EADC. Abbreviation for ethylaluminum dichlo- “Easy Glide” [Swix]. TM for ski wax.

ride. Use: For no-wax skis for better performance and to

avoid icing.

EAK. Abbreviation for ethyl amyl ketone.

“Ebecryl 605a” [Cytec].

CAS: 84593-14-6.

earth. (1) Any siliceous or claylike compound or

Hazard: A mild skin irritant.

mixture, e.g., fuller’s earth, diatomaceous earth. (2)

Use: Industrial coating for wood, plastics, paper, and

A natural metallic oxide, sometimes used as a pig-

electronics including parquet and safety glass inter-

ment, e.g., red and yellow iron oxide, ocher, or

layers.

umber. (3) An oxide of any of a series of chemically

related metals that are difficult to separate from their

ebonite. See rubber, hard.

oxides or other combined forms, specifically, rare

earths, alkaline earths.

ebullator. A solid substance or surface used to

See specific entry.

prevent superheating of liquids above their boiling

point.

earth wax. General name for ozocerite, ceresin,

and montan waxes.

ebullioscope. (ebulliscope). An instrument to

See wax.

determine concentration by means of boiling points

of liquids.

EASC. Abbreviation for ethylaluminum sesqui-

chloride.

ebulliscope. See ebullioscope.

“Easibrom” [Nalco]. TM for microbiological

ecabet sodium.

control.

CAS: 86408-72-2. mf: C

S•Na.

Use: For cooling and water systems.

Hazard: Moderately toxic by ingestion.

“Easperol” [Henkel]. TM for sulfated fatty

“Ecdel” [Eastman]. TM for an elastomer

alcohol–vegetable-oil mixtures.

which imparts excellent low-temperature resistance

Use: Replacement additives for sulfated sperm-oil

that significantly reduces product loss due to flex

types in production of leather.

cracking and shattering during cold weather distri-

bution.

“Eastar” [Eastman]. TM for PETG copolyes-

Use: Applications where low extraction of plasticiz-

ter useful in a variety of processes and applications

ers from the product, flex crack resistance, and utili-

because of its toughness, clarity, and good melt

ty in harsh environments are required.

strength.

Use: For blister packaging and thermoformed con-

echinomycin.

tainers for refrigerated/frozen foods, candies, and

CAS: 512-64-1. C

sundries.

Properties: Colorless crystals. Slightly hygroscopic,

mp 218C. Soluble in fats, chloroform, dioxane; in-

East India. A type of fossil or semirecent resin

soluble in water.

similar to dammar. Varieties are batu, black, and

Use: Medicine (antibiotic).

pale.

Use: In spirit and oleoresinous varnishes.

ECM. See extracellular matrix.

“Eastobond” [Eastman]. TM for a series of

ecology. The study of the interactions between

hot-melt adhesives used in the packaging industry

plant and animal organisms and their environment;

for bonding paper, board, film, foil, and glassine.

the latter is conceived to include everything that is

not an intrinsic part of the organism and thus in-

“Eastone” [Eastman]. TM for disperse dye-

cludes both living and nonliving components.

stuffs for use with acetate and nylon fibers.

Though primarily a branch of biology, ecology does

involve chemistry in respect to plant and animal

“Eastotac” [Eastman]. TM for hydrogenated nutrients, metabolism, photosynthesis, etc., espe-

aliphatic hydrocarbon tackifying resins. cially interferences that may occur in connection

Derivation: Produced from petroleum feedstock by with these. Thus, insecticides, chemical-waste dis-

polymerization followed by hydrogenation. posal, air and water pollution, oil spills, and radioac-

489

490ECONOMIC POISON

tive contaminants have direct bearing on the ecology tion, nor are medicinal oils derived from animal

of a given area. sources (cod liver, mineral oil, etc.).

See environmental chemistry.

Edman degradation. Sequential degradation

economic poison. See pesticide. of peptides beginning at the N-terminal residue

based on the reaction of phenylisocyanate with the

economics, chemical. See chemical eco- ␣-amino group of the terminal amino acid of the

nomics. peptide chain.

economizer. A device that acts like a heat ex- EDTA. Abbreviation for ethylenediaminetetraa-

cetic acid.

changer whereby the heat produced by an operation

is used to warm incoming air or water. It is widely

used in the paper industry, in boilers, and in chemi-

EDTAN. Abbreviation for ethylene diamine tet-

cal processing. Heat recovery up to 30% is possible. raacetonitrile.

ecosystem. The organisms of an ecologic com- EDTA Na

Abbreviation for ethylene diamine

munity together with the physical environment that tetraacetic acid tetrasodium salt.

they occupy. See tetrasodium EDTA.

“Ecozyme” [Swan]. TM for a xylanase-based effect. An evaporation-condensation unit.

enzyme that reduces chemical bleaching agents up See evaporation.

to 25% with enhanced pulp quality.

Use: Reduces chlorinated effluent discharge levels in

effective charge. The value of charge that, mul-

pulp mills.

tiplied by the actual distance between two atoms of a

heteropolar, diatomic molecule, gives the actual di-

ECTEOLA-cellulose. (epichlorohydrin trieth- pole moment.

anolamine cellulose). A dry, powdered cellulose

derivative containing tertiary amine groups.

effervescence. The rapid escape of gas from a

Use: As an anion exchanger in chromatography. It is

liquid or a mixture.

less basic than DEAE-cellulose and serves to sepa-

rate viruses, nucleic acids, and nucleoproteins.

efflorescence. Loss of combined water mole-

cules by a hydrate when exposed to air, resulting in

EDAP. See EDC (reagent).

partial decomposition indicated by presence of a

powdery coating on the material. This commonly

EDB. Abbreviation for ethylene dibromide. occurs with washing soda (Na

•10H

O), which

loses almost all its water constituent spontaneously.

EDC (reagent).

CAS: 25952-53-8. mf: C

•ClH. effluent. Any gas or liquid emerging from a pipe

Use: An antibiotic. or similar outlet; usually refers to waste products

Hazard: A poison. from chemical or industrial plants, as stack gases or

liquid mix.

Edeleanu process. A solvent extraction pro-

cess using liquid sulfur dioxide for the removal of

egg. (1) A large gamete without flagellae that is

undesirable aromatics from heavy lubrication oils. fertilized by a sperm cell. An egg cell is also called

an ovum. (2) A complex multicellular structure in

which an animal embryo develops.

edestin. A protein having a molecular weight of

310,000, obtained from hempseed. Closely similar

proteins occur in seeds of pumpkin, squash, etc.

egg oil. Fatty oil obtained from egg yolk by

extraction with ethylene dichloride; insoluble in wa-

ter, but readily forms emulsions on strong agitation.

edetate. See ethylenediaminetetraacetic acid

Use: Ointments, cosmetic creams.

(note).

egg yolk.

edible oil. As commonly used, the term refers to

Properties: Yellow, semisolid mass. D 0.95, mp

any fatty oil obtained from the flesh or seeds of

22C. High cholesterol content.

plants that is used primarily in foodstuffs (marga-

Grade: Technical, edible.

rine, salad dressing, shortening, etc.). Among these

Use: Baking, dairy products, mayonnaise, pharma-

are olive, safflower, cottonseed, coconut, peanut,

ceuticals, soap, perfumery.

soybean, and corn oils, some of which may be hy-

See albumin, egg.

drogenated to solid form. They vary in degree of

unsaturation, ranging from 78% for safflower to

about 10% for coconut. Castor oil, though technical-

EHEC. Abbreviation for ethyl hydroxyethyl cel-

ly edible, is not usually considered in this classifica- lulose.

491 ELAIDIC ACID

Ehrlich, Paul. (1854–1915). A native of Sile- Einhorn-Brunner reaction. Formation of

sia, Ehrlich is considered the founder of the science substituted 1,2,4-triazoles by condensation of hy-

of chemotherapy, or the treatment of diseases by drazines or semicarbazides with diacylamines in the

chemical agents. He did fundamental work on im- presence of acid catalysts.

munity, which earned him the Nobel Prize in medi-

cine in 1908, and also developed the famous

einstein. The energy acquired by a gram-molecu-

neoarsphenamine (salvarsan or 606) treatment for

lar weight of a substance when each molecule ab-

syphilis (1910), which was not improved upon until

sorbs a quantum of excitation energy.

the discovery of penicillin.

einsteinium. Es. A synthetic radioactive element

with atomic number 99 and aw 253, discovered in

Ehrlich-Sachs reaction. Formation of anils by

the debris from the 1952 hydrogen-bomb explosion.

the base-catalyzed condensation of compounds con-

Einsteinium has since been prepared in a cyclotron

taining active methylene groups with aromatic ni-

by bombarding uranium with accelerated nitrogen

troso compounds.

ions, in a nuclear reactor by irradiating plutonium or

californium with neutrons, and by other nuclear re-

eicosamethyl nonasiloxane. C

actions. The element is named for Albert Einstein. It

Properties: Inert liquid. Bp 173C (5 mm Hg), d

has chemical properties similar to those of the rare-

0.918. Soluble in benzene and light hydrocarbons;

earth metal holmium. Isotopes are known with mass

slightly soluble in alcohol.

numbers ranging from 246 to 253. Einsteinium has

Use: Silicone fluids, foam suppressor in lubricating

valence of 2, and the lowest heat of vaporization of

oils.

any divalent element.

See actinide series.

eicosane. C

. Most technical eicosane is a

mixture of predominantly straight-chain hydrocar-

eka-. Prefix referring to element in next-lower

bons averaging 20 carbon atoms to the molecule.

position in the same group in the periodic system.

Properties: (pure n-eicosane): White, crystalline sol-

id. Fp 36.7C, bp 205C (15 mm Hg), flash p 212F

ekahafnium. One of the last-discovered transu-

(100C), refr index 1.4348 (20C), d 0.778 (at melting

ranic elements; atomic number 104. It has two ␣-

point). Insoluble in water; soluble in ether. Can be

emitting isotopes (257 and 259) and possibly a third

readily chlorinated. Combustible.

(258). The former, made by bombardment of cali-

Grade: Pure normal (99+%), technical.

fornium-249 with carbon-12 nuclei, has a half-life

Use: Cosmetic, lubricants, plasticizers.

of five seconds and decays into nobelium-253. The

259 isotope, made by merging a carbon-13 nucleus

eicosanoic acid. See arachidic acid.

with californium-249, has a half-life of three sec and

decays to nobelium-255.

eicosanoid. Any of a number of biochemically

active compounds resulting from enzymic oxidation

“Ekonol” [Carborundum]. TM for an engi-

of arachidonic acid, e.g., prostaglandins, thrombox-

neering plastic composed of poly-p-oxybenzoate.

anes, prostacyclin, and leukotrienes. As a group,

Resistant to temperatures above 600C, self-lubricat-

they compose what is known as the arachidonic acid

ing surface.

cascade. They have many pharmacological and

Use: In pumps handling corrosive liquids, protective

medical possibilities.

coating for titanium skins on supersonic transports,

See prostaglandin; arachidonic acid.

disk brakes, etc.

1-eicosanol. See arachidyl alcohol.

“ELA” [Du Pont]. Brand name for elastomer

lubricating agent, a mixture of phosphate esters.

5,8,11,14-eicostetraenoic acid. See arachi-

Light-amber liquid.

donic acid.

Use: Unvulcanized rubbers.

eigenenergy. Quantity of energy corresponding

elaboration. A term used in biochemistry to de-

to a time-invarient atomic state.

scribe chemical transformations within an organism

resulting in formation of specific types of sub-

eigenfunction. Wave function corresponding to

stances; for example, plants elaborate proteins and

a state with a definite value of some quantity.

fats, and poisonous snakes elaborate their venom. It

also refers to formation of metabolic end products

such as purines and uric acid.

Eigen, Manfred. (1927– ). A German physicist

who won the Nobel Prize for chemistry in 1967. His

research concerned the rate of hydrogen-ion forma-

elaidic acid. (trans-9-octadecenoic acid).

tion through disassociation of water. He also was CH

[CH

]

HC:CH[CH

]

COOH. The trans form of

concerned with enzyme control. He received his an unsaturated fatty acid of which the cis form is

degree at the University of Gottingen. oleic acid.

492ELAIDINIZATION

high polymers having properties similar to those of

vulcanized natural rubber, namely, the ability to be

stretched to at least twice their original length and to

retract very rapidly to approximately their original

Properties: White solid. D 0.8505 (79/4C), mp

length when released. Among the better-known

43.7C, bp 288C (100 mm Hg), 234C (15 mm Hg),

elastomers introduced since the 1930s are styrene-

refr index 1.4358 (79C). Insoluble in water; soluble

butadiene copolymer, polychloroprene (neoprene),

in alcohol, ether, benzene, and chloroform. Com-

nitrile rubber, butyl rubber, polysulfide rubber

bustible.

(“Thiokol”), cis-1,4-polyisoprene, ethylene-propyl-

Derivation: Synthesized from oleic acid by elaidini-

ene terpolymers (EPDM rubber), silicone rubber,

zation.

and polyurethane rubber. These can be cross-linked

Grade: Purified, 99+%.

with sulfur, peroxides, or similar agents. The term

Use: Medical research, reference standard in chroma-

was later extended to include un-cross-linked polyo-

tography.

lefins that are thermoplastic; these are generally

known as TPO rubbers. Their extension and retrac-

elaidinization. Originally the reaction by which

tion properties are notably different from those of

oleic acid is converted into elaidic acid, but now

thermosetting elastomers, but they are well adapted

used in a more general sense to indicate the conver-

to such specific uses as wire and cable coating,

sion of any unsaturated fatty acid or related com-

automobile bumpers, vibration dampers, and spe-

pound from the geometric cis to the corresponding

cialized mechanical products.

trans form. Nitrous acid and selenium compounds

are commonly used as catalysts for this reaction.

Elbs persulfate oxidation. Hydroxylation of

The resulting trans acids are more stable to oxida-

phenols to p-diphenols by potassium persulfate in

tion.

alkaline solution.

elargin.

Elbs reaction. Formation of anthracenes by in-

CAS: 2169-75-7. mf: C

NO•C

tramolecular condensation of diaryl ketones con-

Hazard: A poison by ingestion.

taining a methyl or methylene substituent adjacent

to the carbonyl group.

elasticity. The ability of a material to recover its

original shape partially or completely after the de-

forming force has been removed. The small amount

elcatonin. See carbocalcitonin.

of deformation that is not recovered is called perma-

nent set or permanent elongation. Among common

electric double layer. A diffuse aggregation

materials, glass and some metals are virtually 100%

of positive and negative electric charges surround-

elastic, whereas vulcanized rubber and other elasto-

ing a suspended colloidal particle which aids in

meric substances are in the range of 90% elastic after

maintaining its stability. According to the Gouy-

extension to rupture. So-called perfect elasticity is a

Freundlich theory, advanced about 1920, a close-

property of atoms that show no energy loss on colli-

packed array of charges is attached to the surface of

sion.

the particle while a diffuse layer of charges of oppo-

See modulus of elasticity; stress; strain; plasticity.

site sign extends into the liquid. The particle is elec-

trically neutral. There is an electrokinetic potential

elastic modulus. See modulus of elasticity.

gradient across the double layer that is called the

zeta potential. The diagram is an approximation of

elastin. A scleroprotein that occurs in connective

this phenomenon. Modifications of this theory have

tissue.

been introduced in recent years, notably by Derja-

Properties: Yellow, fibrous mass. Insoluble in wa-

guin and Landau and by Verwey and Overbeek

ter, dilute acids, alkalies, salt solutions, and alcohol.

(DLVO theory).

Is partially digested by pepsin solution and wholly

See zeta potential.

by trypsin.

“ElastoFlo” [Dow]. TM for ethylene-propyl-

ene rubber polymer.

Properties: A free-flowing granular solid.

Use: For automotive hose, tubing and extrusions,

roofing membranes and gaskets.

“Elastoguard” [Milliken]. TM for an antimi-

crobial, anti-fatigue solution.

elastomer. As originally defined by Fisher

(1940), this term referred to synthetic thermosetting

493 ELECTRODE, GLASS

electric furnace. See furnace. electrical phenomena. It has certain applications in

biochemistry (in nerve reactions and the electric

organs of fish) as well as in organic chemistry. Mi-

electric steel. Steel made in an electric furnace.

chael Faraday (1791–1867) is generally regarded as

the founder of electrochemistry.

electric vehicle propulsion. See storage

battery.

electrocoating. A process of applying primer

paint to household appliances, automobiles, etc., in

electride. An experimental compound composed

which the metal piece to be coated becomes the

of an alkali-metal cation and an electron in which the

anode in a tank of water-based paint. The coating

electron functions as a chemical element (e.g., a

deposited on the metal is uniform regardless of the

halogen) in salt formation. Several such compounds

shape of the article. Large-scale use of electrocoat-

have been made in the U.S. and abroad. The phe-

ing is on automobile bodies.

nomenon is reported to be one that challenges ac-

See electrostatic coating.

cepted concepts of compound formation.

electroconductive polymer. See polymer,

electrochemical equivalent. The number of

electroconductive.

grams of an element or group of elements liberated

by the passage of one coulomb of electricity (one

ampere for one sec).

electrocratic. Descriptive of a liquid colloidal

dispersion of insoluble solid particles whose stabili-

ty is maintained by either positive or negative

“Electrocarb” [Electro Abrasives]. TM for

charges on the particles. As the like charges are

silicon carbide.

mutually repellent, they offset the attraction of grav-

CAS: 409-21-2.

ity and prevent the particles from sinking or coalesc-

Properties: High thermal conductivity, abrasion re-

ing. A colloidal gold suspension is a well-known

sistant, high hardness (2550 knoop). Electrical con-

example. Electrocratic dispersions can be readily

ductor.

precipitated by addition of an oppositely charged

Grade: Grit sizes 8–1600 mesh.

electrolyte, as in the purification of water with

Use: Wear resistant filler, thermal conductor in com-

ions from aluminum sulfate.

pounds, high temperature paints, ceramics, refracto-

ries. As a polishing and lapping abrasive.

“Electrocure.” TM for a process for hardening

electrochemical gradient. The sum of the gra- or curing paint films on plastics by use of low-volt-

dients of concentration and of electric charge of an age electron beams. Paints so treated cure in four sec

ion across a membrane. Used as the driving force for or less at room temperature; the finishes produced

processes, such as oxidative phosphorylation and are said to be superior in resistance to abrasion and

photophosphorylation. chemicals. The process can also be applied to other

substrates such as wood, glass, metals, etc.

electrochemical potential. The energy re-

quired to maintain a separation of charge and of

electrode. Either of two substances having differ-

concentration across a membrane.

ent electromotive activity that enables an electric

current to flow in the presence of an electrolyte.

Electrodes are sometimes called plates or terminals.

Electrochemical Society. (ECS). Established

Commercial electrodes are made of a number of

in 1902, this society was organized to promote the

materials which vary widely in electrical conductiv-

advancement of the science of electrochemistry and

ity, i.e., lead, lead dioxide, zinc, aluminum, copper,

related fields. It comprises 11 divisions, each devot-

iron, manganese dioxide, nickel, cadmium, mercu-

ed to a special branch of electrochemistry, e.g., cor-

ry, titanium, and graphite; research electrodes may

rosion, batteries, rare metals, electrodeposition, etc.

be calomel (mercurous chloride), platinum, glass, or

It publishes a journal and sponsors books relating to

hydrogen. Electrodes are essential components of

its major interests. Its office is at 65 South Main

both batteries and electrolytic cells; in batteries the

Street, Pennington, New Jersey 08534-2839.

negative plate is the anode and the positive plate the

Website: http://www.electrochem.org.

cathode, whereas in electrolytic cells the reverse is

the case.

electrochemistry. That branch of chemistry

Use: Electrodes are also used in welding devices.

concerned primarily with the relationship between

See anode; cathode; battery; electrolytic cell.

electrical forces and chemical reactions. This rela-

tionship is fundamental and farreaching, as the

structure of matter is based on electrical effects.

electrode, glass. A thin, glass membrane that

Electrochemistry is directly involved in chemical when immersed in a suitable liquid medium devel-

bonding, ionization, electrolysis (e.g., production of ops a measurable electrical potential that can be

aluminum), metallurgy, battery science, fuel cells, readily related to the activity of ionic species present

and corrosion—in short, in any situation in which a in the solution. By appropriate manipulation of the

chemical change is caused by or associated with glass composition, careful pretreatment of the glass

494ELECTRODE, HYDROGEN

surface, and reproducible experimental conditions, in a bath without application of an electric current,

i.e., by chemical reduction.

electrodes can be devised that not only yield infor-

mation about the concentration of ions in solution

but also have the ability to discriminate in the sense

electroluminescence. Luminescence generated

of a selective response between a number of differ-

in crystals by electric fields or currents in the ab-

ent ions of similar chemical characteristics. Because

sence of bombardment or other means of excitation.

of their ability to give both qualitative and quantita-

It is a solid-state phenomenon involving p- and n-

tive information about ions in solution, glass elec-

type semiconductors, and is observed in many crys-

trodes are widely used for purposes of chemical

talline substances, especially silicon carbide, zinc

measurement, especially in electrochemical re-

sulfide, and gallium arsenide, as well as in silicon,

search.

germanium, and diamond.

See phosphor.

electrode, hydrogen. A platinum surface coat-

electrolysis. Decomposition of water and other

ed with platinum black immersed in a solution and

inorganic compounds in aqueous solution by means

bathed with a stream of pure hydrogen gas. The

of an electric current, the extent being proportional

potential developed depends on the equilibrium be-

to the quantity of electricity passing through the

tween the hydrogen gas and the hydrogen ions in

solution. The positive and negative ions formed are

solution.

carried by the current to the oppositely charged

Use: Standard reference electrode.

electrodes, where they are collected (if wanted) or

released (if unwanted). Metallic ions deposited on

electrodeposition. The precipitation of a mate-

the electrode form a coating. A simple electrolysis is

rial at an electrode as the result of the passage of an

the separation of water into oxygen and hydrogen;

electric current through a solution or suspension of

this is one method of producing hydrogen. Some-

the material, for example, alkaline-earth carbonates,

what more complicated is electrolysis of brine to

rubber from latex, paint films on metal. A technique

chlorine and sodium hydroxide; this is carried out in

for electrodepositing refractory carbide coatings on

electrolytic cells of the diaphragm or mercury type,

metal has been reported. The electrode is in the

with water taking part in the reaction. In electroplat-

shape of the desired article. An important advantage

ing, metal salts dissociate into their constituent ions,

of electrodeposition is its ability to coat complex

the positively charged metal ions coating the cath-

shapes having small and irregular cavities with exact

ode. There are a number of variations of this process

thickness control.

(electrodeposition, electrocoating, electroforming).

See electrophoresis.

See electrolytic cell; ionization.

electrodialysis. A form of dialysis in which an

electrolyte. A substance that will provide ionic

electric current aids the separation of substances that

conductivity when dissolved in water or when in

ionize in solution. Seawater can be desalted by this

contact with it; such compounds may be either solid

method on a large scale by placing it in the center

or liquid. Familiar types are sulfuric acid and sodi-

chamber of a three-compartment container having

um chloride, which ionize in solution. One solid

two semipermeable membranes and a positive elec-

electrolyte, used originally in fuel cells, is a polymer

trode in one end chamber, and a negative electrode

of perfluorinated sulfonic acid used as the core of a

in the other. The ions migrate to their respective

water electrolysis cell for production of hydrogen

electrodes under a difference of potential, leaving

and oxygen. When saturated with water it has high

the water saltfree.

conductivity. Another solid type is a ceramic mix-

See dialysis; desalination; demineralization.

ture of sodium, aluminum, lithium, and magnesium

used as a separating medium in the liquid-sodi-

electroforming. An electrolytic plating process

um–sulfur (␤) battery under continuing develop-

for manufacturing metal parts. A mold of the object

ment. The most common application of electrolytes

to be reproduced is made in a soft metal or in wax (by

is in electroplating of metals in which dissolved

impression). The mold surface is made conducting

(ionized) metal salts are the electrolytes.

by coating with graphite. Some suitable metal is

See electrolysis; electroplating.

then deposited electrolytically on the mold surface.

This mold is then (in most cases) a negative of the

electrolyte acid. Legal label name for battery

object to be produced. Other industrial applications

acid.

are phonograph records, plastic tile, ducting, tubing,

etc.

electrolytic cell. An electrochemical device in

which electrolysis occurs when an electric current is

electrogenic. Contributing to the generation of

passed through it. Ionizable compounds dissociate

an electrical potential across a membrane.

in the aqueous solution with which the electrodes are

in contact. Such cells are of two types: (1) the dia-

electroless coating. A protective coating of phragm cell, which has two compartments separated

copper, cobalt, nickel, gold, or palladium deposited by a porous membrane; and (2) the mercury cell, in

495 ELECTRONEGATIVITY

which mercury is the cathode. The anodes of both tric energy, or bombardment with high-energy parti-

types have long been made of graphite; because this cles (see radiation, ionizing). In such cases, they are

decomposes rapidly as electrolysis progresses, they totally free from the atomic orbit and their energy

are being replaced with dimensionally stable types can be utilized by means of a conductor (electricity)

consisting of titanium coated with oxides of rutheni- or a vacuum tube or semiconductor. Current is gen-

um and other rare metals, which are also much more erated by detaching the electrons of a metallic con-

efficient. In electrolysis of sodium chloride, the cur- ductor (silver, copper) by means of an electric or

rent causes chloride ion to migrate to the anode, magnetic field; the electrons then flow along the

where it is collected as chlorine gas; sodium hydrox- conductor to a positively charged terminal. The sci-

ide and hydrogen are also formed, the hydrogen ence of electronics was made possible by the ability

being discharged. The overall cell reaction is: 2NaCl of a heated metal cathode to emit a continuous

+2H

O → H

+Cl

+ 2NaOH. This principle is stream of electrons in a vacuum tube. Free electrons,

applied in the electroplating of metals, electrodepo- called ␤ particles, are spontaneously emitted by de-

sition of colloids, and similar processes. caying radioactive nuclei; they have comparatively

See diaphragm cell; mercury cell; electroplating. low energy but can be accelerated to velocities ap-

proaching that of light. The basic nature of the elec-

tron has been the subject of much research of the

electromagnetic separation. Separation of

highest order of mathematical rigor. In simplest

isotopes, especially those of uranium, by first accel-

terms, the electron has the properties of both a parti-

erating them by means of an electrostatic field and

cle and a wave, i.e., a standing wave is associated

then passing them through a magnetic field. The

with an electron moving in its orbit. The energy state

effect of this is to cause all the particles to take a

of any electron in an atom is described by four

curved path; the heavier ones, having higher kinetic

quantum numbers.

energy, describe a wider arc than the lighter ones.

See shell; atom; orbital theory; Lewis electron theory.

Thus, two isotopes of closely similar masses can be

separated and collected.

See mass spectrometry; magnetic separation.

electron acceptor. A substance that receives

electrons in a redox reaction.

electromagnetic spectrum. See radiation.

electron-beam welding. See welding.

electrometallurgy. Application of the princi-

ples and techniques of electrochemistry to the pro-

electron carrier. A protein or other chemical

duction of such metals as aluminum and titanium. species, such as a cytochrome or coenzyme Q, that

can reversibly gain and lose electrons. They func-

tion in the transfer of electrons from organic nutri-

electromotive series. See activity series.

ents to oxygen or some other terminal acceptor as in

the case of anaerobes.

electron. Discovered by J. J. Thompson in 1896,

the electron is a fundamental particle of matter that

electron donor. A substance that donates elec-

can exist either as a constituent of an atom or in the

trons in a redox reaction.

free state. It has a negative electric charge (4.8 × 10

−10

esu) and a mass 1/1837 that of a proton, equivalent to

9.1 × 10

−28

gram. The number of electrons in an atom electronegativity. All atoms (except those of

of any element is the same as the number of protons helium) that have fewer than eight electrons in their

in the nucleus, i.e., the atomic number. Thus, the highest principal quantum level have low-energy

range is from one electron in hydrogen to 103 in orbital vacancies capable of accommodating elec-

lawrencium. As the negative charge of the electrons trons from outside the atom. The existence of these

equals the positive charge of the protons, all atoms vacancies is evidence that within these regions the

are electrically neutral. Electrons are arranged in nuclear charge can exert a significant attraction for

from one to seven shells around the nucleus; the such electrons, even though as a whole the atom is

maximum number of electrons in each shell is strict- electrically neutral. This attraction is called “elec-

ly limited by the laws of physics. The tendency of tronegativity.” To the extent that the initially neutral

electrons to form complete outer shells accounts for atom may be able to acquire electrons from outside,

the valence of an element, and they play an essential it will acquire also their negative charge. The word

part in chemical bonding. The outer shells are not “electronegativity” means “tendency to become

always filled: sodium has two electrons in the first negatively charged.” The concept of electronegativ-

shell, eight in the second, and only one in the third. A ity is an extremely useful one in chemistry, since the

single electron in the outer shell may be attracted attractive force exerted by the nuclei of atoms that

into an incomplete shell of another element, leaving have vacancies in their outer shells makes possible

the original atom with a net positive charge. Each the formation of both covalent and ionic bonds and

atom then is called an ion. Valence electrons are is thus a fundamental factor in the formation of

those that can be captured by or shared with another chemical compounds. The most highly electronega-

atom. Electrons can be removed from the atoms of tive elements are the halogens, sulfur, and oxygen.

metals and some other elements by heat, light, elec- See bond, chemical.

496ELECTRON MICROSCOPE

electron microscope. A microscope in which Use: In recombinant DNA technology.

See transfection.

the source of illumination is a stream of electrons

emanating from a tungsten cathode in a high vacuum

and accelerated by a strong electric impulse (300

electron transport chain. See acceptor con-

kv). The electrons are focused by a series of magnet-

trol.

ic fields that function as lenses in the same way as

glass affects waves of visible light, i.e., the electron

electron-volt. (eV). An extremely small unit

stream curves as it passes through the magnetic

used in measuring the energy of electrons and other

field. Such lenses were developed in Germany by

atomic constituents. It is the energy developed by an

Busch, Knoll, and Tuska in the 1930s, and were

electron in falling through a potential difference of

adapted to microscopy by Zworykin and Hillier at

one V, equivalent to 1.6 × 10

−19

J. The rupture of a

the RCA Laboratories in the early 1940s, when the

carbon-to-carbon bond has been calculated to yield

first commercial instruments were produced. The

approximately 5 eV.

electron microscope is characterized by extremely

high resolving power due to the ultrashort wave-

electrophoresis. Migration of suspended or col-

length of electronic radiation—a small fraction of an

loidal particles in a liquid such as rubber latex due to

angstrom unit (A

). Resolution of 2 A

is possible,

the effect of a potential difference across immersed

which permits determination of the structure of mac-

electrodes. The migration is toward electrodes of

romolecules (DNA) and even observation of large

charge opposite to that of the particles. Most solids,

atoms (uranium). Instruments of the scanning trans-

being negatively charged, migrate to the anode, the

mission type with a resolving power of 0.05 A

were

exception being basic dyes, hydroxide solutions,

developed at the University of Chicago. Two kinds

and colloids that have adsorbed positive ions, all of

of electron microscopies are in general use: the

which are positively charged and migrate to the

transmission type, in which the electrons penetrate

cathode. Migrating particles lose their charge at the

the specimen, and the scanning type introduced in

electrode and generally agglomerate around it. Clay

1970, in which the electrons, condensed to a fine

suspensions can be filtered by means of forced-flow

beam, repeatedly traverse the surface of the speci-

electrophoresis. Electrophoresis is important in the

men, producing a three-dimensional contour effect

study of proteins because the molecules of such

by means of secondary electrons emanating from the

materials act like colloidal particles and their charge

specimen itself. Pictures of astonishing accuracy

is positive or negative according to whether the

have been obtained, especially of surface structures,

surrounding solution is acidic or basic. Thus, the

a matter of great importance in the study of catalysis

acidity of the solution can be used to control the

and other critical phenomena in both industry and

direction in which a protein moves upon electropho-

the biological sciences. A unique combination of

resis. It has been found that electrophoresis can be

these techniques is the scanning transmission elec-

carried out more efficiently under zero-gravity con-

tron microscope (STEM), by means of which col-

ditions in outer space than on earth.

ored motion pictures of uranium atoms on a thin-

Use: Experimentally to separate mixtures of electri-

film carbon substrate have been obtained.

cally charged species such as proteins or nucleic

See optical microscope; resolving power; ultramicro-

acids.

scope; field-ion microscope.

See electrodeposition.

electroplating. The deposition of a thin layer or

electron octet. Group of eight valence elec-

coating of metal (e.g., chromium, nickel, copper,

trons. The most stable configuration of the outer-

silver, etc.) on an object by passing an electric cur-

most, or valency, electron shell of the atom.

rent through an aqueous solution of a salt containing

ions of the element being deposited, for example,

electron paramagnetic resonance. (EPR).

. The material being plated (usually a metal but

A method of spectroscopic analysis similar to nucle-

often a plastic) constitutes the cathode. The anode is

ar magnetic resonance except that microwave radia-

often composed of the metal being deposited; ideal-

tion is employed instead of radio frequencies. It is

ly it dissolves as the process proceeds. The thin layer

used for studying free radicals, crystalline centers,

deposited is sometimes composed of two or more

transition elements, and structures involving un-

metals, in which case it is an alloy. The solution or

paired electrons.

plating bath contains dissolved salts of all the metals

being deposited. Electrolytic cells are used for this

electrophile. An electron-deficient group with a

process. The anode must be an electrical conductor,

strong tendency to accept electrons from an elec-

but may or may not be of the same chemical compo-

tron-rich group (nucleophile).

sition as the material being deposited, and may or

See nucleophile; Lewis acid.

may not dissolve during the process. The purpose of

electroplating is usually protection of the base metal

electroporation. A process using high-voltage from corrosion. Silver is electroplated on copper for

current to make cell membranes permeable to allow economy reasons; plastics may be electroplated for

the introduction of new DNA. decorative effects.

