Enzymatic synthesis of the acrylic esters: a comparative study

被引:18
作者
Athawale, V [1 ]
Manjrekar, N [1 ]
机构
[1] Univ Bombay, Dept Chem, Bombay 400098, Maharashtra, India
关键词
acylation; enzymatic synthesis; lipase; oxime acrylate; transesterification;
D O I
10.1016/S1381-1177(00)00008-4
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Various acrylic esters were synthesized by Candida cylindracea lipase (CCL) catalysed transesterification with different alcohols. A comparative study was carried out using 2,3-butanedione mono-oxime acrylate and vinyl acrylate as acylating agents. The rate of conversion was faster when oxime acrylate was used as acylating agent as compared to vinyl acrylate. Effect of solvents on the rate of conversion was studied and diisopropyl ether (DIPE) was proved to be a better solvent as compared to CHCl3 and THF. The effect of various structural aspects of the substrates on the rate of conversion was studied. Among the linear alcohols studied, ease of conversion was found to be in the order of n-octanol > n-hexanol > n-butanol. Up to 80% conversion was achieved in the case of cyclohexyl methanol. (C) 2000 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:551 / 554
页数:4
相关论文
共 7 条
  • [1] BENNEVILLE P, 1958, J ORG CHEM, V23, P1355
  • [2] ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS
    BIANCHI, D
    CESTI, P
    BATTISTEL, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) : 5531 - 5534
  • [3] ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS
    DEGUEILCASTAING, M
    DEJESO, B
    DROUILLARD, S
    MAILLARD, B
    [J]. TETRAHEDRON LETTERS, 1987, 28 (09) : 953 - 954
  • [4] OXIME ESTERS AS NOVEL IRREVERSIBLE ACYL TRANSFER AGENTS FOR LIPASE CATALYSIS IN ORGANIC MEDIA
    GHOGARE, A
    KUMAR, GS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) : 1533 - 1535
  • [5] PARTITION COEFFICIENTS AND THEIR USES
    LEO, A
    HANSCH, C
    ELKINS, D
    [J]. CHEMICAL REVIEWS, 1971, 71 (06) : 525 - +
  • [6] MERGER F, 1988, Patent No. 4777265
  • [7] WANG Y, 1989, TETRAHEDRON LETT, V15, P1917