Synthesis and properties of N,N′-dialkylimidazolium bis(nonafluorobutane-1-sulfonyl)imides: a new subfamily of ionic liquids |
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Authors: | Ser Kiang Quek Ilya M Lyapkalo Han Vinh Huynh |
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Institution: | a Institute of Chemical and Engineering Sciences Ltd, 1 Pesek Road, Jurong Island, Singapore 627833 b Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 |
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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. |
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Keywords: | Nonafluorobutane-1-sulfonyl fluoride Dialkyl imidazolium Bis(nonafluorobutane-1-sulfonyl)imide Hydrophobicity Ionic liquids |
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