W. Symbol for tungsten. Wallach rearrangement. Acid-catalyzed re-

See tungsten, wolfram. arrangement of azoxybenzenes to p-hydroxyazo-

benzenes.

Wacker reaction. The oxidation of ethylene to

“Wallpol” [Reichhold]. TM for a series of

acetaldehyde in the presence of palladium chloride

vinyl acetate/acrylate and vinyl acetate emulsions.

and cupric chloride.

“Warfarin” [Velsicol]. (3-(␣-acetonylben-

Wagner-Jauregg reaction. Addition of male-

zyl)-4-hydroxycoumarin).

ic anhydride to diarylethylenes with formation of bis

CAS: 81-81-2.

adducts that can be converted to aromatic ring

O(OH)(O)CH(CH

COCH

systems.

Properties: Colorless crystals; odorless; tasteless.

Mw 308.35, mp 161C. Soluble in acetone, dioxane;

slightly soluble in methanol, ethanol; very soluble in

Wagner-Meerwin rearrangement. Carbon-

alkaline aqueous solution; insoluble in water and

to-carbon migration of alkyl, aryl, or hydride ions.

benzene.

The original example is the acid-catalyzed rear-

Hazard: A poison. TLV: 0.1 mg/m

rangement of camphene hydrochloride to isobornyl

Use: Anticoagulant rodenticide.

chloride.

warning odor. A distinctive odor imparted to

Waksman, Selman A. (1888–1973). Ameri-

fuel gases for safety purposes, because they have

can microbiologist (Nobel Prize winner in 1952) and

little or no odor of their own. Ethanethiol and other

professor at Rutgers University. He was the first to

malodorous mercaptan derivatives are added to nat-

use the term antibiotic to designate the mold-pro-

ural gas, SNG, LPG, etc., for this purpose.

duced antibacterial substances discovered by Flem-

ing in 1928. He became the outstanding authority in

warp. The lengthwise threads or strands of a tex-

this field.

tile fabric.

Walden inversion. Inversion of configuration

wash-and-wear fabric. See aminoplast

of a chiral center in bimolecular nucleophilic substi-

resin.

tution reactions.

washing soda. (soda crystals).

Walker, John E. (1941– ). An English chemist

•10H

who won the Nobel Prize in 1997 for his work on

See soda ash; sodium carbonate monohydrate.

elucidating the enzymatic mechanism by which

ATP synthase (ATPase) catalyzes the synthesis of

waste, chemical.

See chemical waste.

adenosine triphosphate (ATP), the energy source of

living cells. He is a senior scientist at the Medical

waste control. Waste materials can be classified

Research Council Laboratory of Molecular Biology,

by type, as gaseous, liquid, solid, and radioactive;

Cambridge, England. He received his Ph.D. from

and by source, as chemical, municipal, agricultural,

Oxford University, Great Britain.

urban, and nuclear. Many methods of treating

See Boyer, Paul D., Skou, Jens C.

wastes, either by converting them to useful by-prod-

ucts or by disposing of them, are in operation or

Wallach, Otto. (1847–1931). A German chem- under experimentation. Dumping in streams and

ist who received the Nobel Prize for chemistry in rivers has long been illegal and ocean dumping has

1910 for his work in alicylic compounds. His men- been prohibited since 1973. Methods of disposal or

tors were Hofmann and Wahler, and he worked at treatment include incineration (garbage, paper, plas-

the University of Bonn under Kekule. He studied tics), precipitation (smoke, solid-in-liquid suspen-

pharmacy and did work on terpenes, camphors, and sions), adsorption (gases and vapors), chemical

essential oils. This was followed by research in aro- treatment (neutralization, ion-exchange, chlorina-

matic oils, perfumes, and spices. He studied thuja oil tion), reclamation of sulfite liquors (paper industry),

and fenchone. His research on terpenes revealed reclaiming (paper, metals, rubber), compaction (ur-

their significance in sex hormones and vitamins. ban wastes), bacterial digestion (sewage), commi-

Ethereal oils and industrial uses were made possible nution, and melting (glass, metals). Some cases may

by his work. involve a combination of these methods.

1324

1325 WATER POLLUTION

The following procedures should also be men- coatings, textile processing, moderator in nuclear

tioned: (1) Flash pyrolysis of certain solid wastes

reactors, debarking logs, industrial coolant, filtra-

yields synthetic fuel oil and other useful products.

tion, washing and scouring, sulfur mining, hydroly-

(2) Urban, animal, and agricultural wastes can be

sis, Portland cement, hydraulic systems, power

fermented by anaerobic bacteria to yield proteins,

source, steam generation, food industry, source of

fuel oil, etc.; the possibilities of converting cannery

hydrogen by electrolysis and thermochemical de-

and other food-processing wastes into protein-rich

composition.

foods and feeds are being investigated. (3) Catalytic

See hydrogen; ice; steam; heavy water; ocean water;

oxidation of exhaust emission gases; devices have

water, hard.

been installed in cars since 1973 for air-pollution

control. (4) Recovery of methane from manures. (5)

“Water Based Ink Wash” [Ulano]. TM

Incorporation of special additives to certain plastics

for liquid cleaner.

(polystyrene bottles) to render them biodegradable.

