Production of l-menthyl acetate through kinetic resolution byCandida cylindracea lipase: effects of alkaloids as additives

被引：11

作者：

Belkacemi, Fatima Zohra ^{[1
]}

Merabet-Khelassi, Mounia ^{[1
]}

Aribi-Zouioueche, Louisa ^{[1
]}

Riant, Olivier ^{[2
]}

机构：

[1] Badji Mokhtar Annaba Univ, Ecocompatible Asymmetr Catalysis Lab LCAE, Annaba, Algeria

[2] Catholic Univ Louvain, Inst Condensed Matter & Nanosci Mol, Solids & React IMCN MOST, Louvain La Neuve, Belgium

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2018年 / 44卷 / 11期

关键词：

l-Menthyl acetate; Kinetic resolution; Candida cylindracea lipase; Alkaloids; Additives; CANDIDA-RUGOSA LIPASE; ORGANIC-SOLVENTS; DL-MENTHOL; ENANTIOSELECTIVE HYDROLYSIS; CATALYZED RESOLUTION; ACID ANHYDRIDES; ACYLATION; ESTERIFICATION; ALCOHOLS; TRANSESTERIFICATION;

D O I：

10.1007/s11164-018-3525-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enzymatic transesterification of dl-menthol with vinyl acetate in tert-Butyl methyl ether (TBME) catalyzed by Candida cylindracea lipase (CCL) was carried out in the presence of cinchona alkaloid as additive. The effects of various reaction parameters, such as lipase nature and loading, acylating agent, molecular sieves, solvents and various additives, on the reactivity as well as on the enantioselectivity were investigated. A significant improvement of CCL reactivity has been recorded after using cinchona alkaloid as additive in TBME. A high enantiomeric ratio (E=80) was achieved when 30mol% of quinidine was added, and l-(-)-menthyl acetate was obtained with 93% optical purity and 49% conversion. This process was easily applied to gram-scale quantities, using commercially inexpensive lipase, providing high yield optically active menthol under mild experimental conditions.Graphical abstract [GRAPHICS] .

引用

页码：6847 / 6860

页数：14

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