Atlantic Richfield Company

Emery Industries, Inc.

Other

Princeton University

Halcon Research and Development Corp.

John F White

Wilfred P Shum

Eva M Beals

Edward C Taylor

Eugene G Harris

Chih-Shu Chiang

Jerome C Bertrand

Roger A Grey

Richard G Fayter

Margaret I Nemet-Mavrodin

Michael R Pollard

A novel method for producing branched carboxylic acids or esters from alpha-unsaturated olefins is disclosed. Such olefins are reacted with a novel, sterically hindered, ortho substituted phenylphosphine palladium halide catalysts in the presence of water or primary or secondary alcohols to produce high branched end product yields. Such catalysts have phosphine ligand cone angles of between about 170.degree. and 180.degree.. Tris(o-methoxyphenyl)phosphine palladium halide and o-trifluoromethylphenyldiphenylphosphine palladium halide catalysts are preferred.

Method for producing branched carbonylation products from alpha

A novel method of converting alkanoic acids, such as isobutyric acid, to alpha-beta unsaturated acids, such as methacrylic acid, is disclosed which exhibits a higher degree of selectivity than those vapor phase oxydehydration methods heretofore known to the art. The preferred method comprises contacting a Dawson structure phosphomolybdic acid catalyst with isobutyric acid under specified reaction conditions to achieve a high selectivity for methacrylic acid.

High selectivity process for vapor phase oxydehydrogenation of alkanoic

A process for producing primary alcohols from terminal epoxides having a mono-substituted epoxy ring and having from 3 to 6 carbon atoms per molecule which process comprises contacting the epoxide and hydrogen gas with Raney cobalt catalyst under vapor phase conditions in a hydrogenation zone.

Method for producing primary alcohols by catalytic hydrogenation of

A novel synthesis of methacrylic acid and methacrolein from isobutylene oxide is provided. This method includes contacting isobutylene oxide with a catalyst, preferably a heteropolyacid catalyst, in the presence of oxygen. Using this method, isobutylene oxide conversion is nearly 100% complete. Depending upon the reaction temperature selected, yields of up to about 60% methacrolein and up to about 12% methacrylic acid may be obtained. A simple, inexpensive high yield process is thus provided for producing reaction mixtures containing methacrylic acid and methacrolein.

Oxidation of isobutylene oxide to methacrylic acid and methacrolein

Process for the oxidation of isobutylene oxide to methacrolein

A novel synthetic procedure is disclosed for producing heteropolyacid catalysts having the general formula H.sub.3+x PV.sub.x W.sub.3-x Mo.sub.9 O.sub.40 where 0&lt;x&lt;3. The synthesis of these catalysts requires the formation of a defect structure wherein three of the twelve transition metals which surround the phosphorus hetero atom are missing. Three metal atoms of two other transition metals are then added to the cluster in a separate step by mixing Na.sub.3 H.sub.6 PMo.sub.9 O.sub.34 with the oxides of such transition metals in the presence of hydrochloric acid. A preferred catalyst having the formula H.sub.3.5 PV.sub.0.5 W.sub.2.5 Mo.sub.9 O.sub.40 is also described.

Vanadotungstomolybdophosphoric acid oxidation catalyst

The present invention provides a novel method for recovering 2-phenylethanol which is produced as a by-product of non-catalytic air oxidation of ethylbenzene, and as a by-product, in the ethylbenzene hydroperoxide epoxidation of an olefinically unsaturated compound, e.g., propylene, to the corresponding alkylene oxide, e.g., propylene oxide. In such processes, 2-phenylethanol accumulates in a process stream typically comprising major proportions of methylbenzyl alcohol, ethylbenzene, alkylene oxide and acetophenone. Conventional distillation-separation procedures may remove most of the alkylene oxide and ethylbenzene, leaving a process stream which is eventually used for styrene monomer production which contains minor amounts, i.e., less than about 20 weight percent, of 2-phenylethanol. The present invention provides a novel method of recovering 2-phenylethanol from that process stream prior to its conversion to other by-products in the dehydration and hydrogenation steps which are utilized to produce styrene monomer. The present invention provides a 2-phenylethanol removal method comprising the preparation of a 2-phenylethanol feed stream having a methylbenzyl alcohol concentration of between about 10 and 70 weight percent, and a 2-phenylethanol concentration of between about 20 and 80 weight percent. This prepared feed stream is then diluted with an organic diluent, such as ethylbenzene, and is subjected to a metal halide addition which results in the formation of an insoluble 2-phenylethanol metal halide complex which is separated, washed and decomposed to produce a crude 2-phenylethanol product, which may be distilled to remove residual diluent to provide a high purity 2-phenylethanol product exhibiting superior fragrance qualities.

Recovery of 2-phenylethanol

Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.

Conversion of aldehydes

This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.

Process for the preparation of vinylcyclopropane derivatives

Improved supported thallium(III) reagents are provided which significantly improve reaction rates and product selectivity of oxythallation reactions. The present reagents have a thallium(III) salt of an acid on the surface and within montmorillonite clay minerals.

Thallium(III) reagents supported on montmorillonite clay minerals and

A process is provided for the continuous or semi-continuous production of hetero-macrocyclic compounds including lactones and cyclic esters. The process involves the catalyzed depolymerization of linear polyesters at elevated temperature and under reduced pressure in the presence of a specified amount of monocarboxylate moieties while providing top-to-bottom mixing throughout essentially the total volume of the reaction mass.

Process for the production of macrocyclic esters

Thallium(III) reagents supported on montmorillonite clay minerals in

A process is provided for the continuous or semi-continuous production of hetero-macrocyclic compounds including lactones and cyclic esters. The process involves the catalyzed depolymerization of a linear polyester at an elevated temperature and under reduced pressure in the presence of a specified amount of monocarboxylate moieties and while providing top-to-bottom mixing throughout essentially the total volume of the reaction mass.

Process for the production of heterocyclic compounds

An improved process is provided herein for the preparation of immobilized transition metal catalysts containing up to about 60 wt. % bound transition metal. These catalysts are obtained by heating a hydroxylic support with an excess of a transition metal alkoxide in an inert hydrocarbon and in the presence of water.

Growing community of inventors

Princeton, NJ, United States of America

John F White