Use: To remove all solvent based inks from screen

(6) High-pressure hydrogenation of garbage to yield

after printing, leaving film stencil intact.

a low-sulfur combustible oil. (7) Deactivating ra-

dioactive wastes by adsorption or ion exchange, as

water, bound. See bound water.

well as by solidification and hydraulic fracturing;

high-activity wastes are buried in steel-lined con-

water of crystallization. Water chemically

crete tanks. (8) Catalytic oxidation of waste chlori-

combined in many crystallized substances; it can be

nated hydrocarbons, with partial recovery of chlo-

removed at or near 100C, usually with loss of crys-

rine. (9) Incineration of semisolid and liquid wastes

talline properties.

at sea in ships designed for that purpose. See

radioactive waste; chemical waste; sewage

water gas. (blue gas). A mixture of gases made

sludge; urban waste.

from coke, air, and steam. The steam is decomposed

by passing it over a bed of incandescent coke or by

waste, hazardous. See chemical waste; ra-

high-temperature reaction with natural gas or simi-

dioactive waste.

lar hydrocarbons. Approximate composition: car-

bon monoxide 40%, hydrogen 50%, carbon dioxide

waste, radioactive. See radioactive waste.

3%, and nitrogen 3%.

Hazard: Flammable, dangerous fire and explosion

waste wool, wet. See wool waste. risk. Explosive limits 7–72% in air. Toxic by inhala-

tion.

Use: Organic synthesis, fuel gas, ammonia synthesis.

“Watchung” [Du Pont]. TM for precipitated

See synthesis gas.

diazo red pigments.

water glass. See sodium silicate.

water. (ice, steam). H

O or HOH.

Properties: Colorless liquid; odorless; tasteless. Al-

water, hard. Water containing low percentages

lotropic forms are ice (solid) and steam (vapor).

of calcium and magnesium carbonates, bicarbon-

Water is a polar liquid with high dielectric constant

ates, sulfates, or chlorides as a result of long contact

(81 at 17C), which largely accounts for its solvent

with rocky substrates and soils. Degree of hardness

power. It is a weak electrolyte, ionizing as H

and

is expressed either as grains per gallon or parts per

−

. At atmospheric pressure it has d 1.00 (4C), fp

million (ppm) of calcium carbonate (1 grain of

0C (32F), and expands about 10% on freezing. Vis-

CaCO

per gal is equivalent to 17.1 ppm). Up to 5

cosity 0.010019 poise (20C), sp heat 1 cal/g, vap

grains is considered soft; more than 30 grains is very

press 760 mm Hg (100C), triple p 273.16K (4.6

hard. Hardness may be temporary (carbonates and

mm), surface tension 73 dynes/cm (20C), latent heat

bicarbonates) or permanent (sulfates, chlorides).

of fusion (ice) 80 cal/g, latent heat of condensation

Treatment with zeolites is necessary to soften per-

(steam) 540 cal/g, bulk d 8.337 lb/gal, 62.3/lb/cu ft,

manently hard water. Temporary hardness can be

refr index 1.333. Water may be superheated by enc-

reduced by boiling. These impurities are responsible

losing in an autoclave and increasing pressure; it

for boiler scale and corrosion of metals on long

may be supercooled by adding sodium chloride or

contact. Hard waters require use of synthetic deter-

other ionizing compound. It has definite catalytic

gents for satisfactory sudsing.

activity, especially of metal oxidation. Physiologi-

See zeolite.

cally water is classed as a nutrient substance.

Derivation: (1) Oxidation of hydrogen; (2) end prod-

watermark. See dandy roll.

uct of combustion; (3) end product of acid-base

reaction; (4) end product of condensation reaction.

Purification: (1) Distillation; (2) ion exchange reac-

water pollution. Contamination of fresh- or

tion (zeolite); (3) chlorination; (4) filtration. saltwater with materials that are toxic, noxious, or

Use: Suspending agent (papermaking, coal slurries), otherwise harmful to fish and other animals and to

solvent (extraction, scrubbing), diluent, beer and humans, including thermal pollution. Disposal of

carbonated beverages, hydration of lime, paper untreated chemical and municipal wastes in streams

1326WATERPROOFING AGENT

and rivers has been illegal since the early 1900s; in

wattle bark. (Australian bark; mimosa bark).

1973 the EPA prohibited dumping of all types of Derivation: From the Australian and South African

wastes into the ocean. Unintentional pollution re- wattles and South African acacias. Bark contains

sults from runoff containing toxic insecticidal resi- 25–35% tannin.

dues. Oil spills at sea are a continual problem and Grade: Based on tannin content.

probably will remain so. Use: Source of wattle bark extract, used in vegetable

See waste treatment; Environmental Protection tanning of leather, especially retannage of upper

Agency; environmental chemistry. leathers and production of heavy leathers.

waterproofing agent. (1) Any film-forming

wave function. In quantum mechanics, a com-

substance that coats a substrate with a water-repel-

plex function extending over the configuration

lent layer, such as paint, a rubber or plastic film, a

space of a system; its complex conjugate yields the

wax, or an asphaltic compound. These are used on a

probability density function, and other mathemati-

wide variety of surfaces, including cement, mason-

cal operations yield other physical quantities.

ry, metals, textiles, etc.

(2) Any metal salt or other chemical that impreg-

wax. A low-melting organic mixture or compound

nates textile fibers in such a way as to give an air-

of high molecular weight, solid at room temperature

permeable, water-resistant product. There are three

and generally similar in composition to fats and oils

types of these: renewable, semidurable, and durable.

except that it contains no glycerides. Some are hy-

Renewable repellents are water dispersions contain-

drocarbons, others are esters of fatty acids and alco-

ing aluminum acetate or formate, emulsifying

hols. They are classed among the lipids. Waxes are

agents and protective colloids in the continuous

thermoplastic, but since they are not high polymers,

phase, and a blend of waxes in the disperse phase.

are not considered in the family of plastics. Com-

Semidurable repellents involve precipitation of in-

mon properties are water repellency, smooth tex-

soluble metal salts on the fibers; water-soluble soaps

ture, low toxicity, freedom from objectionable odor

and waxes are usually added to the mixture, which is

and color. They are combustible and have good

especially effective on synthetic fibers. Durable re-

dielectric properties; soluble in most organic sol-

pellents coat each fiber with a protective film with-

vents; insoluble in water. The major types are as

out bonding them together or sealing the apertures.

follows:

I. Natural

water purification. (water conditioning).