497 ELUATE

See electrophoresis; protective coating; “electroless” heavier than lead are unstable and radioactive.

About 90% of the earth’s crust is made up of ele-

coating; throwing power; current density.

ments with even numbers of protons and neutrons.

No stable elements heavier than nitrogen have an

electropolishing. A nonmechanical method of

odd number of both protons and neutrons. Elements

polishing metal surfaces that is actually the reverse

of even atomic number normally have several iso-

of electroplating. This is achieved by making the

topes, while those of odd atomic number never have

object to be polished the anode in an electrolytic

more than two stable isotopes. All elements beyond

circuit, the cathode usually being carbon. The elec-

uranium (transuranic) were nonexistent in 1940.

trolytes used are phosphoric, hydrofluoric, nitric,

They are artificially created by bombardment of

and sulfuric acids (sometimes called polishing

other elements with neutrons or other heavy parti-

acids).

cles. Research on new elements is actively carried

on at many laboratories including the Lawrence

electrostatic bond. Alternative name for an

Livermore Laboratories, which reported discovery

ionic bond.

of element 106 in 1974. Creation of element 109 was

See bond, chemical.

announced in 1982, and of element 112 in 1996. A

single atom of element 109 was made by West Ger-

electrostatic coating. A metal-painting tech-

man physicists by bombarding

209

Bi with

Fe nuclei.

nique in which electrostatically charged pigment

Controversy continues on the naming of elements

particles are sprayed onto a substrate metal, fol-

104 through 109. Many more (possibly up to 150)

lowed by baking. The electric charge attracts the

are theoretically possible according to Dr. G. T.

particles to the metal and holds them in place until

Seaborg.

heat treatment is applied. Maintenance of the charge

See periodic table; isotope; radioactivity; abundance.

is thus essential; factors affecting this are relative

Note: For origin of elements, see nucleogenesis.

humidity (the lower the better) and the chemical

nature of the pigment, e.g., phthalocyanine blue

retains the charge much longer than titanium di-

elemi. A soft, balsam like resin obtained from a

oxide.

tree in the Philippines, soluble in coal tar hydrocar-

bons, but not in petroleum solvents, alcohols, and

electrostatic precipitator. See Cottrell,

ketones.

Frederick G.

Use: Plasticizer, adhesion of lacquers to metals, ce-

ments and adhesives, wax compositions, printing

electrovalent bond. Alternative name for an

inks, textile and paper coatings, perfumery, water-

ionic bond.

proofing, engraving.

See bond, chemical; ionic bond.

elimination reaction. A chemical reaction in-

electrowinning. The technique of extracting a

volving elimination of a portion of a reactant com-

metal from its soluble salt by an electrolytic cell. It is

pound, resulting in a second compound. Many reac-

used in recovery of zinc, cobalt, chromium, and

tions eliminate water.

manganese, and has been applied to copper when in

the form of a silicate ore. For any specific metal, the

“Elimin-Ox” [Nalco]. TM for chemicals for

salt in solution is subjected to electrolysis and is

scavenging oxygen.

electrodeposited on a cathode made of the metal

Use: In water systems.

being extracted.

element. One of the 112 presently known kinds of

elongation factors. Specific proteins required

substances that compose all matter at and above the

in the elongation of polypeptide chains by ribo-

atomic level. According to a theory that has gained

somes, or DNA strands by replisomes.

acceptance, the lightest elements were formed in

less than half an hour from a primordial complex

Eltekoff reaction. Production of highly

called ylem, a mixture of neutrons and electromag-

branched hydrocarbons by methylation of olefins

netic radiation. The smallest unit of any element is

with methyl choride, or methyl iodide in the pres-

the atom. All the atoms of a given element are

ence of lead oxide, or calcium oxide at high tempera-

identical in nuclear charge and number of electrons

tures.

and protons, but they may differ in mass, e.g., hydro-

gen has mass numbers of 1, 2, and 3, called hydro-

eluant. The liquid used to separate or extract one

gen, deuterium, and tritium, respectively. These are

material from another.

the isotopes of hydrogen; most elements have isoto-

See chromatography.

pic forms that are due to the presence of one or more

extra neutrons in the nucleus. The atomic number of

an element indicates its position in the periodic table

eluate. The solution that results from the elution

and represents the number of protons present, which process.

is the same as the number of electrons. All elements See chromatography.

498ELUTRIATION

elutriation. A process of washing, decantation, Hazard: Toxic by ingestion.

and settling that separates a suspension of a finely

divided solid into parts according to their weight. It

emeralds, synthetic. Artificial crystals pro-

is especially useful for very fine particles below the

duced by a high-pressure, high-temperature process

usual screen sizes, and is used for pigments, clay

from beryllium aluminum silicate containing a

dressing, and ore flotation.

small amount of chromium.

Use: Lasers, masers, semiconductors.

“Elvace” [Reichhold]. TM for a series of vinyl

acetate ethylene emulsions.

emery. See corundum; abrasive.

“Elvacite” [Du Pont]. (butyl methacrylate emetine. (cephaeline methyl ether; 6

′

,10,11-

tetramethoxyemetan).

resins). TM for polymer products.

CAS: 483-18-1. C

. An alkaloid from

Use: Resistance to UV weathering and degrading; as

ipecac.

base for lacquers, paints, coatings, and inks.

Properties: White powder; very bitter taste. Mp 74C.

Darkens on exposure to light. Soluble in alcohol and

“Elvanol” [Du Pont]. TM for various grades

ether, slightly soluble in water.

of polyvinyl alcohol.

Derivation: By extraction from root of Cephalis ipe-

cacuanha (ipecac) or synthetically.

“EMA” resins [Solutia]. TM for ethylene-

Hazard: Toxic by ingestion.

maleic anhydride copolymers. Water-soluble resins

Use: Medicine (antiamebic).

that serve as dispersing agents in cold-water deter-

gents, thickeners, binders, stabilizers, and emulsi-

emission spectroscopy. Study of the composi-

fiers.

tion of substances and identification of elements by

observation of the wavelengths of radiation they

embosser. See fiber roll.

emit as they return to a normal state after excitation

by an external energy source. When atoms or mole-

embrittlement. Hardening of a metal (especially

cules are excited by energy input from an arc, spark,

steel) or of an ABS resin, resulting in loss of strength

or flame, they respond in a characteristic manner;

and impairment of other physical properties. In met-

their identity and composition are signaled by the

als, the primary cause is exposure to hydrogen,

wavelengths of incident light they emit. The spectra

though other factors such as corrosion also are in-

of elements are in the form of lines of distinctive

volved. In copolymer plastics, such as ABS resins,

color, such as the yellow sodium D line of sodium;

embrittlement is due to formation of a vitreous ma-

those of molecules are groups of lines called bands.

trix as well as to oxidation of the butadiene particles

The number of lines present in an emission spectrum

in the matrix. Embrittlement due to thermal shock

depends on the number and position of the outer-

occurs in pressurized-water reactors. This may re-

most electrons and the degree of excitation of the

sult in rupture of reactor walls and is a constant

atoms. The first application of emission spectra was

source of trouble in reactors of this type.

identification of sodium in the solar spectrum

(1814).

embryo. Once a zygote begins to undergo cellular

See spectroscopy.

divisions, it becomes an embryo.

emivirine.

embryonic stem (ES) cells. An embryonic

CAS: 149950-60-7. mf: C

cell that can replicate indefinitely, transform into

Hazard: Moderately toxic by ingestion.

other types of cells, and serve as a continuous source

of new cells.

emmenagogue. A drug used to induce menstrua-

tion.

Emde degradation. Modification of the Hof-

mann degradation method for reductive cleavage of

the carbon-nitrogen bond by treatment of an alco-

Emmert reaction. Formation of 2-pyridyldial-

holic or aqueous solution of a quaternary ammo- kylcarbinols by condensation of ketones with pyri-

nium halide with sodium amalgam. Also used as a dine or its homologs in the presence of aluminum or

catalytic method with palladium and platinum cata- magnesium amalgam.

lysts. The method succeeds with ring compounds

not degraded by the Hofmann procedure.

emodin. (frangula emodin; frangulic acid;

1,3,8-trihydroxy-6-methylanthraquinone).

emedastine difumarate.

CAS: 518-82-1. C

(OH)

CAS: 87233-62-3. mf: C

O•2C

Occurrence: Either free, or combined with a sugar in

Hazard: A poison by ingestion.

a glucoside, in rhubarb, cascara sagrada, and other

plants. A synthetic product is also available.

emerald green. A pigment consisting of copper Properties: Orange crystals. Mp 256C. Soluble in

acetoarsenite. alcohol, insoluble in water.

499 ENANTIOMER

Use: Medicine (cathartic). ules plus water droplets are the disperse phase.

See colloid; protective; phase (2); detergent; surface-

active agent; wetting agent.

emoren.

CAS: 13930-31-9. mf: C

•xClH.

Hazard: Moderately toxic by ingestion.

emulsion breaker. See demulsification.

empirical formula. See formula, chemical.

emulsion paint. See paint emulsion.

EMTS. Abbreviation for ethylmercury-p-toluene

emulsion polymerization. Polymerization re-

sulfonanilide.

action carried out with the reactants in emulsified

form. Performed at normal pressure and −20 to

“Emulmetik” [Lucas Meyer]. TM for hy-

+60C. Many copolymers (synthetic rubbers) are

drogenated lecithin.

made in this way.

emulsifier. A surface-active agent.

“Emulsiphos” [Solutia]. TM for sodium

See emulsion.

phosphate.

CAS: 7601-54-9.

emulsifying oil. See soluble oil.

Grade: Powders.

Use: Food-grade phosphate emulsifying agent used

“Emulsilac-S” [ACH]. (sodium stearoyl lac-

in processed cheese and cheese food.

tylate) TM for emulsifier, dough conditioner-

strengthener, and whipping agent.

“Emulvis” [Hall]. TM for polyoxyethylene

Use: For baked goods, puddings, dips, cheese substi-

stearate.

tutes, sauces, whipped toppings, and fillings.

Use: Viscosity builder and solubility retarder for cos-

metics, soaps, and shampoos.

emulsion. (synaptase; amygdalase; ␤-glucosi-

dase). An enzyme catalyzing the production of glu-

en. Abbreviation for ethylenediamine, used in for-

cose from ␤-glucosides.

mulas for coordination compounds, e.g., the cobalt

Properties: White powder; odorless; tasteless. Capa-

complex Co[en]

(NO

)

ble of hydrolyzing glucosides such as amygdalin to

See dien; pn; py.

glucose and the other component substances. Solu-

ble in water; insoluble in ether and alcohol.

enamel. (1) A type of paint consisting of an inti-

Source: Sweet almonds.

mate dispersion of pigments in a varnish or resin

Derivation: By extracting an emulsion of almonds

vehicle. The vehicle may be an oil-resin mix or

with ether, filtering the clear solution, and precipi-

entirely synthetic resin. Those containing drying

tating the emulsion with alcohol.

oils are converted to films by oxidation; those com-

posed wholly of synthetic resins may be converted

emulsion. A stable mixture of two or more im-

by either heat or oxidation, or both.

miscible liquids held in suspension by small per-

See baking finish.

centages of substances called emulsifiers. These are

(2) Porcelain enamel.

of two types: (1) Proteins or carbohydrate polymers

which act by coating the surfaces of the dispersed fat

enamine. A group of amino olefins; the name

or oil particles, thus preventing them from coalesc-

refers especially to unsaturated tertiary amines of

ing; these are sometimes called protective colloids.

the general formula

(2) Long-chain alcohols and fatty acids, which are

able to reduce the surface tension at the interface of

the suspended particles because of the solubility

properties of their molecules. Soaps behave in this

where R is any alkyl group. Though of little use as end

manner; they exert cleaning action by emulsifying

products, enamines are valuable intermediates for

the oily components of soils. All such substances,

many organic syntheses.

both natural and synthetic, are known collectively as

detergents. Polymerization reactions are often car-

enanthaldehyde. See heptanal.

ried out in emulsion form; a wide variety of food and

industrial products are emulsions of one kind or

enanthic acid. See n-heptanoic acid.

another, e.g., floor and glass waxes, drugs, paints,

shortenings, textile and leather dressings, etc. All

enanthyl alcohol. See heptyl alcohol.

emulsions consist of a continuous phase and a dis-

perse phase: in an oil-in-water (o/w) emulsion, such

as milk, water is the continuous phase and butterfat

enantiomer. (enantiomorph). One of a pair of

(oil) the disperse phase; in a water-in-oil (w/o) emul- optical isomers containing one or more asymmetric

sion, such as butter, free fat (from crushed fat glob- carbon atoms C* whose molecular configurations

ules) is the continuous phase and unbroken fat glob- have left- and right-hand (chiral) forms. These

500ENANTIOMORPH

forms are conventionally designated dextro (

D) and endocytosis. The uptake of extracellular material

by its inclusion within a vesicle (endosome) formed

levo (

L) because they compare to each other structur-

by an invagination of the plasma membrane.

ally as do the right and left hands when the carbon

atoms are lined up vertically. This is apparent in the

endoergic. See Endothermic.

enantiomorphic forms of glyceraldehyde; the two

structures are mirror images of each other and can-

endomycin. An antifungal antibiotic complex

not be made to coincide:

produced by streptomyces.

endonuclease. An enzyme that digests nucleic

acids starting in the middle of the strand (as opposed

to an exonuclease, which must start at an end). Ex-

Several pairs of enantiomers are possible, depending

amples include the restriction enzymes, DNase I and

on the number of asymmetric carbon atoms in the

RNase A.

molecule. Compounds in which an asymmetric carbon

See restriction enzyme.

is present display optical rotation.

See asymmetry; optical isomer; optical rotation.

endoplasmic reticulum. An extensive system

of double membranes in the cytoplasm of eukaryotic

enantiomorph. See enantiomer.

cells. The two major types are smooth and rough

endoplasmic reticulum. Functions in calcium stor-

encapsulation. The process in which a material

age as well as in protein and lipid synthesis.

or an assembly of small, discrete units is coated with

or imbedded in a molten film, sheath, or foam, usual-

“Endor” [Du Pont]. TM for a rubber peptiz-

ly of an elastomer. A foam-forming plastic may be

ing agent containing activated zinc salt of pentachlo-

used to fill the spaces between various electrical or

rothiophenol. (C

Zn and 80% inert filler.

electronic components so that they are imbedded in

Properties: Grayish-green powder. D 2.39.

and supported by the foam. Plastics and other mate-

rials used for this purpose are often called potting

endorphin. Any of a group of polypeptides

compounds. A specialized use of this technique is in

formed in the brain tissue and pituitary gland of

growing crystals for semiconductors, in which a

higher animals that are thought to control the trans-

coating of liquid boric oxide is the encapsulating

fer of signals at nerve junctions, thus ensuring that

agent. Use of a glassy silicate coating to encapsulate

behavior patterns in the individual remain normal.

nuclear waste for permanent disposal is under inves-

Imbalance or malfunction of these polypeptides has

tigation.

been reported to be a factor in irrational and violent

See microencapsulation.

actions and other emotional disorders, as well as in

epilepsy and memory processes. This belongs to a

′

end. The end of a nucleic acid that lacks a

developing field of medicinal chemistry called neu-

nucleotide bound at the 3

′

position of the terminal

ropharmacology.

residue.

␤-endorphin.

endergonic reaction. A chemical reaction that

CAS: 60617-12-1.

consumes energy (that is, for which DG is positive).

Hazard: A reproductive hazard.

This is a nonspontaneous processe.

endosmosis. The passing of a fluid inward

“Endic” anhydride [Velsicol]. TM for

through a porous partition toward another fluid of

endo-cis-bicyclo(2.21)-5-heptene-2,3-dicarboxylic

different character.

anhydride. (C

See exosmosis; Perrin rule.

Properties: White crystals. Mp 163C. Soluble in

aromatic hydrocarbons, acetone, ethanol.

endosulfan. (6,7,8,9,10,10-hexachloro-

Use: Elastomers, plasticizers, fire retardant chemi-

1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzo-

cals, resins, and epoxy curing systems.

dioxathiepin-3-oxide).

CAS: 115-29-7. C

endo-. A prefix used in chemical names to indi-

Properties: (commercial product): Brown crystals.

cate an inner position, specifically (1) in a ring rather

Mp 70–100C (pure: mp 106C). Mixture of two iso-

than a side chain or (2) attached as a bridge within a

mers. Mp 108–109C and 206–208C.

ring.

Hazard: Toxic by ingestion, inhalation, and skin

See exo-.

absorption; use may be restricted. TLV: 0.1 mg/m

;

not classifiable as a human carcinogen.

Use: Insecticide.

endocrine glands. Groups of cells specialized

to synthesize hormones and secrete them into the

blood to regulate other types of cells. The pancreas,

endosymbiosis. When one organism takes up

for example. permanent residence within another, so that the two

501 ENERGY BALANCE

become a single functional organism. Mitochondria

enercology. A coined word defined as the bal-

and plastids are believed to have resulted from endo- anced relationship between energy and ecology. A

symbiosis. foundation devoted to practical applications of this

relationship has been established at Alma College,

Michigan.

endothall. (7-oxalobicyclo-[2.2.1]-heptane-2,3-

dicarboxylic acid disodium salt).

CAS: 145-73-3. C

Ene reaction. Addition of an olefin with an

Hazard: Strong irritant to eyes and skin.

allylic hydrogen (ene) to a compound with a double

Use: Defoliant, herbicide.

bond (enophile), involving the allylic shift of one

double bond, transfer of the allylic hydrogen to the

endothermic. A process or change that takes

enophile, and bonding between the two unsaturated

place with absorption of heat and requires high tem-

termini.

perature for initiation and maintenance. An example

is production of carbon monoxide and hydrogen by

energy. The fundamental active entity in the uni-

passing steam over hot coke.

verse, defined as the capacity for doing work. Two

famous equations relate energy to mass as either E

endothion. [S-(5-methoxy-4-oxo-4H-pyran-2-

(Einstein) or E

h␤n (Planck). These equations

yl)-methyl] O,O-dimethylphosphorothioate).

show that energy cannot be completely divorced

CAS: 2778-04-3.

from mass, as the two are to some extent intercon-

vertible. The law of conservation of energy, simply

stated, is that the sum total of energy in the universe

(CH

P(O)SCH

❘

:CHC(O)C(OCH

):CH

❘

is constant; therefore, energy cannot be either creat-

Properties: Crystals. Mp 90–91C. Very soluble in

ed or destroyed, but only converted from one form to

water; soluble in chloroform and ethanol.

another. Radiant energy (light) comprises the elec-

Hazard: Toxic by ingestion, cholinesterase inhibi-

tromagnetic spectrum; all wavelengths of light are

tor; use may be restricted.

composed of photons or packets of energy traveling

Use: Insecticide.

at the speed of light. Theoretically, they have no

mass except that associated with their speed. Pro-

end point. (1) In chemical analysis, the point

tons, electrons, and neutrons are forms of highly

during a titration at which a marked color change is

condensed energy that possess determinable mass

observed, indicating that no more titrating solution

but move at lower speeds. Energy is directly related

is to be added.

to chemical phenomena in the formation and decom-

See indicator. (2) The highest temperature reached

position of compounds, in the many important reac-

during an assay distillation of hydrocarbon liquids,

tions that occur in electrochemistry, and in the re-

indicating the overall volatility of the liquid

lease of energy in nuclear fission and fusion. Free

(ASTM).

energy is a thermodynamic function; in chemical

reactions, it is a measure of the extent to which a

end-product inhibition. Inhibition of an allo-

substance can react. Kinetic energy (the energy of

steric enzyme at the beginning of a metabolic se-

motion) is most clearly exhibited in gases, in which

quence by the end product of the sequence.

molecules have much greater freedom of motion

than in liquids and solids.

endrin. (1,2,3,4,10,10-hexachloro-6,7-epoxy-

See radiation; matter; thermodynamics; free energy.

1,4,4a,5,6,7,8,8a-octahydro-1,4-endo,endo-5,8-di-

Note: “One of the most difficult challenges we face is

methanonaphthalene).

to find ways to ensure that all peoples of the world

CAS: 72-20-8. C

OCl

. A stereoisomer of dield-

share more equitably the vast human benefits that

rin which is the endo, exo isomer.

energy can bring. The foundation of worldwide en-

Properties: White, crystalline powder. Mp approxi-

ergy policy must be based on energy conservation

mately 200C (rearranges above this point). Insolu-

and the development of additional sources through a

ble in water and methanol; moderately soluble in

judicious application of science and technology.”

other common organic solvents; compatible with

(Glenn T. Seaborg, ACS meeting, April 1976).

nonacidic fertilizers, herbicides, fungicides, and in-

secticides.

energy, activation. The minimum energy

Hazard: Toxic by inhalation and skin absorption, a

which a molecule must acquire before it can be

carcinogen, use may be restricted. TLV: 0.1 mg/m

;

regarded as being activated. The difference between

not classifiable as a human carcinogen.

the energy of an activated molecule and the mean

Use: Insecticide.

energy of all the molecules.

See aldrin.

-ene. (1) Suffix denoting open-chain unsaturated energy balance. (1) Energy required to carry on

hydrocarbons having one double bond, as in pro- an operation or to maintain the desired operating

pene. (2) Suffix denoting an aromatic cyclic hydro- conditions. (2) Calculation of energy required to

carbon, as in benzene. balance a reaction.

502ENERGY BAND

energy band. Energy spectrum of valence elec- cellulose ocean thermal energy

coal oil sands

trons in a polyatomic material.

conversion peat

copaiba petroleum

energy charge. The fractional degree to which

ethyl alcohol (note) plutonium

the ATP/ADP/AMP system is filled with high-ener-

fission radiation

gy phosphate groups.

fuel cell shale oil

fuel oil solar cell

energy converter. Any element or compound

fusion solar energy

having the ability to convert the radiant energy of

gasification solar pond

sunlight into electrical, thermal, or chemical energy.

gasohol storage (4)

Prominent among them are silicon, selenium, and

gasoline thermoelectricity

tellurium, as well as the chlorophyll of plants in

geothermal energy uranium

photosynthesis.

guayule wood

See solar cell; magnetohydrodynamics.

energy coupling. The transfer of energy from

“Energy Smart” [Advanced Ingredients].

one process to another. For example, the coupling of

TM for a nutritive carbo sweetener made from

ATP hydrolysis with glucose phosphorylation.

fruit juice and dextrin.

Use: Nutritive sweetener that is stable at room tem-

energy gap. Forbidden part of energy spectrum

peratures.

of valence electrons.

energy storage. See storage (4).

energy level. See quantum state.

enfleurage. Extraction of odoriferous compo-

energy sources. Nonrenewable energy sources

nents of flowers by means of fats or mixtures of fat

are materials of geologic origin, i.e., petroleum, nat-

and tallow, the process being carried out at room

ural gas, coal, shale oil, and uranium, which cannot

temperature to avoid decomposition of the desired

be replaced once their supply is exhausted. Renew-

perfumes. The latter are separated from the fat by

able sources, on the other hand, are those that can be

washing with alcohol.

replenished on a predictable time basis and are

See essential oil; perfume.

known collectively as biomass; these include such

cellulosic products as wood, bagasse, agricultural

enflurane. (2-choro-1,1,2-trifluoroethyl difluo-

waste, and residue from the forest products indus-

romethyl ether).

tries (shavings, bark, sawdust, etc.), which yield the

CAS: 13838-16-9. C

ClF

same heating value per dry ton as one barrel of crude

Properties: Clear, colorless liquid; mild, sweet odor.

oil. Several of these sources have been in use for

Mw 184.50, D 1.5167 (25C), bp 56.5C, vap press

some years as on-site fuels in the sugarcane, ply-

174.5 mm Hg (20C). Soluble in organic solvents;

wood, and paper pulp industries. Another instance is

slightly soluble in water.

methane obtained from animal manures (biogas),

Hazard: Volatile with anesthetic properties, but non-

which is being developed on a large scale in the west

flammable. TLV: 75 ppm; not classifiable as a hu-

and southwest. Interest in the mass cultivation of

man carcinogen.

algae and hydrocarbon-producing plants such as

Use: Clinical anesthetic.

guayule and copaiba for fuel has been reported.

There are also a number of mechanical energy

engineering material. A metal, alloy, plastic,

sources whose development involves engineering

or ceramic used in the fabrication of machinery and

rather than chemistry, namely, solar radiation, wind,

its components, structural shapes, chemical process

water flow, tides, and thermal gradients in ocean

equipment, castings, tools, instruments, drums,

water. Several of these are already in limited opera-

tanks, piping, ductwork, and auxiliary items (ex-

tion, but in most cases their development will be

cluded are materials used chiefly as protective coat-

slow and costly. Hydroelectric power has long been

ings or as components of alloys). Engineering mate-

an accomplished fact, though it accounts for only

rials are characterized by hardness, strength,

about 1% of electrical needs. Solar energy is being

machinability, dimensional stability, nonflamma-

actively researched, but is unlikely to be a factor of

bility, and resistance to corrosion, most acids, sol-

consequence for at least another decade. The follow-

vents, and heat. The more important of these are

ing entries discuss the chemical sources of energy

listed below; for specific uses, see individual entries.

more specifically:

Metals and alloys Plastics

battery hydrocarbon (note)

biogas hydrogen aluminum ABS resin

biomass methane beryllium acetal resin

breeder natural gas brass acrylic resin

carbohydrate nuclear energy bronze fluorocarbon polymer

503 ENTRAINER

enolase. An enzyme active in glycolysis that cata-

Metals and alloys Plastics

lyzes the conversion of 2-phosphoglyceric acid to

cast iron nylon

the phosphorylated enol of pyruvic acid.

copper phenolformaldehyde resin

lead polybutylene terephthalate

enology. (oenology). The art and science of wine

magnesium polycarbonate

making.

steel polyethylene

tantalum polyphenylene oxide

“Enovid” [Searle]. TM for norethynodrel with

titanium polypropylene

mestranol. Oral contraceptive approved by FDA.

zinc polystyrene

zirconium polyvinyl chloride

enprostil.

various trademarked reinforced plastics (FRP)

CAS: 73121-56-9. mf: C

alloys

Hazard: Moderately toxic by ingestion.

ureaformaldehyde resin

Ceramics

enrichment. (1) In food technology, the addition

glass

to a foodstuff of various nutrient substances during

porcelain

manufacture to increase the dietary value of the

food, e.g., addition to wheat flour of vitamins B

niacin, and iron. In this way, the food is brought up

“Enhance” [Evans Vanodine]. TM for an

to a specific nutritional standard. (2) Increase in the

ultra high solid floor polish.

abundance of certain isotopes of an element by any

of several methods: (a) By a chemical reaction ac-

enhanced oil recovery. Any of several meth-

companied by irradiation from a laser beam; enrich-

ods for increasing the productivity of oil wells (after

ment of boron, chlorine, and sulfur isotopes has been

pumping is no longer effective) by emulsifying as

achieved in this way in a number of research labora-

much as possible of the oil trapped in the rock struc-

tories. Uranium enrichment is also possible, either

ture. Techniques that have been researched and used

by adding previously prepared

235

U to natural urani-

to some extent involve the pumping into the forma-

um or by the laser technique. (b) Uranium can also

tions of pressurized carbon dioxide, water, steam,

be enriched by gas centrifugation and gaseous diffu-

detergent solutions, brine, and a mixture of various

sion. The latter is the usual procedure. (3) Addition

high polymers, guar gum, xanthan biopolymer,

of oxygen to air to increase its combustion-support-

bauxite, or sand. Considerable success has been

ing ability.

achieved, but such methods have proved to be both

slow and inefficient.

enrobe. To coat candy centers, fruits, nuts, etc.,

See chemical flooding; hydraulic fracturing.

with a liquid confection such as chocolate or sugar

solution by mechanical dipping.

enhancer. (1) A food additive that brings out the

taste of a food product without contributing any taste

ensilage. A feed for livestock prepared by long

of its own. Sodium glutamate is the most widely

storage of corn husks, stalks, etc., in an air-tight

used substance of this class; its effective concentra-

vertical cylindrical structure (silo) in which the ma-

tion is in parts per thousand.

terial undergoes anaerobic fermentation. It is a com-

(2) a nucleotide sequence to which transcription

ponent of biomass.

factor(s) bind, and which increases the transcription

of a gene. It is NOT part of a promoter; the basic

enterokinase. An enzyme found in the small

difference being that an enhancer can be moved

intestine which converts trypsinogen into trypsin.

around anywhere in the general vicinity of the gene

(within several thousand nucleotides on either side

enterotoxin b, staphylococcal.

or even within an intron), and it will still function. It

CAS: 11100-45-1.

can even be clipped out and spliced back in back-

Hazard: A poison.

wards, and will still operate. A promoter, on the

Source: Natural product.

other hand, is position- and orientation-dependent.

Some enhancers are “conditional” in that they en-

enthalpy. The increase in heat content of a sub-

hance transcription only under certain conditions.

stance or system that accompanies its change from

See potentiator.

one state to another under constant pressure. The

internal energy plus the product of the volume and

enocianina. See grape skin extract.

pressure of a working substance.

enol. A chemical grouping containing both a dou- entrainer. An additive for liquid mixtures diffi-

ble bond (ene) and a hydroxyl group (OH), forming cult to separate by ordinary distillation. The entrain-

an intermediate and reversible product. Enols are er usually forms an azeotrope with one of the com-

characteristic of racemic compounds. pounds of the mixture and thereby aids in the

504ENTRAINMENT

separation of such a compound from the remainder lar weight from 10,000 to a million or more. An

important characteristic of enzymes is their specific-

of the mixture.

ity, i.e., a given enzyme can catalyze one particular

reaction and no others. Six types are recognized,

entrainment. The presence of minute drops of

which catalyze the following reactions: (1) redox

water or other liquid in the vapor produced by evap-

(oxidoreductases), (2) transfer of specific radicals or

oration or distillation; also small bubbles of air or

groups (transferases), (3) hydrolysis (proteolytic),

other gas in a liquid as a result of turbulence induced

(4) removal from or addition to the substrate of

by agitation. Entrained water or gas is often undesir-

specific chemical groups (lyases), (5) isomerizaton

able, and care needs to be taken to eliminate or

(isomerases), (6) combination or binding together of

prevent it; in certain cases it is beneficial.

substrate units (ligases). The names of enzymes in-

See venturi; entrainer.

variably terminate in either -ase or -in. The follow-

ing partial list indicates some of the more important

entropy (S). Thermodynamic concept referring

functions performed by enzymes; among these are

to heat content. If, during a reversible change at

the ability to cleave the peptide bonds of proteins

temperature T, an ammount dQ of heat enters the

(hydrolysis) with simultaneous formation of water;

substance, its entropy is augmented by:

and to decompose sugars and starches to ethyl alco-

hol and carbon dioxide (fermentation). Enzymes are

essential to many biochemical processes, especially

in the food, beverage, and pharmaceutical indus-

tries.

environmental chemistry. That aspect of

chemistry concerned with air and water pollution,

amylase starch hydrolysis

pesticides, and chemical and radioactive waste dis-

carboxylase decomposes pyruvic acid

posal. A random selection of specific areas of re-

cellulase converts cellulose to glu-

search includes lead and other toxic chemicals in the

cose

air, effects of increased burning of coal, biological

cholinesterase inactivates acetylcholine

modification of wastes, detoxification methods,

chymotrypsin hydrolysis of proteins

pesticide content of fish, environmental analytical

invertase converts sucrose to glucose

and monitoring techniques, utilization of biomass,

and fructose

drinking water quality, organic contaminants in

lipase hydrolysis of fats

lakes and rivers, and effect of deforestation on car-

maltase converts maltose to glucose

bon dioxide and oxygen content of air.

pepsin hydrolysis of proteins

protease hydrolysis of peptide

Environmental Protection Agency. (EPA).

linkages

A federal agency established in 1970. Under the

rennin hydrolysis of proteins

Toxic Substances Control Act of 1976, it is required

ribonuclease decomposes RNA

to ensure the safe manufacture, use, and transporta-

trypsin splits proteins to amino

tion of hazardous chemicals. It includes an Office of

acids

Hazardous Materials Control which administers

urease decomposes urea to NH

Congressional legislation pertaining to this field.

and CO

The EPA may require manufacturers to conduct

zymase converts sugars to alcohol

tests on materials or products that adversely affect

and CO

(fermentation)

the environment or public health and safety. One of

Recent research in biomimetic chemistry has suc-

the most important aspects of its activities is the

ceeded in creating synthetic enzymes that imitate the

establishment and supervision of automotive emis-

behavior of natural enzymes, e.g., chymotrypsin,

sion standards. It is also concerned with pesticides,

and are almost as effective. See catalyst; biomi-

fungicides, and other potentially detrimental materi-

metic chemistry; fermentation; hydrolysis.

als, as well as industrial waste disposal. It operates in

close conjunction with the U.S. Department of Agri-

culture and the Food and Drug Administration. The

eolotropic. See aeolotropic.

construction of new plants for manufacturing prod-

ucts must conform to EPA standards, especially as

regards effluents that contribute to water pollution.

eosin. (bromeosin; CI 45380; tetrabromofluor-

The headquarters are located at 1200 Pennsylvania

escein).

Avenue, N.W., Washington, DC 20460 Website:

CAS: 15086-94-9. C

http://www.epa.gov.

Properties: Red, crystalline powder. Soluble in alco-

See toxic substances; environmental chemistry.

hol and acetic acid; insoluble in water. The potassi-

um and sodium salts are soluble in water.

enzyme. Any of a unique class of proteins that Derivation: Bromination of fluorescein.

catalyze a broad spectrum of biochemical reactions. Use: Dyeing silk, cotton, and wool; red writing ink;

Enzymes are formed in living cells; they are com- cosmetic products; biological stain; coloring motor

prised one or more polypeptide chains with molecu- fuel.

