Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts

Molecules

Mireia Oromí-Farrús¹  Jordi Eras¹  Núria Sala¹  Mercè Torres¹ 

[1] ¹Chemistry Department, Lleida University, 25198-Lleida, Spain ²Food Technology Department, Lleida University, 25198-Lleida, Spain

关键词: (S)-1-bromomethyl-1-heptanol;    (S)-1-chloromethyl-1-heptanol;    lipases;    enzymatic resolution;   

DOI  :  10.3390/molecules14104275

来源: mdpi

【 摘 要 】

Preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol was carried out by the enzymatic hydrolysis of halohydrin palmitates using biocatalysts. Halohydrin palmitates were prepared by various methods from palmitic acid and 1,2-octanediol. A tandem hydrolysis was carried out using lipases from Candida antarctica (Novozym^® 435), Rhizomucor miehei (Lipozyme IM), and “resting cells” from a Rhizopus oryzae strain that was not mycotoxigenic. The influence of the enzyme and the reaction medium on the selective hydrolysis of isomeric mixtures of halohydrin esters is described. Novozym^® 435 allowed preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol after 1–3 h of reaction at 40 °C in [BMIM][PF₆].

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.