1. Animal (beeswax, lanolin, shellac wax,

Any process whereby water is treated in such a way

Chinese insect wax)

as to remove or reduce undesirable impurities. The

2. Vegetable (carnauba, candelilla, bayberry,

following methods are used: (1) sedimentation, in

sugar cane)

which coarse suspended matter is allowed to settle

3. Mineral

by gravity in special tanks or reservoirs; (2) coagula-

(a) Fossil or earth waxes (ozocerite, ceresin,

tion of aggregates (called “floc”) by means of alumi-

montan)

num sulfate, ferric sulfate, or sodium aluminate (the

(b) Petroleum waxes (paraffin, microcrystal-

aggregates are formed from colloidally dispersed

line) (slack or scale wax)

impurities activated by the coagulant); (3) filtration

II. Synthetic

through a bed of fine sand, either by gravity flow or

1. Ethylenic polymers and polyol ether-esters

by pressure, to remove suspended particles; (4)

(“Carboxwax,” sorbitol)

chlorination, which is effective in sterilizing potable

2. Chlorinated naphthalenes (“Halowax”)

water, swimming pools, etc.; (5) adsorption on acti-

3. Hydrocarbon type, i.e., Fischer-Tropsch

vated carbon for removal of organic contaminants

synthesis

causing unpleasant taste and odor; (6) hardness re-

moval by ion-exchange or zeolite process.

Use: Polishes, candles, crayons, sealants, sun-crack-

The USDA has reported that mercury can be re-

ing protection of rubber and plastic products, abher-

moved from water by treatment with low concentra-

ent, cosmetics, paper coating, packaging food prod-

tions of black liquor from kraft papermaking.

ucts, electrical insulation, waterproofing and

cleaning compounds, carbon paper, precision in-

water-soluble gum. See gum, natural.

vestment casting.

water-soluble oil. Ammonia, potash, or sodium

wax, chloronaphthalene.

soaps of oleic, rosin, or naphthenic acids dissolved

Properties: Translucent, black, light and varied col-

in mineral oils.

ors. D 1.40–1.7 (300F), mp 87.7–129.4C, bp

Use: Boring, lathe-cutting, milling, polishing lubri-

287–371C. Soluble in many organic solvent liquids

cants, dressing textile fibers, dust laying.

and oils (when heated together).

See soluble oil.

Derivation: By chlorinating naphthalene.

Hazard: Toxic by ingestion and skin contact.

water-soluble resin. See polymer, water-sol- Use: Condenser impregnation, moisture-, flame-,

uble. acid-, insect-proofing of wood, fabric, and other

1327 WESTON CELL

fibrous bodies; moisture- and flameproofing cov- for metals: (1) An oxyacetylene flame is applied

ered wire and cable; solvent (for rubber, aniline and with a torch to the butted ends or edges of the pieces

other dyes, mineral and vegetable oils, varnish gums to be joined. (2) A method called brazing is similar

and resins, and other waxes when mixed in the mol- to (1), except that a nonferrous filler alloy is inserted

ten state). between the pieces. A number of alloys are used,

e.g., Ag/Cu/Zn; the filler cannot be remelted. It

forms an intermetallic compound at the interfaces.

wax, microcrystalline. A wax, usually

(3) In resistance welding, the heat is provided by the

branched-chain paraffins, characterized by a crys-

resistance to an electric current as it passes through

talline structure much smaller than that of normal

the material. No filler metal is used. (4) In ultrasonic

wax and also by much higher viscosity. Obtained by

welding, the heat source is the friction resulting

dewaxing tank bottoms, refinery residues, and other

from ultrasonic vibrations. It is a type of friction

petroleum waste products; they have an average

welding. (5) Electron-beam welding is a compara-

molecular weight of 500–800 (twice that of paraf-

tively recent technique in which energy is supplied

fin). Viscosity 45–120 sec (SUS at 98.9C), penetra-

by a stream of electrons focused by a magnetic field

tion value 3–33. Petroleum-derived products are

under high vacuum. It is used for complicated weld-

used for adhesives, paper coating, cosmetic creams,

ments of tool steels.

floor wax, electrical insulation, heat-sealing, glass

The following methods are used for welding such

fabric impregnation, leather treatment, emulsions,

thermoplastics as polyvinyl chloride, HDPE, poly-

etc. Some natural products, notably chlorophyll, are

propylene, and polycarbonates: (1) Hot gas tech-

classed as microcrystalline waxes.

nique, in which an electrically or gas-heated “gun”

melts a rod of the same material as the parts to be

wax, polymethylene. White, odorless solid

joined. (2) Friction welding, in which heat is gener-

with congealing point of 96.1C. Offered in flaked

ated by rapid rubbing together of the two surfaces,

form. Approved by FDA.

one of which is held stationary while the other is

rubbed against it at a speed great enough to cause

wax tailings. Brown, sticky, semiasphalt prod-

softening. (3) Ultrasonic welding, which is also used

uct obtained in the destructive distillation of petrole-

for metals. See (4) above. See solder.

um tar just before formation of coke.

