CHEMICALS
C6 Olefins Provide Unique Structures Houdry develops process to make C6 olefins, possible monomers in stereospecific polymerizations 139TH
ACS
NATIONAL
MEETING
Petroleum Chemistry
Low cost Cr) olefins of high purity are now available from Houdry Process in research quantities. They provide a series of compounds having structures that aren't possible with the lower olefins. And one suggested u s e monomers for stereospecific polymerization—shows the practical significance of the selective process developed by Houdry to make the olefins. Details of the process and its products were presented by Dr. W. Lorz and co-workers of Houdry at a Symposium on Monomers and Polymers from Petroleum. The symposium was held jointly with the Division of Polymer Chemistry. Two of five possible C 6 paraffins— 2,2-dimethylbutane (neohexane) and 2,3-dimethylbutane (diisopropyl) —are starting points in making the olefins. Neohexane yields tert-butyl ethylene when catalytically dehydrogenated, and diisopropyl yields 2,3-dimethylbutenes and 2,3-dimethylbutadiene. The first product, tert-butyl ethylene, has some unique features. It is the smallest olefin with a quaternary carbon. It is also an ce-olefin and is the only C 6 olefin possible with that carbon skeleton. Convert Stocks. The two dimethylbutane stocks (99% purity) are converted in flow type, isothermal, catalytic reactors. In some cases, a pilot plant has been run adiabatically. The reactor effluent is cooled in a liquid nitrogen trap, and noncondensed gases pass through a vacuum pump for collection. Products are analyzed by gas chromatography, aided by mass spectrometry, and, in some cases, by infrared. A modified chromia-alumina catalyst of high activity and low isomerizing character was selected after several were tried. 76
C&EN
APRIL
10,
1961
A variety of chemical uses for tertbutyl ethylene have been suggested. These include epoxidation, oxidation, hydration, and hydroformylation. It was originally thought that the olefin would be of immediate polymer interest, since the next higher homolog, 4,4-dimethylpentene-l, has a stereoregulated polymer with a melting point above 400° C. However, polymerization has been unsuccessful so far, probably because of steric hindrance, Dr. Lorz believes. Molecular models show there is an available double bond, but spatial requirements of the catalysts aren't known. Unique Structure. The second starting material, 2,3-dimethylbutane, has another unique skeletal structure. If the compound can be catalytically dehydrogenated without extensive rearrangement or cracking, several possibilities arise. For example, there is a revived interest in 2,3-dimethylbutadiene-1,3, the only possible diolefin from this reaction, according to the Houdry team. It has been used in the past, notably in Germany, as the monomer for synthetic rubber. Other elastomers became available, and methyl rubber was abandoned. But Ziegler polymerization opens up new possibilities. The two monoolefins—2,3-dimethylbutene-1 and -2—coming from the 2,3-dimethylbutane starting material are also potentially useful. The butene-1, an a-olefin, might find some application as a monomer in Ziegler polymerization or as an intermediate in chemical synthesis, Dr. Lorz says. The parent 2,3-dimethylbutane is available commercially. It is made by catalytic alkylation of isobutane with ethylene, using aluminum chloride or its complexes as catalyst.
BRIEFS Dispersing agent for use in paper production is available in commercial quantities from Rohm & Haas, Philadelphia, Pa. Tamol SN is effective in
both acidic and basic solutions and promotes dispersion of solids without frothing or foaming in milling, grinding, and mixing operations, the company says. In paper production, Tamol SN disperses natural pitch in unbleached and mechanical wood pulp and also serves as a conditioning agent in tall oil separation, according to Rohm & Haas. C1
Stabilizer for vinyl plastics, from Allied Asphalt and Mineral Corp., Great Neck, N.Y., serves as a wetting aid for fillers and as a mold or calender lubricant. It also acts as a heat and light stabilizer, the company says. Designated Allied Y-3, it is for use in a variety of industrial, household, and consumer products of vinyl polymers and copolymers. C2
Two sulfamic acid based cleaners are
available from E. F. Drew & Co., New York, N.Y. Saf-acid G is for use in systems containing galvanized metal, and Improved Saf-acid is a powdered scale remover, inhibited to prevent corrosion and foaming, Drew says. C 3 Urethane insulating foam of low density provides dimensional stability at subzero temperatures. The new formulation designated Nopco Lockfoam H-602, developed by Nopco Chemical, North Arlington, N.J., has greater strength in each cell wall, and over-all homogeneity in foam strength, the company says. The foam can be used for insulating refrigerators, freezers, refrigerated warehouses, and in other applications where subzero temperatures are encountered, says Nopco. C4 Polyethylene resin, Dylan 2037, is being produced by Koppers, Pittsburgh, Pa. Film made from the resin has high clarity and high strength, especially in creases, Koppers says. It can be converted into bags or overwrap for packaging materials. C5
Four organic intermediates have been added to the line of Alliance Chemical Corp., Newark, N.J. They are: 5-sulfoisophthalic acid and 5-hydroxyisophthalic acid, available in research quantities, and l-amino-6-naphthol and S^'-dimethoxy-G^'-dichlorobenzidine, available in commercial quanti-
Low Temperature Flexibility? For vinyls requiring the best possible resistance to stiffening and cracking at low temperatures, Argus recommends Drapex 3.2. Where good performance is required under less extremes of cold, you will get it—at lower cost—with Drapex 4.4. Both Drapexes give excellent heat and light stability, low volatility, good weather ability. And their low viscosity and low freezing point prevent solidification when stored at low temperatures. Countless technical problems are continually posed to Argus. Plastisol bubble break, toxicity, better stabilization of clear rigids and of electrical compounds—to name just a few. The answer to your current vinyl problem may be as near at hand as your phone. Call Argus. If one of our line Mark stabilizers or Drapex plasticizers isn't the answer, we'll gladly track it down in our lab.
