Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters

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• 作者：Xiao-Sheng Lin ; Yong Zou ; Kai-Hua Zhao…
• 刊名：Journal of Surfactants and Detergents
• 出版年：2016
• 出版时间：May 2016
• 年：2016
• 卷：19
• 期：3
• 页码：511-517
• 全文大小：766 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Industrial Chemistry and Chemical Engineering
  Surfaces and Interfaces and Thin Films
  Polymer Sciences
  Waste Water Technology, Water Pollution Control, Water Management and Aquatic Pollution
  Analytical Chemistry
  Physical Chemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1558-9293
• 卷排序：19

文摘

As nonionic surfactants derived from naturally renewable resources such as sugars and fatty acids, sugar fatty acid esters have been widely utilized in food, cosmetic and pharmaceutical industries. Our present study has demonstrated that the inexpensive and halogen-free tetraalkylammonium salts (e.g., [Bu₄N][Ac], [Et₄N][Ac] and [Me₄N][Ac]) can act as dual solvents–catalysts for regioselective acylation to produce glucose laurate. This non-enzymatic synthesis can proceed under mild conditions with high specificity, and the conversions obtained were superior to that when an enzyme catalyst (lipase, EC 3.1.1.3) was added. A higher yield was obtained in the ammonium salt with a longer alkyl chain on the cation, while no product was obtained in [Bu₄N][HSO₄] and [Bu₄P][Ac]. A reaction mechanism has been proposed, which is supported by phase-transfer catalysis and law of matching water affinity.KeywordsIonic liquid (IL)Sugar fatty acid ester (SFAE)Glucose laurateTetraalkylammonium saltsDual solvent–catalystPhase-transfer catalysis