Ethylene oxide unit a t Wyandotte's new Geismar Works near Baton Rouge, Louisiana.

WYANDOTTE OXIDES . . building blocks for exciting new chemicals

One of the most rapidly brightening horizons in the chemical industry tod-ay is the field of alkylene oxides. New products based o n the "building block" ability of ethylene and propylene oxides, are coming out of the laboratories a t an ever-increasing rate. Boasting more than 16 years of extensive experience in experimental

and practical oxide chemistry, plus unexcelled research facilities, Wyandotte Chemicals is a leader in this fertile and diversified area. In oxides, as en other chemical frontiers, Wyandotte is Pacing Progress with Creative Chemistry. •

PETROLEUM—Wyandotte products based on alkylene oxides serve the oil industry in drilling muds as demulsifiers, and also find extensive application in the growing area of secondary oil recovery.

NATIONAL DEFENSE—Wyandotte, under the Navy's Bureau of Aeronautics, pioneered in the development of ethylene oxide a s a xnonopropellant for guided missile hardware.

TRANSPORTATION —Many of Wyandotte 's oxide products are used in antifreeze, lubricants and hydraulic fluids. Wyandotte research is working on several new products in this held.

WYANDOTTE n e w milestones in

When ethylene oxide reacts with an "active hydrogen" compound like one of the alcohols, glycols, phenols, amines or organic acids, the new product generally contains a hydroxy 1 group which can, in turn, react with another molecule of ethylene oxide to form another new product. This chain reaction, subject to designed controls, offers unlimited possibilities in the development of new products.

S T A G G E R I N G P O T E N T I A L When you add t o this the fact t h a t you can use ethylene oxide alone, propylene oxide alone, and that you can use them in random mixtures or ordered blocks, you begin to see the infinite variety of products that alkylene oxides can spawn.

T H E B E G I N N I N 6 Wyandotte 's interest in oxide chemistry reached sharp focus in the early- days of World War I I with the synthesis of allyl alcohol from propylene glycol. Then came investigation into the pro­duction of glycol ethers for hydraulic fluids and the production of PLURONIC© block-polymers with their impact on surface-active chemistry^.

A M A J O R D I S C O V E R Y The outgrowth of this work in block-polymers led to what is considered one of Wyandotte 's major contributions in the field of oxide chemistry. Namely, nonionic surfactants produced by sequen­tial condensation of propylene oxide and ethylene oxide with low-molecular-weight reactive hydro­gen compounds . . . and how discovery of this new molecular structure for nonionic surfactants was used to synthesize what are now known as Wyan­dotte PLURONIC polyols and TETRONIC® polyols.

T H E F I R S T C O M I V 1 E R C I A L B L O C K - P O L Y M E R S

The PLURO^STICS were the first block-polymers to be successfully employed commercially as non­ionic surface-active agents. And continuing research into alkylene oxides has led to Wyandot te ' s QUADROL,* M O X O L E N E , * PLURACOL® Ε series of polyethylene glycols, PLURACOL. Ρ series of poly­propylene glycols, PLURACOL T P triols, and many other products still in development stages.

W H A T ' S G O I N G ON N O W ? Present ^Yyandotte work in t h e field of oxide chemistry includes the extension of the block-

research triggers oxide chemistry polymer series towards the development of new uses for our present products, along with new products for urethanes, hydraulic fluids, lubri­cants , improved surfactants, and hundreds of other applications.

W H A T ' S A H E A D ? Continuing research into block-polymers may lead to new methods of bringing about the reactions of oxides with a host of other chemical compounds. Such, new reactions would undoubtedly open up zvhoL· new ranges of products whose resulting appli­cations cannot now even be predicted.

