Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions

Green Chemistry

Volumn 4, Issue 5, 2002, Pages 407-413

  Holbrey, John D ^a   Reichert, W Matthew ^a   Swatloski, Richard P ^a   Broker, Grant A ^a   Pitner, William R ^b   Seddon, Kenneth R ^b   Rogers, Robin D ^a  

^a UNIVERSITY OF ALABAMA   (United States)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67049173080     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b204469b     Document Type: Article

References (44)

1. See, for example: Ionic Liquids: Industrial Applications for Green Chemistry, ed. R. D. Rogers and K. R. Seddon, ACS Symposium Series 818, American Chemical Society, Washington DC, 2002.
2. J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser and R. D. Rogers, Chem. Commun., 1998, 1765; A. E. Visser, R. P. Swatloski, W. M. Reichert, S. T. Griffin and R. D. Rogers, Ind. Eng. Chem. Res., 2000, 39, 3596.
3. J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser and R. D. Rogers, Chem. Commun., 1998, 1765; A. E. Visser, R. P. Swatloski, W. M. Reichert, S. T. Griffin and R. D. Rogers, Ind. Eng. Chem. Res., 2000, 39, 3596.
4. A. E. Visser, R. P. Swatloski, S. T. Griffin, D. H. Hartman and R. D. Rogers, Sep. Sci. Technol., 2001, 36, 785.
5. K. Hong, H. Zhang, J. W. Mays, A. E. Visser, C. S. Brazel, J. D. Holbrey, W. M. Reichert and R. D. Rogers, Chem. Commun., 2002, 1368.
6. M. A. Klingshirn, G. A. Broker, J. D. Holbrey, K. H. Shaughnessy and R. D. Rogers, Chem. Commun., 2002, 1394; C. Hardacre, J. D. Holbrey, S. P. Katdare and K. R. Seddon, Green Chem., 2002, 4, 143.
7. M. A. Klingshirn, G. A. Broker, J. D. Holbrey, K. H. Shaughnessy and R. D. Rogers, Chem. Commun., 2002, 1394; C. Hardacre, J. D. Holbrey, S. P. Katdare and K. R. Seddon, Green Chem., 2002, 4, 143.
8. R. P. Swatloski, S. K. Spear, J. D. Holbrey and R. D. Rogers, J. Am. Chem. Soc., 2002, 124, 4974.
9. J. S. Wilkes, J. A. Levisky, R. A. Wilson and C. L. Hussey, Inorg. Chem., 1982, 21, 1263.
10. B. K. M. Chan, N.-H. Chang and M. R. Grimmett, Aust. J. Chem., 1977, 30, 2005.
11. R. X. Ren and J. X. Wu, Org. Lett., 2002, 3, 3727.
12. A. A. Fannin, D. A. Floreani, L. A. King, J. S. Landers, B. J. Piersma, D. J. Stech, R. L. Vaughn, J. S. Wilkes and J. L. Williams, J. Phys. Chem., 1984, 88, 2614.
13. J. S. Wilkes and M. J. Zaworotko, Chem. Commun., 1992, 965.
14. K. R. Seddon, A. Stark and M.-J. Torres, Pure Appl. Chem., 2001, 72, 2275.
15. Y. Chauvin and H. Olivier-Bourbigou, CHEMTECH, 1995, 30.
16. T. Welton, Chem. Rev., 1999, 99, 2071; J. D. Holbrey and K. R. Seddon, Clean Prod. Proc., 1999, 1, 223; P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772; R. Sheldon, Chem. Commun., 2001, 2399; C. M. Gordon, Appl. Catal. A, 2001, 222, 101.
17. T. Welton, Chem. Rev., 1999, 99, 2071; J. D. Holbrey and K. R. Seddon, Clean Prod. Proc., 1999, 1, 223; P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772; R. Sheldon, Chem. Commun., 2001, 2399; C. M. Gordon, Appl. Catal. A, 2001, 222, 101.
