Ethyl Corporation

Albemarle Corporation

R Carl Herndon, Jr

Ronny W Lin

G Patrick Stahly

Tse-Chong Wu

Thanikavelu Manimaran

Gary D Focht

W Dirk Klobucar

Robert H Allen

William J Layman, Jr

Kannappan C Chockalingam

Thorsten W Brockmann

Gary D Heidebrecht

E E Atkinson, Jr

Ranjit K Roy

Joseph D McLean

Karl R Jones

Yaping Zhong

A process of producing benzoic acids from phthalimides is described. The ability to dramatically reduce the reaction time in comparison to currently practiced processes by the addition of readily available compounds is demonstrated.

Process for making benzoic acids

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

The co-formation of diarylalkane by-product in the chloroalkylation of an aromatic compound with an aldehyde is minimized by conducting the reaction in a continuous manner in a concentration with agitation and in the presence of both hydrogen sulfate and hydrogen chloride.

Chloroalkylation of aromatic compounds

A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process utilizes first an enantiomerically enriched mixture the of aryl-substituted aliphatic carboxylic acid obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with a base producing a salt that has the following properties:

Enantiomeric resolution of aryl-substituted aliphatic carboxylic acids

Enantiomeric resolution

A process for preparing ibuprofen is described. The improved process involves the treatment of spent palladium carbonylation catalyst with oxygen at about 300.degree. C. to about 850.degree. C. The treated material then used with a phosphine ligand to carbonylate 1-halo-1-(4-isobutyl-phenyl)ethane, 1-hydroxyl-1-(4-isobutylphenyl)ethane, or isobutylstyrene to produce ibuprofen.

Process for recycling and regenerating carbonylation catalyst used in

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Baton Rouge, LA, United States of America

R Carl Herndon, Jr