Use: Wood preservative, roofing paper.

“Wellbrom” [Albemarle]. TM for sodium

“Weatherometer.” See aging (c).

bromide solution, completion fluid.

Use: Completion, work-over and packer fluid in oil-

web. A roll of paper as it comes from the fourdrini-

field applications.

er machine and used to feed a rotary printing press.

Werner, A. (1866–1919). A native of Switzer-

weedkiller. See herbicide.

land, Werner was awarded the Nobel Prize for his

development of the concept of the coordination

Weerman degradation. Formation of an al-

theory of valence, which he advanced in 1893. His

dose with one less carbon atom from an aldonic acid

ideas revolutionized the approach to the structure of

by a Hoffmann-type rearrangement of the corre-

inorganic compounds and in recent years have per-

sponding amide. This is a general reaction of ␣-

meated this entire area of chemistry. The term Wer-

hydroxy carboxylic acids.

ner complex has largely been replaced by “coordina-

tion compound.”

weight. See mass.

Wessely-Moser rearrangement. Rearrange-

weighting agent. (1) In soft drink technology,

ment of flavones and flavanones possessing a 5-hy-

an oil or oil-soluble compound of high specific grav-

droxyl group, through fission of the heterocyclic

ity, such as a brominated olive oil, which is added to

ring and reclosure of the intermediate diaroylmeth-

citrus flavoring oils to raise the specific gravity of

anes in the alternate direction.

the mixture to about 1.00, so that stable emulsions

with water can be made for flavoring. (2) In the

Western blot. A technique for analyzing mix-

textile industry a compound used both to deluster

tures of proteins to show the presence, size, and

and lower the cost of a fabric, at the same time

abundance of one particular type of protein.

improving its “hand” or feeling. Zinc acetylaceto-

See DNA; Northern blot; protein; RNA; Southern

nate, clays, chalk, etc. are used.

blot.

welding. Joining or bonding of metals or thermo-

plastics by application of temperatures high enough

Weston cell. An electrical cell used as a standard

to melt the materials so that they fuse to a permanent that consists of an amalgamated cadmium anode

union on cooling. In general, the temperatures used covered with crystals of cadmium sulfate dipping

for thermoplastics are considerably lower than re- into a saturated solution of the salt, and a mercury

quired for metals. The following methods are used cathode covered with solid mercury sulfate.

1328WESTPHALEN-LETTRE

Westphalen-Lettre rearrangement. Dehy- (corn, rye, or barley). After distillation whiskey is

dration of 5-hydroxycholesterol derivatives accom- aged in wooden containers for several years. The

panied by C-10 to C-5 methyl migration in com- following changes occur during aging: extraction of

pounds with a ␤-substituent in C-6. wood components (acids and esters), oxidation of

the components of the liquid, and reaction between

organic compounds in the liquid, forming new

wet deposition. See acid precipitation.

flavors.

Hazard: Flammable, moderate fire risk. A noncumu-

wetting agent. A surface-active agent that,

lative poison; usually harmless in moderate amounts

when added to water, causes it to penetrate more

but may be toxic when habitually taken in large

easily into, or to spread over the surface of, another

amounts.

material by reducing the surface tension of the wa-

Use: Beverage, medicine (stimulant, antiseptic, vaso-

ter. Soaps, alcohols, and fatty acids are examples.

dilator).

See detergent.

See ethanol; proof.

WFNA. Abbreviation for white fuming nitric

acid.

white acid. A mixture of ammonium bifluoride

See nitric acid, fuming.

and hydrogen fluoride used for etching glass.

Hazard: Strong irritant to skin and tissue.

Wharton reaction. Reduction of ␣,␤-epoxy

ketones by hydrazine to allylic alcohols.

white arsenic. See arsenic trioxide.

wheat germ oil. Light-yellow, fat-soluble oil

white copperas. See zinc sulfate.

extracted from wheat germ.

Use: A food supplement.

white dye. An optical bleach or, in general, any

See tocopherol.

substance, such as bluing, that may be added to a

white article to increase its apparent whiteness.

whey. The serum remaining after removal of the

solids (fat and casein) from milk. Dried whey con-

white gasoline. See gasoline.

tains about 13% protein, 71% lactose, 2.3% lactic

acid, 4.5% water, and 8% ash, including a low con-

white gold. Alloy of 90% gold and 10% palladi-

centration of phosphoric anhydride. Besides its val-

um, or 59% nickel and 41% gold.

ue as an inexpensive source of protein for animal

feeds, whey is used as a source of lactose and lactic

white lead. Name primarily applied to lead car-

acid, as well as for the synthesis of riboflavin, ace-

bonate, basic, but also used for lead sulfate, basic

tone, butanol, and fuel-grade ethanol by fermenta-

(white lead sulfate), and lead silicate, basic (white

tion processes. Some types of cheese are made from

lead silicate).

whey, and it is also a possible culture medium. Dried

Hazard: Toxic by ingestion and skin absorption.

whey may be used to replace up to 75% of the polyol

Content in paints limited to 0.05% (FDA).

component of rigid polyurethane foams.

Use: Paint pigment.