Argus Has the Answer Technical
bulletins and samples on request
ARGUS CHEMICAL Corporation 633 Court Street, Brooklyn 3 1 , N.Y. Branch: Frederick Building, Cleveland 15, Ohio Rep's.: H. M. Royal, Inc., 11911 Woodruff Ave., Downey, Cal.; Philipp Bros. Chemicals, Inc., 10 High St., Boston; H. L. Blachford, Ltd., 977 Aqueduct St., Montreal. European Affiliates: SA Argus Chemical NV; 33, Rue d'Anderlecht, Drogenbcs, Belgium - Lankro Chemicals, Ltd.; Salters Lane, Eccles, Manchester, England.
ties. All are used in the manufacture of dyes and other organic chemicals, the company says. C6
far and away the most versatile viscometer on the market...
Two functional group monomers, 2hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate, are now available in development quantities from Rohm & Haas, Philadelphia, Pa. These two compounds are proposed for use as chemical intermediates, and in the production of various copolymers, especially thermosetting plastics and elastomers, the company says. C 7
Viscosity determination is an exacting science the benefits of which have not been fully exploited — or even utilized — by many researchers who have great need for its application. Rotovisco is the most versatile viscometer for measurements on Newtonian and non-Newtonian materials.
Two organic intermediates have been added to the line of Pfister Chemical Works, Ridgefield, N.J. 3-Nitro-4methoxybenzanilide is a pale yellow% powder rated at 98.5% minimum purity. 3-Nitro-4-chlorobenzanilide is a water-insoluble, yellow powder with a melting point of 133° to 136° C. Both are available in commercial quantities and can be used in manufacturing dyes and other organic chemicals. C8
1) The only viscometer which offers both a cup and bob (Couette) and a plate-cone measuring system. 2) Will measure viscosities in the range of 5x10 - 3 to 4 x 1 0 7 poises. 3) Temperature control from - 6 0 to +300°C possible. 4) Measurements on sample quantities as small as 0.1 ml 5) Readings direct in Centipoise. Does not require use of calibration charts. Standard recorders may be used. 6) Rotor speeds from 0.03 to 486 r.p.m.
Antistatic fluid for use on plastic faced instruments has been introduced by Daystrom Inc., Newark, N.J. The fluid, Statnul, which is effective even under extremely dry conditions, provides a thin transparent coating which drains off static electricity from meter windows, thereby improving instrument performance, the company claims. Statnul also provides a cleaning action at the same time that it removes static. C9
HAAKE
Rotovisco's are now being used for research
R0T0VISGO
and control projects by U. S. manufacturers of; Paints and Lacquers Films and photographic products Pharmaceuticals Starch and glues Inks Chocolates and Foodstuffs Cosmetics Petroleum products Chemicals Cement
For complete information, write ROTOVISCO —
I
BRINKMANN
I 78
INSTRUMENTS,INC. 115
Cutter Mill Road, Great Neck,N.Y.
Philadelphia • Cleveland • Houston • Miami • Menlo Park. Cal.
C&EN
APRIL
10,
1961
Self-bonding silicone rubber compound, which bonds directly to ferrous metals such as steel, chrome steel, and stainless steel by direct reaction with the metal surface, has been developed by General Electric, Waterford, N.Y. Designated SE-5504U, the gray, highstrength compound will be of use in manufacturing such items as shock mounts, rubber rolls, and oil seals, GE says. C 10
Further useful information on keyed Chemical items mentioned is readily available . . . Use handy coupon on page 84 ^
