Abstract

Sugar fatty acid esters (SFAEs) are biocompatible nonionic surfactants with broad applications in food, cosmetic, and pharmaceutical industries. They can be synthesized enzymatically with many advantages over their chemical synthesis. In this study, SFAE synthesis was investigated by using two reactions: (1) transesterification of glucose with fatty acid vinyl esters and (2) esterification of methyl glucoside with fatty acids, catalyzed by Lipozyme TLIM and Novozym 435 respectively. Fourteen ionic liquids (ILs) and 14 deep eutectic solvents (DESs) were screened as solvents, and the bisolvent system composed of 1-hexyl-3-methylimidazolium trifluoromethylsulfonate ([HMIm][TfO]) and 2-methyl-2-butanol (2M2B) was the best for both reactions, yielding optimal productivities (769.6 and 397.5 µmol/h/g, respectively) which are superior to those reported in the literature. Impacts of different reaction conditions were studied for both reactions. Response surface methodology (RSM) was employed to optimize the transesterification reaction. Results also demonstrated that as co-substrate, methyl glucoside yielded higher conversions than glucose, and that conversions increased with an increase in the chain length of the fatty acid moieties. DESs were poor solvents for the above reactions presumably due to their high viscosity and high polarity.

Highlights

  • IntroductionSugar fatty acid esters (SFAEs) are produced from renewable resources such as sugars and fatty acids

  • The development of new eco-friendly surfactants has been an ongoing issue

  • Both Lipozyme TLIM and Novozym 435 are able to catalyze the synthesis of glucose laurate, either through transesterification of glucose and vinyl laurate or through esterification of methyl glucoside and lauric acid

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Summary

Introduction

Sugar fatty acid esters (SFAEs) are produced from renewable resources such as sugars and fatty acids. They are biodegradable, odorless, non-irritating, and non-toxic, and broad applications in the food, cosmetic, and pharmaceutical industries have been found [1,2,3,4]. When catalyzed by a lipase (EC 3.1.1.3), sugars can be acylated to produce an SFAE by esterification with fatty acids or transesterification with active carboxylic esters. Both reactions are required to Molecules 2016, 21, 1294; doi:10.3390/molecules21101294 www.mdpi.com/journal/molecules

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