See lactose.

white liquor. See liquor (c).

whiskers. Single, axially oriented, crystalline fi-

laments of metals (iron, cobalt, aluminum, tungsten,

white metal. (1) Any of a group of alloys having

rhenium, nickel, etc.), refractory materials (sap-

relatively low melting points. They usually contain

phire, aluminum oxide, silicon carbide), carbon, bo-

tin, lead, or antimony as the chief component. Type

ron, etc. They have tensile strengths of 3–6 million

metal, Babbitt, pewter, and Britannia metal are of

psi and very high elastic moduli. Their upper tem-

this group. (2) Copper matte containing about 75%

perature limit in oxidizing atmospheres may be as

copper, as obtained in copper smelting operations.

high as 1700C and in inert atmospheres up to 2000C.

See copper.

Length may be up to two inches, with diameter up to

10 microns. Their chief use is in the manufacture of

whitener. (1) Any of several oil-in-water emul-

composite structures with plastics, glass, or graphite

sions in powder form that are dried and concentra-

that have many applications in the aircraft and space

ted; when added to an aqueous medium they form

vehicle field, where their high heat capacity and

stable emulsions, giving a white color and a cream-

tremendous strength are invaluable, especially as

like body to coffee. A typical formulation contains

ablative agents.

vegetable fat, protein, sugar, corn syrup solids, plus

emulsifier and stabilizers. (2) A white pigment or

whiskey.

colorant used in the paper and textile industries.

Properties: Light-yellow to amber liquid. D

0.923–0.935 (15.56C), 47–53% alcohol by volume,

flash p 26.6C (CC).

white oil. Any of several derivatives of paraffin-

Derivation: Distillation of fermented malted grains ic hydrocarbons having moderate viscosity, low vol-

1329 “WILUBE 655”

atility, and high flash point. Available in USP grade.

Wij’s solution. ICl

and I

Combustible. Source: Iodine chloride (9.4 g) and iodine (7.2 g) are

Use: Textile lubricant and finishing agent, plastics dissolved separately in glacial acetic acid and the

modifier. solutions added together.

Use: Determination of iodine values of fats and oils.

white phosphorus. See phosphorus.

wild type. The form of an organism that occurs

most frequently in nature.

white precipitate. See mercury, ammoniated.

Wilkinson, Geoffrey. (1921–1996). A British

white shellac. See shellac, bleached.

organic chemist who won the Nobel Prize for chem-

istry in 1973 with Fischer. Their work involved

white vitriol. See zinc sulfate.

research on organometallic compounds. He was a

professor at the University of California and Har-

whitewash. A suspension of hydrated lime or

vard before returning to University of London as

calcium carbonate in water used for temporary anti-

professor of inorganic chemistry.

septic coatings of interiors of chicken houses and the

like.

willemite. Zn

SiO

. Natural zinc orthosilicate.

See calcimine.

Troostite is a manganese-bearing variety.

Properties: Color yellow, green, red, brown, white;

whiting. Finely ground, naturally occurring calci-

luster vitreous to resinous; sometimes fluoresces in

um carbonate, CaCO

, 98% pure, contaminated with

UV light. Mohs hardness 5.5, d 3.3.

silica, iron, aluminum, or magnesium.

Occurrence: New Jersey, New Mexico, Africa,

Properties: White or off-white powder. D 2.7. Insol-

Greenland.

uble in water; soluble in acids. It has no tinctorial

Use: Ore of zinc, a phosphor.

power and hence is not a pigment.

Derivation: Traditionally from chalk, obtained from

Willgerodt reaction. Discovered in 1887, this

England, France, Belgium. A pure limestone or cal-

reaction involves heating a ketone, e.g., ArCOCH

cite is the principal commercial source. Crude chalk

with an aqueous solution of yellow ammonium sul-

or limestone is ground dry or wet, air- or water-

fide (sulfur dissolved in ammonium sulfide). It re-

floated, and sieved. Grades are based on particle

sults in formation of an amide derivative of an aryla-

size, softness, and light reflectance. Dry ground, air-

cetic acid and in some reduction of the ketone:

floated limestone whiting can be as fine as 99%

ArCOCH

+ (NH)

→ ArCH

CONH

through 300-mesh.

ArCH

. The dark reaction mixture usually is

Grade: Various. Paris white is the finest; coarser

refluxed with alkali to hydrolyze the amide, the

grades are extra gilders whiting, gilders whiting, and

arylacetic acid being recovered from the alkaline

commercial, the last being quite coarse and of poor

solution (L. & M. Fieser).

color. A putty grade is also sold.

Use: Filler in rubber, plastics, and paper coatings;

Williamson synthesis. An organic method for

putty (with linseed oil); whitewashes; sealants.

preparing ethers by the interaction of an alkyl halide

See calcium carbonate; chalk.

with a sodium alcoholate (or phenolate).

Whiting reaction. Alkynediols are reduced by

Willstater, Richard. (1872–1942). A German

lithium aluminum hydride in ether or tertiary amines

chemist who won the Nobel Prize for chemistry in

to dienes.

1915 for his work with plant pigmentation. His edu-

cation was at the University of Munich where he

Wichterle reaction. Modification of the Rob-

studied and taught before going to Zurich, Switzer-

inson annellation reaction in which 1,3-di-

land. He researched chlorophylls and pigments of

chloro-cis-2-butene is used instead of methyl vinyl

plants and the relationship of cornflower blue to rose

ketone.

red. Work included the study of alkaloids including

cocaine, tropine, and atropine. His work perfected

Widman-Stoermer synthesis. Synthesis of

the process of chromatographic partition.

cinnolines by cyclization of diazotized o-aminoaryl-

ethylenes at room temperature.

“Wilube 139” [Wilube]. TM for a semisyn-

thetic machine and grinding coolant with lubricating

and pressure additives.