505 EPINEPHRINE

EP. (1) Abbreviation for extreme pressure as ap- flash p 93F (33.9C) (TOC). Miscible with most

plied to lubricants. (2) Abbreviation for ethylene- organic solvents; slightly soluble in water.

Derivation: By removing hydrogen chloride from

propylene.

dichlorohydrin.

Hazard: Toxic by inhalation, ingestion, and skin

EPA. Abbreviation for Environmental Protection

absorption; strong irritant, a carcinogen. Flamma-

Agency.

ble, moderate fire risk. TLV: 0.5 ppm; animal car-

cinogen.

“EPAL” [Albemarle]. TM for linear primary

Use: Major raw material for epoxy and phenoxy

alcohols.

resins, manufacture of glycerol, curing propylene-

based rubbers, solvent for cellulose esters and

EPC black. Abbreviation for easy-processing

ethers, high-wet-strength resins for paper industry.

channel black.

See carbon black.

epichlorohydrin-bis(3-

aminopropyl)methylamine copolymer.

EPDM. Abbreviation for a terpolymer elastomer

CAS: 41941-50-8. mf: (C

•C

ClO)

made from ethylene-propylene diene monomer.

Hazard: Low toxicity by ingestion.

See ethylene-propylene terpolymer.

epichlorohydrin-dimethylamine copolymer.

ephedrine. (1-phenyl-2-methylaminopropanol).

See dimethylamine-epichlorohydrin co-

CAS: 299-42-3. C

CH(OH)CH(NHCH

)CH

polymer.

Optically active (levorotatory) form.

Properties: White to colorless granules, pieces, or

crystals; unctuous to touch. Mp 33–40C, bp 255C

epichlorohydrin triethanolamine cellulose.

(decomposes). Hygroscopic, gradually decomposes

See ECTEOLA-cellulose.

on exposure to light. Soluble in water, alcohol, ether,

chloroform, and oils.

epigallocatechin 3-gallate.

Derivation: Isolation from stems or leaves of Ephe-

CAS: 989-51-5. mf: C

dra, especially Ma huang (China and India).

Hazard: Moderately toxic by ingestion.

Grade: Technical, NF.

Hazard: Toxic by ingestion.

epimer. An isomer that differs from the com-

Use: Medicine (bronchodilator).

pound with which it is being compared only in the

See racephedrine.

relative positions of an attached hydrogen and hy-

droxyl. The isomerism may be represented as

epi. (1) A prefix denoting a bridge or intramolecu-

−HCOH− and −HOCH−. It is common in sugars.

lar connection, e.g., epoxide. (2) An abbreviation for

See diastereoisomer.

epichlorohydrin.

epimerases. Enzymes that catalyze the revers-

“EPI” [Epi-Products]. TM for a cleaning

ible interconversion of two epimers.

agent.

Use: For cleaning thermoplastic processing equip-

epimers. Two stereoisomers differing in configu-

ment.

ration at one asymmetric center in a compound hav-

ing two or more asymmetric centers.

(+−)-epibatidine dihydrochloride.

CAS: 162885-01-0. mf: C

ClN

•2ClH.

epinephrine. (l-methylaminoethanolcatechol;

Hazard: A poison.

“Adrenalin”).

Use: Agricultural chemical.

CAS: 51-43-4.

epichlorohydrin. (chloropropylene oxide).

CAS: 106-89-8. An epoxide.

❘

CHCH

Cl.

A hormone of the adrenal glands.

Properties: (l-Form) Light-brown or nearly white,

crystalline powder; odorless. Affected by light. Mp

211–212C, specific rotation −50 to −53.5 (25C).

Properties: Highly volatile, unstable liquid; chloro- Sparingly soluble in water; insoluble in alcohol,

form-like odor. D 1.1761 (20/20C); bp 115.2C; bulk chloroform, ether, acetone, oils; readily soluble in

d 9.78 lb/gal; vap press 12.5 mm Hg (20C); fp −25C; aqueous solutions of mineral acids, sodium hydrox-

viscosity 1.12 cP (20C) refr index 1.4358 (25C); ide, and potassium hydroxide.

506“EPIPHEN”

Derivation: From the adrenal glands of sheep and

“Epotuf” [Reichhold]. TM for epoxy resins,

cattle or synthetically from pyrocatechol. epoxy hardeners, and epoxy esters used as coating

Grade: USP. vehicles.

Use: Medicine (vasoconstrictor).

epoxidation. Reaction in which olefinic unsatu-

“Epiphen” [Borden]. TM for an epoxy resin in

ration is converted to a cyclic, three-membered ether

liquid form. “Epiphen” ER-823 is used in adhesives

by active oxygen agents.

for rubber, steel, aluminum, or glass. Catalyst is

supplied for specific end uses.

epoxide. An organic compound containing a re-

active group resulting from the union of an oxygen

3-episarmentogenin.

atom with two other atoms (usually carbon) that are

CAS: 465-12-3. mf: C

joined in some other way as indicated:

Hazard: A poison.

Source: Natural product.

epistasis. One gene interfers with or prevents the

This group, commonly called “epoxy,” characterizes

expression of another gene located at a different

the epoxy resins. Epichlorohydrin and ethylene oxide

locus.

are well-known epoxides. The compounds are also

used in certain types of cellulose derivatives and fluo-

epitaxy. An oriented crystalline growth between

rocarbons.

two crystalline solid surfaces of different chemical

composition in which the surface of one crystal

epoxidized linseed oil. See “Drapex”

offers suitable positions for deposition of a second

[Crompton & Knowles].

crystal. This behavior is characteristic of some types

of high polymers.

epoxidized soybean oil.

Properties: Iodine number maximum of 6, oxirane

“EPI-TDPA” [Epi-Products]. TM for plastic

oxygen minimum of 6.0 percent.

film products.

Use: Food additive.

Use: For films that will will degrade in landfills,

photo degrade and biodegrade.

1,2-epoxybutane. See 1,2-butylene oxide.

epithelial cell. Any cell that forms part of the

outer covering of an organism or organ.

3,4-epoxycyclohexane carbonitrile.

O(C

)CN.

epitope. A portion of an antigenic macromolecule

Properties: Liquid. D 1.0929 (20/20C), bp 244.5C,

recognized and bound by a specific antibody.

fp −33C. Soluble in water.

Hazard: Toxic by skin absorption, ingestion, and

EPN. (o-ethyl-o,p-nitrophenyl phenylphospho-

inhalation.

rothioate).

Use: Intermediate, stabilizer.

CAS: 2104-64-5. C

P(C

O)(S)OC

Properties: Light-yellow crystals. Mp 36C, d 1.5978

epoxyethane. See ethylene oxide.

(30C). Insoluble in water; soluble in most organic

solvents. Decomposes in alkaline solutions.

2,3-epoxy-2-ethylhexanol.

Grade: Wettable powders and dusts.

Hazard: A cholinesterase inhibitor, absorbed by

❘

C(C

)CH

OH.

skin, use may be restricted. TLV: 0.1 mg/m

(skin);

Properties: Liquid. D 0.9517 (20/20C), bp (decom-

not classifiable as a human carcinogen.

poses), fp −65C. Slightly soluble in water. Combus-

Use: Cotton insect pest control, acaricide.

tible.

Hazard: Skin irritant.

epolamine. See 1-pyrrolidineethanol.

Use: Stabilizer, intermediate.

“Eponol” Resins. TM for high molecular

epoxyheptachlor. (HCE; heptachlor epoxide).

weight linear copolymers of bisphenol A and epi-

CAS: 1024-57-3. C

chlorohydrin; produce outstanding surface coatings

Hazard: Confirmed carcinogen and poison by inges-

by solvent evaporation alone.

tion. TLV: 0.05 mg/m

; animal carcinogen.

“Epon” resins [Shell]. TM for a series of

condensation products of epichlorohydrin and bis-

11,13-(epoxymethano)-13h-cyclopenta(a)

phenol-A having excellent adhesion, strength, phenanthrene, pregn-4-ene-3,20-deriv.

chemical resistance, and electrical properties when CAS: 6251-69-0. mf: C

formulated into protective coatings, adhesives, and Hazard: A reproductive hazard.

structural plastics. Use: Hormone.

507 EQUILIBRIUM CONSTANT

epoxy novolak. Epoxy resin made by the reac- Derivation: Naphthalene-1,5- and 1,6-sulfonic acids

tion of epichlorohydrin with a novolak resin (phe-

are nitrated and reduced, giving 1-naphthylamine-

nol-formaldehyde; see novolak). These have a re-

3,8- and 4,8-disulfonic acids. Separation is effected

peating epoxide structure that offers better

by crystallizing out the acid sodium salts of 1-naph-

resistance to high temperatures than the epichloro-

thylamine-3,8-disulfonic acid.

hydrin—bisphenol A type, and are especially useful

Use: Azo-dye intermediate.

as adhesives.

Epsom salts. See magnesium sulfate.

2,3-epoxy-1-propanol. See glycidol.

EPT. Abbreviation for ethylene-propylene terpo-

lymer.

epoxy resin. A thermosetting resin based on the

reactivity of the epoxide group. One type is made

“Eptac No.1” [Du Pont]. TM for zinc dime-

from epichlorohydrin and bisphenol A. Aliphatic

thyldithiocarbamate, an ultraaccelerator for rubber.

polyols such as glycerol may be used instead of the

aromatic bisphenol A. Molecules of this type have

EPTC. (S-ethyl di-N,N-propylthiocarbamate).

glycidyl ether structures,

CAS: 759-94-4. C

SC(O)N(C

)

Available forms: Liquid and granular formulations.

−OCH

❘

Use: A preemergence herbicide.

in the terminal positions, have many hydroxyl

groups, and cure readily with amines.

eq. Abbreviation for gram equivalent weight, i.e.,

Another type is made from polyolefins oxidized

the equivalent weight in grams. Recommended as an

with peracetic acid. These have more epoxide

international unit.

groups, within the molecule as well as in terminal

positions, and can be cured with anhydrides, but

“Equanil.” [Wyeth-Ayerst] Proprietary name

require high temperatures. Many modifications of

for meprobamate.

both types are made commercially. Halogenated

Use: Sedative.

bisphenols can be used to add flame-retardant prop-

erties. See epoxy novolak.

equation of state. The mathematical formula

The reactive epoxies form a tight, cross-linked poly-

that expresses the relationships between pressure,

mer network and are characterized by toughness,

volume, and temperature of a substance in any state

good adhesion, corrosive-chemical resistance, and

of aggregation.

good dielectric properties.

Most epoxy resins are the two-part type which hard-

equilibrium. (1) Chemical equilibrium is a con-

en when blended. A one-component liquid type for

dition in which a reaction and its opposite or reverse

filament winding and a pelletized type for injection

reaction occur at the same rate, resulting in a con-

molding are available under the TM “Arnox.”

stant concentration of reactants; for example, am-

Hazard: Strong skin irritant in uncured state.

monia synthesis is at equilibrium when ammonia

Use: Surface coatings, as on household appliances

molecules form and decomposes at equal velocities

and gas storage vessels; adhesive for composites and

+3H

←→ 2NH

for metals, glass, and ceramics; casting metal-form-

(2) Physical equilibrium is exhibited when two or

ing tools and dies; encapsulation of electrical parts;

more phases of a system are changing at the same

filament-wound pipe and pressure vessels; floor sur-

rate so that the net change in the system is zero. An

facing and wall panels; neutron-shielding materials;

example is the liquid-to-vapor–vapor-to-liquid in-

cements and mortars; nonskid road surfacing; rigid

terchange in an enclosed system, which reaches

foams; oil wells (to solidify sandy formations); ma-

equilibrium when the number of molecules leaving

trix for stained-glass windows; low-temperature

the liquid is equal to the number entering it.

mortars.

equilibrium constant. A number that relates

(3-␣)-12,13-epoxytrichothec-9-ene-3,4,15-

the concentrations of starting materials and products

triol 15-acetate.

of a reversible chemical reaction to one another. For

CAS: 2623-22-5. mf: C

example, for a chemical reaction represented by the

Hazard: A poison by ingestion. A mild skin irritant.

equation aAB + bCD ←→ cAD + dBC the equilibri-

Source: Natural product.

um constant would be K

[(AD)

(BD)

[(AB)

(CD)

] where a, b, c, and d are the numbers of

EPR. Abbreviation for ethylene propylene rub-

molecules of AB, CD, AD, and BC that occur in the

ber, also for electron paramagnetic resonance.

balanced equation, and (AD), (BC), (AB), and (CD)

are the molecular concentrations of AD, BC, AB,

epsilon acid. (1-naphthylamine-3,8-disulfonic and CD in any mixture that is at equilibrium. At any

acid). C

(NH)

(SO

. one temperature, K is usually at least approximately

Properties: White, crystalline scales. Soluble in hot constant, regardless of the relative quantities of the

water. several substances, so that when K is known it is

508EQUILIBRIUM DIAGRAM

often possible to predict the concentrations of the Properties: Soft, malleable solid with metallic lus-

products when those of the starting materials are

ter. Salts are pink to red. D 9.16 (15C), mp 1522C,

known. The constant changes markedly with tem-

bp approximately 2500C, high electrical resistivity.

perature. The constant can often be calculated from

Insoluble in water; soluble in acids.

the relations of thermodynamics if the free energy

Derivation: Reduction of the fluoride with calcium,

for the chemical reaction is known, or by measuring

electrolysis of the fused chloride.

all concentrations in one or more carefully conduct-

Source: Rare-earth minerals.

ed experiments.

Available forms: Lumps, ingots of high purity,

sponge, powder.

Hazard: Flammable in finely divided form.

equilibrium diagram. (constitutional dia-

Use: Nuclear controls, special alloys, room-tempera-

gram). (1) A simplified boiling-point diagram,

ture laser.

showing for a liquid mixture the composition of the

vapor in equilibrium with the liquid. (2) A chart

showing the relation between a solution and the

erbium nitrate. Er(NO

)

•5H

solids that may be crystallized from it. (3) A diagram

Properties: Large, reddish crystals. Loses 4H

Oat

showing the limits of composition and temperature

130C. Soluble in water, alcohol, ether, and acetone.

in which the various phases or constituents of an

Derivation: Treatment of oxides, carbonates, or hy-

alloy are stable.

droxides with nitric acid.

Grade: 99%.

equipartition, law of. Every particle, heavy or

Hazard: May explode if shocked or heated.

light, gaseous or liquid, and independent of its

chemical nature or form, always possesses the same

erbium oxalate. Er

)

•10H

mean energy of translation at a given temperature.

Properties: Reddish, microcrystalline powder. De-

composes at 575C, d 2.64. Soluble in water and

equipotential energy. The energy existing at a

dilute acids.

constant potential throughout a system.

Hazard: Corrosive.

Use: Oxalates of the rare-earth metals are used to

equivalent electrons. Electrons of equal azi-

separate the latter from common metals.

muthal quantum numbers and principal quantum

numbers. They have identical orbital properties but

erbium oxide. (erbia). Er

may have a difference in sign of their orbital mo-

Properties: Pink powder that readily absorbs mois-

ments.

ture and carbon dioxide from the atmosphere. D

8.64, specific heat 0.065, infusible. Insoluble in wa-

equivalent weight. (combining weight). The

ter; slightly soluble in mineral acids.

weight of an element that combines chemically with

Derivation: By heating the oxalate or other oxy-acid

8 g of oxygen or its equivalent. Since 8 g of oxygen

salts.

combines with 1.008 g of hydrogen, the latter is

Grade: 98–99%.

considered equivalent to 8 g of oxygen. When 8 g is

Use: Phosphor activator, infrared-absorbing glass.

selected for the combining weight of oxygen, no

See rare earth.

element has a combining-weight value greater than

one. The equivalent weight of an acid is the weight

erbium sulfate. Er

(SO

)

•8H

that contains one atomic weight of acidic hydrogen,

Properties: Pink, monoclinic crystals. D 3.68, dehy-

i.e., hydrogen that reacts during neutralization of

drated at 400C. Soluble in water.

acid with base. The equivalent weight of a base or

Derivation: Dissolving hydroxides, carbonates, or

hydroxide is the weight that will react with an equiv-

oxides in dilute sulfuric acid.

alent weight of acid. Equivalent weights of other

Grade: 99.9%.

substances are defined in a similar manner.

Use: To determine atomic weight of a rare-earth

element.

Er. Symbol for erbium.

ERE. (estrogen response element). A binding

ER. See endoplasmic reticulum.

site in a promoter to which the activated estrogen

receptor can bind. The estrogen receptor is essential-

ERAD. Endoplasmic reticuluum-associated deg-

ly a transcription factor which is activated only in

radation (of protein). Incorrectly formed proteins

the presence of estrogens. The activated receptor

are destroyed in the ER instead of being secreted.

will bind to an ERE, and transcription of the adjacent

gene will be altered. See also “Response element”.

erbia. See erbium oxide.

erbium. Er. Element with atomic number 68, aw erbon. (generic name for 2-(2,4,5-trichloro-

167.26, valence of 3; one of the rare-earth elements phenoxy)ethyl-2,2-dichloropropionate).

of the yttrium subgroup. CAS: 136-25-4. (Cl)

OC(O)C(Cl)

See rare earth. Properties: Solid. Mp 49–50C (technical), bp 161C

509 ERNST, RICHARD R

(0.5 mm Hg). Insoluble in water; soluble in most tion in the bony structure (thus preventing rickets),

organic solvents.

overdosage of vitamin D may be harmful.

Hazard: Toxic by inhalation and ingestion, strong

Use: Antirachitic vitamin; when irradiated with UV

irritant to eyes and skin.

light, it has vitamin D activity; source of estradiol.

Use: Herbicide.

ergot. (secale cornutum; rye ergot). A fungus

growth, Claviceps purpurea, on rye.

erepsin. A mixture of peptidase enzymes former-

Occurrence: Europe, cultivated in Spain and Russia.

ly thought to be a single enzyme that catalyzes the

Grade: Spanish, Russian.

hydrolysis of peptides in the small intestine.

Hazard: Toxic by ingestion.

Use: Source of many alkaloids, medicine (vasocon-

ergamine. See histamine.

strictor).

ergocalciferol. (calciferol; vitamin D

ergotamine.

CAS: 50-14-6. C

CAS: 113-15-5. Alkaloid present in rye ergot.

Properties: Mw 581.73.

ergovaline mesylate. See ergovaline mono-

methanesulfonate.

ergovaline monomethanesulfonate.

CAS: 3398-46-7. mf: C

•CH

Hazard: A reproductive hazard.

erionite.

CAS: 66733-21-9. mf: Al

•

Ca•7H

O•

Na.

Hazard: Confirmed human carcinogen.

Source: Natural product.

Properties: White, odorless crystals. Affected by air

“Erionyl” [Novartis]. TM for a group of con-

and light. Mp 115–118C, specific rotation +103 to

densation products of aromatic sulfonic acids used

+106 degrees. Insoluble in water; soluble in alcohol,

as fixative/reserving agents in dyeing nylon and

chloroform, ether, and fatty oils.

nylon-cellulosic blends.

Derivation: From ergosterol by irradiation with UV

light.

Erlenmeyer flask. A useful type of laboratory

Grade: USP, FCC, as vitamin D

glassware, it is an open container whose dimensions

Use: Nutrition, dietary supplement.

are, for example, about 8 inches tall with a relatively

narrow neck section about 1.5 inches in diameter

ergocornine, dihydro-. See 9,10-dihydroer-

and 2 inches long, below which the contour becomes

gocornine.

cone shaped. The bottom is flat. It was named after

its inventor, a German chemist.

Use: Numerous experiments involving liquids, espe-

ergosterol. (provitamine D

). C

OH. A

cially titrations and extractive testing.

plant sterol widely distributed in nature.

Erlenmeyer-Plochl azlactone and amino

acid synthesis. Formation of azlactones by

intramolecular condensation of acylglycines in the

presence of acetic anhydride. The reaction of azlac-

tones with carbonyl compounds followed by hydrol-

ysis to the unsaturated ␣-acylamino acid and by

reduction yields the amino acid; drastic hydrolysis

gives the ␣-oxo acid.

Ernst, Richard R. (1933– ). A native of Swit-

Properties: Colorless crystals. Mp 166C (with 1.5 zerland who won the Nobel Prize in chemistry in

O), bp 250C (0.01 mm Hg), d 1.04, specific rota- 1991 for important methodological developments in

tion −135 (in chloroform). Insoluble in water; solu- NMR spectroscopy. He invented Fourier-transform

ble in alcohol, benzene, ether. NMR (FT-NMR), which multiplied sensitivity 10 to

Derivation: Synthesized by yeast from simple sug- 100 times compared to dispersive instruments. He

ars, obtained from fungus ergot. also devised two-dimensional NMR techniques, in-

Hazard: Due to its ability to catalyze calcium deposi- creasing resolution and enabling structure determi-

510ERUCAMIDE

nations of biologically important macromolecules. Occurrence: U.S. (California, Colorado, Idaho, Ne-

Ernst received his Ph.D from the Federal Technical vada), Ontario.

Institute (ETH) in Zurich, Switzerland. Hazard: Toxic by ingestion and inhalation.

Use: Coloring glass and ceramics.

erucamide. (erucylamide). C

CONH

erythritol. (tetrahydroxybutane).

Properties: Solid. D 0.888, mp 75–80C, iodine value

CAS: 149-32-6. CH

OHCH

OCH

OH. A tet-

70–80. Soluble in isopropanol; slightly soluble in

rahydric alcohol found in Protococcus vulgaris and

alcohol and acetone. Combustible.

other lichens of Rocella species. Can be made syn-

Use: Foam stabilizer, solvent for waxes and resins,

thetically.

emulsions, antiblock agent for polyethylene.

See “Crodamide” [Croda].

erucic acid. (cis-13-docosenoic acid).

CH:CH(CH

)

COOH. A C

(solid) fatty acid

with one double bond; a homolog of oleic acid with

four more carbons.

Properties: Mp 33–34C, bp 264C (15 mm Hg), io-

dine value 75. Combustible.

Properties: White, sweet crystals. Mp 121–122C, bp

Derivation: Fats and oils from mustard seed, rape-

329–331C, d 1.45. Soluble in water; slightly soluble

seed, and crambe seed.

in alcohol; insoluble in ether.

Use: Preparation of dibasic acids and other chemi-

Use: Manufacture of erythrityl tetranitrate.

cals, polyethylene-film additive, water-resistant

nylon.

erythritol anhydride. (butadiene dioxide).

CAS: 564-00-1. C

“Erucical H-102” [Lambent]. TM for a high

Properties: Colorless liquid. Bp 138C, fp −18C, d

erucic acid rapeseed oil referred to as HEAR oil.

1.11. Hydrolyzed to erythritol when dissolved in

Use: For lubricity in metal working fluids, as a base

water.

oil in hydraulic fluid applications.

Hazard: Quite toxic.

Use: Cross-linking agent, biocide, bacteriostat.

erucyl alcohol. C

OH. A C

(solid) fatty

alcohol having one double bond.

erythrityl tetranitrate. (erythrol tetranitrate).

Properties: White, soft solid; almost odorless. D CH

ONO

(CHONO

)

ONO

0.8486, cloud point 27.2C, boiling range 334–376C, Properties: Crystals. Mp 61C. Soluble in alcohol,

iodine value 83, flash p 395F (201C). Soluble in ether, and glycerol; insoluble in water.

alcohol and most organic solvents. Combustible. Derivation: By nitration of erythritol.

Derivation: Sodium reduction of erucic acid. Hazard: Severe explosion risk when shocked or

Use: Lubricants, surfactants, petrochemicals, plas- heated.

tics, textiles, rubber. Use: Medicine (diluted with lactose in nonexplosive

tablets).

erythorbic acid. (d-erythroascorbic acid;

erythroascorbic acid. See erythorbic acid.

isoascorbic acid). C

Properties: Shiny, granular crystals. Decomposes

164–169C. Soluble in water, alcohol, pyridine;

erythrocyte. A red blood cell, containing hemo-

moderately soluble in acetone; slightly soluble in

globin, the iron-carrying protein of the blood.

glycerol.

See leucocyte.

Grade: FCC.

Use: Antioxidant (industrial and food), especially in

erythrogenic acid. See isanic acid.

brewing industry, reducing agent in photography.

erythromycin.

erythorbic acid sodium salt.

CAS: 114-07-8. C

. An antibiotic produced

CAS: 6381-77-7. mf: C

•Na.

by growth of Streptomyces erythreus Waksman. It is

Hazard: Low toxicity by ingestion. A mild eye irri-

effective against infections caused by Gram-posi-

tant.

tive bacteria, including some ␤-hemolytic strepto-

cocci, pneumococci, and staphylococci.

erythrite. (1) Synonym for erythritol. Properties: White or slightly yellow crystalline

(2) Cobalt bloom. Co

(As)

)

•8H

O. A natural hyd- powder; odorless; bitter. Mp 133–138C. Freely sol-

rated cobalt arsenate. uble in alcohol, chloroform, and ether; very slightly

Properties: Crimson, peach, red, pink, or pearl gray. soluble in water; slightly hygroscopic; pH (saturated

Contains 37.5% cobalt oxide. D 2.91–2.95, Mohs solution) 8–10.5; pH <4 is destructive. Alcoholic

hardness 1.5–2.5, mp (decomposes). Soluble in hy- solution is levorotatory.

drochloric acid. Grade: USP.

511 ESSENTIAL OIL

Use: Medicine (antibiotic); various salts are avail- taglio color printing. A wax derived from this plant

able. is used as a substitute for carnauba, especially in

Note: The erythromycin molecule was synthesized carbon paper.

by the Harvard chemist Robert Woodward. The syn-

thesis was almost completed at the time of his death

ESR. See spin resonance.

in 1979, and was finished by his associates in 1981.

It is an extremely complex structure containing a

essential. (1) Containing the characteristic odor

lactone ring of 14 members with 10 asymmetric

or flavor, (i.e., the essence) of the original flower or

centers; it also has two specialized sugar molecules,

fruit: an essential oil, usually obtained by steam

L-cladinose and D-desosamine. The reported molec-

distillation of the flowers or leaves or cold-pressing

ular configuration is:

of the skin. (2) As applied to certain amino acids,

fatty acids, and vitamins, this term is used by bio-

chemists to mean that the compound in question is a

necessary nutritional factor that is not synthesized

within the body of the animal and thus must be

obtained from external sources. Eight amino acids

are classified as essential on this basis.

See amino acid.

essential amino acids. Amino acids that can-

not be synthesized by humans (or other vertebrates)

and must be obtained from the diet.

erythromycin thiocyanate.

Properties: White or almost white powder.

essential fatty acids. The group of polyunsat-

Use: Food additive; drug (veterinary).

urated fatty acids produced by plants, but not hu-

mans, and thus required in the human diet: linoleic,

erythrosine. (Sodium or potassium salt of

linolenic and arachidonic acids.

iodeosin; CI 45430; FD&C Red No.3).

CAS: 16423-68-0. C

essential oil. A volatile oil derived from the

Properties: Brown powder, forms cherry-red solu-

leaves, stem, flower, or twigs of plants, and usually

tion in water. Soluble in alcohol.

carrying the odor or flavor of the plant. Chemically,

Use: Biological stain, certified food color.

they are often principally terpenes (hydrocarbons),

but many other types also occur. Essential oils (ex-

Es. See einsteinium.

cept for those containing esters) are unsaponifiable.

Some are nearly pure single compounds, as oil of

ESCA. Electron spectroscopy for chemical

wintergreen, which is methyl salicylate. Others are

analysis.

mixtures, as turpentine oil (pinene, dipentene) and

oil of bitter almond (benzaldehyde, hydrocyanic

eschka mixture. Consists of two parts magne-

acid). Some contain resins in solution and are called

sium oxide and one part anhydrous sodium car-

oleoresins or balsams.

bonate.

Properties: Pungent taste and odor; usually nearly

Use: As a fusion mixture for determining sulfur in

colorless when fresh but becoming darker and thick

coal.

on exposure to the air. Optically active, d

0.850–1.100. Soluble in alcohol, carbon disulfide,

Eschweiler-Clarke reaction. Reductive

carbon tetrachloride, chloroform, petroleum ether,

methylation of primary or secondary amines with

and fatty oils; insoluble in water except for individu-

formaldehyde and formic acid (special form of the

al constituents of some oils which may be partially

Leuckart-Wallach reaction).

water-soluble, resulting in a loss of these constitu-

ents during steam distillation.

ESD. Electron-stimulated desorption.

Derivation: (1) By steam distillation; (2) by pressing

(fruit rinds); (3) by solvent extraction; (4) by macer-

eserine. See physostigmine.

ation of the flowers and leaves in fat and treating the

fat with a solvent; (5) by enfleurage.

-esis. Suffix denoting state, condition, or process.

Use: Perfumery, flavors, thinning precious-metal

preparations used in decorating ceramic ware.

esmolol. See methyl 4-(2-hydroxy-3-((1.

See terpeneless oil. Further information can be ob-

tained from the Essential Oil Association of U.S.

esparto. The leaves of a desert plant (Stipa tena- Note: Many essential oils are now made synthetically

cissima and Lygeum spartum) of the Mediterranean for a wide variety of fragrances and flavoring agents.

area. Relatively high content of cellulose and ␣-cel- Use of these synthetics is increasing because of a

lulose make it usable for high-quality paper for in- shortage of natural products.

512EST

EST. See expressed sequence tag. soluble in alcohol, acetone, dioxane, and solutions

of alkali hydroxides; sparingly soluble in vegetable

oils.

ester. An organic compound corresponding in

Derivation: Isolated from human and mare pregnan-

structure to a salt in inorganic chemistry. Esters are

considered as derived from acids by the exchange of cy urine, commercial synthesis from cholesterol or

the replaceable hydrogen of the latter for an organic ergosterol.

radical. The usual reaction is that of an acid (organic Grade: NF (␤-form).

or inorganic) with an alcohol or other organic com- Hazard: A carcinogen (OSHA).

pound rich in OH groups. Esters of acetic acid are Use: Medicine (estrogenic hormone).

called acetates, and esters of carbonic acid carbon-

ates.

estradiol monopamitate.

See fatty ester.

Use: Food additive; drug (veterinary).

esterase-lipase.

estragole. (chavicol methyl ether; methyl

Properties: Derived from Mucor miehei.

chavicol).

Use: Food additive.

CAS: 140-67-0. C

)(OCH

Properties: Colorless liquid; anise odor. D

ester gum. Hard, semisynthetic resin produced

0.965–0.975 (20/4C), 1.5230 (17.5C), bp 216C. Sol-

by esterification of natural resins (especially rosin)

uble in alcohol and chloroform.

with polyhydric alcohols (principally glycerol but

Occurrence: In tarragon oil, basil oils, anise bark oil,

also pentaerythritol). Flash p 375F (190C). Com-

and others.

bustible.

Use: Perfumes, flavors.

Grade: By color, also as gum rosin or wood rosin.

Use: Paints, varnishes, and cellulosic lacquers.

4,9,11,-estratrien-17␤-ol-3-one. See trenbo-

esterification. The process of producing an ester

lone.

by reaction of an alcohol with an acid.

estriol.

ester interchange. (transesterification; interi-

CAS: 50-27-1. C

fication). The reaction between an ester and another

Properties: White, odorless, microcrysalline pow-

compound with exchange of alkoxy or acyl groups

der. Mp 282C. Exhibits reddish fluorescence under

to form a different ester.

filtered UV light. Undergoes phase change at

270–275C. Practically insoluble in water; soluble in

ester number. (1) The number of milligrams of

alcohol, dioxane, and oils.

alkali necessary for saponification of the glyceryl

Derivation: Isolation from pregnant human urine,

esters in a fat or oil. (2) The difference between acid

isolated from human placenta, organic synthesis.

number and saponification number.

Hazard: A carcinogen (OSHA).

Use: Medicine (estrogenic hormone).

“Esteron” [Dow]. TM for a series of weed- and

brush-control products; they are formulated esters

of 2,4-D and 2,4,5-T.

estrogen. A general term for female sex hor-

mones. They are responsible for the development of

estradiol.

the female secondary sex characteristics, such as the

CAS: 50-28-2. C

. A female sex hormone. It

deposition of fat and the development of the breasts.

occurs in two isomeric forms, ␣ and ␤. ␤-estradiol

The naturally occurring estrogens, such as estradiol,

has the greatest physiological activity of any natu-

estrone, and estriol, are steroids. Estrogens are pro-

rally occurring estrogen. The ␣ form is relatively

duced by the ovary and, to a lesser degree, by the

inactive. Commonly used preparations are the ben-

adrenal cortex and testis. Some synthetic nonsteroid

zoate, dipropionate, and valerate, as well as ethiny-

compounds such as diethylstilbestrol and hexestrol

lestradiol.

have estrogenic activity.

Hazard: Carcinogenic, damaging side effects

(thromboembolism).

Use: Medicine, biochemical research, oral contra-

ceptives.

See antifertility agent.

estrogen response element. See ERE.

Properties: (␤-form) White or slightly yellow, small

estrone.

crystals or crystalline powder; odorless. Mp CAS: 53-16-7. C

. A steroid with some estro-

173–179C, stable in air. Almost insoluble in water; genic activity.

513 ETHANETHIOL

n,n

′

-(1,2-ethanedioxysulfinyl)bis(s-methyl-n-

methylcarbamoyloxythioacetimidate).

CAS: 81861-89-4. mf: C

Hazard: A poison by ingestion.

Use: Agricultural chemical.

ethanedioyl chloride. See oxalyl chloride.

Properties: Small, white crystals or white, crystal-

1,2-ethanedithiol. (dithioethyleneglycol; ethy-

line powder; odorless. Mp 258–262C, stable in air.

lenedimercaptan).

