Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1981-05-15
1982-06-29
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
562506, C07B 1900, C07B 2100
Patent
active
043373526
ABSTRACT:
A process for the separation of enantiomers of a chiral carboxylic acid, comprising reacting an alkali metal salt of the acid with an amount of an optically active amine salt which is equivalent to only one enantiomer, in an aqueous weakly alkaline buffered solution as the reaction medium, the reaction medium having a pH value at which the entire acid is present in the ionized form but at which no amine salt is yet deprotonated. Advantageously the carboxylic acid is of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently is hydrogen, alkyl, with 1-4 C atoms, halogen, optionally substituted phenyl or optionally substituted phenylmercapto,
the optically active amine salt is a mineral acid salt of a phenylglycine alkyl ester, .alpha.-methylbenzylamine, phenylethylamine, phenylethanolamine, 1-phenyl-2-dimethyl-amino-1,3-propanediol or abietylamine, the buffered solution contains potassium carbonate, sodium carbonate, sodium bicarbonate or sodium hydrogen phosphate as the buffering agent, and the reaction is effected at about 0.degree. to 100.degree. C., the process including the further steps of separating the precipitated ammonium salt from the alkali metal salt that remains in solution, treating the ammonium salt with a strong acid whereby the free carboxylic acid enantiomer is liberated, and treating the alkali metal salt that remains in solution with a strong acid whereby the free carboxylic enantiomer is liberated.
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Bayer Aktiengesellschaft
Killos Paul J.
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