Inventors:
Robert H. Allen - Baton Rouge LA
R. Carl Herndon - Baton Rouge LA
Kannappan C. Chockalingam - Baton Rouge LA
W. Dirk Klobucar - Baton Rouge LA
Gary D. Focht - Baton Rouge LA
Tse-Chong Wu - Baton Rouge LA
Gary D. Heidebrecht - Orangeburg SC
Joseph D. McLean - Orangeburg SC
Yaping Zhong - Columbia SC
Thorsten W. Brockmann - Columbia SC
Ronny W. Lin - Baton Rouge LA
William J. Layman - Baton Rouge LA
Ranjit K. Roy - Baton Rouge LA
Assignee:
Albemarle Corporation - Richmond VA
International Classification:
C07C 5110
Abstract:
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.