Insoluble in water; soluble in alcohol, acetone, diox-

CAS: 540-63-6. HSCH

SH.

ane, and solutions of fixed alkali hydroxides.

Properties: Liquid. Mw 94.20, bp 144–146C, d

Derivation: Isolated from pregnant human urine,

1.123. Soluble in alcohol and alkalies.

synthesis from ergosterol.

Hazard: Vapors cause severe headache and nausea.

Hazard: A carcinogen (OSHA).

Use: Metal-complexing agent. Reverses the inhibi-

tion by ␣-keto aldehydes on mitosis in E. coli.

estrone 17-methoxime.

n,n

′

-(1,2-ethanedithiosulfinyl)bis(2,3-

CAS: 3342-64-1. mf: C

dihydro-2,2-dimethylbenzofuranyl-7)

Hazard: A reproductive hazard.

methylcarbamate.

CAS: 81861-95-2. mf: C

Et. Informal abbreviation for ethyl. Example:

Hazard: A poison by ingestion.

EtOH, ethyl alcohol.

Use: Agricultural chemical.

etamycin.

n,n

′

-(1,2-ethanedithiosulfinyl)bis(s-methyl-n-

CAS: 299-20-7. mf: C

methylcarbamoyloxythioacetimidate).

Hazard: Moderately toxic by ingestion.

CAS: 81861-94-1. mf: C

Hazard: A poison by ingestion.

Use: Agricultural chemical.

Etard reaction. Oxidation of an arylmethyl

group to an aldehyde by means of chromyl chloride.

1,1

′

-(1,2-ethanediyl)bis(1-methylhydrazine).

CAS: 20247-50-1. mf: C

“Ethacure” [Albemarle]. TM for curing

Hazard: Moderately toxic by ingestion and inhala-

agents for thermosetting plastics.

tion.

“Ethafoam” [Dow]. TM for a lightweight,

1,1

′

-(1,2-ethanediylbis(oxy))bis(2,3,4,5,6-

low-density polyethylene foam.

pentabromobenzene).

CAS: 61262-53-1. mf: C

Hazard: Moderately toxic by inhalation and skin

ethanal. See acetaldehyde.

contact. Low toxicity by ingestion.

ethanamide. See acetamide.

ethane hydrate. See gas hydrate.

ethane. (dimethyl; methylmethane). ethanethiol. (ethyl sulfhydrate; ethyl mercap-

CAS: 74-84-0. C

. tan).

Properties: Colorless gas; odorless.Bp −88.63C, fp CAS: 75-08-1. C

SH.

−183.23C (triple point), d of liquid 0.446 (0C), d of Properties: Colorless liquid, has one of the most

vapor (air

1) 1.04 (0C), critical temp 32.1C, criti- penetrating and persistent odors known (skunk). D

cal press (absolute) 718 psi, specific heat at constant 0.83907 (20/4C), bp 36C, fp −121C, refr index

press 0.897, specific heat at constant vol 0.325, ratio 1.4305 (20C), flammable limits in air 2.8–18.2% by

of specific heats (cp/cv) 1.224, heat of combustion volume, flash p approximately 80F (26.6C) (CC),

approximately 22,300 Btu/lb or 1800 Btu/cu ft, flash autoign temp 570F (298C). Slightly soluble in wa-

p −211F (−135C), autoign temp 959F (515C). Insol- ter; soluble in alcohol, ether, petroleum naphtha.

uble in water; soluble in alcohol. Relatively inactive Derivation: By saturating potassium hydroxide solu-

chemically. tion with hydrogen sulfide, mixing with calcium

Derivation: Fractionation of natural gas. ethylsulfate solution, and distilling in a water bath.

Grade: 95%, 99%, research, 99.98%. Hazard: Toxic by ingestion and inhalation. Flamma-

Hazard: Severe fire risk if exposed to sparks or open ble, dangerous fire risk. TLV: 0.5 ppm.

flame. Flammable limits in air 3–12%. An asphyxi- Use: LPG odorant, adhesive, stabilizer, chemical in-

ant gas. termediate.

Use: Petrochemicals (source of ethylene, halogenat- Note: Tomato juice is reported to deodorize materials

ed ethanes), refrigerant, fuel. contaminated with this compound.

514ETHANETHIOLIC ACID

ethanethiolic acid. See thioacetic acid. Use: Agricultural chemical.

ethanoic acid. See acetic acid. ethaverine. (1-[(3,4-diethoxyphenyl)methyl]-

6,7-diethoxyisoquinoline; isoquinoline).

CAS: 486-47-5. C

ethanol. See ethyl alcohol.

Properties: Crystals. Mw 395.48 (99–101C). Insolu-

ble in water; very soluble in hot alcohol; slightly

ethanolamine. (MEA; monoethanolamine; co-

soluble in ether and chloroform.

lamine; 2-aminoethanol; 2-hydroxyethylamine).

Use: Antispasmodic drug.

CAS: 141-43-5. HOCH

Properties: Colorless; ammoniacal odor. D 1.0179

“Ethazcate” [Uniroyal]. TM for zinc diethyl-

(20/20C), bp 170.5C, mp 10.5C, vap press 0.48 mm

dithiocarbamate.

Hg (20C), flash p 200F (93.3C) (OC), bulk d 8.5 lb/

See zinc diethyldithiocarbamate.

gal (20C). Hygroscopic, viscous liquid. Strong base.

Miscible with water, methanol, acetone. Combus-

tible.

ethchlorvynol. (1-chloro-3-ethyl-1-penten-4-

Derivation: Reaction of ethylene oxide and ammo- yn-3-ol; ␤-chlorovinylethylethynylcarbinol).

nia gives a mix of mono-, di-, and triethanolamines. CAS: 113-18-8. HC≡CCOH(C

)CH==CHCl.

Grade: Technical, NF. Properties: Colorless to yellow liquid; pungent aro-

Hazard: Skin irritant. TLV: 3 ppm; STEL 6 ppm. matic odor. Darkens on exposure to light and air. D

Use: Scrubbing acid gases (H

S, CO

), especially in 1.068–1.071, refr index 1.4765–1.4800 (25C), bp

synthesis of ammonia, from gas streams; nonionic 173–181C. Immiscible with water; miscible with

detergents used in dry cleaning, wool treatment, most organic solvents.

emulsion paints, polishes, agricultural sprays; Grade: NF.

chemical intermediates, pharmaceuticals, corrosion Hazard: Abuse may cause addiction.

inhibitor, rubber accelerator. Use: Medicine (sedative).

ethanol formamide. HOCH

NHOCH. ethene. See ethylene.

Properties: Somewhat viscous liquid. Bp 143C (2.5

mm Hg), fp approximately −72C, d 1.170 (25/4C),

ethenol. See vinyl alcohol.

flash p 347F (175C). Miscible with water, alcohol,

and glycerol. Compatible with polyvinyl alcohol,

ethenylbenzene tribromo deriv.

many cellulosic and natural resins. Combustible.

homopolymer.

CAS: 57137-10-7. mf: (C

)

ethanol hydrazine. See ␤-hydroxyethylhy-

Hazard: Moderately toxic by skin contact. Low tox-

drazine.

icity by ingestion. A mild eye irritant.

Use: Fragrance chemical.

ethanolurea. NH

CONHCH

OH.

Properties: Liquid. Solidification point 71–74C.

ethenyl 2-propenoate.

Formaldehyde condensation products are perma-

CAS: 2177-18-6. mf: C

nently thermoplastic and water soluble. As increas-

Hazard: A poison by ingestion. Low toxicity by

ing amounts of simple urea are mixed with ethanolu-

inhalation. A severe skin and eye irritant.

rea, the condensation products gradually change

from pliable film-forming resins into the brittle

ethephon. See 2-chloroethylphosphonic acid.

types. Thus, almost any degree of water solubility

and flexibility may be obtained in the final resin. The

ether. A class of organic compounds in which an

modified resins formed with ethanolurea are com-

oxygen atom is interposed between two carbon

patible with polyvinyl alcohol, methyl cellulose,

atoms (organic groups) in the molecular structure,

cooked starch, and other water-dispersible mate-

giving the generic formula ROR. They may be de-

rials.

rived from alcohols by elimination of water, but the

major method is catalytic hydration of olefins. Only

ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-

the lowest member of the series, methyl ether, is

hexamethyl-2-naphthalenyl)-.

gaseous; most are liquid, and the highest members

CAS: 21145-77-7. mf: C

are solid (cellulose ethers). The term ether is often

Hazard: A poison by ingestion. Low toxicity by skin

used synonymously with ethyl ether and is the legal

contact.

label name for it.

Hazard: The lower molecular weight ethers are dan-

“Ethanox” [Albemarle]. TM for hindered

gerous fire and explosion hazards; when containing

phenolic antioxidants.

peroxides they can detonate on heating.

Use: See ethyl ether; polymer, water-soluble; ethyl-

ethaphos. ene oxide; propylene oxide; diethylene glycol;

CAS: 38527-91-2. mf: C

PS. ethylcellulose; polyether.

Hazard: A poison by ingestion. Note: An illogical and archaic use of the term ether

515

-ETHOXYCHRYSOIDINE

survives in such names as petroleum ether. (22C). Solutions are yellow, fluorescent, and stable

See crown ether. to boiling.

Purity: 97% (dry basis).

Use: Bactericide, surgical antisepsis, preparation of

ethereal. Descriptive of a liquid characterized by

pure ␥-globulin.

high volatility, often a mixture of ethyl ether and an

essential oil.

ethofumesate. (2-ethoxy-2,3-dihydro-3,3-di-

methyl-5-benzofuranol methanesulfonate).

ethical drug. A prescription drug.

CAS: 26225-79-6. C

See drug.

Properties: Whitish crystals. Mp 71C. Does not hy-

drolyze with water at neutral pH.

ethinylestradiol. (ethynylestradiol; 19-nor-17-

Use: Herbicide, silvicide.

␣-pregna-1,3,5(1)-trien-20-yne-3,17-diol).

CAS: 57-63-6. C

ethoheptazine. (ethyl heptazine; 1-methyl-4-

Properties: Fine, white to creamy white crystalline

carbethoxy-4-phenylhexamethyleneimine).

powder; odorless. Sensitive to light. Mp 142–146C.

May also exist in a polymorphic modification with

Properties: Liquid. D 1.038 (26/4C), bp 133–134C

mp 180–186C. Soluble in acetone, alcohol, chloro-

(1.0 mm Hg), refr index 1.5210 (26C).

form, dioxane, ether, and vegetable oils; practically

Use: Medicine (analgesic).

insoluble in water; soluble in solutions of sodium

hydroxide or potassium hydroxide; slightly dextro-

ethohexadiol. USP name for 2-ethylhexanediol-

rotatory in dioxane solution.

1,3.

Derivation: Preparation from estrone.

Grade: USP.

“ETHONIC” [Albemarle]. TM for ethoxylat-

Use: Medicine (estrogenic hormone).

ed alcohol surfactants.

ethion. (generic name for O,O,O

′

-tetrae-

“ETHONIC 11” [Albemarle]. TM for

thyl-S,S

′

-methylenediphosphorodithioate).

ethoxylated alcohols.

CAS: 563-12-2. [(C

P(S)S]

Use: As wetting agents and emulsifiers in detergents,

Properties: Liquid. D 1.220 (20C), fp −13C. Slightly

personal care, textiles, and paper.

soluble in water; soluble in acetone, xylene, chloro-

form, and methylated naphthalene.

ethopabate.

Hazard: Cholinesterase inhibitor, use may be re-

CAS: 59-06-3. mf: C

stricted. TLV: 0.4 mg/m

Properties: Odorless white to pink crystals from

Use: Insecticide and miticide.

MeOH (aq). Mp: 148−149°. Sol in methanol, etha-

nol, acetone, acetonitrile, isopropanol, p-dioxane,

ethisterone. (preneninolone; anhydrohydroxy-

ethyl acetate, and methylene chloride.

progesterone; ethynyltestosterone).

Use: Drug (veterinary); food additive.

CAS: 434-03-7. C

Properties: White or slightly yellow crystals or crys-

ethoxazene. See p-ethoxychrysoidine.

talline powder; odorless. Stable in air. Affected by

light. Mp 267–275 (decomposes). Almost insoluble

p-ethoxyacetanilide. See acetophenetidin.

in water; slightly soluble in alcohol, chloroform,

ether, and vegetable oils.

4-ethoxyamphetamine hydrochloride.

Derivation: From progesterone and other steroids.

CAS: 135014-87-8. mf: C

NO•ClH.

Grade: NF.

Hazard: A reproductive hazard.

Use: Medicine (estrogenic hormone).

ethoxycarbonyl isothiocyanate. (ethyl iso-

“Ethocel” [Dow]. TM for ethylcellulose resins

thiocyanateformate). C

CNCS.

are able to withstand shock and maintain toughness

Properties: Moisture-sensitive solid. Mw 131.15, bp

over a temperature range of +93 to −40C. Available

56C (18 mm Hg), d 1.112.

in transparent, translucent, and opaque colors. Insol-

Hazard: Lachrymator.

uble in water, soluble in most organic solvents.

Use: Versatile reagent for organic synthesis.

Use: Household articles, automotive parts, tools for

aircraft industry.

o-(4-(1-(((ethoxycarbonyl)oxy)imino)ethyl)

phenyl) o,o-diethyl phosphorothioate.

CAS: 22936-34-1. mf: C

PS.

ethodin. (6,9-diamino-2-ethoxyacridine lactate

Hazard: Moderately toxic by ingestion.

monohydrate).

Use: Agricultural chemical.

CAS: 1837-57-6. C

O•C

•H

Properties: Pale-yellow crystals. Darkens at 200C,

mp 235C. Slowly soluble in 15 parts water; soluble

p-ethoxychrysoidine.

in 9 parts boiling water; soluble in 110 parts alcohol CAS: 94-10-0. mf: C

5162-ETHOXY-3,4-DIHYDRO

Hazard: A poison.

“Ethoxylan” [Henkel]. TM for additive lan-

olin.

Available forms: Paste, waxy solid.

2-ethoxy-3,4-dihydro-2H-pyran.

Use: Emollient conditioner; lubricant emulsifier for

creams, lotions, makeup, lip products, and nail and

❘

H:CHCH

❘

CHOC

suntan products.

Properties: Liquid. D 0.970 (20/20C), bp 143C, fp

−100C, flash p 111F (OC). Sets to glass below this

ethoxylated glyceryl monostearate. See

temperature. Very slightly soluble in water. Com-

“Durfax EOM” [PPG].

bustible.

Hazard: Moderate fire risk.

ethoxylated mono- and diglycerides.

Use: Stabilizer, intermediate.

Properties: Mix of stearate, palmitate, and lesser

amounts of myristate partial esters of glycerin con-

6-ethoxy-1,2-dihydro-2,2,4-

densed with approx. 20 moles of ethylene oxide per

trimethylquinoline. (ethoxyquin).

mole of ␣-monoglyceride reaction mixtures. (FCC

CAS: 91-53-2. C

NO.

III) Pale, sltly yellow, oily liquid; mildly bitter taste.

Properties: Yellow liquid. Bp 125C (2 mm Hg), mp

Sol in water, alc, xylene; sltly sol in mineral oil,

approximately 0C, refr index 1.569–1.572 (25C), d

vegetable oil.

1.029–1.031 (25C). Discolors and stains badly.

Use: Food additive.

Hazard: Toxic by ingestion.

Use: Insecticide, antioxidant, flex-cracking inhibitor,

4-ethoxy-3-methoxybenzaldehyde.

postharvest preservation of apples (scald inhibitor).

(OC

)(OCH

)CHO.

Properties: White to light-brown crystals; slight

ethoxydimethylsilane. (dimethylethoxysi-

vanillin odor. Mp 62–64C. Combustible.

lane).

Use: Intermediate.

CAS: 14857-34-2. C

OSi.

Hazard: An inhalation hazard. TLV: TWA 0.5 ppm;

4-ethoxy-3-methoxyphenylacetic acid.

STEL: 1.5 ppm.

(OC

)(OCH

)CH

COOH.

Properties: An off-white powder. Mp 119–122C.

Use: Intermediate.

2-ethoxyethanol. See ethylene glycol monoe-

thyl ether.

1-ethoxy-2-methoxy-4-propenylbenzene.

See isoeugenyl ethyl ether.

2-ethoxyethyl acetate. See ethylene glycol

monoethyl ether acetate.

2-ethoxy-4-methyl-2,3-dihydro-4h-pyran.

CAS: 10138-44-0. mf: C

n-(2-ethoxyethyl)-4,5-dihydro-3-

Hazard: Moderately toxic by ingestion. mild skin

(phenylamino)-2h-benz(g)indazole-2-

and eye irritant.

acetamide.

CAS: 301644-19-9. mf: C

ethoxymethylenemalononitrile.

Hazard: A poison by ingestion.

OCH:C(CN)

Properties: Colorless liquid. Bp 160C, mp 64C,

2-ethoxyethyl-p-methoxycinnamate.

flash p 311F (155C). Combustible.

CH:CHCOOC

Use: Chemical intermediate.

Properties: Slightly yellow, viscous liquid; practi-

cally odorless. D 1.1000–1.1035 (25/25C), refr in-

4-ethoxyphenol. See hydroquinone monoe-

dex 1.5650–1.5675 (20C), flash p >212F (>100C)

thyl ether.

(TCC). Miscible with alcohol and isopropyl alcohol;

almost insoluble in water. Combustible.

r-(−)-5-(2-((2-(2-ethoxyphenoxy)ethyl)

Use: UV absorber in suntan preparations.

amino)propyl)-2-methoxybenzene-

sulfonamide hydrochloride.

3-ethoxy-4-hydroxybenzaldehyde. See eth-

CAS: 106463-17-6. mf: C

S•ClH.

yl vanillin.

Hazard: Moderately toxic by ingestion.

1-ethoxy-2-hydroxy-4-propenylbenzene.

2-(m-ethoxyphenyl)imidazo(2,1-

See propenyl guaethol.

a)isoquinoline.

CAS: 61001-14-7. mf: C

Hazard: A reproductive hazard.

2-[1-(ethoxyimino)butyl]-5-[2-

(ethylthio)propyl]-3-hydroxy-2-

cyclohexene-1-one. ethoxyquin.

Coined name for 6-ethoxy-1,2-

Use: Food additive; herbicide. dihydro-2,2,4-trimethylquinoline.

517 ETHYL ACRYLATE

ethoxytriglycol. synthesis, smokeless powders, pharmaceuticals,

CAS: 112-50-5. C

O(C

synthetic fruit essences.

Properties: Colorless liquid. D 1.0208 (20/20C),

bulk d 8.5 lb/gal (20C), bp 255.4C, vap press <0.01

ethyl-o-acetate. CH

C(OC

)

(20C), fp −18.7C, viscosity 7.80 cP (20C). Com-

Properties: Colorless liquid. Bp 144–148C, refr in-

pletely soluble in water. Flash p 275F (135C) (CC).

dex 1.395 (25C). Insoluble in water; soluble in alco-

Combustible.

hol and ether, flash p 131F (55C). Combustible.

Use: Chemical intermediate.

Hazard: Moderate fire risk.

Use: Intermediate.

ethy abietate. C

COOC

ethyl acetate, anhydrous. ethyl acetate,

Properties: Amber-colored, viscous liquid; hardens

grade 99%.

upon oxidation. Bp 350C, flash p 352F (177C), mp

45C, refr index 1.4980, d 1.02. Soluble in ether and

ethyl acetic acid. See butyric acid.

most varnish solvents, insoluble in water. Combus-

tible.

ethyl acetoacetate. (diacetic ester; acetoacet-

Derivation: (1) By heating together ethyl chloride

ic ester). CH

COCH

COOC

(keto form),

and an alcoholic solution of rosin and caustic soda.

C(OH):CHCOOC

(enol form). This com-

(2) By reacting ethyl iodide with silver abietate.

pound is a tautomer at room temperature consisting

Hazard: Irritant.

of about 93% keto form and 7% enol form.

Use: Varnishes, lacquers, and coating compositions.

Properties: Colorless liquid; fruity odor. D 1.0250

(20/4C), fp (enol) −80C; (keto) −39C, bp 180–181C,

n-ethylacetamide. CH

CONHC

bulk d 8.5 lb/gal, vap press 0.8 mm Hg (20C), flash p

Properties: Colorless liquid; faint odor. D 0.920 (20/

185F (85C) (COC), coefficient of expansion

20C), boiling range 206–208.5C, flash p 230F

0.00101/C. Soluble in water and common organic

(110C). Combustible.

solvents. Combustible.

Derivation: Action of metallic sodium on ethyl ace-

ethyl acetamidocyanoacetate. (acetamido-

tate with subsequent distillation.

cyanoacetic ester; ethyl-n-acetyl-␣-cyanogly-

Grade: Technical, 98%.

cine). NCCH(NHCOCH

)COOC

Hazard: Toxic by ingestion and inhalation; irritant to

Properties: Solid. Mp 129C.

skin and eyes.

Use: Synthesis of amino acids and related com-

Use: Organic synthesis; antipyrine, lacquers, dopes,

pounds.

plastics; manufacture of dyes, pharmaceuticals anti-

malarials, vitamin B; flavoring.

n-ethylacetanilide. (ethylphenylacetamide).

COCH

ethyl acetone. See methyl propyl ketone.

Properties: White, crystalline solid; faint odor. D

0.994, bp 258C, flash p 126F (52.2C), mp 54C.

ethyl-n-acetyl-␣-cyanoglycine. See ethyl

Soluble in most organic solvents; insoluble in water.

acetamidocyanoacetate.

Combustible.

Grade: Technical.

ethylacetylene. (1-butyne).

Hazard: Toxic by ingestion, moderate fire risk.

CAS: 107-00-6. C

C≡CH.

Use: Substitute for camphor in nitrocellulose.

Properties: Available as liquefied gas. Bp 8.3C, d

0.669 (0/0C), fp −130C, flash p <20F (−6.6C)

(TOC), sv 7.2 cu ft/lb (21.2C). Insoluble in water.

ethyl acetate. (acetic ether; acetic ester; vin-

Hazard: Flammable, dangerous fire risk.

egar naphtha).

Use: Specialty fuel, chemical intermediate.

CAS: 141-78-6. CH

COOC

Properties: Colorless, fragrant liquid. Bp 77C, vap

␣-ethylacrolein.

press 73 mm Hg (20C), fp −83.6C, bulk density

CAS: 922-63-4. mf: C

0.8945 g/ml (25C), flash p 24F (−4.4C), autoign

Hazard: Moderately toxic by inhalation.

temp 800F (426C). Soluble in chloroform, alcohol,

and ether; slightly soluble in water.

Derivation: By heating acetic acid and ethyl alcohol

ethyl acrylate.

in the presence of sulfuric acid and distilling. CAS: 140-88-5. CH

:CHCOOC

Grade: Commercial 85–88%, 95–98%, 99%, NF Properties: Colorless liquid. Bp 99.4C, fp −72.0C, d

(99%), FCC. 0.9230 (20/20C), refr index 1.4037 (25C), bulk d 7.6

Hazard: Toxic by inhalation and skin absorption; lb/gal (20C), flash p 60F (15.5C) (OC). Soluble in

irritant to eyes and skin. Flammable, dangerous fire alcohol and ether. Readily polymerized.

and explosion risk, flammable limits in air 2.2–9%. Derivation: (1) Ethylene cyanohydrin, ethyl alcohol,

TLV: 400 ppm; not classifiable as a human carcin- and dilute sulfuric acid; (2) Oxo reaction of acety-

ogen. lene, carbon monoxide, and ethyl alcohol in the

Use: General solvent in coatings and plastics, organic presence of nickel or cobalt catalyst.

518␣-ETHYLACRYLALDEHYDE

Grade: Technical (inhibited, usually with hydroqui-

ethyl ␣-allylacetoacetate.

none or its monomethyl ether), pure uninhibited.

COCH(CH

CH:CH

)COOC

Hazard: Toxic by ingestion, inhalation, skin absorp-

Properties: Water-white liquid. D 0.989 (20C), bulk

tion; irritant to skin and eyes. Flammable, dangerous

d 8.24 lb/gal (20C). Combustible.

fire and explosion hazard. TLV: 5 ppm; STEL 15

Use: Intermediate for pharmaceuticals, perfumes,

ppm; suspected human carcinogen.

fungicides, insecticides, fine chemicals.

Use: Monomer for acrylic resins.

See acrylate; acrylic resin.

ethylaluminum dichloride. (EADC).

AlCl

Properties: Clear, yellow, pyrophoric liquid. Bp (ex-

␣-ethylacrylaldehyde. See ␣-ethylacrolein.

trapolated) 194C, fp 32C, d 1.222, bulk d 10.28 lb/

gal (25C).

Derivation: Reaction of aluminum chloride with

ethyl alcohol. (alcohol; grain alcohol; etha- ethylaluminum sesquichloride.

nol; EtOH). Hazard: Ignites on contact with air, dangerous fire

CAS: 64-17-5. C

OH. risk, reacts violently with water. Skin irritant.

Properties: (Pure 100% absolute alcohol, dehy- Use: Catalyst for olefin polymerization, aromatic hy-

drated) Colorless, limpid, volatile liquid; ethereal drogenation; intermediate.

vinous odor; pungent taste. Bp 78.3C, fp −117.3C,

refr index 1.3651 (15C), surface tension 22.3 dynes/

ethylaluminum sesquichloride. (EASC).

cm (20C), viscosity 0.0141 cP (20C), vap press 43

)

mm Hg (20C), specific heat 0.618 cal/g K (23C),

Properties: Clear, yellow, pyrophoric liquid. Bp

flash p 55F (12.7C), d 0.816 (15.56C), bp 78C, fp

204C, fp −50C, d 1.08.

−114C, autoign temp 793F (422C). Miscible with

Derivation: Reaction of ethyl chloride and alu-

water, methanol, ether, chloroform, and acetone.

minum.

(95% alcohol)

Grade: Commercial.

Derivation: (1) From ethylene by direct catalytic

Hazard: Ignites on contact with air, dangerous fire

hydration or with ethyl sulfate as intermediate; (2)

risk, reacts violently with water.

fermentation of biomass, especially agricultural

Use: Catalyst for olefin polymerization, aromatic hy-

wastes; (3) enzymatic hydrolysis of cellulose

drogenation; intermediate.

See cellulase.

Grade: USP (95% by volume), absolute, pure, com-

ethylamine. (monoethylamine; aminoethane).

pletely denatured, specially denatured, industrial,

CAS: 75-04-7. CH

various proofs (one-half the proof number is the

Properties: Colorless, volatile liquid (or gas). Am-

percentage of alcohol by volume).

monia odor, strong alkaline reaction, bp 16.6C, fp

Hazard: Classified as a depressant drug. Though it is

−81.2C, d 0.689 (liquid 15/15C), bulk d 5.7 lb/gal

rapidly oxidized in the body and is therefore noncu-

(20C), flash p approximately 0F (−17.7C) (OC),

mulative, ingestion of even moderate amounts

autoign temp 723F (383C). Miscible with water,

causes lowering of inhibitions, often succeeded by

alcohol, and ether.

dizziness, headache, or nausea. Larger intake causes

Derivation: From ethyl chloride and alcoholic am-

loss of motor nerve control, shallow respiration, and

monia under heat and pressure.

in extreme cases unconsciousness and even death.

Grade: Technical (anhydrous and 70% aqueous so-

Degree of intoxication is determined by concentra-

lution), pure 98.5% min.

tion of alcohol in the brain. Of primary importance is

Hazard: Strong irritant. Flammable, dangerous fire

the fact that intake of moderate amounts together

risk, flammable limits in air 3.5–14%. TLV: 5 ppm;

with barbiturates or similar drugs is extremely dan-

15 ppm STEL.

gerous and may even be fatal. Flammable, danger-

Use: Dye intermediate, solvent extraction, petroleum

ous fire risk; flammable limits in air 3.3–19%. TLV:

refining, stabilizer for rubber latex, detergents, or-

1000 ppm; not classifiable as a human carcinogen.

ganic synthesis.

Use: Solvent for resins, fats, fatty acids, oils, hydro-

carbons; extraction medium; manufacture of acetal-

ethylamine hydrobromide. C

•HBr.

dehyde, acetic acid, ethylene, butadiene, 2-ethyl

Properties: White, almost odorless granules. Mp

hexanol, dyes, pharmaceuticals, elastomers, deter-

158–161C. Very soluble in water.

gents, cleaning preparations, surface coatings, cos-

Use: Intermediate (where liquid ethylamine or liquid

metics, explosives, antifreeze, beverages, antisep-

hydrobromic acid cannot be used).

sis, gasohol, yeast-growth medium; octane booster

in gasoline.

ethyl-o-aminobenzoate. See ethyl anthrani-

See alcohol, denatured; alcohol, industrial; biomass.

late.

Note: Ethanol from fermentation of biomass and

hydrolysis of cellulose is a significant alternate ener-

gy source, especially as an automotive fuel. Its use in

ethyl-p-aminobenzoate hydrochloride.

gasoline will continue to increase. (anesthesol; benzocaine; procaine hydrochlo-

519

-ETHYLBENZENESULFONAMIDE

ride).

ethyl anthranilate. (ethyl-o-aminobenzoate).

CAS: 51-05-8. C

•HCl. CAS: 87-25-2. C

(NH

)COOCH

Properties: White, crystalline; odorless; tasteless Properties: Colorless liquid; fruity odor. D 1.117,

powder. Stable in air. Mp 88–92C. Soluble in dilute

refr index 1.564, bp 260C. Soluble in alcohol and

acids; less soluble in chloroform, ether, and alcohol;

propylene glycol. Combustible.

very slightly soluble in water.

Grade: Technical, FCC.

Derivation: Ethylation of p-nitrobenzoic acid fol-

Use: Perfumery and flavors, similar to methyl anthra-

lowed by reduction.

nilate.

Grade: Technical, pure, NF (as benzocaine).

Hazard: Toxic by ingestion.

2-ethylanthraquinone. C

Use: Medicine (local anesthetic), suntan prepara-

Properties: Buff to light-yellow paste. Mp 108C.

tions.

Use: Synthesis, especially of hydrogen peroxide.

ethylaminoethanol. See N-ethylethanolamine.

“Ethyl” Antiknock Compounds

Mixed ethylaminoethanols; may also contain die-

[Albemarle]. TM for a series of fuel additives

thylaminoethanol.

containing various percentages of tetraethyl lead,

ethylene dibromide, ethylene dichloride, dye, kero-

2-ethylamino-4-isopropylamino-6-

sene, and antioxidant. All are used to improve the

methylthio-s-triazine.

octane rating of motor fuels.

HNC

(SCH

)NHCH(CH

)

Properties: White, crystalline powder. Mp 84–85C.

ethylarsenious oxide. C

AsO.

Slightly soluble in water; soluble in organic sol-

Properties: Colorless oil; garliclike, nauseating

vents.

odor. D 1.802 (11C); bp 158C (10 mm Hg). Oxidizes

Hazard: Toxic by ingestion.

in air and forms colorless crystals. Soluble in ace-

Use: Weed-killing agent in pineapple and sugarcane.

tone, benzene, ether.

Hazard: Highly toxic.

ethyl-1-(p-aminophenyl)-4-

Use: Organic synthesis.

phenylisonipecotate. See anileridine.

2-ethylaziridine. See ethylethyleneimine.

ethyl amyl ketone. (EAK; 5-methyl-3-hepta-

none).

ethyl p-benzamidobenzoate.

CAS: 541-85-5. CH

CO(CH

)

CAS: 736-40-3. mf: C

Properties: Colorless liquid; pungent odor. Bp

Hazard: Moderately toxic by ingestion.

157C, bulk d 83 lb/gal, d 0.819–0.824, refr index

Use: Agricultural chemical.

1.416, flash p 138F (58C). Insoluble in water; solu-

ble in four volumes of 60% alcohol. Combustible.

ethylbenzene. (phenylethane).

Hazard: Narcotic in high concentration. Moderate

CAS: 100-41-4. C

fire risk. TLV: 25 ppm.

Use: Perfumery, solvent for nitrocellulose and vinyl

resins.

n-ethylaniline.

CAS: 103-69-5. C

NHC

Properties: Colorless liquid; aromatic odor. Vapor

Properties: Colorless liquid, becoming brown on

heavier than air, bp 136.187C, refr index 1.49594

exposure to light. Soluble in alcohol; insoluble in

(20C), d 0.867 (20C), fp −95C, bulk d 7.21 lb/gal

water. D 0.9631, fp −63.5C, bp 206C, refr index

(25C), flash p 59F (15C), autoign temp 810F

1.5559 (20C), flash p 185F (85C) (OC). Combus-

(432C), specific heat 0.41 cal/gal/K, viscosity 0.64

tible.

cP (25C). Soluble in alcohol, benzene, carbon tetra-

Derivation: By heating aniline and ethyl alcohol in

chloride, and ether; almost insoluble in water.

the presence of sulfuric acid, with subsequent distil-

Derivation: (1) By heating benzene and ethylene in

lation.

the presence of aluminum chloride, with subsequent

Hazard: Toxic by ingestion, inhalation, and skin

distillation; (2) by fractionation directly from the

absorption.

mixed xylene stream in petroleum refining.

Use: Organic synthesis.

Grade: Technical, pure, research.

Hazard: Toxic by ingestion, inhalation, and skin

o-ethylaniline.

absorption; irritant to skin and eyes. Flammable,

CAS: 578-54-1. C

(NH

dangerous fire risk. TLV: 100 ppm; STEL 125 ppm.

Properties: Brown liquid. Fp −44C, d 0.982 (20C),

Use: Intermediate in production of styrene, solvent.

bp 214C, flash p 185F (85C) (OC). Soluble in alco-

hol and toluene; insoluble in water. Combustible.