*Quadrol®—trademark for Ny Λ7, Ν', N'-tetrakis (2-hydroxypro-pyl) ethylenediamine

Monolene®—trademark for .V-(2-hydroxy propyl) ethylenedia m ine

Milestones in Wyandotte's oxide progress

U.S. Pat. Patent No. Granted

Ο ΑΑΛ CA(\ C 1 1 ΛΟ

2,479,632 8-23-49

2,503,050 4-4-50

2,521,170

2,577,256

2,600,654

2,690,655

2,601,538

2,674,619 2,677,700

9-5-50

12-4-51

6-17-52

6-17-52

6-24-52

4-6-54 5-4-54

2,716,137 8-23-55

2,718,509 9-20-55 2,786,080 3-19-57

2,855,370 10-7-58

Title

Production of ally! alcohol. Catalytic production of ally! alcohol from Propylene Oxide Process for producing aldehydes by isomerization of olefin alpha oxides. Process for aldehydo isomeriza­tion of olefin alpha oxides. Polyoxypropylene-benzene-sulfonamides Chromic oxide-cadmium chloride-cadmium oxide catalyst. Chromium oxide-tungsten oxide-iron oxide gel catalyst Catalytic isomerization of propy­lene oxide to propionaidehyde, catalyst therefor and synthesis of catalyst. Polyoxyalkylene compounds. Polyoxyalkylene surface active agents. Catalytic condensation of α, β, alkylene oxides. Plasticized resin compositions. Stabilized polyoxyalkylene compositions. Catalyst

PLASTICS—Wyandotte oxide products are widely used in the mush­rooming production of many grades of polyurethane foams—in flexible, semi-rigid and rigid forms—for myriad uses tliroughout industry.

CHEMICALS—Because they are versatile, reactive, and meet high industrial standards, Wyandotte oxides are widely employed as chemi­cal intermediates.

Please turn page ψ MEDICINE—Pîuronie F68, one of Wyandotte 's many oxide products, is employed as an emulsifying agent in therapeutic fat emulsions . . a n emergency source of calories for the injured-

(Continued from previous page)

Where can you use Wyandot te 's exper ience in a lky lene oxides?

Whatever ox ide products y o u use , it will pay you to investigate their purchase in tank-car quantities from Wyandotte. The savings are substantial and the quality is uniformly high.

WHATEVER YOUR BUSINESS, if it involves oxide chemistry there's a good chance

you can effectively use Wyandotte's experience.

It's quite possible one of Wyandotte's oxide products can improve your present product or assist in one you're developing—broaden its application by adding or changing chemical or physical properties.

For skilled assistance in the use of Wyandotte oxide products—detailed technical data—or other specific information—fill in and mail the coupon below.

Find out what Wyandotte's experience in oxide chemistry can do for you.

CHEMICALS M I C H I G A N A L K A L I D I V I S I O N

Wyandotte, Michigan · Offices in Principal Cities

| ) Send me more data as indicated below. j_J Have your representative call with data indicated below

1 1 Ethylene Oxide Π DIIP-MP [ 1, 4-bis-("2-hydroxypropyl) 2-methylpiperazine]

I I Diehloroethyl Ether L J Dichloroisopropyl Ether I I Diethylene Glycol I I Ethylene Dichloride Π Ethylene Gl}

I I Monolene [ X-(*2-hydroxypropyl) ethylenediamine]

I I Pluracol Ε (polyethylene glycols)

LJ Pluracol Ρ (polypropylene glycols)

Π Pluracol T P Triols

I I Pluronic Polyols.

I I Tetronic Polyols

Π Quadrol [X, X, N \ X'-tetrakis (v2-hydroxypro-pyl) ethylenediamine]

I I Propylene Oxide

D Propylene Dichloride

I I The advantages of buying oxide products in tank-car — quantities from Wyandotte.

I I Custom ethyoxylation by Wyandotte.

I I Data on using oxides for

Position_

Name of Firm

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City

IViÂIL TO: Wyandotte Chemicals Corporation, Michigan Alkali Division, Dept. 82S, Wyandotte, Michigan.

.Zone State.

Name

Wyandotte