18. T. Welton, Chem. Rev., 1999, 99, 2071; J. D. Holbrey and K. R. Seddon, Clean Prod. Proc., 1999, 1, 223; P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772; R. Sheldon, Chem. Commun., 2001, 2399; C. M. Gordon, Appl. Catal. A, 2001, 222, 101.
19. T. Welton, Chem. Rev., 1999, 99, 2071; J. D. Holbrey and K. R. Seddon, Clean Prod. Proc., 1999, 1, 223; P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772; R. Sheldon, Chem. Commun., 2001, 2399; C. M. Gordon, Appl. Catal. A, 2001, 222, 101.
20. T. Welton, Chem. Rev., 1999, 99, 2071; J. D. Holbrey and K. R. Seddon, Clean Prod. Proc., 1999, 1, 223; P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772; R. Sheldon, Chem. Commun., 2001, 2399; C. M. Gordon, Appl. Catal. A, 2001, 222, 101.
21. A. S. Larsen, J. D. Holbrey, F. S. Tham and C. A. Reed, J. Am. Chem. Soc., 2000, 122, 7264.
22. (a) P. Bonhôte, A. P. Dias, N. Papageorgiou, K. Kalyanasundaram and M. Grätzel, Inorg. Chem., 1996, 35, 1168;
23. (b) K. R. Seddon, A. J. Carmichael and M. J. Earle, World Pat., WO 01/40146, June 7 2001.
24. M. Ue, M. Takeda, T. Takahashi and M. Takehara, Electrochem. Solid-State Lett., 2002, 5, A119.
25. D. Delledonne, F. Rivetti and U. Romano, Appl. Catal. A, 2001, 221, 241.
26. Z. Kricsfalussy, H. Waldmann and H.-J. Traenckner, Ind. Eng. Chem. Res., 1998, 37, 856.
27. A. J. Ardeuengo III, US Pat., 5, 077, 414, Dec 31, 1991.
28. A. J. Arduengo III, H. V. R. Dias, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1992, 114, 5530.
29. W. A. Herrmann, L. J. Goossen, G. R. J. Artus and C. Köcher, Organometallics, 1997, 16, 2472.
30. M. J. Earle and K. R. Seddon, World Pat., WO 01/77081 October 18, 2001.
31. W. B. McCormack and B. C. Lawes, Sulfuric and Sulfurous Esters, in Kirk Othmer Encyclopedia of Chemical Technology, Wiley, New York, 4th Edition, 1997, vol. 23, p. 409.
32. S. H. Schöfer, N. Kaftzik, P. Wasserscheid and U. Kragl, Chem. Commun., 2001, 425.
33. R. A. Sheldon, R. M. Lau, M. J. Sorgedrager, F. van Rantwijk and K. R. Seddon, Green Chem., 2002, 4, 147.
34. A. Bösmann, L. Datsevich, A. Jess, A. Lauter, C. Schmitz and P. Wasserscheid, Chem. Commun., 2001, 2494.
35. L. A. Blanchard, Z. Gu and J. F. Brennecke, J. Phys. Chem. B, 2001, 105, 2437.
36. J. D. Holbrey and K. R. Seddon, J. Chem. Soc., Dalton Trans., 1999, 2133.
37. J. Golding, S. Forsyth, D. R. MacFarlane, M. Forsyth and G. B. Deacon, Green Chem., 2002, 4, 223.
38. J. G. Huddleston, A. E. Visser, W. R. Reichert, H. D. Willauer, G. A. Broker and R. D. Rogers, Green Chem., 2001, 3, 156.
39. C. M. Gordon, J. D. Holbrey, A. R. Kennedy and K. R. Seddon, J. Mater. Chem., 1998, 8, 2627.
40. J. D. Holbrey and R. D. Rogers, Melting Points and Phase Diagrams, in Ionic Liquids in Synthesis, ed. P. Wasserscheid and T. Welton, Wiley-VCH, Weinheim, 2002, pp. 41-55.
41. J. D. Holbrey, A. E. Visser and R. D. Rogers, Solubility and Solvation in Ionic Liquids, inIonic Liquids in Synthesis, ed. P. Wasserscheid and T. Welton, Wiley-VCH, Weinheim, 2002, pp. 68-81.
42. J. Fuller, R. T. Carlin and R. A. Osteryoung, J. Electrochem. Soc., 1987, 144, 3881.
43. A. J. Arduengo III, US Pat., 6, 177, 575, Jan 23, 2001.
44. S. V. Dzyuba and R. A. Bartsch, Chem. Commun., 2001, 1466.