Process for producing D(-)mandelic acid

US4489208A · kind A · utility

Assignee

• E.N.I. Nazionale Idrocarburi · IT

Inventors

• Roberto Olivieri · Siena, IT
• Giancarlo Eletti Bianchi · Roma, IT
• Eugenio Fascetti · Roma, IT
• Felice Centini · Roma, IT
• Ludwig Degen · Roma, IT
• Walter Marconi · San Donato Milanese, IT

Key dates

• Filing date: Feb 16, 1982
• Grant date: Dec 18, 1984
• Expiry date: Feb 16, 2002

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C12P13/02
• WIPO field: Biotechnology
• WIPO sector: Chemistry

Abstract

This invention relates to a process for the preparation of D(-) mandelic acid by the acid hydrolysis of the corresponding carbamate in an aqueous environment at a temperature of between 40.degree. and 100.degree. C. and at a pH of between 1 and 3.5. The invention also relates to a process for the enzymatic hydrolysis of racemic 5-substituted 2,4-oxazolidinediones to give only one of the two possible optical isomers, i.e., the D-carbamyl-.alpha.-hydroxy acid. The free D-.alpha.-hydroxy acid can be obtained from the optically active carbamyl derivative by simple hydrolysis. Of particular interest is the case in which the D-.alpha.-hydroxy acid is D(-)mandelic acid. The enzymatic activity required for preparing the carbamyl derivative of D(-)mandelic acid has been found both in homogenised veal liver and in a series of microorganisms, including Agrobacterium radiobacter, Bacillus brevis, Bacillus stearothermophilus, Pseudomonas sp., Pseudomonas desmolytica, Pseudomonas fluorescens, Pseudomonas putida.