Wieland, Heinrich O. (1877–1957). A Ger-

Use: As a machine and grinding coolant.

man chemist who won the Nobel Prize for chemistry

in 1927. His research included work on bile acids,

organic radicals, nitrogen compounds, toxic sub-

“Wilube 655” [Wilube]. TM for a synthetic

stances, and chemical oxidation, as well as the dis- fluid grinding lubrication.

covery of the structure of cholesterol. He received Use: Provides hard water stability and low foam

his Ph.D. from the University of Munich. characteristics.

1330“WILUBE BLUE”

“Wilube Blue” [Wilube]. TM for a premium Derivation: Products from coconut oil.

grade oil containing extreme pressure additives. Grade: Liquid, hard fats, flake, and powder form.

Use: To inhibit growth of bacteria and fungus in hard Use: As dispersants, cream bases, emollients, refat-

ting agents, emulsifiers, suppository bases, and con-

water.

sistency regulators.

Wilzbach procedure. Exposure of organic

witherite. BaCO

. A natural barium carbonate

compounds to tritium gas yields tritiated products of

usually found in veins with lead ores.

high activity without extensive radiation damage.

Properties: White, yellowish, or grayish; vitreous,

Concentrations of tritium ranging from 1 to 90 milli-

inclining to resinous, luster. D 4.27–4.35, Mohs

curies per gram have been obtained with quite varied

hardness 3–3.75.

compounds.

Occurrence: U.S. (Kentucky, Lake Superior re-

gion), England (most important source).

Windaus, Adolf. (1876–1959.) A German

Hazard: Toxic by ingestion, skin irritant.

chemist who won the Nobel Prize for chemistry in

Use: Chemicals (barium dioxide, barium hydroxide,

1928. His work involved the study of steroids and

blanc fixe), plate glass and porcelain, brick making,

the effect of ultraviolet light activity, ergosterol, and

rodenticide.

vitamin D

. He also researched digitalis and hista-

mine. Although he studied medicine, he received his

Wittig, George. (1897–1987). A University of

doctorate in chemistry at the University of Freiburg.

Heidelberg professor who won the Nobel Prize for

chemistry in 1979 along with Brown of Purdue.

wine. The fermented juice of grapes or other fruits

Wittig’s research showed that phosphorous ylids

or plants. Contains 7–20% alcohol (by volume). The

react with ketones and aldehydes to form alkenes.

higher percentages are obtained by addition of pure

This reaction is used a great deal in the synthesis of

alcohol (fortifying). Coloring matter, sugars, and

pharmaceuticals and other complex organic sub-

small amounts of acetic acid, salts, higher fatty

stances.

acids, etc. give wines their distinctive appearance

and flavor.

Wittig reaction. Preparation of olefins from

Hazard: Flammable, moderate fire risk.

alkylidene phosphoranes (ylids) and carbonyl com-

pounds.

wine ether. See ethyl pelargonate.

Wittig rearrangement. Rearrangement of

wine gallon. Same as U.S. gallon.

ethers with alkyl lithiums to yield alcohols via a 1,2

shift.

wine lees. A deposit or sediment formed in the

bottom of wine casks during fermentation. Wine

“Wizard” [Velocity]. TM for an aqueous solu-

lees vary greatly in quality, but usually contain

tion for degreasing commercial kitchens.

20–35% potassium acid tartrate and up to 20% calci-

um tartrate. They also contain yeast cells, proteins,

and other solid matter that was suspended in the

WLN. (Wiswesser Line-Formula notation). A

grape juice. system for converting chemical structural diagrams

Use: Source of tartaric acid and tartarates. to a linear string of symbols of letters and numbers.

See Pasteur, Louis; tartaric acid.

wobble. The relatively loose base pairing be-

“Wingstay 29” [Goodyear]. TM for p-orient-

tween the base at the 3

′

end of a codon and the

ed styrenated diphenyl amine.

complementary base at the 5

′

end of the anticodon.

Available forms: Liquid or powder.

Use: Stabilizer for SBR and NBR, back-loaded com-

Wohl degradation. Method for the conversion

pounds using diene polymer systems.

of an aldose into an aldose with one less carbon atom

by the reversal of the cyanohydrin synthesis. In the

wintergreen oil. See methyl salicylate.

Wohl method, the nitrile group is eliminated by

treatment with ammoniacal silver oxide.

winterize. A process of refrigerating edible and

lubricating oils to crystallize the saturated glycer-

Wohler, Friedrich. (1800–1882). A native of

ides, which are then removed by filter pressing.

Germany, Wohler, working with Berzelius, placed

the qualitative analysis of minerals on a firm founda-

wire cloth. See screen; filter media.

tion. In the early 19th century, chemists still thought

it impossible to synthesize organic compounds. In

Wiswesser Line-Formula notation. See

1828, Wohler publicized his laboratory synthesis of

WLN.

urea, which he had obtained four years previously

by heating the inorganic substance ammonium cya-

“Witepsol” [Degussa]. TM for fatty acid nate; the synthesis is a result of intramolecular rear-

esters. rangement:

1331 WOOD FLOUR

Properties: Black to brown color, submetallic to

resinous luster, black to brown streak. Mohs

hardness 5–5.5, d 7.0–7.5.

Occurrence: Colorado, South Dakota, Nevada, Aus-

This was the beginning of the science of synthetic

tralia, Bolivia, Europe.

organic chemistry.

Use: Chief ore of tungsten.

Wohler synthesis. Classical synthesis of urea

wolfram white. See barium tungstate.

by heating an aqueous solution of ammonium cya-

nate extended to preparation of urea derivatives.

wollastonite.

