DISPLACEMENT OF THE EQUILIBRIUM IN LIPASE CATALYZED TRANSESTERIFICATION IN ETHYL OCTANOATE BY CONTINOUS EVAPORATION OF ETHANOL

被引:24
作者
OHRNER, N
MARTINELLE, M
MATTSON, A
NORIN, T
HULT, K
机构
[1] ROYAL INST TECHNOL,DEPT BIOCHEM & BIOTECHNOL,S-10044 STOCKHOLM 70,SWEDEN
[2] ROYAL INST TECHNOL,DEPT ORGAN CHEM,S-10044 STOCKHOLM 70,SWEDEN
关键词
D O I
10.1007/BF01022321
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
A simple method to overcome low equilibrium conversion in lipase catalysed resolution of alcohols by transesterification was developed. Ethyl octanoate was used as acyl donor as well as solvent and the reaction equilibrium was shifted by applying reduced pressure, forcing the co-product ethanol to evaporate during the reaction. Using a lipase from Candida antarctica 2-octanol, 1-phenyl ethanol, 1-cyclohexyl ethanol and trans-2-methylcyclohexanol were resolved in good optical and chemical yields.
引用
收藏
页码:263 / 268
页数:6
相关论文
共 15 条
[1]  
ADELHORST K, 1990, SYNTHESIS-STUTTGART, V2, P112
[2]   IMMUNIZATION OF LIPASE AGAINST ACETALDEHYDE EMERGING IN ACYL TRANSFER-REACTIONS FROM VINYL-ACETATE [J].
BERGER, B ;
FABER, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) :1198-1200
[3]   ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS [J].
BIANCHI, D ;
CESTI, P ;
BATTISTEL, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5531-5534
[4]   CHIRAL SYNTHESIS VIA ORGANOBORANES .15. SELECTIVE REDUCTIONS .42. ASYMMETRIC REDUCTION OF REPRESENTATIVE PROCHIRAL KETONES WITH POTASSIUM 9-O-(1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSYL)-9-BORATABICYCLO[3.3.1]-NONANE [J].
BROWN, HC ;
CHO, BT ;
PARK, WS .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1231-1238
[5]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTION OF ENANTIOMERS .2. ENZYME-CATALYZED ESTERIFICATIONS IN WATER ORGANIC-SOLVENT BIPHASIC SYSTEMS [J].
CHEN, CS ;
WU, SH ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2812-2817
[6]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[7]  
DEGUEILCASTAING M, 1987, TETRAHEDRON LETT, V28, P935
[8]  
GERLACH D, 1989, BIOCATALYSIS, V2, P257
[9]   CATALYTIC ASYMMETRIC HYDROBORATION OF STYRENES [J].
HAYASHI, T ;
MATSUMOTO, Y ;
ITO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3426-3428
[10]   A PROCEDURE FOR ALCOHOL INVERSION USING CESIUM ACETATE [J].
HUFFMAN, JW ;
DESAI, RC .
SYNTHETIC COMMUNICATIONS, 1983, 13 (07) :553-557