Use: Intermediate for pharmaceuticals, dyestuffs,

n-ethylbenzenesulfonamide.

pesticides, and other products. CAS: 5339-67-3. mf: C

5204-ETHYLBENZENESULFONIC ACID

Hazard: Moderately toxic by ingestion.

ethylbenzyl chloride. (1-chloromethylethyl-

Use: Agricultural chemical.

benzene). ClCH

. Consists of 70% p- and

30% o-ethylbenzyl chloride.

Properties: Colorless liquid. D 1.0460–1.0475 (25/

4-ethylbenzenesulfonic acid. (p-ethylben-

25C), refr index 1.5290–1.5305 (25C). Soluble in

zenesulfonic acid). C

alcohols; insoluble in water.

Properties: Solid. Mw 186.23, d 1.229, fp >110C.

Hazard: Irritant to eyes, a lachrymator.

Hazard: Corrosive.

Use: Intermediate.

ethyl benzoate.

ethyl biscoumacetate. (ethyl bis(4-hydroxy-

CAS: 93-89-0. C

coumarinyl)acetate).

Properties: Colorless aromatic liquid. D

CAS: 548-00-5. C

. A synthetic derivative of

1.043–1.046, fp −32.7C, bp 212.9C, refr index

bishydroxycoumarin.

1.505, flash p 200F (93C). Soluble in alcohol and

Properties: White, crystalline solid; odorless; bitter

ether; insoluble in water. Combustible.

taste. Mp 177–182C. Another form melts at

Derivation: By heating ethanol and benzoic acid in

154–157C. Soluble in acetone and benzene; slightly

the presence of sulfuric acid.

soluble in alcohol and ether; insoluble in water.

Grade: Technical, FCC.

Grade: NF.

Use: Flavoring, perfumery, solvent mixture, lac-

Use: Medicine (anticoagulant).

quers, solvent for many cellulose derivatives and

natural and synthetic resins.

ethyl borate. Legal label name for triethyl bo-

rate.

ethyl benzoylacetate.

CAS: 94-02-0. C

COCH

COOC

ethyl bromide. (bromoethane).

Properties: Light-yellow oil. Bp 265C (decom-

CAS: 74-96-4. C

Br.

poses), d 1.111–1.117 (20C), flash p 275F (135C).

Properties: Colorless liquid. D 1.431 (20/4C), bp

Soluble in most organic solvents; insoluble in water.

38.4C, bulk d 12–12.1 lb/gal, vap press 386 mm Hg

Combustible.

(20C), autoign temp 952F (511C), fp −119C, flash p

Derivation: Reaction of ethyl acetate and ethyl ben-

approximately 80F (26C). Soluble in alcohol and

zoate with metallic sodium.

ether; sparingly soluble in water.

Method of purification: Vacuum distillation.

Derivation: From ethanol or ethylene and hydrobro-

Grade: 95% pure.

mic acid. One process uses ␥-radiation to initiate the

Use: Dye and pharmaceutical intermediate.

combination.

Grade: Technical (98%).

Hazard: Toxic by ingestion, inhalation, and skin

ethyl-o-benzoyl benzoate.

absorption; strong irritant. TLV: TWA 5 ppm; ani-

COC

COOC

mal carcinogen. Flammable, dangerous fire hazard,

Properties: Yellowish-white solid; odorless. Mp

explosion limits in air 6–11%.

56–58C; bp 325C. Insoluble in water; soluble in

Use: Organic synthesis, medicine (anesthetic), re-

alcohol, acetone, ethyl acetate, and benzene. Com-

frigerant, solvent, grain and fruit fumigant.

bustible.

Use: Plasticizer for nitrocellulose and synthetic

ethyl bromoacetate.

resins.

CAS: 105-36-2. CH

BrCOOC

Properties: Clear, colorless liquid. Partially decom-

1-ethylbenzyl alcohol. (1-phenyl-1-propanol;

posed by water. D 1.53 (4C), bp 168C, fp −13.8C,;

ethylphenylcarbinol).

vap d 5.8. Soluble in alcohol, benzene, ether; insolu-

CAS: 93-54-9. C

OH.

ble in water.

Properties: Oily liquid. Bp 220C, d 0.99, refr index

Derivation: Interaction of bromine and acetic acid in

1.51. Soluble in ethanol and methanol alcohols, ben-

the presence of red phosphorus.

zene, and toluene.

Grade: Technical.

Derivation: Benzaldehyde or phenyl ethyl ketone.

Hazard: Toxic by ingestion, inhalation, and skin

Use: Heat-transfer fluid.

absorption; strong irritant.

ethylbromopyruvate. BrCH

COCO

ethylbenzylaniline. C

N(C

)CH

Properties: Light-yellow liquid. Mw 195.02, bp

Properties: Light-yellow liquid. D 1.034, bp 286C.

90–100C (10 mm Hg), d 1.554, fp 98C.

Soluble in alcohol and ether; insoluble in water.

Hazard: Severe poison, lachrymator, irritant.

Combustible.

Use: Pharmaceutical intermediate.

Derivation: By heating ethylaniline, benzyl chlo-

ride, and aqueous caustic soda, with subsequent

distillation.

2-ethylbutadiene.

Hazard: Toxic by ingestion and inhalation. CAS: 3404-63-5. mf: C

Use: Dyestuffs, organic synthesis. Hazard: A poison.

521 ETHYL BUTYRATE

ethyl butanoate. See ethyl butyrate. ethyl-n-butyl ether. (n-butyl ethyl ether).

CAS: 628-81-9. C

Properties: Liquid. D 0.7528 (20C), fp −103C, bp

2-ethylbutanol. See 2-ethylbutyl alcohol.

92.2C, flash p 40F (4.4C), vap press 43 mm Hg

(20C). Slightly soluble in water.

2-ethyl-1-butene. (uns-diethylethylene).

Hazard: Flammable, dangerous fire risk.

)C:CH

Use: Extraction solvent, inert reaction medium.

Properties: Colorless liquid. D 0.6894 (20/4C), bp

64.95C, refr index 1.3969 (20C). Soluble in alcohol,

ethyl butyl ketone. (3-heptanone).

acetone, ether, and benzene; insoluble in water.

CAS: 106-35-4. CH

COCH

Combustible.

Properties: Clear liquid. D 0.8191 (20/20C), fp

Grade: 95% pure.

−39C, boiling range 142.8−147.8C, 95% purity,

Use: Organic synthesis of flavors, perfumes, medi-

bulk d 6.8 lb/gal, flash p 115F (46C) (OC). Insoluble

cines, dyes, resins.

in water; soluble in alcohol. Combustible.

Hazard: Moderate fire risk. TLV: 50 ppm.

3-(2-ethylbutoxy)propionic acid.

Use: Solvent mix for air-dried and baked finishes, for

CH(C

)CH

OCH

COOH.

polyvinyl and nitrocellulose resins.

Properties: Water-white liquid. D 0.9600 (20/20C),

bp 200C (100 mm Hg), vap press <0.1 mm Hg

2-ethyl-2-butylpropanediol-1,3. (2-butyl-2-

(20C), fp (glass at approximately −90C), flash p

ethylpropanediol-1,3).

280F (137C). Insoluble in water. Combustible.

HOCH

C(C

)(C

)CH

OH.

Use: Preparation of metallic salts for paint driers and

Properties: White crystals or liquid. D 0.931 (50/

gelling agents.

20C), bp 178C (50 mm Hg), fp 41.4C. Solubility in

water 0.8% by wt (20C), flash p 280F (137C). Com-

2-ethylbutyl acetate.

bustible.

CAS: 123-66-0. C

CH(C

)CH

OOCCH

Use: Synthesis of lubricants, emulsifying agents, in-

Properties: Colorless liquid; mild odor. D

sect repellents, plastics.

0.875–0.881 (20/20C), boiling range 155–164C, pu-

rity not less than 90% ethylbutyl acetate, bulk d 7.33

2-ethylbutyl silicate.

lb/gal (20C), flash p 130F (54.4C) (OC).

[CH

CH(C

)CH

Si.

Hazard: Moderate fire risk.

Properties: Colorless liquid. Bp 164C (1 mm Hg).

Use: Solvent for nitrocellulose lacquers, flavoring.

Derivation: Reaction of silicon tetrachloride with 2-

ethylbutanol.

2-ethylbutyl alcohol. (2-ethylbutanol; pseu-

Use: Hydraulic fluid, heat-transfer liquid.

do-hexyl alcohol).

CAS: 97-95-0. CH

CH(C

)CH

OH.

2-ethylbutyraldehyde. (diethylacetaldehyde).

Properties: Colorless liquid. Bp 148.9C, fp −114C, d

CAS: 97-96-1. (C

)

CHCHO.

0.8328 (20/20C), bulk d 6.93 lb/gal (20C), refr index

Properties: Colorless liquid. D 0.8164 (20/20C), bp

1.4229 (20C), flash p 137F (58.3C) (ASTM OC),

116.8C, vap press 13.7 mm Hg (20C), flash p 70F

vap press 0.9 mm Hg (20C). Stable; miscible with

(21.1C) (OC), bulk d 6.8 lb/gal (20C), fp −89C.

most organic solvents; slightly soluble in water.

Insoluble in water.

Combustible.

Grade: Technical.

Hazard: Moderate fire risk.

Hazard: Irritant to eyes and skin. Flammable, dan-

Use: Solvent for oils, resins, waxes, dyes; diluent;

gerous fire risk.

synthesis of perfumes, drugs; flavoring.

Use: Organic synthesis, pharmaceuticals, rubber ac-

celerators, synthetic resins.

n-ethylbutylamine.

CAS: 617-79-8. C

NHCH

ethyl butyrate. (ethyl butanoate).

Properties: Water-white liquid. Bp 108C, fp −78C, d

CAS: 105-54-4. C

0.7401 (20/20C), refr index 1.407 (20C), flash p 65F

Properties: Colorless liquid; pineapple-like odor. D

(18.3C). Partly soluble in water.

0.8788, fp −93.3C, bp 120.6C, refr index 1.400

Hazard: Flammable, dangerous fire risk. Toxic by

(20C), flash p 78F (25.5C) (CC), autoign temp 865F

ingestion.

(462C). Soluble in alcohol and ether; almost insolu-

Use: Intermediate.

ble in water and glycerol.

Derivation: Ethyl alcohol and butyric acid heated in

ethylbutyl carbonate. C

. the presence of sulfuric acid, with subsequent distil-

Properties: Colorless liquid. D 0.92–0.93 (20C), bp lation.

135–175C, flash p 122F (50C) (CC). Combustible. Grade: Technical, FCC.

Hazard: Moderate fire risk. Hazard: Irritant to eyes and mucous membranes,

Use: Solvent for many natural and synthetic resins, in narcotic in high concentration. Flammable, danger-

mixtures for nitrocellulose ous fire risk.

5222-ETHYLBUTYRIC ACID

Use: Flavoring extracts, perfumery, solvent mixture Properties: Off-white crystals. Mw 104.11, mp

for cellulose esters and ethers. 44–47C, bp 108–110C (22 mm Hg), fp 86C.

Hazard: Irritant.

Use: Synthetic intermediate.

2-ethylbutyric acid. (diethylacetic acid).

CAS: 88-09-5. (C

)

CHCOOH.

Properties: Water-white liquid, resembles butyric

N-ethylcarbazole. (9-ethylcarbazole).

acid in most properties except that its odor is less

)

(tricyclic).

pronounced and its water solubility limited. D

Properties: Leaflets.Mp 69–70C, bp 175C (5 mm

0.9225 (20/20C), bp 190C, vap press 0.08 mm Hg

Hg). Soluble in ether and hot alcohol.

(20C), flash p 210F (98C), bulk d 7.7 lb/gal, fp

Derivation: Action of ethyl chloride on the potassi-

−15C. Combustible.

um salt of carbazole.

Use: Ester formation; intermediate for drugs, dye-

Use: Intermediate for dyes, pharmaceuticals; agricul-

stuffs, chemicals; flavoring.

tural chemicals.

ethyl caffeate. (ethyl-3,4-dihydroxycinna-

ethylcarbitol acrylate.

mate). C

(OH)

CH:CHCOOC

CAS: 7328-17-8.

Properties: Yellow to tan crystals; characteristic ar-

Properties: Liquid.

omatic odor. Insoluble in water; very soluble in

Hazard: Moderately toxic. A severe skin irritant.

alcohol.

Grade: CP.

ethyl carbonate. See diethyl carbonate.

Use: Food antioxidant.

ethylcellulose. An ethyl ether of cellulose.

ethyl caprate. (ethyl decanoate).

Properties: White, granular thermoplastic solid,

CAS: 110-38-3. C

COOC

lowest density of the commercial cellulose plastics;

Properties: Colorless liquid; fragrant odor. D 0.862,

properties vary with extent to which hydroxyl radi-

bp 243C. Soluble in alcohol and ether; insoluble in

cals of cellulose have been replaced by ethoxy

water. Combustible.

groups. Standard commercial product has 47–48%

Derivation: By heating capric acid, absolute alcohol,

ethoxy content, d 1.07–1.18, refr index 1.47, high

and sulfuric acid, with subsequent distillation.

dielectric strength, softening point 100–130C. Solu-

Use: Organic synthesis, flavoring agent.

ble in most organic liquids; compatible with resins,

waxes, oils, and plasticizers; inert to alkalies and

ethyl caproate. (ethyl hexoate; ethyl hexa-

dilute acids; insoluble in water and glycerol. Com-

noate).

bustible.

CAS: 123-66-0. C

COOC

Derivation: From alkali cellulose and ethyl chloride

Properties: Colorless to yellowish liquid; pleasant

or sulfate; from cellulose and ethanol in the presence

odor. D 0.873, bp 167. Soluble in alcohol and ether;

of dehydrating agents.

insoluble in water and glycerol. Combustible.

Grade: Technical, NF, FCC.

Derivation: Heating absolute alcohol and n-caproic

Use: Hot-melt adhesives and coatings for cables,

acid in the presence of sulfuric acid, with subsequent

paper, textiles, etc.; extrusion-wire insulation; pro-

distillation.

tective coatings; pigment-grinding bases; toughen-

Grade: Technical, FCC.

ing agent for plastics; printing inks; molding pow-

Use: Organic synthesis, artificial fruit essences.

ders; proximity fuses; vitamin preparations; casing

for rocket propellants; food and feed additive.

2-ethylcaproic acid sodium salt. See sodi-

um 2-ethylhexanoate.

ethyl centralite. See sym-diethyldiphenylurea.

ethyl caprylate. (ethyl octoate; ethyl octa-

Ethylch [Albemarle]. TM for antiknock fuel

noate).

additive, tetraethyl lead.

CAS: 106-32-1. CH

(CH

)

COOC

Properties: Colorless liquid; pineapple odor. D

0.865–0.869 (25C), fp −48C, bp 207–209C. Soluble

ethyl chloride. (chloroethane).

in alcohol and ether; insoluble in water and glycerol.

CAS: 75-00-3. C

Cl.

Combustible.

Properties: Gas at room temperature; when com-

Derivation: Heating caprylic acid, alcohol, and sul-

pressed, a colorless volatile liquid; etherlike odor;

furic acid, with subsequent distillation.

burning taste. D 0.9214, fp −140.85C, bp 12.5C,

Grade: Technical, FCC.

critical point 187.2C (52 atm, d 0.33), vap press

Use: Flavoring, fruit essences.

1000 mm Hg (20C), flash p −58F (−50C) (CC)

autoign temp 966F (518C). Stable and noncorrosive

ethyl carbamate. See urethane.

when dry, but will hydrolyze in the presence of

water or alkalies. Miscible with most of the com-

ethyl carbazate. monly used solvents; slightly soluble in water.

CAS: 4114-31-2. H

NNHCO

. Derivation: (1) From ethylene and hydrogen chlo-

523 ETHYL CYANIDE

ride; (2) by passing hydrogen chloride into a solu-

ethyl 4-chloro-2-oxo-3(2h)-

tion of zinc chloride and ethanol.

benzothiazoleacetate.

Grade: Technical, USP.

CAS: 25059-80-7. mf: C

ClNO

Hazard: Highly flammable, severe fire and explo-

Hazard: Moderately toxic by ingestion and skin con-

sion risk; flammable limits in air 3.8–15.4%. Irritant

tact.

to eyes. TLV: 1000 ppm.

Use: Agricultural chemical.

Use: Manufacture of tetraethyl lead and ethylcellu-

lose; anesthetic; organic synthesis; alkylating agent;

o-ethyl s-4-chlorophenyl

refrigeration; analytical reagent; solvent for phos-

ethylphosphonodithioate.

phorus, sulfur, fats, oils, resins, and waxes; insecti-

CAS: 2984-64-7. mf: C

ClOPS

cides.

Hazard: A poison by skin contact. Moderately toxic

by ingestion and inhalation.

ethyl chloroacetal. ClCH

CH(OC

)

Use: Agricultural chemical.

Properties: Water-white liquid; pleasant odor. D

1.022 (20C), boiling range 54–61C (20 mm Hg),

ethyl chlorosulfonate. C

OClSO

149–153C, fp −32C, flash p 117F (47.2C), refr index

Properties: Colorless, oily liquid; pungent odor. D

1.418 (20C). Soluble in alcohol and ethyl ether;

1.379 (0C); bp 153C; vap d 5 (air

1.29); volatility

insoluble in water. Combustible.

18,000 mg/m

(20C). Fumes in moist air. Decom-

Hazard: Moderate fire risk.

posed by water. Attacks lead and tin but copper only

mildly; iron and steel not affected. Soluble in chlo-

ethyl chloroacetate.

roform and ether; insoluble in water.

CAS: 105-39-5. CCH

ClCO

Derivation: (1) Action of fuming sulfuric acid on

Properties: Water-white, mobile liquid; pungent fru-

ethylchloroformate; (2) interaction of ethylene and

ity odor. Decomposed by hot water and alkalies. D

chlorosulfonic acid.

1.1585 (20C), bp 144.2C, vap d 4.23–4.46, flash p

Grade: Technical.

131F (55C), refr index 1.4227 (20C). Soluble in

Hazard: Strong irritant to eyes and skin, evolves

alcohol, benzene, and ether; insoluble in water.

phosgene when heated.

Combustible.

Use: Organic synthesis, military poison.

Derivation: (1) Action of chloroacetyl chloride on

alcohol; (2) by treating chloroacetic acid with alco-

3-ethylcinchoninic acid ethyl ester.

hol and sulfuric acid.

CAS: 21233-74-9. mf: C

Hazard: Strong irritant to eyes.

Hazard: Moderately toxic by ingestion.

Use: Solvent, organic synthesis, military poison, vat

Use: Agricultural chemical.

dyestuffs.

ethyl cinnamate. (ethyl phenylacrylate; cin-

ethyl chlorobenzoxazoline-2-thione-3-

namylic ether). C

CH:CHCOOC

carboxylate.

Properties: Limpid, oily liquid; strawberry-like

CAS: 33388-24-8. mf: C

ClNO

odor. D 1.045–1.048, refr index 1.560 (20C), con-

Hazard: Moderately toxic by ingestion.

gealing point 7C (min), bp 271C. Soluble in alcohol

Use: Agricultural chemical.

and ether. Insoluble in water. Combustible.

Derivation: Heating ethyl alcohol and cinnamic acid

in the presence of sulfuric acid.

ethyl chlorocarbonate. (ethyl chlorofor-

Use: Perfumery, flavoring extracts.

mate).

CAS: 541-41-3. ClCOOC

Properties: Water-white liquid; irritating odor. D

ethyl citrate. See triethyl citrate.

1.135–1.139 (20/20C), bp 93–95C, refr index

1.3974 (20C), flash p 61F (16.1C) (CC). Decom-

ethyl crotonate.

poses in water and alcohol; soluble in benzene, chlo-

CAS: 623-70-1. CH

CH:CHCOOC

roform, and ether.

Properties: Water-white solid or liquid; characteris-

Derivation: Reaction of carbon monoxide with gas-

tic, pungent, persistent odor. D 0.9207 (20/20C), mp

eous chlorine, producing phosgene (COCl

), which

(solid) 45C, bp (solid) 209C, (liquid) 139C, flash p

is then treated with anhydrous ethanol, giving ethyl

36F (2.2C), refr index 1.4242 (20C), bulk d 7.65 lb/

chlorocarbonate and splitting off hydrogen chloride.

gal (20C). Soluble in alcohol and ether, insoluble in

Grade: Technical.

water.

Hazard: Flammable, dangerous fire risk. Strong irri-

tant to eyes and skin.

tant.

Use: Organic synthesis, intermediate in making die-

Use: Solvent and softening agent, lacquers, organic

thyl carbonate, flotation agents, polymers, isocya-

synthesis.

nates.

ethyl cyanide. (propionitrile; propanenitrile).

ethyl chloroformate. See ethyl chlorocarbo- CAS: 107-12-0. C

CN.

nate. Properties: Mobile, colorless liquid; ethereal odor.

524ETHYL CYANOACETATE

D 0.7829 (20/20C), refr index 1.3664 (20C), bp

ethyl cyclopentanone-2-carboxylate. See

2-carbethoxycyclopentanone.

97.4C, fp −92.9C, flash p 61F (16.1C) (OC). Soluble

in alcohol and water.

ethyl 2-cyano-2-propenoate. See ethyl cya-

Derivation: Heating barium ethyl sulfate and KCN

noacrylate.

with subsequent distillation.

Hazard: Toxic by ingestion and inhalation. TLV: 5

mg(CN)/m

. Flammable, dangerous fire risk. ethyl decanoate. See ethyl caprate.

Use: Solvent, dielectric fluid, intermediate.

ethyl diazoacetate.

ethyl cyanoacetate. (malonic ethyl ester ni- CAS: 623-73-4. N

CHCO

trile). Properties: Liquid. Mw 114.10, mp 22C, bp

CAS: 105-56-6. CNCH

COOC

. 140–141 (720 mm Hg), d 1.085.

Properties: Colorless liquid. Bp 206–208C, fp Available forms: Research quantities.

−22.5C, refr index 1.41751 (20C). Soluble in alco- Hazard: Flammable liquid that explodes when

hol and ether; soluble in alkaline solutions. Flash p heated.

230F (110C). Combustible.

Derivation: Esterification of cyanoacetic acid with

ethyl 2,3-dibromopropanoate.

ethanol; reaction of an alkali cyanide and chloroa-

CAS: 3674-13-3. mf: C

cetic ethyl ester.

Hazard: A poison by ingestion and skin contact. A

Method of purification: Vacuum distillation.

severe skin and eye irritant.

Grade: Reagent, technical.

Hazard: Toxic by ingestion and inhalation.

ethyldichloroarsine. (dichloroethylarsine).

Use: Organic synthesis, pharmaceuticals, dyes.

CAS: 598-14-1. C

AsCl

Properties: Colorless, mobile liquid; becomes yel-

ethyl cyanoacrylate. (ethyl ␣-cyanoacrylate;

lowish under the action of light and air. Fruitlike

ethyl 2-cyanoacrylate; ethyl 2-cyano-2-prope-

odor (high dilution). Decomposed by water. Attacks

noate).

brass but not iron (dry). D 1.742 (14C), bp 156C

CAS: 7085-85-0. C

(decomposes), fp −65C, coefficient of thermal ex-

Hazard: An inhalation hazard.

pansion 0.0011, vap d 6 (air

1.29), volatility

Use: An adhesive.

20,000 mg/m

(20C), vap press 2.29 mm Hg (21.5C).

Soluble in alcohol, benzene, ether, and water.

ethyl ␣-cyanoacrylate. See ethyl cyanoacry- Derivation: Chlorination of ethyl arsenious oxide.

late. Hazard: Toxic by ingestion, inhalation, and skin

absorption; strong irritant.

Use: Military poison.

5-ethyl-5-cycloheptenylbarbituric acid.

See heptabarbital.

ethyl-4,4

′

-dichlorobenzilate. See “Chloro-

benzilate.”

ethylcyclohexane. C

Properties: Colorless liquid. D 0.787, bp 131.8C,

refr index 1.4330 (20C), flash p 95F (35C), autoign

ethyl dichlorophenoxyacetate. See 2,4-D.

temp 504F (262C).

Hazard: Flammable, moderate fire risk; flammable

ethyldichlorosilane.

limits in air 0.9–6.6%.

CAS: 1789-58-8. C

SiHCl

Use: Organic synthesis.

Properties: Colorless liquid. Bp 75.5C, d 1.088 (25/

25C), flash p 30F (−1.1C) (COC). Readily hydro-

N-ethylcyclohexylamine. lyzed by moisture, with the liberation of hydrogen

CAS: 5459-93-8. C

NHC

. and hydrogen chloride.

Properties: Liquid. Mw 127.23, bp 165C, d 0.844, fp Derivation: By Grignard reaction of trichlorosilane

43C. and ethylmagnesium chloride.

Hazard: Corrosive and toxic. Hazard: Flammable, dangerous fire risk. Strong irri-

Use: Intermediate in production of herbicides and tant to eyes and skin.

pharmaceuticals. Use: Intermediate for silicones.

ethyl 2-cyclohexylpropionate. ethyldiethanolamine. C

N(CH

OH)

CAS: 2511-00-4. mf: C

. Properties: Water-white liquid; amine odor. D 1.015

Hazard: Low toxicity by inhalation. (20C), boiling range 246–252C, flash p 255F

(123C). Combustible.

Use: Solvent, detergents.

ethylcyclopentane. C

Properties: Colorless liquid. D 0.766, bp 103.5C,

refr index 1.4198 (20C), autoign temp 504F (262C).

ethyl-2-(diethoxyphosphinyl)-3-

Hazard: Flammable, moderate fire risk; flammable oxobutanoate.

limits in air 1.1–6.7%. CAS: 3730-54-9. mf: C

525 ETHYLENE BROMOHYDRIN

Hazard: A poison by ingestion. temp 9.5C, autoign temp 1009F (543C), critical

Use: Agricultural chemical. press (absolute) 744 psi. Purity not less than 96%

ethylene by gas volume, not more than 0.5% acety-

ethyl 3-((diethylphosphinothioyl)oxy)-2- lene, not more than 4% methane and ethane. Sp vol

butenoate. 13.4 cu ft/lb (15.6C). Slightly soluble in water, alco-

CAS: 73263-81-7. mf: C

PS. hol, and ethyl ether.

Hazard: A poison by ingestion. Derivation: (1) Thermal cracking of hydrocarbon

gases (800–900C), (2) dehydration of ethanol, (3)

from synthesis gas with Ru as catalyst.

ethyl diglyme. See diethylene glycol diethyl

Grade: Technical (95% min), 99.5% min, 99.9 mole

ether.

Hazard: Highly flammable, dangerous fire and ex-

20-ethyl-6-␤,8-dihydroxy-1-␣-methoxy-4-

plosion risk; explosive limits in air 3–36% by vol-

methylheteratisan-14-one.

ume. TLV: Simple asphyxiant; Not Classifiable as a

CAS: 3328-84-5. mf: C

Human Carcinogen.

Hazard: A poison.

Use: Manufacture of polyethylene, polypropylene,

Source: Natural product.

ethylene oxide, ethylene dichloride, ethylene gly-

cols, aluminum alkyls, vinyl chloride, vinyl acetate,

ethyldimethylmethane. See isopentane.

ethyl chloride, ethylene chlorohydrin, acetaldehyde,

ethyl alcohol, polystyrene, styrene, polyvinyl chlo-

ethyldimethyl-9-octadecenylammonium

ride, SBR, polyester resins, trichloroethylene, etc.;

bromide. C

NBr. Cationic surfactant and

as a refrigerant, in welding and cutting of metals, an

algicide, soluble in propylene glycol and isopropyl

anesthetic, and in orchard sprays to accelerate fruit

alcohol.

ripening.

n-ethyl-1,2-dimethylpropylamine.

ethylene azelate.

CAS: 2738-06-9. mf: C

CAS: 4471-27-6. mf: C

Hazard: Low toxicity by ingestion. A severe skin

Hazard: Low toxicity by ingestion and skin contact.

and moderate eye irritant.

A mild skin and eye irritant.

ethyldiphenyltin acetate.

ethylene bis(iminodiacetic acid). See ethy-

CAS: 77405-29-9. mf: C

Sn.

lenediaminetetraacetic acid.

Hazard: A poison by ingestion. TWA 0.1 mg(Sn)/

. STEL 0.2 mg/m

(skin). Not classifiable as a

ethylene bis(oxyethylenenitrilo)tetraacetic

human carcinogen

acid. See ethylene glycol-bis(␤-aminoethyl

ether)-N,N-tetraacetic acid.

ethyldipropylmethane. See 4-ethylheptane.

ethylene bis(pentabromophenoxide). See

S-ethyl di-N,N-propylthiocarbamate. See

1,1

′

-(1,2-ethanediylbis(oxy))bis(2,3,4,5,6-penta-

EPTC.

bromobenzene).

ethyl diselenide.

ethylene bis(tetrabromophthalimide).

CAS: 628-39-7. mf: C

CAS: 32588-76-4. mf: C

Hazard: A poison by ingestion and skin contact.

Hazard: Low toxicity by ingestion, inhalation, and

Low toxicity by inhalation. A moderate eye irritant.

skin contact. A mild eye irritant.

ethyl enanthate. (ethyl heptanoate; cognac

ethylene bromide. See ethylene dibromide.

oil). CH

(CH

)

COOC

Properties: Clear, colorless oil; fruity odor and taste.

D 0.87; bp 187C. Soluble in alcohol, chloroform,

ethylene bromohydrin. (glycol bromohyd-

and ether; insoluble in water. Combustible.

rin; 2-bromoethyl alcohol).

Derivation: By heating enanthic acid and ethanol in

CAS: 540-51-2. BrCH

OH.

the presence of sulfuric acid and subsequent recov-

Properties: Hygroscopic liquid. D 1.7629 (20C), bp

ery by distillation.

149–150C (750 mm Hg), refr index 1.4915 (20C).

Grade: Technical.

Soluble in most organic solvents; completely misci-

Use: Artificial cognac flavor, flavor for liquors and

ble with water. Aqueous solutions have a sweet,

fruity-type soft drinks.

burning taste. Hydrolysis of aqueous solutions is

accelerated by heat, acids, and alkalies. Combus-

ethylene. (bicarburetted hydrogen; ethene). tible.

CAS: 74-85-1. H

C:CH

. Derivation: Action of hydrogen bromide on ethylene

Properties: Colorless gas; sweet odor and taste. Fp oxide.

−169C, bp −103.9C, flash p −213F (−135C), d (liq- Hazard: Irritant to eyes and mucous membranes.

uid) 0.610 (0C), vap d 0.975 (air

1.29), critical Use: Organic synthesis.

526ETHYLENE CARBONATE

ethylene carbonate. (glycol carbonate; diox- 227–228C (decomposes) d 1.0404 (25/4C), vap

olone-2).

press 0.08 mm Hg (25C), 20 mm Hg (117C). Misci-

CAS: 96-49-1. (−CH

CO.

ble with water, acetone, methyl ethyl ketone, etha-

Properties: Colorless, solid or liquid; odorless. Mp

nol, chloroform, and diethyl ether; insoluble in ben-

36.4C, bp 248C, d 1.3218 (39/4C), refr index 1.4158

zene, carbon tetrachloride, and naphtha.

(50C), flash p 290F (143C) (OC). Miscible (40%)

Combustible.

with water, alcohol, ethyl acetate, benzene, and

Derivation: Ethylene oxide and hydrogen cyanide.

chloroform; soluble in ether, n-butanol, and carbon

Hazard: Toxic by ingestion.

tetrachloride. Combustible.

Use: Solvent for certain cellulose esters and inorgan-

Derivation: Interaction of ethylene glycol and phos-

ic salts; organic intermediate for acrylates.

gene.

Use: Solvent for many polymers and resins, plasticiz-

ethylenediamine. (1,2-diaminoethane).

er, intermediate for pharmaceuticals, rubber chemi-

CAS: 107-15-3. NH

cals, textile finishing agents, hydroxyethylation re-

Properties: Colorless, alkaline liquid; ammonia

actions.

odor. D 0.8995 (20/20C), bulk d 7.50 lb/gal (20C),

bp 116–117C, vap press 10.7 mm Hg (20C), mp

ethylene chloride. See ethylene dichloride.

8.5C, viscosity 0.0154 cP (25C), flash p 93F (33.9C)

(CC), refr index 1.4540 (26C), pH of 25% solution

ethylene chlorohydrin. (2-chloroethyl alco-

11.9 (25C). Strong base, soluble in water and alco-

hol; glycol chlorohydrin).

hol; slightly soluble in ether; insoluble in benzene.

CAS: 107-07-3. ClCH

OH.

Readily absorbs carbon dioxide from air.

Properties: Colorless liquid; faint ethereal odor. D

Derivation: Catalytic reaction of ethylene glycol or

1.2045 (20/20C), bp 128.7C, refr index 1.4419

ethylene dichloride and ammonia (nickel or copper

(20C), vap press 4.9 mm Hg (20C), flash p 140F

catalysts are used).

(60C) (OC), bulk d 10.0 lb/gal (20C), coefficient of

Method of purification: Redistillation.

expansion 0.00089 (20C), fp −62.6C, viscosity

Grade: Technical, USP 97%, solutions of various

0.0343 cP (20C), autoign temp 797F (425C). Solu-

strengths.

ble in most organic liquids and completely miscible

Hazard: Toxic by inhalation and skin absorption,

with water. Combustible.

strong irritant to skin and eyes. Flammable, moder-

Derivation: Action of hypochlorous acid on eth-

ate fire risk. TLV: 10 ppm; not classifiable as a

ylene.

human carcinogen.

Grade: Anhydrous, 38%.

