Ethyl Corporation

Albemarle Corporation

Ranjit K Roy

Ronny W Lin

Tse-Chong Wu

W Dirk Klobucar

Robert H Allen

William J Layman, Jr

Keith G Anderson

Kannappan C Chockalingam

Ali M Dadgar

Gary D Focht

R Carl Herndon, Jr

Donald O Hutchinson

Thorsten W Brockmann

Gary D Heidebrecht

Joseph D McLean

Yaping Zhong

Palladium-catalyzed arylation of an olefin (e.g., ethylene) with an aromatic halide (e.g., 2-bromo-6-methoxynaphthalene, m-bromobenzophenone, or 4-isobutyl-1-bromobenzene) is conducted in specified media. After a special acid or base phase separation procedure, palladium-catalyzed carbonylation of the olefinically-substituted aromatic intermediate is conducted in specified media using CO and water or an alcohol to form arylalkylcarboxylic acid or ester or substituted arylalkylcarboxylic acid or ester (e.g., racemic 2-(6-methoxy-2-naphthyl)propionic acid, 2-(3-benzoylphenyl)propionic acid, or 2-(4-isobutylphenyl)propionic acid). Catalyst recovery procedures enabling recycle of catalyst residues and efficient recovery of amine hydrogen halide scavenger and solvent used in the arylation reaction are described, as well as novel, highly efficient methods of conducting the carbonylation reaction. The technology is economical and suitable for use on an industrial scale whereby reaction mixtures can be efficiently separated into the desired component mixtures without need for excessive capital investment or tedious, time-consuming operations. High yields of high purity products can be achieved.

Preparation of carboxylic compounds and their derivatives

This invention relates to a process for preparing a white bisimide product which principally contains N,N'-alkylene-bis(tetrabromophthalimide) or N,N'-bis(tetrabromophthalimide). The process features: providing, in a reaction vessel, a solution containing tetrabromophthalic anhydride and a solvent which contains at least about 15 weight percent of a mono-, di- or tri- carboxylic acid having a dissociation constant not higher than 1.0.times.10.sup.-3 at 25.degree. C.; forming a reaction mass by adding to the solution a diamine or a diamine salt formed by the partial or total diamine neutralization of a mono-, di- or tri- carboxylic acid having a dissociation constant not higher than 1.0.times.10.sup.-3 at 25.degree. C., such formation of the reaction mass resulting in the production of a bisimide precipitate which becomes a constituent of the reaction mass; during the formation of the reaction mass, (i) retaining, in the reaction mass, at least a portion of the water produced during such formation, (ii) maintaining a substantially constant pressure in the reaction vessel, and (iii) not allowing the temperature of the reaction mass to reach a temperature below about 135.degree. C.; terminating the addition of the diamine or diamine salt when the molar ratio of the tetrabromophthalic anhydride initially present in the solution to the diamine or diamine salt added is from about 1.9:1 to about 2.1:1; and recovering, as the bisimide product, the bisimide precipitate.

Process for preparing bisimide products

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Baton Rouge, LA, United States of America

Ranjit K Roy