Synthesis of chiral epichlorohydrin by chloroperoxidase-catalyzed epoxidation of 3-chloropropene in the presence of an ionic liquid as co-solvent

被引：36

作者：

Wu, Jinyue ^{[1
]}

Liu, Chen ^{[1
]}

Jiang, Yucheng ^{[1
,2
]}

Hu, Mancheng ^{[1
,2
]}

Li, Shuni ^{[1
,2
]}

Zhai, Quanguo ^{[1
,2
]}

机构：

[1] Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China

[2] Shaanxi Normal Univ, Key Lab Macromol Sci Shaanxi Prov, Xian 710062, Peoples R China

来源：

CATALYSIS COMMUNICATIONS | 2010年 / 11卷 / 08期

基金：

中国国家自然科学基金;

关键词：

Chloroperoxidase; Asymmetric epoxidation; Chiral epichlorohydrin; Ionic liquids; CALDARIOMYCES-FUMAGO;

D O I：

10.1016/j.catcom.2010.02.003

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Asymmetric epoxidation of 3-chloropropene can be catalyzed by chloroperoxidase (CPO) from Caldariomyces fumago to prepare (R)-epichlorohydrin (ECH) in homogenous phosphate buffer/ionic liquid mixtures using r-butyl hydroperoxide (TBHP) as O-2 donor. Reaction conditions were optimized by the investigation of the choice of oxidants, the presence of ionic liquids (ILs), pH effect and CPO consumption. The best ECH yield reached 88.8% within a duration of 60 min with high enantiomeric excesses (e.e. 97.1%) at pH 5.5 and room temperature, using 1-ethyl-3-methylimidazolium [EMIM][Br] as co-solvent. The ILs with shorter carbon chain was more efficient on chiral ECH preparation. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：727 / 731

页数：5