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使用脂肪酶 TL IM 改进 α-甘油单月桂酸酯的合成。

Improved Synthesis of α-Glycerol Monolaurate Using Lipozyme TL IM.

机构信息

Department of Chemistry, Faculty of Science and Engineering, University of Nusa Cendana.

Department of Animal Diseases and Veterinary Public Health, Faculty of Veterinary Medicine, University of Nusa Cendana University.

出版信息

J Oleo Sci. 2022;71(7):1013-1020. doi: 10.5650/jos.ess21312.

Abstract

This study aimed to synthesize α-Glycerol Monolaurate from protected glycerol (glycerol 1,2-acetonide) using Lipozym TL IM as a catalyst. In the first step, transesterification of methyl laurate and glycerol 1,2-acetonide with Lipozyme TL IM produced 1,2-acetonide-3-lauryl glycerol. In the second step, deprotection of 1,2-acetonide-3-lauryl glycerol with Amberlyst-15 produced α-Glycerol Monolaurate. Furthermore, the optimum yield (82.1%) of 1,2-acetonide-3-lauryl glycerol (light yellow liquid, purity of 92%) was achieved at a reactant mole ratio of 1, n-hexane (4 mL) with a reaction time of 12 hours, and total Lipozyme TL IM of 5% (w/w of the total weight of reactants) at a temperature of 35°C. Deprotection of 1,2-acetonide-3-lauryl glycerol with Amberlyst-15 was conducted at room temperature for 24 hours. At a melting point of 62.8°C, and purity of 100% α-Glycerol Monolaurate in the form of a white solid was obtained with a yield of 74.6% after the recrystallization of the crude product. This α-glycerol monolaurate synthesis reaction pathway can be referred to as a green α-monoacylglyceride synthesis method.

摘要

本研究旨在使用 Lipozym TL IM 作为催化剂,从保护甘油(甘油 1,2-缩酮)合成 α-甘油单月桂酸酯。在第一步中,脂肪酶 TL IM 使月桂酸甲酯和甘油 1,2-缩酮进行转酯化反应,生成 1,2-缩酮-3-月桂基甘油。在第二步中,用 Amberlyst-15 脱保护 1,2-缩酮-3-月桂基甘油,生成 α-甘油单月桂酸酯。此外,在反应物摩尔比为 1、n-己烷(4 mL)、反应时间为 12 小时、温度为 35°C 的条件下,使用总 Lipozym TL IM 为 5%(反应物总重量的 w/w),可获得 1,2-缩酮-3-月桂基甘油的最佳收率(82.1%),产物为浅黄色液体,纯度为 92%。用 Amberlyst-15 脱保护 1,2-缩酮-3-月桂基甘油在室温下进行 24 小时。粗产物经重结晶后,得到熔点为 62.8°C、纯度为 100%的白色固体 α-甘油单月桂酸酯,收率为 74.6%。这种α-甘油单月桂酸酯的合成反应途径可以作为一种绿色的α-单酰基甘油合成方法。

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