Enzymatic synthesis of glucose-based fatty acid esters in bisolvent systems containing ionic liquids or deep eutectic solvents

Kai-Hua Zhao, Yu-Zheng Cai, Xiao-Sheng Lin, Jun Xiong, Peter J. Halling, Zhen Yang

Research output: Contribution to journalArticle

14 Citations (Scopus)
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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.

Original languageEnglish
Article number1294
Number of pages13
JournalMolecules
Volume21
Issue number10
Early online date27 Sep 2016
DOIs
Publication statusE-pub ahead of print - 27 Sep 2016

Keywords

  • alkyl glucoside
  • deep eutectic solvents
  • esterification
  • ionic liquids
  • lipase
  • sugar fatty acid esters
  • transesterification

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