Allied Chemical Corporation

Allied Corporation

Guido P Pez

Roger A Grey

Lowell R Anderson

Wim J Pieters

John N Armor

Emery J Carlson

Irving L Mador

Benzene, or an alkylbenzene, is hydrogenated by reaction with hydrogen in the presence of a Group IVa or Va metal hydride catalyst. The catalyst may be a simple hydride such as ZrH.sub.2 or a hydride of an alloy such as Cu.sub.3 Zr or may be a complex material. One complex material is the reaction product of a Group IVa or Va metal halide, such as ZrCl.sub.4 with an alkyllithium or aryllithium, such as n-butyllithium, in a hydrocarbon solvent.

Group IVa metal hydride catalysts and preparation thereof

A novel class of compounds, anionic Group VIII metal hydrides containing phosphorus, arsenic and antimony organoligands is described, such as potassium tris and bis(triphenylphosphine) ruthenium hydride. The compounds are useful as homogeneous catalysts in the hydrogenation of aldehydes, ketones, olefins or alkynes. Processes for producing the compounds are also described.

Improved process for hydrogenating aldehydes and ketones by employing

Benzene, or an alkylbenzene, is hydrogenated by reaction with hydrogen in the presence of a Group IVa (titanium family) or Va metal hydride catalyst. The catalyst may be a simple hydride such as ZrH.sub.2 or a hydride of an alloy such as Cu.sub.3 Zr or may be a complex material. One complex material is the reaction product of a Group IVa or Va metal halide, such as ZrCl.sub.4 with an alkyllithium or aryllithium, such as n-butyllithium, in a hydrocarbon solvent.

Process of hydrogenating benzenes and group IVa metal hydride catalysts

Electrically conducting polyacetylene compositions are described having incorporated therein a fluorine-containing peroxide, such as FSO.sub.2 --O--O--SO.sub.2 F. Preferred compositions exhibit novel metal-like conductivity at temperatures above about 150.degree. K., and specific conductivities above about 10.sup.2 ohm.sup.-1 -cm.sup.-1 at room temperature, as measured by the standard four-probe method. A process for producing the compositions is also described in which polyacetylene is contacted with the peroxide, preferably in an inert liquid solvent at low temperatures.

Electrically conducting polyacetylenes

A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.

Hydrogenation of esters using alkali doped heterogeneous Group VIII

Benzene or an alkylbenzene is reacted with hydrogen and an alkali metal such as potassium in the presence of a polyamine to produce cyclohexene or alkylcyclohexene and alkali metal hydride. The polyamine contains only C, N and H and has at least three nitrogens. Each nitrogen is linked to three carbons and each carbon bridge is at least two methylenes long. Representative polyamines are hexamethyl hexacyclen, hexamethyl triethylene tetraamine, tris(2-dimethylamino ethyl)amine and octamethyl pentaethylene hexamine. Cyclohexene is produced at high ratios with respect to cyclohexane.

Producing cyclohexene or alkylcyclohexene

Hydrogenation of esters using alkali doped heterogeneous group VIII

Monolefins such as ethylene are reacted with ammonia using alkali metal amide catalysts such as cesium or rubidium amides, or low melting mixtures of amides such as cesium/potassium, cesium/sodium or sodium/potassium amides. Conversions are improved compared to reactions using sodium or potassium amide alone. Conversions of ethylene are improved also when liquid ammonia is present.

Alkali metal amide catalyst

Producing alkylamines from olefins with alkali metal amide catalyst

Electrically conducting polymers

Anionic group VIII metal hydride catalysts

A novel process is described for the homogeneous hydrogenation of nitriles to primary amines utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the high yield hydrogenation of nitriles to primary amines to be conducted under mild conditions of temperature and pressure with high selectivity and eliminates the need for the presence of ammonia to suppress the formation of significant amounts of secondary and tertiary amines.

Process for hydrogenation of nitriles

Novel lithium dicyclopentadienyl titanium hydride type compositions are described, useful as catalysts in converting ethylene to 1-butene, which is used in producing 'polymer gasoline' for increasing the octane number of automotive gasolines. Methods for synthesizing the novel compositions are also described.

Lithium dicyclopentadienyl titanium hydride compositions

A novel process is described for the homogeneous hydrogenation of carboxylic acid esters to primary alcohols utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the process to be conducted in solution under mild conditions of temperature and pressure with high selectivity and eliminates the disadvantages of utilizing heterogeneous catalysts. A process is also described for decarbonylating formate esters utilizing said compositions as catalysts.

Process for homogeneous hydrogenation of esters

A process is described for producing partially crystalline polyacetylene in the cis or trans configurations utilizing.mu.-(.eta..sup.1 :.eta..sup.5 -cyclopentadienyl)-tris(.eta.-cyclopentadienyl)dititanium(Ti-Ti) catalyst. The resulting polyacetylene when 'doped' with halogen additives is useful as an electrical conductor or semiconductor. Also described are polyacetylene 'gels,' consisting essentially of a solid polyacetylene and gel-forming liquid therefor, also containing up to about 10 percent by weight of catalyst, per weight of acetylene, which is used for production of the polyacetylene. The gels are stable to phase separation at room temperature in a closed system, and are useful in preparing randomly and partially chain-aligned polyacetylene films and articles.

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Boonton, NJ, United States of America

Guido P Pez