Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters
| Autor: | Xiao-Sheng Lin, Kai-Hua Zhao, Tao-Xiang Yang, Yong Zou, Zhen Yang, Peter J. Halling |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
biology 010405 organic chemistry General Chemical Engineering Fatty acid Salt (chemistry) 010402 general chemistry 01 natural sciences 0104 chemical sciences Surfaces Coatings and Films Enzyme catalysis Catalysis Acylation chemistry.chemical_compound chemistry Ionic liquid biology.protein Organic chemistry Physical and Theoretical Chemistry Lipase Alkyl |
| Zdroj: | Journal of Surfactants and Detergents. 19:511-517 |
| ISSN: | 1558-9293 1097-3958 |
| DOI: | 10.1007/s11743-016-1798-7 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full text from SpringerLink