Use: Fungicide, manufacture of chelating agents

Hazard: Deadly via ingestion, inhalation, and skin

(EDTA), dimethylolethylene-urea resins, chemical

absorption; strong irritant, penetrates ordinary rub-

intermediate, solvent, emulsifying agent, textile lu-

ber gloves and protective clothing. Moderate fire

bricants, antifreeze inhibitor.

hazard. TLV: ceiling 1 ppm; not classifiable as a

human carcinogen.

ethylenediamine carbamate. See “Diak.”

Use: Solvent for cellulose acetate, ethylcellulose;

introduction of hydroxyethyl group in organic syn-

ethylenediamine dihydroiodide.

thesis; to activate sprouting of dormant potatoes;

(−CH

)

•2HI.

manufacture of ethylene oxide and ethylene glycol;

Use: Feed additive.

insecticides.

ethylenediamine-di-o-hydroxyphenylacetic

ethylene chlorothioarsenate(III).

acid. [−CH

NHCH(COOH)C

OH]

. A phe-

CAS: 3741-32-0. mf: C

AsClS

nolic analog of ethylenediaminetetraacetic acid.

Hazard: A poison by ingestion.

Properties: Mp 218C (decomposes). Insoluble in

Use: Agricultural chemical.

water and most organic solvents; soluble in sulfuric

acid; also forms water-soluble alkali-metal and am-

ethylene cyanide. (ethylene dicyanide; succi-

monium salts.

nonitrile).

Use: Chelating iron in mildly alkaline solutions.

CAS: 110-61-2. C

(CN)

Properties: Colorless, waxy solid. Mp 57–57.5C; bp

ethylenediamine tartrate.

265.7C; flash p 270F (132C). Soluble in alcohol,

Use: To make piezoelectric crystals for control of

water, and chloroform. Combustible.

electric frequencies, etc., as in television.

Derivation: Interaction of ethylene dibromide and

potassium cyanide in the presence of alcohol.

Hazard: TLV: 5 mg(CN)/m

ethylenediaminetetraacetic acid. (EDTA;

ethylenebisiminodiacetic acid; ethylenedinitrilo-

ethylene cyanohydrin. (␤-hydroxypropioni- tetraacetic acid).

trile). CAS: 60-00-4.

CAS: 109-78-4. HOCH

CN. (HOOCCH

)

NCH

N(CH

COOH)

. An organic

Properties: Straw-colored liquid. Fp −46C, bp chelating agent.

527 ETHYLENE GLYCOL

tion, ingestion, and skin absorption;strong irritant to

eyes and skin.

Use: Scavenger for lead in gasoline, grain fumigant,

general solvent, waterproofing preparations, organ-

ic synthesis, fumigant for tree crops.

Note: May poison platinum catalysts.

Properties: Colorless crystals. Decomposes at 240C.

ethylene dichloride. (sym-dichloroethane;

Slightly soluble in water; insoluble in common or-

1,2-dichloroethane; ethylene chloride; Dutch

ganic solvents; neutralized by alkali metal hydrox-

oil).

ides to form a series of water-soluble salts contain-

CAS: 107-06-2. ClCH

Cl.

ing from one to four alkali metal cations.

Properties: Colorless, oily liquid; chloroform-like

Derivation: (a) Addition of sodium cyanide and

odor; sweet taste. Bp 83.5C, fp −35.5C, d 1.2554

formaldehyde to a basic solution of ethylenediamine

(20/4C) (10.4 lb/gal), refr index 1.444, flash p 56F

(forms the tetrasodium salt); (b) heating

(13.3C). Stable to water, alkalies, acids, or active

tetrahydroxyethylethylenediamine with sodium hy-

chemicals; resistant to oxidation, will not corrode

droxide or potassium hydroxide with cadmium ox-

metals. Miscible with most common solvents;

ide catalyst.

slightly soluble in water.

Use: Detergents; liquid soaps; shampoos; agricultur-

Derivation: Action of chlorine on ethylene, with

al chemical sprays; metal cleaning and plating; met-

subsequent distillation with metallic catalyst; also

al chelating agent; treatment of chlorosis; decon-

by reaction of acetylene and hydrochloric acid.

tamination of radioactive surfaces; metal

Grade: Technical, spectrophotometric.

deactivator in vegetable oils, oil emulsions, pharma-

Hazard: Toxic by ingestion, inhalation, and skin

ceutical products, etc.; anticoagulant of blood; elut-

absorption; strong irritant to eyes and skin; a carcin-

ing agent in ion exchange; to remove insoluble de-

ogen. Flammable, dangerous fire risk, explosive

posits of calcium and magnesium soaps; in textiles

limits in air 6–16%. TLV: 10 ppm; not classifiable as

to improve dyeing, scouring, and detergent opera-

a human carcinogen.

tions; antioxidant; clarification of liquids; analytical

Use: Production of vinyl chloride, trichloroethylene,

chemistry, spectrophotometric titration; aid in re-

vinylidene chloride, and trichloroethane; lead scav-

ducing blood cholesterol; in medicine to treat lead

enger in antiknock gasoline; paint, varnish, and fin-

poisoning and calcinosis; food additive (preserva-

ish removers; metal degreasing; soaps and scouring

tive).

compounds; wetting and penetrating agents; organic

Note: A number of salts of EDTA are available with

synthesis; ore flotation; solvent, fumigant.

uses identical or similar to the acid. The USP salts

are called edetates (calcium disodium, disodium

ethylene dicyanide. See ethylene cyanide.

edetates); others are usually abbreviated to EDTA

(tetrasodium, trisodium EDTA). Other salts, known

3,3

′

-(ethylenediiminodimethylene)bis(5,5-

chiefly under trademark names, are the sodium fer-

diphenylhydantoin).

ric, dihydrogen ferrous and a range of disodium salts

CAS: 21322-39-4. mf: C

with magnesium, divalent cobalt, manganese, cop-

Hazard: A poison.

per, zinc, and nickel.

ethylenedinitrilotetraacetic acid. See ethy-

lenediaminetetraacetic acid.

ethylenediaminetetraacetonitrile. (ED-

TAN). [−CH

NCH

]

ethylenedinitrilotetra-2-propanol. See

Properties: White, crystalline solid. Melting range

N,N,N

′

-tetrakis(2-hydroxypro-

126–132C, bulk d 48.4 lb/cu ft. Slightly soluble in

pyl)ethylenediamine.

water; soluble in acetone.

Hazard: Toxic by ingestion and inhalation.

ethylenediphenyldiamine. See N,N-dipheny-

Use: Chelating agent and intermediate.

lethylenediamine.

1,1

′

-ethylene-2,2

′

-dipyridinium dibromide.

ethylene dibromide. (EDB; 1,2-dibromoe-

See diquat.

thane; ethylene bromide).

CAS: 106-93-4. BrCH

Br.

ethylenedithiocyanate.

Properties: Colorless, liquid; sweetish odor. D

CAS: 629-17-4. mf: C

2.17–2.18 (20C), bulk d 18.1 lb/gal, bp 131C, vap

Hazard: A poison by ingestion and skin contact.

press 17.4 mm Hg (30C), fp 9C, refr index 1.5337

(25C), flash p none. Emulsifiable; miscible with

most solvents and thinners; slightly soluble in water.

ethylene glycol. (ethylene alcohol; glycol;

Nonflammable. 1,2-ethanediol).

Derivation: Action of bromine on ethylene. CAS: 107-21-1. CH

OHCH

OH. The simplest

Hazard: TLV: animal carcinogen. Toxic by inhala- glycol.

528ETHYLENE GLYCOL

Properties: Clear, colorless, syrupy liquid; odorless; 0.8374 (20/20C), bulk d 7.0 lb/gal (20C), bp 203.1C,

sweet taste. D 1.1155 (20C), bp 197.2C, fp −13.5C, vap press 0.09 mm Hg (20C), fp −69.1C, flash p

bulk d 9.31 lb/gal (15/15C), refr index 1.430 (25C), 185F (85C). Slightly soluble in water. Combustible.

flash p 240.8F (116C), autoign temp 775F (412C).

Use: High-boiling inert solvent; specialized solvent

Hygroscopic, lowers fp of water, relatively nonvola-

and extraction applications.

tile. Soluble in water, alcohol, and acetone. Com-

bustible.

ethylene glycol dibutyrate. (glycol dibuty-

Derivation: (1) Air oxidation of ethylene followed

rate). (−CH

OCOC

)

by hydration of the ethylene oxide formed; (2) ace-

Properties: Colorless liquid. D 1.024 (0C), refr in-

toxylation; (3) from carbon monoxide and hydrogen

dex 1.424 (25C), bp 240C, fp <−80C. Solubility in

(synthesis gas) from coal gasification; (4) Oxirane

water 0.050% by weight. Combustible.

process.

Use: Plasticizer.

Grade: Technical.

Hazard: TLV: (vapor) ceiling 50 ppm. Toxic by

ethylene glycol diethyl ether. (ethyl

ingestion and inhalation. Lethal dose reported to be

glyme). C

OCH

100 cc.

Properties: Colorless liquid; slight odor. Stable, d

Use: Coolant and antifreeze; asphalt-emulsion

0.8417 (20/20C), bp 121.4C, vap press 9.4 mm Hg

paints; heat-transfer agent; low-pressure laminates,

(20C), flash p 95F (35C), bulk d 7 lb/gal (20C), fp

brake fluids; glycol diacetate; polyester fibers and

−74C. Immiscible with water.

films; low-freezing dynamite; solvent; extractant

Grade: Technical.

for various purposes; solvent mixture for cellulose

Hazard: Flammable, moderate fire risk.

esters and ethers, especially cellophane; cosmetics

Use: Organic synthesis (reaction medium), solvent

(up to 5%); lacquers; alkyd resins; printing inks;

and diluent for detergents.

wood stains; adhesives; leather dyeing; textile pro-

cessing; tobacco; ingredient of deicing fluid for air-

port runways; humectant; ballpoint pen inks; foam

ethylene glycol diformate. (glycol difor-

stabilizer.

mate). HCOOCH

OOCH.

Properties: Water-white liquid. D 1.2277 (20/20C),

ethylene glycol-bis(␤-aminoethyl

bulk d 10.2 lb/gal (20C), bp 177.1C, flash p 200F

ether)-N,N-tetraacetic acid. (ethylene

(93C), vap press 0.5 mm Hg (20C), fp −10C; hydro-

bis(oxyethylenenitrilo)tetraacetic acid).

lyzes slowly, liberating formic acid. Soluble in wa-

[−CH

N(CH

COOH)

]

ter, alcohol and ether. Combustible.

Properties: Crystals. Mp 241C (decomposes). Solu-

Hazard: Toxic by ingestion.

ble in water.

Use: Embalming fluids.

Use: Chelating agent.

ethylene glycol dimethyl ether. (GDME;

ethylene glycol bis(chloromethyl)ether.

glycol dimethyl ether; 1,2-dimethoxyethane;

See bis-1,2-(chloromethoxy)ethane.

monoglyme). CH

OCH

Properties: Water-white liquid; mild odor. D 0.8683

ethylene glycol bis(mercaptopropionate).

(20C), bp 85.2C, fp −69C, refr index 1.3792 (20C),

See glycol dimercaptopropionate.

flash p 104F (40C). Soluble in water and hydrocar-

bons, pH 8.2.

ethylene glycol bisthioglycolate. See gly-

Hazard: Moderate fire risk.

col dimercaptoacetate.

Use: Solvent.

ethylene glycol diacetate. (glycol diacetate).

CAS: 111-55-7. CH

COOCH

OOCCH

ethylene glycol dinitrate.

Properties: Colorless liquid; faint odor. D 1.1063

CAS: 628-96-6. A freezing-point depressant for ni-

(20/20C), bp 190.5C, vap press 0.3 mm Hg (20C),

troglycerine.

flash p 205F (96C) (OC), bulk d 9.2 lb/gal (20C), fp

Use: Low-freezing dynamites.

−31C, refr index 1.415 (20C). Soluble in alcohol,

Hazard: Toxic by skin absorption. TLV: 0.05 ppm.

ether, benzene; slightly soluble in water (10%).

Combustible.

ethylene glycol dipropionate. (glycol pro-

Derivation: (a) Ethylene glycol and acetic acid; (b)

pionate; glycol dipropionate). (−CH

OCOC

)

ethylene dichloride and sodium acetate.

Properties: Liquid. D 1.054 (15C), refr index 1.419

Use: Solvent for cellulose esters and ethers, resins,

(25C), bp 211C, fp <−80C. Soluble in water 0.16%

lacquers, printing inks; perfume fixative; nondisco-

by weight. Combustible.

loring plasticizer for ethyl and benzyl cellulose.

Use: Plasticizer.

ethylene glycol dibutyl ether.

CAS: 112-48-1. C

. ethylene glycol distearate. See “MAPEG”

Properties: Almost colorless liquid; slight odor. D [PPG].

529 ETHYLENE GLYCOL

ethylene glycol monoacetate. (glycol mon- ethylene glycol monobutyl ether oleate.

oacetate). (butoxyethyl oleate). C

COOCH

Properties: Liquid. D 0.892 (25C), fp <−45C. Insol-

CAS: 542-59-6. HOCH

OOCCH

uble in water. Combustible.

Properties: Colorless liquid; almost odorless. Bp

Use: Plasticizer.

181–182C, d 1.108, flash p 215F (101C). Soluble in

water, alcohol, ether, benzene, and toluene. Com-

bustible.

ethylene glycol monobutyl ether stearate.

Derivation: (a) Heating ethylene glycol with acetic

(butoxyethyl stearate). C

COOC

acid (glacial) or acetic anhydride; (b) passing ethyl-

Properties: Colorless liquid. D 0.882 (20C), vap

ene oxide into hot acetic acid containing sodium

press <0.01 mm Hg (20C), bp 210–233C (4 mm Hg),

acetate or sulfuric acid.

mp 16.5C. Insoluble in water. Combustible.

Use: Solvent for nitrocellulose, cellulose acetate,

Use: Plasticizer and solvent.

camphor.

ethylene glycol mono-dicyclopentenyl

ethylene glycol monobenzyl ether. (benzyl

ether.

“Cellosolve”). C

OH.

CAS: 68586-17-4. mf: C

Properties: Water-white liquid; faint roselike odor.

Hazard: Moderately toxic by ingestion and skin con-

D 1.070 (20/20C), bp 255.9C, vap press 0.02 mm Hg

tact. A severe eye and moderate skin irritant.

(20C), flash p 265F (129C), bulk d 8.9 lb/gal (20C),

autoign temp 665F (351C). Combustible.

ethylene glycol monoethyl ether. (2-

Hazard: Toxic by ingestion.

ethoxyethanol; “Cellosolve” solvent).

Use: Solvent for cellulose acetate, dyes, inks, resins,

CAS: 110-80-5. HOCH

perfume fixative; organic synthesis (selective hy-

Properties: Colorless liquid; practically odorless. Bp

droxyethylating agent); coating compositions for

135.6C, d 0.9311 (20/20C), bulk d 7.74 lb/gal (20C),

leather, paper, and cloth; lacquers.

refr index 1.4060 (25C), flash p 120F (48.9C), pour

point <100F (37.7C), autoign temp 460F (237C).

Miscible with hydrocarbons and water. Combus-

ethylene glycol monobutyl ether. (2-bu-

tible.

toxyethanol; butyl “Cellosolve”).

Grade: Technical.

CAS: 111-76-2. HOCH

Hazard: TLV: 5 ppm, toxic by skin absorption. Mod-

Properties: Colorless liquid; mild odor. Bp 171.2C,

erate fire risk.

d 0.9019 (20/20C), bulk d 7.51 lb/gal (20C), refr

Use: Solvent for nitrocellulose, natural and synthetic

index 1.4190 (25C), vap press 0.76 mm Hg (20C),

resins; mutual solvent for formulation of soluble

flash p 142F (61C), autoign temp 472F (244C). High

oils; lacquers and lacquer thinners; dyeing and print-

dilution ratio with petroleum hydrocarbons. Soluble

ing textiles; varnish removers; cleaning solutions;

in alcohol and water. Combustible.

leather; antiicing additive for aviation fuels.

Grade: Technical.

Hazard: A toxic material. TLV: 25 ppm.

Use: Solvent for nitrocellulose resins, spray lacquers,

ethylene glycol monoethyl ether acetate.

quick-drying lacquers, varnishes, enamels, dry-cle-

(“Cellosolve” acetate; 2-ethoxyethyl acetate).

aning compounds, varnish removers, textile (pre-

CAS: 111-15-9. CH

COOCH

venting spotting in printing or dyeing); mutual sol-

Properties: Colorless liquid; pleasant esterlike odor.

vent for “soluble” mineral oils to hold soap in

Bp 156.3C, d 0.9748 (20/20C), bulk d 8.1 lb/gal

solution and to improve the emulsifying properties.

(20C), refr index 1.4030 (25C), viscosity 1.32 cP

(20C), flash p 120F (48.9C), fp −61.7C, vap press 2

mm Hg (20C). Miscible with aromatic hydrocar-

ethylene glycol monobutyl ether acetate.

bons; slightly miscible with water. Combustible.

(butyl “Cellosolve” acetate).

Grade: Technical.

OCH

OOCCH

Hazard: Toxic by ingestion and skin absorption.

Properties: Colorless liquid; fruity odor. Bp 192.3C,

TLV: 5 ppm, toxic by skin absorption.

d 0.9424 (20/20C), fp −63.5C, flash p 190F (87.7C).

Use: Solvent for nitrocellulose, oils, and resins; re-

Soluble in hydrocarbons and organic solvents; in-

tards “blushing” in lacquers, varnish removers,

soluble in water. Combustible.

wood stains, textiles, and leather.

Grade: Technical.

Use: High-boiling solvent for nitrocellulose lacquers,

epoxy resins, multicolor lacquers; film-coalescing

ethylene glycol monoethyl ether laurate.

aid for polyvinyl acetate latex.

COO(CH

)

Properties: Liquid. D 0.89 (25C), fp −7to−11C.

Insoluble in water. Combustible.

ethylene glycol monobutyl ether laurate.

Use: Plasticizer.

(butoxyethyl laurate). C

COO(CH

)

Properties: Liquid. D 0.985 (25C), fp −10 to −15C.

Insoluble in water. Combustible.

ethylene glycol monoethyl ether

Use: Plasticizer. ricinoleate. C

(OH)COO(CH

)

530ETHYLENE GLYCOL

Properties: Liquid. D 0.929 (25C), fp <−10C. Insol- Properties: Liquid. D 0.890, mp 21C. Insoluble in

uble in water. Combustible. water. Combustible.

Use: Plasticizer. Use: Plasticizer.

ethylene glycol monohexyl ether. (n-hexyl ethylene glycol mononitrate vinyl ether.

“Cellosolve”). C

OCH

OH.

CAS: 53987-27-2. mf: C

Properties: Water-white liquid. D 0.8887 (20/20C),

Hazard: Moderately toxic by ingestion. Low toxicity

bulk d 7.4 lb/gal (20C), bp 208.1C, vap press 0.05

by inhalation.

mm Hg (20C), fp −50.1C, flash p 195F (90.5C).

Combustible.

ethylene glycol monooctyl ether.

Use: High-boiling solvent.

CHC

OCH

OH.

Properties: Colorless liquid; odorless. Bp 228.3C, d

ethylene glycol monomethyl ether. (2-me- 0.8859, flash p 230F (110C), vap press 0.02 mm Hg

thoxyethanol; methyl “Cellosolve”). (20C). Combustible.

CAS: 109-86-4. CH

OCH

OH. Use: Solvent for cellulose esters, plasticizers.

Properties: Colorless liquid; mild agreeable odor;

stable. Bp 124.5C, d 0.9663 (20/20C), bulk d 8.0 lb/

ethylene glycol monophenyl ether. (2-

gal (20C), refr index 1.4021 (20C), flash p 110F

phenoxyethanol; phenyl “Cellosolve”).

(43.3C), fp −85.1C, autoign temp 551F (288C).

CAS: 122-99-6. C

OCH

OH.

Miscible with hydrocarbons, alcohols, ketones, gly-

Properties: Colorless liquid; faint aromatic odor.

cols, and water. Combustible.

Stable in presence of acids and alkalies, partially

Derivation: From ethylene oxide.

soluble in water. D 1.1094 (20/20C), bp 244.9C, fp

Grade: Technical.

14C, vap press <0.01 mm Hg (20C), flash p 250F

Hazard: Toxic by ingestion and inhalation. Moder-

(121C), phenol 0.3% (max), bulk d 9.2 lb/gal. Com-

ate fire risk. TLV: 5 ppm, toxic by skin absorption.

bustible.

Use: Solvent for nitrocellulose, cellulose acetate, al-

Grade: Technical.

cohol-soluble dyes, natural and synthetic resins, sol-

Use: Solvent for cellulose acetate, dyes, inks, resins;

vent mixtures, lacquers, enamels, varnishes, leather;

perfume fixative; bactericidal agent; organic syn-

perfume fixative; wood stains; sealing moisture-

thesis of plasticizers, germicides, pharmaceuticals;

proof cellophane; jet fuel deicing additive.

insect repellent.

ethylene glycol monomethyl ether acetate.

ethylene glycol monoricinoleate.

(methyl “Cellosolve” acetate).

(OH)COO(CH

)

OH.

CAS: 110-49-6. CH

COOCH

OCH

Properties: Clear, moderately viscous, pale-yellow

Properties: Colorless liquid; pleasant odor. D

liquid; mild odor. Miscible with most organic sol-

1.0067 (20/20C), bp 145C, vap press 2 mm Hg

vents. D 0.965 (25/25C), saponification number

(20C), flash p 120F (48.9C), bulk d 8.4 lb/gal (20C),

170, hydroxyl value 270, solidifies at −20C, insolu-

fp −65.1C. Stable, miscible with common organic

ble in water. Combustible.

solvents; soluble in water. Combustible.

Derivation: Castor oil and ethylene glycol.

Hazard: Toxic by ingestion, inhalation, and skin

Grade: Technical.

absorption. Moderate fire risk. TLV: 5 ppm, toxic by

Use: Plasticizer, greases, urethane polymers.

skin absorption.

Use: Solvent for nitrocellulose, cellulose acetate,

ethylene glycol monostearate. (glycol stea-

various gums, resins, waxes, oils; textile printing;

rate).

photographic film; lacquers; dopes.

CAS: 111-60-4. C

COO(CH

)

OH.

Properties: Yellow, waxy solid. Mp 57–60C; d 0.96

ethylene glycol monomethyl ether acetyl (25C). Soluble in alcohol, hot ether, and acetone;

ricinoleate. insoluble in water. Combustible.

(OCOCH

)COOCH

OCH

Properties: Liquid. D 0.966, refr index 1.460, boil-

ethylene glycol silicate. (HOCH

)

SiO

ing range 220–260C, fp <−60C, flash p 425F

Properties: Colorless liquid. Slowly hydrolyzed by

(218C). Insoluble in water. Combustible.

acids; miscible with water.

Use: Plasticizer.

Use: Nonvolatile bonding agent for pigments; weath-

erproofing paints for protecting concrete, stone,

brick, and plastic surfaces.

ethylene glycol monomethyl ether

ricinoleate. C

(OH)COOCH

OCH

Properties: Liquid. D 0.935 (25C), fp <−60C. Insol-

ethylene hexene-1-copolymer. Product de-

uble in water. Combustible.

veloped especially for use in blow-molded items.

Use: Plasticizer.

Other possible uses are coatings for pipe, wire, and

cables; sheeting; and monofilament.

ethylene glycol monomethyl ether stearate.

COOCH

OCH

. ethylene hydrate. See gas hydrate.

531 ETHYLENE UREA

ethyleneimine. (aziridine; ethylenimine). gerous fire and explosion risk, flammable limits in

air 3–100%.

CAS: 151-56-4.

Use: Manufacture of ethylene glycol and higher gly-

cols, surfactants, acrylonitrile, ethanolamines; pe-

troleum demulsifier; fumigant; rocket propellant;

industrial sterilant (e.g., medical plastic tubing);

fungicide.

Properties: Clear, colorless liquid; amine odor. Bp

57C, d 0.832 (20/4C), refr index 1.4123 (25C), fp

ethylene oxide and propylene oxide block

−78C, flash p 12F (−11.1C), autoign temp 612F

polymer. See poloxamer 331.

(322C). Miscible with water and most organic sol-

vents.

ethylene oxide polymer.

Derivation: From ethylene dichloride and ammonia

Use: Food additive.

by use of an acid acceptor.

Hazard: Corrosive, absorbed by skin, causes tumors;

exposure should be minimized; a carcinogen. Dan-

ethylene-propylene-diene monomer. See

gerous fire and explosion hazard, flammable limits

ethylene propylene terpolymer.

in air 3.6–46%. TLV: 0.5 ppm, toxic by skin absorp-

tion; animal carcinogen.

ethylene-propylene rubber. (EPR). An elas-

Use: Intermediate and monomer for fuel-oil and lu-

tomer made by the stereospecific copolymerization

bricant refining, ion exchange, protective coatings,

of ethylene and propylene. Has no unsaturation;

pharmaceuticals, adhesives, polymer stabilizers,

cannot be vulcanized with sulfur but can be cured

surfactants. Alkyl-substituted forms, called alkyl

with peroxides.

aziranes, are used as intermediates and for microbial

control; aziridinyl compounds are also used as poly-

ethylene-propylene terpolymer. (EPT;

mers and intermediates.

EPDM). An elastomer based on stereospecific lin-

ear terpolymers of ethylene, propylene, and small

ethylene–maleic anhydride copolymer.

amounts of a nonconjugated diene, e.g., a cyclic or

CAS: 9006-26-2.

aliphatic diene (hexadiene, dicyclopentadiene, or

Properties: Fine, water-soluble powder available as

ethylidene norbornene). The unsaturated part of the

both straight-chain and cross-linked polymers in a

polymer molecule is pendant from the main chain,

variety of molecular weights. May be in form of free

which is completely saturated. Can be vulcanized

acid, sodium, or amide-ammonium salts. Reacts

with sulfur.

readily with alcohols and amines.

Properties: (Vulcanizate) Light-cream to white; ex-

Hazard: Low toxicity by ingestion and skin contact.

cellent resistance to ozone, to high and low tempera-

A mild eye irritant.

tures (from −51 to +148C), and to acids and alkalies;

Use: Oil-well drilling muds; stabilizers and thicken-

good electrical resistance, susceptible to attack by

ers in liquid detergents, cosmetics, paints; textile

oils; pelletized forms available.

sizes; printing inks; suspending agents; ceramic

Use: Automotive parts, gaskets, cable coating, me-

binders.

chanical rubber products, cover strips for tire side-

walls, tire tubes, safety bumpers, coated fabrics,

ethylenenaphthalene. See acenaphthene.

footwear, wire and cable coating, thermoplastic res-

in modifier.

See “Nordel.”

ethylene oxide. (epoxyethane; oxirane).

CAS: 75-21-8.

ethylene thiourea.

CAS: 96-45-7.

❘

HCH

❘

CS (2-imidazolidinethione).

Properties: White to pale-green crystals; faint amine

Properties: Colorless gas at room temperature, liq-

odor. Mp 199–204C. Slightly soluble in cold water;

uid at approximately 12C. Fp −111.3C, bp 10.73C, d

very soluble in hot water; slightly soluble at room

0.8711 (20/20C), bulk d 7.25 lb/gal (20C), viscosity

temperature in methanol, ethanol, acetic acid,

0.32 cP (0C), flash p approximately 0F (−17.7C)

naphtha.

(TOC), autoign temp 805F (429C). Soluble in or-

Use: Electroplating baths; intermediate for antioxi-

ganic solvents; miscible with water.

dants, insecticides, fungicides, vulcanization accel-

Derivation: (1) Oxidation of ethylene in air or oxy-

erators, dyes, pharmaceuticals, synthetic resins.

gen with silver catalyst; (2) action of an alkali on

ethylene chlorohydrin.

Grade: Technical, pure (99.7%).

ethylene urea. (2-imidazolidinone; dihydro-

Hazard: Irritant to eyes and skin. TLV: 1 ppm; sus- 2(3)-imidazolone; 2-imidazolidone).

pected human carcinogen. Highly flammable, dan- CAS: 120-93-4.

532ETHYLENE-VINYL

ethylethylene. See butene-1.

❘

NHCO

❘

NH.

Properties: White, lumpy powder; odorless. Mp

ethylethyleneimine. (2-ethylaziridine).

125–128C. Soluble in water.

Derivation: From ethylenediamine and urea.

❘

Use: Drip-dry textile products, ingredient of plasti-

Properties: Water-white liquid. Bp 87–90C, d

cizers and adhesives, insecticide.

0.812–0.816 (25/25C).

Use: Organic intermediate whose derivatives are

used in the textile, paper, rubber, and pharmaceuti-

ethylene-vinyl acetate copolymer. (EVA).

cal industries.

An elastomer used to improve adhesion properties

of hot-melt and pressure-sensitive adhesives, as well

as for conversion coatings and thermoplastics.

ethyl(5-ethylmercuri-3-(1,2,4-thiadiazolyl)

See “Ultrathene.”

thio)mercury(ii).

CAS: 73928-12-8. mf: C

Hazard: A poison. TWA 0.01. STEL 0.03 mg/m

ethylenimine. See ethyleneimine.

(skin).

N-ethylethanolamine. (ethylaminoethanol).

ethyl 3-ethyl-4-quinolinecarboxylate. See

NHCH

OH.

3-ethylcinchoninic acid ethyl ester.

Properties: Colorless liquid; amine odor. D 0.914

(20C), boiling range 167–169C flash p 160F (71.1C)

2-ethyl fenchol. mf: C

(OC). Soluble in water, alcohol and ether. Combus-

Properties: Pale yellow liquid; camphor, earthy

tible.

odor. D: 0.946−0.967, refr index: 1.470−1.491. Sol

Use: Solvent, intermediate.

in alc, propylene glycol, fixed oils; insol in water.

Use: Food additive.

ethyl ether. (ether; diethyl ether; sulfuric

ether; ethyl oxide; diethyl oxide).

ethyl ferrocenoate. (ferrocenecarboxylic acid

CAS: 60-29-7. (C

)

ethyl ester). (C

COOC

)

Fe.

Properties: Colorless, volatile, mobile liquid. Hy-

Properties: Orange, crystalline solid. Mp 63–64C.

groscopic, aromatic odor, burning and sweet taste.

Use: Intermediate.

Bp 34.5C, fp −116.2C, d 0.7147 (20/20C), surface

tension 17.0 dynes/cm (20C), refr index 1.3526

“Ethylflo” [Albemarle]. TM for synthetic hy-

(20C), viscosity 0.00233 cP (20C), vap press 442

drocarbon fluids.

mm Hg (20C), specific heat 0.5476 cal/g (30C),

flash p −49F (−45C), autoign temp 356F (180C),

ethylfluoroformate. FCOOC

latent heat of evaporation 83.96 cal/g at bp, electric

Properties: Liquid. D 1.11 (33C), bp 57C.

conductivity 4 × 10

−3

mho/cm (25C), bulk d 6 lb/gal

Derivation: Interaction of ethylchloroformate and a

(20C). Soluble in alcohol, chloroform, benzene, sol-

reactive fluoride.

vent naphtha, and oils; slightly soluble in water.

Hazard: Strong irritant.

Derivation: By the action of sulfuric acid on ethanol

or ethylene followed by distillation.

Method of purification: Rectification, dehydration,

ethylfluorosulfonate. C

OFSO

treatment with alkali and charcoal.

Properties: Liquid; ethereal odor.

Grade: USP (for anesthesia), ACS Reagent, ACS

Hazard: Strong irritant.

Absolute, CP, concentrated, USP 1880, washed,

motor, electronic.

ethyl formate.

Hazard: CNS depressant by inhalation and skin ab-

CAS: 109-94-4. HCOOC

sorption. Very flammable, severe fire and explosion

Properties: Water-white, unstable liquid; pleasant

hazard when exposed to heat or flame. TLV: 400

aromatic odor. Flash p −4F (−20C) (CC); explosive

ppm; STEL 500 ppm. Forms explosive peroxides.

limits in air 2.8–13.5%; autoign temp 851F (455C),

Explosive limits in air 1.85–48%.

d 0.9236 (20/20C); fp −80.5C, bp 54.3C, vap press

Use: Organic synthesis; smokeless powder; industri-

200 mm Hg (20.6C), 300 mm Hg (30.2C); wt/gal

al solvent (nitrocellulose, alkaloids, fats, waxes,

7.61 lb (68F); refr index 1.35975 (20C). Miscible

etc.); analytical chemistry; anesthetic, extractant.

with benzene, ether, alcohol; slightly soluble in wa-

ter; gradual decomposition in water.

ethyl-3-ethoxypropionate. Derivation: Heating ethanol with formic acid in the

OOCCH

. presence of sulfuric acid.

Properties: Liquid. D 0.9496 (20C), bp 170.1C, vap Grade: Technical, FCC.

press 0.9 mm Hg (20C), sets to glass at −100C, flash Hazard: Narcotic and irritant to skin and eyes; use in

p 180F (82.2C) (OC). Slightly soluble in water. foods restricted to 0.0015%. Highly flammable,

Combustible. dangerous fire and explosion risk. TLV: 100 ppm.

Use: Intermediate for vitamin B

, other chemicals. Use: Solvent for cellulose nitrate and acetate, acetone

533 2-ETHYLHEXOIC ACID

substitute, fumigant, larvicide, synthetic flavors, or-

2,2

′

-(2-ethylhexamido)diethyl di(2-

ethylhexoate). (“Flexol” 8N8).

ganic synthesis.

