Albemarle Corporation

Ethyl Corporation

Robert E Young

Hao V Phan

Thanikavelu Manimaran

Deepak R Patil

Azfar A Choudhury

William T Murray

Ronald C Zumstein

W Bryan Waites

Phillip R DeVrou

Sodium (S)-2-(6-methoxy-2-naphthyl)propionate of at least 99% chiral purity is formed from (S)-2-(6-methoxy-2-naphthyl)propionic acid having a chiral purity of at least about 82%, but below 99%. This is done by distilling a two-phase mixture formed from (i) the (S)-2-(6-methoxy-2-naphthyl)propionic acid, (ii) water, (iii) sodium hydroxide, sodium oxide and/or at least one basic inorganic sodium salt in an amount proportioned to neutralize from about 50 to about 99% of said acid, and optionally but preferably, (iv) an inert organic solvent that has a boiling point of at least 95.degree. C. at 760 mm Hg such that water is removed from said mixture, and a pot residue containing sodium (S)-2-(6-methoxy-2-naphthyl)propionate of at least 99% chiral purity is formed.

Preparation of high purity sodium (S)-2(6-methoxy-2-naphthyl)propionate

Optically active carboxylic acids, salts or esters, such as the profen-type compounds, are racemized in the presence by nitrogenous bases such as methylbenzylamine by heating an aqueous solution of such optically active compounds in the presence of a suitable excess of an alkali metal hydroxide relative to the amount optically active carboxylic compound present in the solution. The process not only enables conversion of inactive or undesirable enantiomers of compounds such as naproxen or ibuprofen into a usable, desirable enantiomers in an efficient and economical manner, but avoids conversion of the nitrogenous base into amide. Thus the deleterious consequences of amide formation are avoided.

Racemization process for optically active carboxylic acids or salts or

The yield of acetyl chloride from the reaction between acetic anhydride and hydrogen chloride is increased by withdrawing acetyl chloride, optionally together with at least some of the acetic acid by-product, from the reaction mixture as the reaction proceeds and recycling the remainder of the reaction mixture to the reactor for reaction with additional hydrogen chloride.

Process for preparing acetyl chloride

A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. In this process, the aryl-substituted aliphatic carboxylic acid is reacted with an inorganic base in the presence of an organic base to substantially enrich the precipitate in one of the enantiomers and an improved yield. Substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and aryl-substituted aliphatic carboxylic acid enriched in the other enantiomer.

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West Columbia, SC, United States of America

Robert E Young