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|Title:||Synthesis and properties of N,N′-dialkylimidazolium bis(nonafluorobutane-1-sulfonyl)imides: A new subfamily of ionic liquids|
|Citation:||Quek, S.K., Lyapkalo, I.M., Huynh, H.V. (2006-03-27). Synthesis and properties of N,N′-dialkylimidazolium bis(nonafluorobutane-1-sulfonyl)imides: A new subfamily of ionic liquids. Tetrahedron 62 (13) : 3137-3145. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tet.2006.01.015|
|Abstract:||A series of N,N′-dialkylimidazolium bis(nonafluorobutane-1-sulfonyl) imides was synthesized in high yields by quaternization of imidazole derivatives with various readily available alkylating reagents, followed by anion exchange with highly stable and non-hygroscopic potassium bis(nonafluorobutane-1- sulfonyl)imide. The latter was obtained by an improved method starting from ammonium chloride and nonafluorobutane-1-sulfonyl fluoride. The quaternary imidazolium salts thus obtained constitute a new subfamily of thermally stable and remarkably hydrophobic ionic liquids with melting points in the range 0-40°C and solubilities in water and organic solvents (aromatic hydrocarbons, dialkyl ethers) in the range of 0.5-1.5 wt%. The ionic liquids can be easily purified from ionic byproducts (e.g., halogenide salts) by aqueous extraction followed by thorough drying in a high vacuum without loss of yield. Due to the above features, these new ionic fluids may be considered as promising recyclable media in repeated catalytic processes. © 2006 Elsevier Ltd. All rights reserved.|
|Appears in Collections:||Staff Publications|
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