OCOC

)

NCOC

Properties: Light-colored liquid. D 0.9564 (20/

ethyl-o-formate. CH(OC

)

20C), bulk d 8.0 lb/gal (20C), bp 256C (5 mm Hg),

Properties: Colorless liquid. Bp 145.9C, fp <−18C,

flash p 420F (215C), vap press 0.60 mm Hg (200C),

refr index 1.392 (20C), flash p 85F (29.4C). Slightly

viscosity 139.2 cP (20C). Insoluble in water. Com-

soluble in water; soluble in alcohol and ethers.

bustible.

Hazard: Flammable, moderate fire risk.

Use: Plasticizer.

Use: Intermediate.

2-ethylhexanal. See 2-ethylhexaldehyde.

ethyl-3-formylpropionate.

OOCC

C(O)H.

2-ethylhexanediol-1,3. (ethohexadiol; 2-eth-

Properties: Liquid. D 1.0625 (20/20C), bp 190.9C,

yl-3-propyl-1,3-propanediol).

fp <−80C, bulk d 8.9 lb/gal, flash p 200F (93.3C).

CAS: 94-96-2. C

CH(OH)CH(C

)CH

OH.

Somewhat soluble in water. Combustible.

Hazard: Toxic by ingestion and inhalation.

Use: Solvent for lacquers, antibiotic extraction, ace-

tic acid separation, coalescing acids for emulsion

paints.

2-ethylfuran.

Properties: Colorless, slightly viscous, liquid;

Properties: Liquid. Mw 96.13, bp 92–93C (768 mm

odorless. Hygroscopic. D 0.9422 (20/20C), bulk d

Hg), d 0.912.

7.8 lb/gal (20C), bp 244C, vap press <0.01 mm Hg

Grade: Food.

(20C), flash p 260F (126C), fp approximately −40C,

Hazard: Flammable liquid.

refr index 1.4465–1.4515, viscosity 323 cP (20C).

Soluble in alcohol and ether, partially soluble in

water. Combustible.

ethyl furoate. C

OCO

Grade: USP (as ethohexadiol), industrial.

Properties: White leaflets or prisms. D 1.1174 (20.8/

Use: Insect repellent, cosmetics, vehicle and solvent

4C), mp 34C, bp 195C (706 mm Hg). Insoluble in

in printing inks, medicine, chelating agent for boric

water; soluble in alcohol and ether.

acid.

ethyl glycolate isocyanate. See ethyl isoc-

(r)-2-ethylhexanoic acid sodium salt.

yanatoacetate.

CAS: 139906-72-2. mf: C

•Na.

Hazard: A reproductive hazard.

ethyl glyme. See ethylene glycol diethyl

ether.

2-ethylhexanol. See 2-ethylhexyl alcohol.

4-ethylheptane. (ethyldipropylmethane).

((2-ethylhexanoyl)oxy)tributylstannane.

(CH

)

CHC

(CH

)

See tributyltin-2-ethylhexanoate.

Properties: Colorless liquid. D 0.730, bp 141.2C,

refr index 1.4109 (20C). Combustible.

2-ethylhexenal. See 2-ethyl-3-propylacrolein.

Grade: Technical.

Use: Organic synthesis.

2-ethyl-1-hexene. CH

(CH

)

)C:CH

Properties: Colorless liquid. D 0.7270 (20/4C), bp

ethyl heptanoate. See ethyl enanthate.

120C, refr index 1.4157 (20C). Soluble in alcohol,

acetone, ether, petroleum, coal tar solvents; insolu-

ethyl heptazine. See ethoheptazine. ble in water. Combustible.

Grade: 95% min purity.

Hazard: Toxic by ingestion and inhalation.

2-ethylhexaldehyde. (butylethylacetaldehyde;

Use: Organic synthesis of flavors, perfumes, medi-

octylaldehyde; 2-ethylhexanal).

cines, dyes, resins.

CH(C

)CHO.

Properties: Colorless high-boiling liquid; mild odor.

ethyl hexoate. See ethyl caproate.

Miscible with most organic solvents; slightly solu-

ble in water. D 0.8205 (20C), bp 163.4C, vap press

1.8 mm Hg (20C), flash p 125F (51.6C) (OC), bulk d

2-ethylhexoic acid. (butylethylacetic acid).

6.8 lb/gal. Combustible. CAS: 78-42-2. C

CH(C

)COOH.

Grade: Technical. Properties: Mild-odored liquid. D 0.9077 (20/20C),

Hazard: Ignites in air. bulk d 7.6 lb/gal (20C), bp 226.9C, vap press 0.03

Use: Organic synthesis, perfumes. mm Hg (20C), fp −83C, viscosity 7.73 cP (20C),

5342-ETHYLHEXYL

acid number 370, flash p 260F (126C). Slightly (20C), viscosity 1.11 cP (20C), flash p 140F (60C)

soluble in water. Combustible. (OC). Solubility in water 25.3% (20C). Combus-

Grade: 99%. tible.

Use: Paint and varnish driers (metallic salts).

Hazard: Moderate fire risk. Toxic by ingestion and

Ethylhexoates of light metals are used to convert

inhalation.

some mineral oils to greases. Its esters are used as

Use: Synthesis of detergents, rubber chemicals, oil

plasticizers.

additives, and insecticides.

2-ethylhexyl. CH

(CH

)

CH(C

)CH

−.An8-

n-2-ethylhexylaniline.

carbon radical. Many of its compounds were for-

NHCH

CH(C

merly called octyl.

Properties: Light-yellow liquid; mild odor. D

0.9119 (20/20C), bp 194C (50 mm Hg), vap press

<0.01 mm Hg (20C), fp (sets to a glass at approxi-

2-ethylhexyl acetate.

mately −70C), viscosity 7.4 cP (20C), flash p 325F

CAS: 103-09-3. CH

COOCH

CHC

(162C) (COC). Solubility in water <0.01% (20C).

Properties: Water-white stable liquid. D 0.8733

Combustible.

(20C), bp 198.6C, fp −93C, vap press 0.4 mm Hg

Hazard: Chronic exposure is toxic.

(20C), flash p 180F (82.2C), bulk d 7.3 lb/gal (20C).

Use: Solvent, organic synthesis.

Very slightly soluble in water; miscible with alco-

hol. Combustible.

Grade: Technical (approximately 95%).

2-ethylhexyl bromide. C

CH(C

)CH

Br.

Use: Solvent for nitrocellulose, resins, lacquers, bak- Properties: Water-white liquid. Bp 56–58C (6 mm

ing finishes. Hg). Insoluble in water.

Use: Introduction of the 2-ethylhexyl group in organ-

ic synthesis; preparation of disinfectants, pharma-

2-ethylhexyl acrylate.

ceuticals.

CAS: 103-11-7. CH

:CHCOOCH

CH(C

Properties: Liquid; pleasant odor. D 0.8869, bp

2-ethylhexyl chloride.

214–218C, vap press 0.1 mm Hg (20C), sets to glass

CAS: 123-04-6. C

CH(C

)CH

Cl.

at −90C, flash p 180F (82.2C) (OC). Insoluble in

Properties: Colorless liquid. D 0.8833 (20C), bp

water. Combustible.

172.9C, refr index 1.4310, bulk d 7.33 lb/gal, flash p

Use: Monomer for plastics, protective coatings, pa-

140F (60C) (OC), fp −135C. Insoluble in water.

per treatment, water-based paints.

Combustible.

Hazard: Moderate fire risk.

2-ethylhexyl acrylate-hydroxyethyl

Use: Synthesis of cellulose derivatives, dyestuffs,

acrylate-methyl acrylate polymer.

pharmaceuticals, textile auxiliaries, insecticides,

CAS: 50601-74-6. mf: (C

•C

)

resins.

Hazard: Low toxicity by ingestion and skin contact.

A moderate eye irritant.

2-ethylhexyl cyanoacetate.

CNCH

COOCH

CH(C

2-ethylhexyl alcohol. (2-ethylhexanol; octyl

Properties: Liquid. Bp 150C, refr index 1.4389

alcohol).

(20C). Insoluble in water; soluble in alcohol, ben-

CAS: 104-76-7. CH

(CH

)

CHC

OH.

zene, and ether. Combustible.

Properties: Colorless liquid. D 0.83 (20C), bp

Use: Organic intermediate.

183.5C, fp −76C, vap press 0.36 (20C), refr index

1.4300 (20C), bulk d 6.9 lb/gal (20C), flash p 178F

2-ethylhexyl-2-cyano-3

′

-diphenyl acrylate.

(81.1C). Miscible with most organic solvents,

See “Uvinul” [BASF].

slightly soluble in water. Combustible.

Derivation: (a) Oxo process from propylene and

2-ethylhexyl 2-cyano-3-phenylcinnamate.

synthesis gas; (b) aldolization of acetaldehyde or

See octocrilene.

butyraldehyde, followed by hydrogenation; (c) from

fermentation alcohol.

Grade: Technical.

2-ethylhexyl (3-isocyanatomethylphenyl)

Use: Plasticizer for PVC resins, defoaming agent,

carbamate.

wetting agent; organic synthesis; solvent mix for

CAS: 58240-57-6. mf: C

nitrocellulose, paints, lacquers, baking finishes;

Hazard: A poison by ingestion and skin contact. A

penetrant for mercerizing cotton; textile finishing

severe eye irritant.

compounds; plasticizers; inks; rubber; paper; lubri-

cants; photography; dry cleaning.

2-ethylhexylisodecyl phthalate. C

Properties: Colorless, high-boiling liquid. Good die-

2-ethylhexylamine. lectric properties, refr index 1.478–1.488 (25C), d

CAS: 104-75-6. C

CH(C

)CH

. 0.969–0.977 (25/25C). Miscible with most common

Properties: Colorless liquid. D 0.7894 (20/20C), solvents, thinners, and oils. Combustible.

bulk d 6.56 lb/gal (20C), bp 169.2C, vap press 1.2 Use: Plasticizer.

535 ETHYL IODOACETATE

2-ethylhexylmagnesium chloride. ethyl 4-hydroxy-2-methyl-2h-1,2-benzo-

thiazine-3-carboxylate 1,1-dioxide.

CH(C

)CH

MgCl. Grignard reagent

CAS: 24683-26-9. mf: C

available commercially in tetrahydrofuran solution.

Hazard: Low toxicity by ingestion and inhalation.

2-ethylhexyloctylphenyl phosphite.

2-ethyl-2-(hydroxymethyl)-1,3-propanediol

O)P.

triacetoacetate.

Properties: Colorless to light-yellow liquid; charac-

CAS: 22208-25-9. mf: C

teristic odor. D 0.935–0.950 (20/4C), flash p 385F

Hazard: A poison by ingestion and skin contact.

(196C). Insoluble in water. Combustible.

Use: Antioxidant, plasticizer, flame-retardant, lubri-

cating-oil additive.

3-((10-ethyl-11-(p-hydroxyphenyl)dibenz

(b,f)oxepin-3-yl)oxy)-1,2-propanediol

hydrate (4:1).

3,3

′

-(2-ethylhexyl) thiodipropionate. (dioc-

CAS: 85850-93-7. mf: C

•1/

tyl thiopropionate). (C

OOCCH

)

Hazard: A reproductive hazard.

Properties: Colorless liquid. D 0.952 (25C). Insolu-

ble in water; soluble in most organic solvents. Com-

bustible.

ethylidene chloride. (1,1-dichloroethane).

Use: Antioxidant, stabilizer, and lubricant. CAS: 75-34-3. CH

CHCl

Properties: Colorless, neutral, mobile liquid; aro-

matic ethereal odor; saccharin taste. D 1.174 (17C),

ethyl(hydrogen p-mercaptobenzene-

bp 57–59C, fp −98C, refr index 1.4166 (20C). Solu-

sulfonato)mercury sodium salt. See so-

ble in alcohol, ether, fixed and volatile oils; very

dium thimerfonate.

sparingly soluble in water. Combustible.

Hazard: Toxic. TLV: 100 ppm; not classifiable as a

ethyl-2-hydroxy-2,2-bis(4-chlorophenyl)

human carcinogen.

acetate. See “Chlorobenzilate.”

Use: Extraction solvent, fumigant.

ethyl-3-hydroxybutyrate.

ethylidenediethyl ether. See acetal.

CH(OH)CH

Properties: A solid. Mw 132.16, bp 170C, d 1.017,

ethylidenedimethyl ether. See dimethy-

fp 64C.

lacetal.

Grade: Food.

ethylidene fluoride. See 1,1-difluoroethane.

ethyl hydroxyethyl cellulose. (EHEC). A

cellulose ether.

Properties: White, granular solid. Soluble in mix-

5-ethylidene-2-norbornene. (ENB).

tures of aliphatic hydrocarbons containing alcohol; CAS: 16219-75-3. A diene used as the third mono-

soluble in water. Combustible. mer in EPDM elastomers.

Available forms: Extra low- and high-viscosity Hazard: Toxic. TLV: ceiling 5 ppm.

types.

Use: Stabilizer, thickener, binder, formation of film

4,4

′

′′

-ethylidynetrisphenol.

in silk-screen and gravure printing inks; protective

CAS: 27955-94-8. mf: C

coatings; aqueous, aqueous-organic, and organic

Hazard: Low toxicity by ingestion and skin contact.

solvent systems.

A mild eye irritant.

n-ethyl-n-(2-hydroxyethyl)-3-methyl-4-

ethyl iodide. (iodoethane).

nitrosoaniline.

CAS: 75-03-6. C

CAS: 58066-96-9. mf: C

Properties: Colorless liquid, turning brown on expo-

Hazard: A poison by ingestion.

sure to light. D 1.90–1.93 (25/25C), fp −108C, bp

72C, refr index 1.5168 (15C). Soluble in alcohol and

ethyl-␣-hydroxyisobutyrate. (CH

)

COH- ether; slightly soluble in water. Combustible.

COOC

. Derivation: By digesting red phosphorus with abso-

Properties: Water-white liquid. D 0.978–0.986 lute ethanol, after which iodine is added and the

(20C), bp 149–150C. Soluble in water, alcohol, and mixture distilled.

ether. Combustible. Hazard: Toxic by inhalation and skin absorption,

Use: Solvent for nitrocellulose and cellulose acetate; narcotic in high concentration.

solvent mixture for cellulose ethers, organic synthe- Use: Medicine, organic synthesis.

sis, pharmaceuticals.

ethyl iodoacetate. CH

ICOOC

4-ethyl-7-hydroxy-3-(p-methoxyphenyl) Properties: Dense, colorless liquid. Decomposed by

coumarin. light and air, also (very slowly) by alkaline solutions

CAS: 5219-17-0. mf: C

. and water. D 1.8, bp 179C, vapor d 7.4, vap press

Hazard: A reproductive hazard. 0.54 mm Hg (20C).

5365-ETHYL-5-ISOAMYLBARBITURIC

Derivation: Interaction of potassium iodide with eth- 135C, fp −99C, d 0.864 (20/20C), refr index

yl bromo- or chloroacetate. 1.3950–1.3990 (20C). Slightly soluble in water;

Hazard: Strong irritant to eyes and skin. miscible with alcohol, ether, and benzene. Combus-

tible.

Derivation: Heating sodium valerate and ethanol in

5-ethyl-5-isoamylbarbituric acid. See

the presence of sulfuric acid or hydrochloric acid,

amobarbital.

with subsequent distillation.

Grade: Technical, FCC.

ethylisobutrazine hydrochloride.

Use: Essential oils, perfumery, artificial fruit es-

CAS: 3737-33-5. mf: C

S•ClH.

sences, flavoring.

Hazard: A poison.

ethyl lactate.

ethylisobutylmethane. See 2-methylhexane.

CAS: 97-64-3. CH

OCOOC

Properties: Colorless liquid; mild odor. D

ethyl isobutyrate.

1.020–1.036 (20/20C), bp 154C, flash p 115F

CAS: 97-62-1. (CH

)

CHCOOC

(46.1C) (CC); bulk d 8.55 lb/gal (20C), autoign

Properties: Colorless, volatile liquid. D 0.870, bp

temp 752F (400C). Miscible with water, alcohols,

110–111C, fp −88C, refr index 1.3903 (20C). Solu-

ketones, esters, hydrocarbons, oil. Combustible.

ble in alcohol and ether; slightly soluble in water.

Derivation: (a) By the esterification of lactic acid

Combustible.

with ethanol; (b) by combining acetaldehyde with

Derivation: Heating isobutyric acid and ethyl alco-

hydrogen cyanide to form acetaldehyde cyanohyd-

hol, with subsequent distillation.

rin, which is converted into ethyl lactate by treat-

Use: Organic synthesis, flavoring extracts.

ment with ethanol and an inorganic acid.

Grade: Technical (96%).

ethyl isocyanate.

Hazard: Moderate fire risk.

CAS: 109-90-0. C

NCO.

Use: Solvent for nitrocellulose, cellulose acetate,

Properties: Liquid. D 0.898, bp 60C. Soluble in

many cellulose ethers, resins; lacquers; paints;

chlorinated and aromatic hydrocarbons.

enamels; varnishes; stencil sheets; safety glass; fla-

Hazard: Strong irritant to tissue.

voring.

Use: Pharmaceutical and pesticide intermediate.

ethyl levulinate. CH

CO(CH

)

COOC

ethyl isocyanatoacetate.

Properties: Colorless liquid. D 1.012, bp 205–206C,

CAS: 2949-22-6. mf: C

refr index 1.4229 (20C). Soluble in water; miscible

Hazard: Moderately toxic by ingestion and inhala-

with alcohol. Combustible.

tion.

Use: Solvent for cellulose acetate and starch ethers,

flavoring.

ethyl 4-isocyanobenzoate.

CAS: 1983-99-9. mf: C

ethyllithium. (lithium ethyl).

Hazard: Low toxicity by ingestion.

Properties: Transparent crystals. Decomposed by

Use: Agricultural chemical.

water. The commercial product is a 2 M suspension

of C

Li in benzene.

2-ethylisohexanol.

Hazard: Ignites in air, reacts with oxidizing mate-

(CH

)

CHCH

CH(C

)CH

OH.

rials.

Properties: Liquid. D 0.825–8.035 (20/20C), boiling

Use: Grignard-type reactions.

range 173.0–181.0C, refr index 1.4235 (20C), bulk

d 6.89 lb/gal (20C), flash p 170F (76.6C) (COC).

ethylmagnesium bromide. C

MgBr.

Combustible.

Properties: Liquid. D 1.01.

Use: Chemical intermediate.

Available forms: Dissolved in ether.

Hazard: Flammable, dangerous fire risk.

ethyl isopropenyl ketone. See isopropenyl

Use: Grignard-type reactions.

ethyl ketone.

ethylmagnesium chloride. C

MgCl.

ethyl isothiocyanate. See ethyl thiocarbi-

Available forms: Dissolved in ether (also offered

mide.

commercially in tetrahydrofuran).

Properties: Liquid. D 0.85.

ethyl 4-isothiocyanatobutanoate.

Hazard: Flammable, dangerous fire risk.

CAS: 17126-65-7. mf: C

Use: Grignard-type reactions.

Hazard: A poison.

ethyl isovalerate. (ethyl valerate; ethyl 2- N-ethylmaleimide. (1-ethyl-1-H-pyrrole-2,5-

methylbutyrate). dione).

CAS: 108-64-5. (CH

)

CHCH

COOC

. CAS: 128-53-0. C

Properties: Colorless, oily liquid; fruity odor. Bp Properties: Crystals. Mw 125.13, mp 45C.

537 ETHYL-2-METHYLBUTYRATE

Hazard: Lachrymator when liquid, a strong irritant.

n-ethylmercuri-p-toluenesulfonanilide.

Use: Cancer research. CAS: 517-16-8. C

NHg.

Properties: Crystalline solid; strong, garlic like

odor. Insoluble in water.

ethyl malonate. (malonic ester; diethyl malo-

Hazard: Ingestion may be fatal.

nate).

Use: Agricultural chemical (grain smut control).

CAS: 105-53-3. CH

(COOC

)

Properties: Colorless liquid; sweet ester odor. Bp

198C, fp −50C, d 1.055 (25/25C), flash p 200F

ethylmercury-2,3-dihydroxypropyl

(93.3C). Insoluble in water; soluble in alcohol, mercaptide. C

HgSCH

OCH

OH. Or-

ether, chloroform, and benzene. Combustible. ganic mercurial.

Derivation: By passing hydrogen chloride into cya- Hazard: Very toxic; see mercury.

noacetic acid dissolved in absolute alcohol with Use: Fungicidal dust, or in slurry treatment, for con-

subsequent distillation. trol of seed borne disease and to reduce losses from

Use: Intermediate for barbiturates and certain pig- seed decay and damping off of wheat, oats, rye, etc.

ments, flavoring. See mercury.

ethylmemazine monohydrochloride. See ethylmercury-p-toluenesulfonanilide.

ethylisobutrazine hydrochloride. (EMTS; “Ceresan” M).

N(HgC

)SO

Properties: Crystals; pungent odor. Mp 154–157C.

ethyl mercaptan. Legal label name for ethane-

Nearly insoluble in water; soluble in acetone and

thiol.

chloroform.

Hazard: Very toxic.

ethylmercuric acetate.

Use: Dust or slurry for control of seed-borne diseases

CAS: 109-62-6. C

HgOOCCH

of fungi by treatment of seeds or bulbs.

Properties: White, crystalline powder. Mp 178C.

See mercury.

Slightly soluble in water; soluble in many organic

solvents. May be steam distilled.

ethylmercury toluenesulfonate.

Hazard: Strong irritant; see mercury.

CAS: 2654-47-9. mf: C

HgO

Use: Seed fungicide as dust or slurry with water.

Properties: IDLH 10 mg/m

(as Hg).

See mercury.

Hazard: A poison. TWA 0.1 mg(Hg)/m

(skin).

ethylmercuric chloride.

ethyl methacrylate.

CAS: 107-27-7. C

HgCl.

CAS: 97-63-2. H

C:CCH

COOC

Properties: Crystals. D 3.482, mp 193C, sublimes

Properties: Colorless liquid. Bp 119C, fp approxi-

readily. Insoluble in water; slightly soluble in ether;

mately −75C, d 0.911, refr index 1.4116 (25C), flash

soluble in hot alcohol.

p 70F (21.1C) (OC). Insoluble in water; readily

Derivation: Reaction of zinc diethyl and mercuric

polymerized.

chloride.

Derivation: Reaction of methacrylic acid or methyl

Hazard: Strong irritant.

methacrylate with ethanol.

Use: Fungicide for seed or bulb treatment, either

Grade: Technical (inhibited).

alone or with other organic mercury compounds.

Hazard: Flammable, dangerous fire and explosion

See mercury.

hazard. An irritant.

Use: Polymers, chemical intermediates.

ethylmercuric dicyandiamide.

See acrylic resin.

CAS: 63869-03-4. mf: C

HgN

Properties: IDLH 10 mg/m

(as Hg).

n-(2-(5-ethyl-2-methoxyphenyl)ethyl)

Hazard: A poison. TWA 0.01. STEL 0.03 mg/m

propionamide.

(skin).

CAS: 156482-87-0. mf: C

Hazard: Moderately toxic by ingestion.

ethylmercuric phosphate.

CAS: 2440-45-1. (C

HgO)

PO.

N-ethyl-3-methylaniline. See n-ethyl-m-tolu-

Properties: White powder; garlic like odor. Soluble

idine.

in water.

Derivation: Reaction of ethylmercuric acetate with

phosphoric acid.

n-ethyl-2(or 4)-methylbenzenesulfonamide.

Hazard: Strong irritant. CAS: 8047-99-2. mf: C

Use: Seed fungicide, timber preservative. Hazard: Moderately toxic by ingestion. Low toxicity

See mercury. by skin contact. A mild eye irritant.

ethylmercurithiosalicylic acid, sodium salt. ethyl-2-methylbutyrate. See ethyl isoval-

See thimerosal. erate.

538ETHYL METHYL CELLULOSE

ethyl methyl cellulose. A water-soluble cellu- Properties: Colorless to sltly yellow liquid; strong,

lose ether used for thickening, sizing, emulsifying, raw potato odor. D: 0.980−0.999 @ 20°, refr index:

and dispersing. 1.502. Sol in water, org solvs.

See polymer, water-soluble. Hazard: Moderately toxic by ingestion.

Use: Food additive.

o-ethyl-s-(3-methyl-4-chlorophenyl)ethyl

phosphonodithioate.

5-ethyl-2-methylpyridine. See 2-methyl-5-

CAS: 1942-78-5. mf: C

ClOPS

ethylpyridine.

Hazard: A poison by ingestion and skin contact.

Use: Agricultural chemical.

O-ethyl-O-[4-(methylthio)phenyl] S-propyl

phosphorodithioate. See sulprofos.

n-ethyl-3,4-methylenedioxyamphetamine.

CAS: 82801-81-8. mf: C

7-ethyl-2-methyl-4-undecanol. (tetradeca-

Hazard: Human systemic effects.

nol). C

CH(C

CH(OH)CH

CH(CH

)

Properties: Liquid. D 0.8355 (20/20C), bp 264C,

ethyl methyl ether.

flash p 285F (140C). Insoluble in water. Combus-

CAS: 540-67-0. C

OCH

tible.

Properties: Colorless liquid. D 0.725, bp 10.8C,

Use: Intermediate for synthetic lubricants, defoam-

flash p −35F (−37.2C), autoign temp 374F (190C).

ers, and surfactants.

Soluble in water; miscible with alcohol and ether.

Hazard: Highly flammable, dangerous fire and ex-

ethylmorphine hydrochloride.

plosion risk.

CAS: 125-30-4. C

•HCl•2H

Use: Medicine (anesthetic).

Properties: White, crystalline powder; odorless. Mp

approximately 123C (decomposes). Soluble in wa-

ethyl (4-(1-methylethyl)phenyl)methyl 3-

ter and alcohol; slightly soluble in ether and chloro-

pyridinylcarbonimidodithioate.

form.

CAS: 51308-73-7. mf: C

Derivation: Action of hydrochloric acid on ethyl-

Hazard: Moderately toxic by ingestion.

morphine, which is made by action of ethyl iodide

Use: Agricultural chemical.

on morphine in alkaline solution.

Grade: Technical, NF.

2-ethyl-4-methylimidazole. C

. Hazard: Toxic by ingestion; habit-forming narcotic.

Properties: A supercooled amber liquid that if crys- Use: Medicine (analgesic).

tallized is a low-melting solid. Mp 45C, bp 154C (10

mm Hg).

N-ethylmorpholine.

Use: Curing epoxy-resin systems.

CAS: 100-74-3.

ethyl methyl ketone. See methyl ethyl ke-

❘

OCH

❘

NCH

tone.

Properties: Colorless liquid; ammoniacal odor. D

0.916 (20/20C), fp −63C, bp 138C, bulk d 7.6 lb/gal

ethyl 3-methyl-4-(methylthio)phenyl(1-

(20C), flash p 90F (32.3C) (OC). Miscible with

methylethyl) phosphoramide. See fen-

water.

amiphos.

Grade: Technical.

Hazard: Irritant to skin and eyes, absorbed by skin.

ethyl methylphenylglycidate. (so-called al-

Flammable, moderate fire risk. TLV: 5 ppm, toxic

dehyde C-16; “strawberry aldehyde”).

by skin absorption.

Use: Intermediate for dyestuffs, pharmaceuticals;

rubber accelerators and emulsifying agents; solvent

❘

CHCOOC

for dyes, resins, oils; catalyst in making polyure-

Properties: Colorless to yellowish liquid; strong

thane foams.

odor suggestive of strawberry. D 1.104–1.123, refr

index 1.509–1.511. Soluble in three volumes of 60%

ethyl mustard oil. See ethyl thiocarbimide.

alcohol. Combustible.

Grade: Technical, FCC (as aldehyde C-16).

Use: Perfumery, flavors.

ethyl myristate. (ethyl tetradecanoate).

(CH

)

COOC

Properties: Liquid. D 0.856, mp 12C, bp 295C. In-

o-ethyl s-1-methylpropyl s-1,1-

soluble in water, soluble in alcohol; slightly soluble

dimethylethyl phosphorodithioate.

in ether. Combustible.

CAS: 86073-23-6. mf: C

Use: Flavoring.

Hazard: A poison by ocular route.

2-ethyl-3-methylpyrazine. n-ethyl-␣-naphthylamine. (n-ethyl-1-naph-

CAS: 15707-23-0. mf: C

. thylamine). C

NCH

539 3-ETHYLPENTANE

Properties: Colorless liquid. Refr index 1.6475, bp Use: Intermediate.

305C. Insoluble in water; soluble in alcohol and

ether. Combustible.

ethyl oxalate. (diethyl oxalate).

Use: Intermediate.

CAS: 95-92-1. (COOC

)

Properties: Colorless, unstable, oily, aromatic liq-

ethyl nitrate.

uid. D 1.09 (20/20C), bp 186C, fp −40.6C, bulk d

CAS: 625-58-1. C

approximately 8.96 lb/gal (20C), flash p 168F

Properties: Colorless liquid; pleasant odor; sweet

(75.5C) (CC). Miscible with alcohol, ether, ethyl

taste.D 1.116, fp −112C, bp 87.6C, vapor three times

acetate, and other common organic solvents; slight-

heavier than air, flash p 50F (10C) (CC), lower

ly soluble in water and gradually decomposed by it.

explosive limit 3.8%. Soluble in alcohol and ether;

Combustible.

insoluble in water.

Derivation: By standard esterification procedure us-

Derivation: By heating alcohol, urea nitrate, and

ing ethanol and oxalic acid. The final purification

nitric acid, with subsequent distillation.

calls for unusual technique and equipment. The last

Hazard: Flammable, dangerous, fire and explosion

traces of water are most difficult to remove, and this

risk.

is accomplished by a special step in the rectification.

Use: Organic synthesis, drugs, perfumes, dyes, rock-

Hazard: Toxic by ingestion, strong irritant to skin

et propellant.

and mucous membranes.

Use: Solvent for cellulose esters and ethers, many

ethyl nitrite. natural and synthetic resins; radio-tube cathode fix-

CAS: 109-95-5. C

. ing lacquers; dye intermediate; pharmaceuticals,

Properties: Yellowish volatile liquid. D 0.90, bp perfume preparations; organic synthesis.

16.4C, flash p −31F (−35C), decomposes spontane-

ously at 194F (90C), explosive limits in air 3–50%.

ethyl-2-oxocyclopentanecarboxylate. See

Soluble in alcohol and ether; decomposes in water.

2-carbethoxycyclopentanone.

Narcotic in high concentration.

Hazard: Highly flammable, dangerous, explodes!!

ethyl oxyhydrate.

Use: Organic reactions, synthetic flavoring.

Properties: Colorless liquid; sharp rum-like odor.

Miscible in alc, glycerin, propylene glycol.

ethyl 2-(m-nitrobenzylidene)acetoacetate.

Use: Food additive.

CAS: 39562-16-8. mf: C

Hazard: Moderately toxic by ingestion, inhalation,

ethyl pabate. See ethopabate.

and skin contact.

ethylparaben. (ethyl-p-hydroxybenzoate).

ethyl 2-nitrophenyl sulfide.

CAS: 120-47-8. C

CAS: 3058-46-6. mf: C

Properties: Colorless crystals. Mp 115C, decom-

Hazard: Moderately toxic by ingestion and skin con-

poses at 297C. Soluble in alcohol and ether; almost

tact. A mild skin and moderate irritant.

insoluble in water.

Derivation: Esterification of p-hydroxybenzoic

ethyl nonanoate. See ethyl pelargonate.

acid.

Use: Pharmaceutical preservative.

ethyl octanoate. See ethyl caprylate. See “Parabens.”

ethyl octoate. See ethyl caprylate. ethyl parathion. See parathion.

ethyl oenanthate. See ethyl enanthate. ethyl PCT. See O,O-diethyl phosphorochlo-

riodothioate.

ethyl oleate. C

COOC

Properties: Light-colored, yellowish, oily liquid.

ethyl pelargonate. (ethyl nonanoate; wine

Bulk d 7.27 lb/gal (20C), refr index 1.45189 (20C), ether). CH

(CH

)

COOC

bp 205C, fp approximately −32C, d 0.867, flash p Properties: Colorless liquid; fruity odor. Refr index

348F (175C). Insoluble in water, soluble in alcohol 1.4220 (20C), d 0.866 (18/4C), bp approximately

and ether; solubility of water in ethyl oleate 1.0 cc/ 220C, fp −44C. Insoluble in water; soluble in alco-

100 cc (202C). Combustible. hol and ether. Combustible.

Use: Solvent, plasticizer, lubricant, water-resisting Grade: Technical, FCC.

agent, flavoring. Use: Flavoring alcoholic beverages; perfumes;

chemical intermediate.

ethyl orthopropionate. CH

C(OC

)

Properties: Colorless liquid. Bp 155–160C, refr in-

3-ethylpentane. (triethylmethane). (C

)

CH.

dex 1.401 (20C), flash p 140F (60C). Insoluble in Properties: Colorless liquid. Bp 93.5C, fp −118.6C,

water; soluble in alcohol and ether. Combustible. d 0.69818 (20C), refr index 1.3934 (20C). Soluble in

Hazard: Moderate fire risk. alcohol; insoluble in water. Combustible.

540

-ETHYLPHENOL

Grade: Technical. Properties: White, crystalline powder. Melting

Use: Organic synthesis. range 85–87C. Saturated solution is slightly acid.

Freely soluble in acetone, ethyl acetate, and chloro-

m-ethylphenol. (3-ethylphenol). HOC

. form; soluble in ethanol and methanol; practically

Properties: Colorless liquid. Fp −4C, bp 214C, d insoluble in water.

1.001. Very slightly soluble in water; miscible with Grade: NF (as glutethimide).

alcohol and ether. Combustible. Hazard: Manufacture and use controlled by law.

Hazard: Toxic material. Use: Medicine (sedative).