CAS: 13983-17-0. CaSiO

. A natural calcium sili-

Wohlwill process. The official process of the

cate found in metamorphic rocks.

U.S. mints for refining gold. It consists in subjecting

Properties: White to brown, red, gray, yellow solid;

gold anodes to electrolysis in a hot solution of hy-

vitreous to pearly luster. Mohs hardness 4.5–5, d

drochloric acid containing gold chloride, the solu-

2.8–2.9.

tion being continuously agitated with compressed

Occurrence: New York, California.

air.

Grade: Fine, medium paint grades.

Use: Ceramics; paint extender; welding rod coatings;

Wohl-Ziegler reaction. Allylic bromination

rubber filler; silica gels; paper coating; filler in plas-

of olefins with N-bromosuccinimide. Peroxides or

tics, cements, and wallboard; mineral wool; soil

ultraviolet light is used as initiators.

conditioner.

Wolffenstein-Boters reaction. Simultaneous

“Women Plus” [Fu-E Life]. TM for a rich

oxidation and nitration of aromatic compounds to

source of soybean protein essence with a wealth of

nitrophenols with nitric acid or the higher oxides of

vitamins.

nitrogen in the presence of a mercury salt as catalyst.

Hydroxynitration of benzene yields picric acid.

wood. A mixture composed of 67–80% holocellu-

Wolff-Kishner reaction. This reduction reac- lose and 17–30% lignin, together with low percent-

tion was discovered independently in Germany ages of resins, sugars, a variable amount of water,

(Wolff, 1912) and in Russia (Kishner, 1911). A and potassium compounds. Its fuel value varies

ketone (or aldehyde) is converted into the hydra- widely around 3000–6000 Btu/lb according to vari-

zone, and this derivative is heated in a sealed tube or ety, moisture, etc. Combustible.

an autoclave with sodium ethoxide in absolute eth- Use: Pulp and paper, construction, packaging and

anol. cooperage, furniture, destructive distillation prod-

After preliminary technical improvements, Huang ucts (charcoal), extraction products (turpentine, ro-

Minlon (1946) introduced a modified procedure by sin, tall oil, pine oil, etc.), methanol, plywood, fuel,

which the reduction is conducted on a large scale at rayon and cellophane, flock.

atmospheric pressure with efficiency and economy Note: Catalytic conversion of wood chips to fuel oil

(L. & M. Fieser). and methanol is under development.

See biomass.

Wolff rearrangement. Rearrangement of dia-

zoketone to ketenes by action of heat, light or some

wood alcohol. See methanol.

metallic catalysts. The rearrangement is the key step

in the Arndt-Eistert synthesis.

wood ash. The inorganic residue of wood com-

bustion.

wolfram. Wolfram is the official international

Use: Fertilizer for its potash content, which averages

alternate name for tungsten. Tungsten is preferred in

about 4% K

the U.S.

See tungsten.

wood flour. (wood flock). Pulverized dried

wolframic acid, anhydrous. See tungstic

wood from either soft- or hardwood wastes. Graded

oxide.

according to color and fineness.

Grade: Domestic standard, domestic fine, imported

wolframite. (Fe,Mn)WO

. A natural tungstate of 40–60 mesh, 70–80 mesh, etc.

iron and manganese. Ferberite is the iron-rich mem- Hazard: Flammable, dangerous fire risk, especially

ber of the series, and huebnerite is the manganese- suspended in air.

rich member. Use: Extender and filler in dynamite, plastics, rubber,

1332WOOD, INDURATED

paperboard; fur cleaning; polishing agents; Sorel

wool. Staple fibers, usually 2–8 in. long, obtained

cement. from the fleece of sheep (and also alpaca, vicuna,

and certain goats). Physically, wool differs from hair

wood, indurated. A wood hardened by impreg- in fineness and by the presence of prominent cortical

nation with a phenol-formaldehyde product. scales and a natural crimp. The latter properties are

Use: Storage batteries. responsible for the felting properties of wool and the

ability of the fibers to cling together when spun into

wood, petrified. Wood in which the original yarns. Chemically, wool consists essentially of pro-

chemical components have been replaced by silica. tein chains (keratin) bound together by disulfide

The change occurs in such a way that the original cross linkages.

Properties: Tenacity ranges from 1 to 2 g/denier;

form and structure of the wood are preserved. The

elongation 25–50%, d 1.32, moisture regain 16%

most famous instance is the Petrified Forest of Ari-

(21.2C, 65% relative humidity), decomposes at

zona.

126C, scorches at 204C, resistant to most acids ex-

cept hot sulfuric, destroyed by alkalies and chlorine

wood pulp. See pulp, paper.

bleach, resistant to mildew but attacked by insects,

amphoteric to dyes. Combustible.

wood rosin. See rosin.

Source: Australia, Argentina, U.S., New Zealand,

Uruguay, the former U.S.S.R., England.

Wood’s metal. A four-component fusible alloy

Use: Outerwear, blankets, carpets, upholstery, felt,

used largely in sprinkler systems, it melts at 70C, the

clothing source of lanolin.

composition being bismuth 50%, cadmium 10%, tin

13.3%, lead 26.7%.

wool fat. See lanolin.

See alloy, fusible; eutectic.

wool waste. Wool from scrap materials cut up

wood sugar. See D(+)-xylose.

for remaking into cloth. Used as a fertilizer. Wool

waste usually contains from 4 to 7% ammonia. Pure

wood tar. See pine tar; creosote, coal tar;

wool shoddy may contain as much as 15% nitrogen

wood-tar.

and is particularly valued by hop growers.

