Optical Resolution of <SUB>DL</SUB>-Mandelic Acid by Preferential Crystallization Procedure

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  • <SUB>DL</SUB>-マンデル酸の優先晶出法による光学分割
  • 光学分割　Ｉ　　ＤＬ‐マンデル酸の優先晶出法による光学分割

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Description

This paper describes the possibility of optical resolution of DL-mandelic acid (DL-MA) amine salts by preferential crystallization procedure. The DL-MA amine salts of primary amines such as butylamine and aniline, secondary amines such as dipropylamine, diisopropylamine (DIPA), diphenylamine, and dicyclohexylamine were prepared. The salts forming racemic mixture, racemic compound, and racemic solid solution were classified by comparing the infrared spectra, melting point, and solubilities of racemic modifications with those of optically active modifications. The results were as follows. ( 1 ) The DIPA salt formed racemic mixture. ( 2 ) The dicyclohexylamine and the diphenylamine salts formed racemic solid solutions. (3)The butylamitie, aniline, and diethylamine salts formed racemic compounds. The resolutions of the DL amine salts of diethylamine, DIPA, dicyclohexylamine and diphenylamine. were carried out. As the results it was possible to resolv eonly the DIPA salt. Optical resolution of DL-MA DIPA salts was studied under the conditions of several temperatures and supersaturations. It was found that the optically active isomer resolved at supersaturation from 116% to 125% had high optical purity. The time course of resolution with several temperatures and supersaturations was additionally studied.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1979 (8), 1092-1096, 1979-08-10

    The Chemical Society of Japan

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