See phenol.

ethyl phenyl ketone. See propiophenone.

p-ethylphenol. (4-ethylphenol). HOC

4-ethyl-n-(phenylmethylene)benzenamine n-

Properties: Colorless needles. Mp 46C, bp 219C,

oxide.

flash p 219F. Soluble in alcohol or ether; slightly

CAS: 42790-35-2. mf: C

NO.

soluble in water. Combustible.

Hazard: Moderately toxic by ingestion and skin con-

Hazard: Toxic material.

tact. A mild eye irritant.

See phenol.

␣-(5-ethyl-1-phenyl-1h-pyrazol-4-yl)-1-

3-(2-ethylphenoxy)-1-((1s)-1,2,3,4-

piperidinebutanol.

tetrahydronaphth-1-ylamino)-(2s)-2-

CAS: 296269-54-0. mf: C

propanol oxalate.

Hazard: A poison by ingestion.

CAS: 174689-39-5. mf: C

•C

Hazard: A poison.

ethyl phenylurethane. See ethyl phenylcar-

bamate.

ethylphenylacetamide. See n-ethylacetani-

lide.

ethylphosphoric acid. C

Properties: Pale-straw-colored liquid. D 1.33 (25C).

ethyl phenylacetate.

Can be neutralized with alkalies or amines to give

CAS: 101-97-3. C

COOC

water-soluble salts. Combustible.

Properties: Colorless liquid; honeylike odor. D

Grade: Purity: 97%, remainder being orthophospho-

1.027–1.032, refr index 1.498, bp 226C. Soluble in 8

ric acid and ethanol.

parts of 60% alcohol; insoluble in water. Combus-

Hazard: An irritant.

tible.

Use: Catalyst, rust remover, soldering flux, interme-

Grade: Technical, FCC.

diate.

Use: Perfumery; flavors; intermediate, especially for

phenobarbital; herbicide.

ethyl phthalate. See diethyl phthalate.

ethyl phenylacrylate. See ethyl cinnamate.

ethyl phthalyl ethyl glycolate.

OCOC

COOCH

COOC

5-ethyl-5-phenylbarbituric acid. See phe-

Properties: Liquid with slight odor. D 1.180 (25C),

nobarbital.

refr index 1.498 (25C), bp 190C (5 mm Hg). Solubil-

ity in water 0.018% by weight; miscible with most

ethyl phenylcarbamate. (phenylurethane;

organic solvents. Combustible.

ethyl phenylurethane). C

NHCOOC

Use: Plasticizer; food additive.

Properties: White, crystalline solid; aromatic odor;

clovelike taste. Mp 51C. Soluble in alcohol, ether,

5-ethyl-2-picoline. See 2-methyl-5-ethylpyri-

and boiling water; insoluble in cold water.

dine.

Derivation: Action of ethanol on phenyl isocyanate.

2-ethylpiperidine.

ethylphenyldichlorosilane. C

)SiCl

Properties: Liquid. Mw 113.20, bp 143C, d 0.850.

Properties: Colorless liquid that fumes strongly in

Hazard: Flammable; irritant.

moist air.

Hazard: Toxic by inhalation and ingestion, strong

irritant to eyes and skin.

1-ethyl-1-propanol. See 3-pentanol.

N,N-ethylphenylethanolamine. ethyl propiolate. HC≡CCO

OH. Properties: Liquid. Mw 98.10, bp 120C, d 0.968.

Properties: Liquid. D 1.04 (20/20C), bp 268C (740 Hazard: Flammable; lachrymator.

mm Hg), bulk d 8.7 lb/gal. Combustible.

Use: Organic synthesis, dyestuffs.

ethyl propionate.

CAS: 105-37-3. C

COOC

2-ethyl-2-phenylglutarimide. (glutethimide). Properties: Water-white liquid; pineapple odor. D

. 0.888 (25C), bp 99C, fp −73C, flash p 54F (12.2C)

541 ETHYLSULFONYLETHYL

(CC), autoign temp 890F (476C), refr index 1.3844

ethyl silicate. (tetraethyl orthosilicate).

(20C). Soluble in alcohol and ether; solubility in CAS: 78-10-4. (C

)

SiO

water 2.5% 15C. Properties: Colorless liquid; faint odor. D 0.9356

Derivation: Treating ethanol with propionic acid. (20/20C), bp 168.1C, mp 110C (sublimes), vap

Grade: Commercial 85–90% ester content, FCC. press 1.0 mm Hg (20C), flash p 125F (51.6C) (OC),

Hazard: Flammable, dangerous fire risk. bulk d 7.8 lb/gal (20C), fp −77C, viscosity 0.0179 cP

Use: Solvent for cellulose ethers and esters, various (20C). Miscible with alcohol; hydrolyzed to an ad-

natural and synthetic resins; flavoring agent; fruit hesive form of silica. Combustible.

syrups; cutting agent for pyroxylin. Grade: 29% silicon, 40% silicon.

Hazard: Moderate fire risk. Strong irritant to eyes,

nose, throat. TLV: 10 ppm.

ethylpropionyl. See diethyl ketone.

Use: Weatherproof and acid-proof mortar and ce-

ments, refractory bricks, other molded objects, heat-

2-ethyl-3-propylacrolein. (2-ethylhexenal).

resistant paints, chemical-resistant paints, protec-

CAS: 645-62-5. C

CH:C(C

)CHO.

tive coatings for industrial buildings and castings,

Properties: Yellow liquid; powerful odor. D 0.8518

lacquers, bonding agent, intermediate.

(20/20C), bp 175.0C, vap press 10 mm Hg (20C),

flash p 155F (68.3) (OC), bulk d 7.1 lb/gal (20C),

ethyl silicate, condensed. Light-yellow liq-

viscosity 0.113 cP (20C). Combustible.

uid with mild odor consisting of 85% by weight

Hazard: Toxic by inhalation and ingestion; strong

tetraethyl orthosilicate and 15% polyethoxysi-

irritant.

loxanes.

Use: Insecticide, organic synthesis (intermediate),

Properties: Yields high-purity, refractory silica on

warning agents, and leak detectors.

hydrolysis or ignition.

Hazard: Toxic.

␣-ethyl-␤-propylacrylanilide.

Use: Intermediate for siloxane compounds; for preci-

NHCOC(C

):CH(CH

)

sion casting of high-melting alloys; pigment binder

Use: Rubber accelerator.

for paints; surface hardener for sandstones.

See ethyl silicate.

2-ethyl-3-propylacrylic acid.

CH:C(C

)COOH.

ethyl sodium oxalacetate.

Properties: Liquid. D 0.9484 (20C), fp −7.8C, bp

OOCC(ONa):CHCOOC

232.1C, vap press <0.1 mm Hg (20C), flash p 330F

Properties: Light-yellow powder, 92% pure.

(165C). Insoluble in water. Combustible.

Derivation: Reaction of pure ethyl acetate and die-

Use: Pharmaceuticals, resins and plastics, lubricants.

thyl oxalate with metallic sodium.

Use: Dyes, synthesis.

ethyl propyl ketone. See 3-hexanone.

ethyl sulfate. See diethyl sulfate.

ethyl propyl phosphorothioate.

CAS: 20195-06-6. mf: C

PS.

Hazard: A poison.

ethyl sulfhydrate. See ethanethiol.

3-ethyl-3-propyl-1,3-propanediol. See 2-

ethyl sulfide. (diethyl sulfide).

ethylhexanediol-1,3.

CAS: 352-93-2. (C

)

Properties: Colorless, oily liquid; garliclike odor. D

2-(5-ethyl-2-pyridyl)ethyl acrylate.

0.837, fp −102C, bp 92–93C, refr index 1.4423

:CHCOOC

(20C). Soluble in alcohol and ether, slightly soluble

Properties: Liquid. D 1.0458 (20C), bp 181C (50

in water. Combustible.

mm Hg), fp −75C. Very slightly soluble in water.

Derivation: Heating sodium ethyl sulfate and potas-

Combustible.

sium sulfide, with subsequent distillation.

Use: Manufacture of plastics and fibers, adhesives,

Use: Organic synthesis, solvent for mineral salts,

textile finishes and sizes.

electroplating baths.

ethyl pyrophosphate. See tepp.

ethylsulfonylethyl alcohol. (2-(ethylsulfo-

nyl)ethanol). CH

OH.

ethyl salicylate. Properties: Colorless crystals. Mp 45C, bp 153C

CAS: 118-61-6. C

(OH)COOC

. (2.5 mm Hg). Soluble in water and common organic

Properties: Colorless liquid; faint odor of methyl solvents; hygroscopic.

salicylate. D 1.127–1.130, refr index 1.523, bp Derivation: Reaction of 2-ethylthioethanol with hy-

231–234C. Soluble in ether and alcohol; slightly drogen peroxide.

soluble in water. Combustible. Use: Solvent and organic intermediate, antistatic

Use: Perfumery, flavors. agent, humectant.

542ETHYLSULFURIC ACID

ethylsulfuric acid. (acid ethylsulfate). Properties: Colorless crystals. Mp 64C, flash p 260F

(126C). Soluble in alcohol. Combustible.

HSO

Grade: A mixture of the o- and p-isomers is available

Properties: Colorless, oily liquid. D 1.316; bp 280C

commercially.

(decomposes). Soluble in water, alcohol, and ether.

Use: Plasticizer.

Combustible.

Derivation: Action of sulfuric acid on ethanol.

Hazard: Toxic by ingestion and inhalation; strong

ethyl-p-toluenesulfonate.

irritant to eyes and skin. CAS: 80-40-0. CH

Use: Precipitant for casein, organic synthesis. Properties: Unstable solid. Mp 33C, bp 221.3C, d

1.17, flash p 316F (157C). Soluble in many organic

solvents; insoluble in water. Combustible.

4-ethyl-1,4-thiazane. C

NSC

Use: Plasticizer for cellulose acetate, ethylating

Properties: Colorless, mobile liquid. D 0.9929

agent.

(15C); bp 184C (763 mm Hg). Soluble in water.

Combustible.

Derivation: Interaction of dichlorodiethyl sulfide

N-ethyl-m-toluidine. (N-ethyl-3-methylani-

and an aliphatic amine in the presence of alcohol and line).

sodium carbonate. CAS: 102-27-2. CH

NHC

Properties: Light-amber liquid. Refr index 1.5451

(20C), bp 221C. Combustible.

3-(ethylthio)butyraldehyde.

Use: Chemical intermediate.

CAS: 27205-24-9. mf: C

OS.

Hazard: Moderately toxic by ingestion and skin con-

tact. Low toxicity by inhalation. An eye irritant.

N-ethyl-o-toluidine. CH

NHC

Properties: Colorless to yellowish oil. D 0.9534; bp

214C. Soluble in alcohol, ether, and hydrochloric

ethyl thiocarbimide. (ethyl mustard oil; eth-

acid; insoluble in water. Combustible.

yl isothiocyanate). C

NCS.

Derivation: Heating ethanol with o-toluidine and

Properties: Colorless liquid; pungent odor. D 1.004

hydrochloric acid.

(15/4C), fp −5.9C, bp 131–132C. Soluble in alcohol;

insoluble in water.

Hazard: Toxic by inhalation; strong irritant to skin

ethyl triacetylgallate. C

OOCC

(O-

and mucous membranes. OCCH

)

Use: Military poison gas. Properties: Colorless crystals or white crystalline

powder; insipid taste; odorless. Mp 134–136C. Sol-

uble in warm alcohol and acetone; slightly soluble in

ethyl thioethanol. C

OH.

ether and alcohol; insoluble in water.

Properties: Pale-straw-colored liquid. D

1.015–1.025 (20/20C), distillation range 180–184C,

refr index 1.486 (20C). Combustible.

ethyl-3,5,6-tri-o-benzyl-d-glucofuranoside.

Grade: 95% min. CAS: 10310-32-4. mf: C

Use: Organic intermediate (pesticides, plasticizers, Hazard: Low toxicity by ingestion.

etc.).

ethyltrichlorosilane.

ethylthiopyrophosphate. See sulfotepp. CAS: 115-21-9. C

SiCl

Properties: Colorless liquid. Bp 99.5C, d 1.236 (25/

25C), refr index 1.4257 (25C), flash p 72F (22.2C)

(ethylthio)trioctylstannane.

(OC). Soluble in benzene, ether, heptane, perchloro-

CAS: 70303-46-7. mf: C

SSn.

ethylene; readily hydrolyzed with liberation of hy-

Hazard: Moderately toxic. TWA 0.1 mg(Sn)/m

;

drogen chloride.

STEL 0.2 mg/m

(skin)

Derivation: By reaction of ethylene and trichlorosi-

Use: Drug.

lane in the presence of a peroxide catalyst.

Hazard: Flammable, dangerous fire risk, may form

ethyltin trichloride.

explosive mixture with air. A strong irritant.

CAS: 1066-57-5. mf: C

Sn.

Use: Intermediate for silicones.

Properties: Colorless liquid. Mp: –10°, bp:

196−198°.

“Ethyl Tuex” [Uniroyal]. TM for tetrame-

Hazard: A poison by ingestion. TWA 0.1 mg(Sn)/

thylthiuran disulfide.

; STEL 0.2 mg(Sn)/m

(skin).

ethyl urethane. See urethane.

m-ethyltoluene.

CAS: 620-14-4. mf: C

Hazard: Moderately toxic. Low toxicity by inhala-

ethyl valerate. See ethyl isovalerate.

tion.

ethyl vanillate. (CH

O)HOC

COOC

n-ethyl-p-toluenesulfonamide. Properties: Solid. Mp 44C, bp 291–293C. Insoluble

NHSO

. in water; soluble in alcohol and ether.

543 EUROPIUM

Use: Food preservative, medicine, sunburn preven- miscible with alcohol, chloroform, ether, glacial

acetic acid, and fixed or volatile oils. Combustible.

tive.

Derivation: By fractionally distilling eucalyptus oil

followed by freezing. The oil is imported from

ethyl vanillin. (3-ethoxy-4-hydroxybenzaldeh-

Spain, Portugal, and Australia.

yde).

Grade: Technical, NF.

CAS: 121-32-4. OHC

(OC

)CHO.

Use: Pharmaceuticals (cough syrups, expectorants),

Properties: Fine, white crystals; intense odor of van-

flavoring, perfumery.

illin. Affected by light, mp 76.5C. Soluble in alco-

hol, chloroform, and ether; slightly soluble in water.

euchromatin. Chromatin, which is in an uncon-

Combustible.

densed form, is more accessible and contains the

Grade: NF, FCC.

majority of actively expressed genes. See also heter-

Use: Flavors, to replace or fortify vanillin.

ochromatin.

ethyl vinyl ether. See vinyl ethyl ether.

eucryptite. A lithium silicate mineral (LiAlSiO

)

containing up to 4.8% lithia.

ethyl vinyl ether polymer.

Use: Glass manufacture; source of lithium.

CAS: 25104-37-4.

Hazard: Moderately toxic.

eugenic acid. See eugenol.

ethylxanthic acid. See xanthic acid.

eugenics. The study of improving a species by

artificial selection; usually refers to the selective

ethylzinc. See diethylzinc.

breeding of humans.

ethyne. See acetylene.

eugenol. (4-allyl-2-methoxyphenol; caryophyl-

lic acid; eugenic acid).

ethynylation. Condensation of acetylene with a

CAS: 97-53-0. C

(OH)OCH

reagent such as an aldehyde to yield an acetylenic

Properties: Colorless or yellowish liquid, oily; be-

derivative. The best example is the union of formal-

comes brown in air; spicy odor and taste. D

dehyde and acetylene to produce butynediol.

1.064–1.070, bp 253.5C, fp −9C, refr index

1.5400–1.5420 (20C), optically inactive. Soluble in

ethynylenebis(carbonyloxy)bis

alcohol, chloroform, ether, and volatile oils; very

(triphenylstannane). See

slightly soluble in water. Combustible.

bis(triphenyltin)acetylenedicarboxylate.

Derivation: By extraction of clove oil with aqueous

potash, liberation with acid, and rectification in a

1-ethynylcyclohexanol.

stream of carbon dioxide.

CAS: 78-27-3. HC≡CC

OH.

Grade: Technical, USP, FCC.

Properties: Colorless, low-melting solid; sweet

Use: Perfumes, essential oils, medicine (analgesic),

odor. Mp 30–31C, bp 180C, d 0.967 (20/20C).

production of isoeugenol for the manufacture of

Slightly soluble in water; soluble in most organic

vanillin, flavoring.

solvents.

Use: Stabilization of chlorinated organic compounds,

eugenyl methyl ether. See methyl eugenol.

intermediate, corrosion inhibitor for mineral acids,

medicine (sedative).

eukaryote. A unicellular or multicellular organ-

ism with cells having a membrane-bounded nucleus.

ethynylestradiol. See ethinylestradiol.

All possess, in addition, multiple chromosomes and

internal organelles.

ethythrin. Ethyl analog of allethrin.

Use: Insecticide with applications similar to allethrin.

“Eureka” [Du Pont]. TM for a soldering flux

See barthrin; cyclethrin; furethrin.

crystalline composition based on zinc chloride and

ammonium chloride.

ETU. See ethylene thiourea.

europia. See europium oxide.

Eu. Symbol for europium.

europium. Eu. Atomic number 63, one of the

eucalyptol. (cineol; cajeputol). lanthanide or rare-earth elements of the cerium sub-

CAS: 470-82-6. C

O. group, aw 151.96, valences of 2, 3; two stable iso-

Properties: Colorless essential oil; a terpene ether topes.

having a camphorlike odor and pungent, cooling, Properties: Steel-gray metal, difficult to prepare,

spicy taste. D 0.921–0.923 (25C); bp 174–177C; quite soft and malleable (DPH

20). Mp 826C, bp

congealing point not less than about 0C, refr index approximately 1489C, d 5.24, oxidizes rapidly in

1.4550–1.4600 (20C). Slightly soluble in water; air. May burn spontaneously. Most reactive of the

544EUROPIUM CHLORIDE

rare-earth metals. Liberates hydrogen from water.

eutectic. The lowest melting point of an alloy or

Reduces metallic oxides. solution of two or more substances (usually metals)

Derivation: Reduction of the oxide with lanthanum that is obtainable by varying the proportion of the

or misch metal.

components. Eutectic alloys have definite and mini-

Source: Rare-earth minerals.

mum melting points in contrast to other combina-

Grade: High purity (ingots, lumps).

tions of the same metals.

Hazard: Highly reactive, may ignite spontaneously

See alloy, fusible.

in powder form.

Use: Neutron absorber in nuclear control, color-TV

eutectic point. Melting point of eutectic mix-

phosphors to activate yttrium, phosphors in postage-

ture. The lowest temperature at which the eutectic

stamp glues to permit electronic recognition of first-

mixture can exist in liquid phase.

class mail.

eutrophication. The unintentional enrichment

or “fertilization” of either fresh or saltwater by

europium chloride.

chemical elements or compounds present in various

CAS: 10025-76-0. EuCl

•6H

types of industrial wastes. Phosphates and nitroge-

Properties: Yellow needles. D 4.89 (20C), mp 850C.

nous compounds in detergent and chemical-pro-

Soluble in water.

cessing wastes are particularly effective eutrophy-

Derivation: Obtained by treating the oxide with hy-

ing agents. They supply nutrients to algae, which

drochloric acid.

proliferate so abundantly that a large proportion die

for lack of light; their decomposition products de-

europium fluoride. EuF

•3H

plete the water of its dissolved oxygen and thus

Properties: Crystals. Mp 1390C, bp 2280C. Insolu-

cause the death of fish and other marine life. One

ble in water and dilute acids.

process for removing phosphates involves addition

of a metal-ion source to waste effluents so as to

europium nitrate. Eu(NO

)

•6H

O. Colorless

insolubilize dissolved phosphates, after which the

to pale-pink crystals, mp 85C (sealed tube), soluble

particles are agglomerated by anionic polymers.

in water, obtained by treating the oxide with nitric

See algae; nitrilotriacetic acid.

acid.

eutropic series. Series of substances in which

europium oxalate. Eu

)

•10H

O. White

the physical properties and crystal form show regu-

powder, insoluble in water, slightly soluble in acids.

larity in their variation.

Grade: 25–50% and 99.8% Eu salt. Impure grade

may be colored.

eV. Abbreviation for electron-volt.

EVA. Abbreviation for ethylene–vinyl acetate co-

europium oxide. (europia). Eu

polymer.

Properties: Pale-rose powder. D 7.42. Insoluble in

water; soluble in acids to give the corresponding

evaporation. The change of a substance from the

salt.

solid or liquid phase to the gaseous or vapor phase.

Derivation: Calcination of the oxalate, solvent ex-

In some cases (e.g., ice, snow, dry ice), the sub-

traction, or liquid ion-exchange processes.

stances do not go through a liquid phase; the phe-

Grade: 25–50%, 99.9%.

nomenon is called sublimation. The rate of evapora-

Use: Nuclear-reactor control rods, especially in red-

tion of liquids varies with their chemical nature and

and infrared-sensitive phosphors.

the temperature; in general, organic liquids (ben-

zene, gasoline) evaporate at lower temperatures and

europium sulfate. Eu

(SO

)

anhydrous and

higher rates than water. The thermal energy required

to vaporize a given volume of a liquid is known as its

Properties: Colorless to pale-pink crystals. D (anhy-

latent heat of vaporization; it remains in the vapor

drous) 4.99 (20C). Hydrate loses 8H

O at 375C;

(steam, in the case of water heated to its boiling

slightly soluble in water.

point) and is released when the vapor condenses. For

water, this latent-heat value is 540 cal/g. In chemical

“Eurovanillan” [Borregaard]. TM for aro-

processing installations requiring a series of evapo-

matic ethyl vanillan.

rations and condensations, the units are set up in

Use: An aroma additive.

series and the latent heat of vaporization from one

unit is utilized to supply energy for the next. Such

units are called “effects” in engineering parlance, as,

eutactic. Characterized by precise molecular or-

e.g., a triple-effect evaporator.

der, like that of a perfect crystal, the interior of a

See distillation.

protein molecule, or a machine-phase system; con-

trasted to the disorder of bulk materials, solution

environments, or biological structures on a cellular

evaporite. A mineral or rock formed by precipi-

scale. tation of crystals from evaporating water.

545 EXON

EVE. Abbreviation for ethyl vinyl ether. the absorbed photons or by transferring the energy to

See vinyl ethyl ether. other atoms or molecules. The emission by the atom

or molecule yields line or band spectra characteristic

of its structure, thus permitting identification. Pho-

eve carbamate.

tochemical reactions are induced by excited chemi-

CAS: 204442-82-0. mf: C

cal entities, which are also responsible for the phe-

Hazard: Low toxicity by ingestion. A mild skin and

nomena of luminescence (phosphorescence and

moderate eye irritant.

fluorescence).

See spectroscopy; photochemistry; absorption (2).

“Everflex” [Grace]. TM for vinyl acetate poly-

mer emulsions.

exciton. An energetic entity induced in semicon-

Use: Paints, paper coating, and acoustic tile coatings.

ductor crystals by incident radiation and occurring

in the field area between a hole and its displaced

evolution. Emission of a gas as a result of a

electron. It is conceived as behaving like an unc-

chemical reaction, as hydrogen from acids reacted

harged particle having quantum-mechanical prop-

with a metal or carbon dioxide from the action of an

erties.

acid on a carbonate. In formulas it may be indicated

by an upward vertical arrow.

excluded volume. The presence of one mole-

cule reduces the volume available for other mole-

cules; resulting reductions in their entropy are

termed excluded volume effects.

exell.

evolutionarily conserved. See conserved se-

CAS: 104559-06-0.

quence.

Hazard: Moderately toxic by ingestion.

evolutionary rootprinting. One can infer

exemestane. See 6-methylenandrosta-1,4-di-

which portions of a gene are important by compar-

ene-3,17-dione.

ing the sequence of that gene with its cognates from

other species. A plot showing the regions of high

exergonic reaction. A chemical reaction that

conservation indicates the regions that are function-

proceeds with the release of free energy (that is, for

al in all the test species.

which DG is negative and the reaction spontaneous).

exchange reaction. A chemical reaction in

exhaust emission control. See air pollution.

which atoms of the same element in two different

molecules or in two different positions in the same

Exkin 1,2,3. TM for a series of antiskinning

molecule change places. Exchange reactions are

agents of the volatile oxime type.

usually studied with the aid of a tracer or tagged

Use: Paints.

atom.

exo-. A prefix used in chemical names to indicate

excimer. A transient excited dimer formed be-

attachment to a side chain rather than to a ring.

tween a solute and a solvent molecule.

See endo-.

excipient. A natural, inert, and somewhat tacky exocarbon. Cyclic compound in which all or

material used in the pharmaceutical industry as a most carbon atoms are in the form of carbonyl

binder in tablets, etc. Commonly used materials are groups or their equivalents.

gum arabic, honey, and beet pulp.

exocytosis. The fusion of an intracellular vesicle

with the plasma membrane, releasing the vesicle

excitation. Addition of energy to a system where-

contents to the extracellular space.

by it is transferred from its ground state to a state of

higher energy.

exoergic. See exothermic.

excited state. A higher than normal energy level

exogenous DNA. DNA originating outside an

of the electrons of an atom, radical, or molecule,

organism that has been introducted into the or-

typically resulting from absorption of photons

ganism.

(quanta) from a radiation source (arc, flame, spark,

etc.) in any wavelength of the electromagnetic spec-

trum. X-ray, UV, visible, infrared, microwave, and

exon. Those portions of a genomic DNA sequence

radio frequencies are used for excitation in various which will be represented in the final, mature

types of spectroscopy. When the energizing source mRNA. The term “exon” can also be used for the

is removed or discontinued, the atom or molecule equivalent segments in the final RNA. Exons may

returns to its normal or stable state either by emitting include coding sequences, the 5

′

untranslated re-

546EXONUCLEASE

gion, or the 3

′

untranslated region. explosive limits. The range of concentration of

See: Intron. a flammable gas or vapor (% by volume in air) in

which explosion can occur upon ignition in a con-

fined area. Explosive limits for some common sub-

exonuclease. An enzyme that digests nucleic

stances are

acids starting at one end. An example is Exonu-

clease III, which digests only double-stranded DNA

Substance Lower (%) Upper (%)

starting from the 3

′

end.

carbon disulfide 1 50

benzene 1.5 8

exosmosis. Osmosis in an outward direction.

methane 5 15

See endosmosis.

butadiene 2 11.5

butane 1.9 8.5

exothermic. Decribes a process or chemical re-

propane 2.4 9.5

action that is accompanied by evolution of heat, for

natural gas 3.8 17

example, combustion reactions.

hydrogen 4 75

acetylene 2.5 80

exotic. A term applied to materials of various

functional types that have extra power and that are

explosive, low. An explosive, such as black

often derived from unusual sources. Examples are

powder, that deflagrates rather than detonates.

rocket propellants derived from boron hydrides and

See deflagration.

certain special-purpose solvents.

explosive, permissible. Explosives approved

expander. (1) A mixture of lampblack, barium

for use in coal mines. Usually they are modified

sulfate, and an organic material usually derived

dynamites.

from lignin that increases the capacity of storage

batteries, presumably by coating the anode and thus

exposure testing. Determination of the degra-

preventing the deposit of lead sulfate on the underly-

dation of a material by exposing samples to an envi-

ing lead metal.

ronment selected for its adverse effect. Materials

(2) A substance used in medicine as a substitute for

most frequently tested are paints, metals and alloys,

blood plasma, e.g., dextran, gelatin, or polyvinylpy-

rubber, and plastics. An area frequently chosen is the

rollidone.

coast of southern Florida, where the combination of

high temperature, strong sunlight, salt air, and mois-

expeller. See extractor; expression.

ture is particularly severe, especially as regards met-

al corrosion. Burial of metals in acid soils for long

periods and immersion of impregnated wood sam-

explosive, high. A chemical compound, usually

ples in seawater are other exposure-testing tech-

containing nitrogen, that detonates as a result of

niques.

shock or heat see detonation. Dynamite was the

See testing.

most widely used explosive for blasting and other

industrial purposes until 1955, when it was largely

replaced by prills-and-oil and slurry types. The for-

expressed sequence tag. (EST). A short

mer consists of 94% ammonium nitrate prills and

strand of DNA that is a part of a cDNA molecule and

6% fuel oil (ANFO). Slurry blasting agents (SBA)

can act as identifier of a gene. Used in locating and

are based on thickened or gelatinized ammonium

mapping genes.

nitrate slurries sensitized with TNT, other solid ex-

See cDNA; sequence tagged site.

plosives, or aluminum. An unusual type of explosive

is represented by acetylides of copper and silver,

expression. (1) Removal of a liquid from a solid

which are examples of commercially used explo-

by hydraulic pressure, as in manufacture of vegeta-

sives that contain neither oxygen nor nitrogen.

ble oils from seeds, rinds, or meal cake. Worm de-

High explosives vary greatly in their shock sensitivi-

vices similar to extrusion machines are also used for

ty; most sensitive are mercury fulminate and nitro-

this purpose; they are called expellers or extractors.

glycerin, whereas TNT and ammonium nitrate are

(2) To “express” a gene is to cause it to function. A

comparatively difficult to detonate, requiring the

gene which encodes a protein will, when expressed,

use of blasting caps or similar activating device.

be transcribed and translated to produce that protein.

A gene which encodes an RNA rather than a protein

(for example, a rRNA gene) will produce that RNA

explosive, initiating. An explosive composi-

when expressed.

tion used as a component of blasting caps, detona-

tors, and primers. They are highly sensitive to flame,

heat, impact, or friction. Examples are lead azide,

expression clone. This is a clone designed to

silver acetylide, mercury fulminate, diazodinitro- produce a protein from the DNA insert. Since mam-

phenol, nitrosoguanidine, lead styphnate, and penta- malian genes do not function in bacteria, to get

erythritol tetranitrate. bacterial expression from mammalian cDNA. It is

547 “EZN-CHEK”

required to put its coding region (i.e. no introns) or for extracting the juice from fruits. It is similar in

immediately adjacent to bacterial transcription/ principle to an extrusion machine having a tapering

translation control sequences. screw rotating in a cylindrical barrel; the oil or juice

is delivered to a container while the residual pulp

and fiber are extruded as waste material. Fruit is fed

Ext. D&C. Product certified for external use

into the machine after being crushed and preheated.

only in drugs and cosmetics.

Juices can also be separated centrifugally. Machines

of this type are also called expellers.

extender. A low-gravity material used in paint,

ink, plastic, and rubber formulations chiefly to re-

“Extrema” [Schumacher]. (trichloroethane).

duce cost per unit volume by increasing bulk. Ex-

TM for a chlorine source.

tenders include diatomaceous earth, wood flock,

Use: Thermal oxidation of silicon and furnace-tube

mineral rubber, liquid asphalt, etc. Microscopic

cleaning.

droplets of water fixed permanently in a plastic

matrix are an efficient extender for polyester resins.

In the food industry, the term refers to certain ex-

extreme-pressure additive. (EP additive).

truded proteins, especially those derived from soy-

(1) Material added to cutting fluids to impart high

beans, which are used in meat products to provide

film strength. They are mainly sulfur, chlorine, and

equivalent nutrient values at lower cost. Made from

occasionally phosphorus compounds. Actual condi-

defatted soy flour, they are often called textured

tions, amounts, etc. are proprietary. (2) Lubricating

proteins.

oil and grease additives that prevent metal-to-metal

See diluent (2); filler.

contact in highly loaded gears. Some react with the

metal gears to form a protective coating. Saponified

lead salts are often used.

extinction. When all the members of a clade or

taxon die, the group is said to be extinct.

“Extru Seal” [Pecora]. TM for a butyl glaz-

ing tape for construction.

extinguishing agent. See fire extinguish-

ment.

extrusion. A fundamental processing operation

extracellular matrix. (ECM). Region outside in many industries in which a material is forced

of metazoan cells which includes compounds at- through a metal forming die, followed by cooling or

tached to the plasma membrane, as well as dissolved chemical hardening. The material may be liquid

substances attracted to the surface charge of the (molten glass or a polymer dispersion); a viscous

cells. The ECM functions both to keep animal cells polymer, as in injection molding; a semisolid mass,

adhered together as well as to buffer them from their such as a rubber or plastic mix; or a hot metal billet.

environment. High-viscosity materials are fed into a rotating

screw of variable pitch that forces the materials

through the die with considerable pressure; a ram is

extraction, solvent. See solvent extraction.

used for metals at temperatures from 537 to 1093C.

Film is made by passing a low-viscosity mixture

extractive distillation. A variety of distillation

through a narrow slit. Molten glass and polymer

that always involves use of a fractionating column

suspensions are forced through a nozzle having a

and is characterized by use of a purposely added

tiny orifice (spinnerette); the latter are hardened

substance that modifies the vaporization character-

after extrusion by immersion in a bath of formalde-

istics of the materials undergoing separation to make

hyde or similar agent. Food items (spaghetti, etc.)

them easier to separate. The additive is often called a

are also extruded. Extrusion involves rheological

solvent and is usually chosen to be much less vola-

principles of some complexity, critical factors being

tile than any of the substances being separated. It is

viscosity, temperature, flow rate, and die design.

added to the down flowing liquid-reflux stream near

See injection molding.

the top of the column and is removed from the still

pot or reboiler at the base. The addition of furfural to

eyespot. Light-sensitive organelle found in many

mixtures of butadiene and butene hydrocarbons to

groups of protists, and in some metazoans.

separate the butadiene more easily is an example of

extractive distillation.

“E-Z Mulse” [Florida Chemicals]. TM for

an emulsifier.

extractive metallurgy. That portion of metal-

Use: To combine d-limonene and water to make

lurgical science devoted to the technology of mining

stable formulations; emulsifies solvents or oil with

and processing of metals and their ores.

water.

extractor. A machine designed for expression of

the oil from seeds such as cottonseed, flaxseed, etc.,

“Ezn-Chek” [Ferro]. TM for heat stabilizers.