Hazard: Wet wool waste is flammable and a danger-

wood turpentine. See turpentine (oil).

ous fire risk.

Woodward-Hoffmann rules. Rules that pre-

work function. The energy needed to transport

dict the stereochemical course of concerted reac-

electrons, ions, and molecules from the inside of one

tions in terms of the symmetry of the interacting

medium into an adjoining medium.

molecular orbitals.

working draft DNA sequence. See Draft

Woodward cis-hydroxylation. The hydrox-

DNA Sequence.

ylation of an olefin with iodine and silver acetate in

acetic acid to give cis-glycols. The method involves

work, internal. The work done by a system

the trans addition of iodine and silver acetate to give

against internal forces or between its parts or upon

a trans-iodo-acetoxy derivative. The latter is hydro-

the system by these forces.

lyzed to a cis-mono-glycol acetate with acetic acid

and water. Alkaline hydrolysis results in the final

work, theoretical. Ideal reversible work calcu-

cis-glycol.

lated from properties.

Woodward, Robert B. (1917–1979). An

wormseed oil. See chenopodium oil.

American chemist born in Quincy, MA, and widely

regarded as one of the world’s leading synthetic

wormwood. See absinthium.

organic chemists. After receiving his doctorate from

M.I.T. (the youngest student in the history of the

wort. A clear infusion of grain extract (usually

institute to do so), he joined the Harvard faculty in

malt) used as the basis of fermentation in the brew-

1937 as instructor and attained full professorship in

ing industry.

1950. He was recipient of the Nobel Prize in 1965

See brewing.

for his brilliant work in synthesizing complex organ-

ic compounds, among them quinine, cholesterol,

wove. (paper).

chlorophyll, reserpine, and cobalamin (vitamin B

See dandy roll.

When he died in 1979, his synthesis of the antibiotic

erythromycin was virtually complete; it was fin-

ished by his associates two years later. He was direc-

writing ink. A solution of colorant in water,

tor of the Woodward Research Institute in Basel, usually containing also low concentrations of tannic

Switzerland, and a member of the governing board or gallic acid. Washable inks contain glycerol. Vari-

of the Weizmann Institute in Israel. ous water-soluble dyes are used for colored inks;

1333 WUTHRICH, KURT

dispersions of carbon black stabilized with a protec- lene and ethylene are produced in 1:1 ratio.

See acetylene.

tive colloid are used for drawing inks. Fountain pen

inks retain the fluidity of water; for ballpoint pens

the mixture is of a pastelike consistency.

Wurtz reaction. A method of synthesizing hy-

drocarbons discovered by Wurtz in 1855. It consists

wrought iron. A ferrous material, aggregated

in treatment of an alkyl halide with metallic sodium,

from a solidifying mass of pasty particles of highly

which has a strong affinity for bound halogen and

refined metallic iron into which 1–4% of slag is

acts on methyl iodide in such a way as to strip iodine

uniformly dispersed without subsequent melting.

from the molecule and produce sodium iodide. The

Wrought iron is distinguished by its low carbon and

reaction involves two molecules of methyl iodide

manganese contents. Carbon seldom exceeds

and two atoms of sodium.

0.035%, and manganese content is held at 0.06%

The reaction probably proceeds through the forma-

maximum. Phosphorus usually ranges from 0.10%

tion of methylsodium, which interacts with methyl

to 0.15%; it adds about 1000 psi for each 0.01%

iodide:

above 0.10%. Sulfur content is normally low, rang-

ing from 0.006% to less than 0.015%. Silicon con-

tent ranges from 0.075% to 0.15%; silicon content of

base metals is 0.015% or less. Residuals such as

chromium, nickel, cobalt, copper, and molybdenum

The Wurtz reaction can be applied generally to syn-

are generally low, totaling less than 0.05%. Wrought

thesis of hydrocarbons by the joining together of

iron is readily fabricated by standard methods and is

hydrocarbon residues of two molecules of an alkyl

quite corrosion resistant.

halide (usually the bromide or iodide). With halides

of high molecular weight the yields are often good

and the reaction has been serviceable in the synthe-

“WS-Extra 400” [Millenium]. TM for a

sis of higher hydrocarbons starting with alcohols

cooling agent blend for oral products.

found in nature.

wulfenite. PbMoO

, sometimes with calcium,

chromium, vanadium.

Wuthrich, Kurt. (1938– ). Born in Aarberg,

Properties: Yellow, orange, or bright-orange-red

Switzerland, Wuthrich won the Nobel Prize for

mineral of resinous luster. D 6.7–7.0, Mohs

chemistry in 2003 for his pioneering work concern-

hardness 2.75–3.

ing for the development of nuclear magnetic reso-

Occurrence: Found in veins with ores of lead in U.S.

nance spectroscopy for determining the three-di-

(Massachusetts, New York, Pennsylvania, Nevada,

mensional structure of biological macromolecules

Utah, New Mexico, Arizona), Europe, Australia.

in solution. He earned an undergraduate degree from

Use: Ore of molybdenum.

the University of Bernborn in Aarberg and a Ph.D. in

chemistry from the University of Basel, Switzer-

Wulff process. Production of acetylene by land. Currently a Professor of Biophysics in Eidgen-

treating a hydrocarbon gas with superheated steam rich, Switzerland and Cecil H. and Ida M. Green

in a regenerative type of refractory furnace at Visiting Professor of Structural Biology, The

1148–1371C. Contact times are very short. Acety- Scripps Research Institute, La Jolla, CA.