Ethyl Corporation

Albemarle Corporation

Other

Kannappan C Chockalingam

Tse-Chong Wu

William J Layman, Jr

Ronny W Lin

W Dirk Klobucar

Robert H Allen

R Carl Herndon, Jr

Gary D Focht

Thorsten W Brockmann

Gary D Heidebrecht

Joseph D McLean

Ranjit K Roy

Yaping Zhong

Jean-Pierre Lecouv E

Methods are provided for preparing branched alkyl-substituted-anilines, such as 2-(1,3-dimethylbutyl)aniline. Such methods comprise combining aniline, an alkyl-substituted-1-alkene, such as 4-methyl-i-pentene, and an aluminum alkyl catalyst.

Preparation of 2-(1,3-dimethylbutyl)aniline and other branched alkyl-substituted-anilines

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 the production of a solid calcium [S,S]-ethylenediamine-N,N'-disuccinate by the reaction of calcium aspartate and dihaloethane in an aqueous solvent.

Method for producing calcium salts of

A new process for preparing aryl-substituted aliphatic carboxylic acids is provided. Aryl-substituted aliphatic ether or thioether compound is reacted with carbon monoxide in aqueous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An acid such as hydrochloric acid may be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.

Process for preparing carboxylic acids by carbonylation of ethers and

A new process for preparing aliphatic carboxylic acid esters is provided. A substituted aliphatic ether or thioether compound is reacted with carbon monoxide in the presence of an alcohol in anhydrous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An excess of several moles of anhydrous alcohol is preferred. An acid such as hydrochloric acid may also be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.

Catalytic carbonylation of ethers and thioethers

A new process for preparing alkyl esters of ibuprofen is provided. A 1-halo-1-(4-isobutylphenyl)ethane is reacted with carbon monoxide in the presence of an anhydrous alcohol at a temperature between about 10.degree. C. and about 200.degree. C. An excess of several moles of alcohol is preferred. An acid such as trifluoroacetic acid is also added. As catalyst, a palladium compound and at least one acid-stable ligand over palladium are present; however, an excess of ligand over palladium is advantageous.

Process for preparing aryl-substituted aliphatic carboxylic acid esters

A new process for preparing alkyl esters of ibuprofen is provided. A 1-halo-1-(4-isobutylphenyl)ethane is reacted with carbon monoxide in the presence of an anhydrous alcohol at a temperature between about 10.degree. C. and about 200.degree. C. An excess of several moles of alcohol is preferred. An acid such as trifluoroacetic acid is also added. As catalyst, a mixture of a copper compound and a palladium or a palladium compound and at least one acid-stable ligand are present.

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Baton Rouge, LA, United States of America

Kannappan C Chockalingam