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The Distillation and Volatility of Ionic Liquids

The Distillation and Volatility of Ionic Liquids. Martyn J. Earle, Jose M.S.S. Esperanca, Manuela A. Gilea, Jose N. Canongia Lopes, Luis P.N. Rebelo, Joseph W. Magee, Kenneth R. Seddon & Jason A. Widegren. Nature 2006 , 439 , 831-834. 1-ethyl-3-methylimidazolium chloride.

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The Distillation and Volatility of Ionic Liquids

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  1. The Distillation and Volatility of Ionic Liquids Martyn J. Earle, Jose M.S.S. Esperanca, Manuela A. Gilea, Jose N. Canongia Lopes, Luis P.N. Rebelo, Joseph W. Magee, Kenneth R. Seddon & Jason A. Widegren Nature2006, 439, 831-834.

  2. 1-ethyl-3-methylimidazolium chloride • [C2mim]Cl - AlCl3 system with a greater than 2:1 excess of AlCl3, a detectable vapour pressure of Al2Cl6 was observed above 191 oC. • [C2mim]Cl2 190 oC in vacuum decompose (transalkylation):1-methylimidazole, 1-ethylimidazole, chloromethane, chloroethane, ethene and hydrogen chloride recondense:[C1mim]Cl - [C2mim]Cl- [C2eim]Cl Dymek, C. J. Jr, Hussey, C. L., Wilkes, J. S. & Øye, H. A. in Joint (Sixth) International Symposium on Molten Salts (eds Mamantov, G. et al.) 93–-104 (The Electrochemical Society, Pennington, New Jersey, 1987). Øye, H. A. & Wahnsiedler, W. E. in The Fourth International Symposium on Molten Salts (eds Blander, M., Newman, D. S., Saboungi, M. L., Mamantov, G. & Johnson, K.) 58–-73 (The Electrochemical Society, Pennington, New Jersey, 1984). Jeapes, A. J. et al. Process for recycling ionic liquids. World Patent WO 01/15175 (2001).

  3. Yoshizawa, M., Xu, W. & Angell, C. A. J. Am. Chem. Soc.2003, 125, 15411–-15419. Kreher, U. P., Rosamilia, A. E., Raston, C. L., Scott, J. L. & Strauss, C. R. Self-associated, “distillable” ionic media. Molecules, 2004, 9, 387–-393.

  4. Apparatus 1. Kugelrohr apparatus 2. Sublimation apparatus

  5. [NTf2]- is bis{(trifluoromethyl)-sulphonyl}amide, also known as bistriflamide, [N(SO2CF3)2]-

  6. cholinium [CxyzN(C2H4OH)]+ tetraalkylammonium [NCwx y z]+ tetraalkylphosphonium [PCwx y z ]+

  7. cholinium [CxyzN(C2H4OH)]+ tetraalkylammonium [NCwx y z]+ tetraalkylphosphonium [PCwx y z ]+ ˇ

  8. Ionic liquids with other anions • (for example, halides, sulphates, or carboxylates) • decomposed on distillation. • The principal mechanism of decomposition was by • dealkylation or transalkylation of the cation. • This is aided by a nucleophilic anion.

  9. No feasible mechanism to transfer a proton to the anion R = H , CH3

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