Review of ionic liquids with fluorine-containing anions

Journal of Fluorine Chemistry

Volumn 127, Issue 2, 2006, Pages 159-176

  Xue, Hong ^a   Verma, Rajendar ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

Anion; Fluorination; Fluorine; Ionic liquids; Quaternization

Indexed keywords

EID: 32344439993     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.11.007     Document Type: Review

References (155)

1. T. Welton Chem. Rev. 99 1999 2083 2171
2. P. Wasserscheid, and W. Keim Angew. Chem. Int. Ed. 39 2000 3772 3789
3. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim, Germany
4. R. Hagiwara, and Y. Ito J. Fluorine Chem. 105 2000 221 227
5. R. Hagiwara, and Y. Ito Electrochemistry 70 2 2002 130 136 (Tokyo)
6. R.A. Sheldon Chem. Commun. 2001 2399 2407
7. R.D. Rogers, and K.R. Seddon Ionic Liquids: Industrial Applications to Green Chemistry, ACS Symposium Series 818 2002 American Chemical Society Washington, DC
8. R.D. Rogers, and K.R. Seddon Ionic Liquids as Green Solvents: Progress and Prospects, ACS Symposium Series 856 2003 American Chemical Society Washington, DC
9. R.D. Rogers, and K.R. Seddon Ionic Liquids IIIA: Fundamentals, Progress, Challenges, and Opportunities: Properties and Structure, ACS Symposium Series 901 2005 American Chemical Society Washington, DC
10. R.D. Rogers, and K.R. Seddon Ionic Liquids IIIB: Fundamentals, Progress, Challenges, and Opportunities: Transformations and Processes, ACS Symposium Series 902 2005 American Chemical Society Washington, DC
11. P. Kubisa Prog. Polym. Sci. 29 2004 3 12
12. J.H. Davis Jr. Chem. Lett. 33 9 2004 1072 1077
13. J.H. Davis Jr., and P.A. Fox Chem. Commun. 2003 1209 1212
14. N. Jain, A. Kumar, S. Chauhan, and S.M.S. Chauhan Tetrahedron 61 2005 1015 1060
15. A. Heintz J. Chem. Thermodyn. 37 6 2005 525 535
16. M.C. Buzzeo, R.G. Evans, and R.G. Compton Chem. Phys. Chem. 5 8 2004 1106 1120
17. K.N. Marsh, J.A. Boxall, and R. Lichtenthaler Fluid Phase Equilib. 219 1 2004 93 98
18. H. Xue, and J.M. Shreeve Eur. J. Inorg. Chem. 13 2005 2573 2580
19. Y. Gao, S.W. Arritt, B. Twamley, and J.M. Shreeve Inorg. Chem. 44 2005 1704 1712
20. H. Xue, B. Twamley, and J.M. Shreeve Adv. Mater. 17 2005 2142 2146
21. G. Drake, T. Hawkins, A. Brand, L. Hall, M. Mckay, A. Vij, and I. Ismail Propellants, Explosives, Pyrotechnics 28 4 2003 174 180
22. G. Drake, US Patent 6,509,473, January 21, 2003.
23. G. Drake, and T. Hawkins AFOSR Ionic Liquids Workshop Dulles, VA, October 2002
24. G. Drake AFOSR Ionic Liquids Workshop Aberdeen, MD, September 2003
25. G. Kaplan, G. Drake, K. Tollison, L. Hall, and T. Hawkins J. Heterocyclic Chem. 42 2005 19 27
26. G.W. Drake, T.M. Hawkins, J. Boatz, L. Hall, and A. Vij Propellants, Explosives, Pyrotechnics 30 2 2005 156 163
27. G. Drake, T. Hawkins, K. Tollison, L. Hall, A. Vij, and S. Sobaski R.D. Rogers K.R. Seddon (1R)-4-Amino-1,2,4-triazolium Salts: New Families of Ionic Liquids. In Ionic Liquids IIIB: Fundamentals, Progress, Challenges and Opportunities: Transformations and Processes, ACS Symposium Series 902 2005 American Chemical Society Washington, DC 259 302
28. P. Wasserscheid, R. van Hal, A. Boesmann, J. Esser, and A. Jess R.D. Rogers K.R. Seddon Ionic Liquids as Green Solvents, ACS Symposium Series 856 2003 57 69
29. J.D. Holbrey, W.M. Reichert, R.P. Swatloski, G.A. Broker, W.R. Pitner, K.R. Seddon, R. Kenneth, and R.D. Rogers Green Chem. 4 5 2002 407 413
30. K.O. Christe, W.W. Wilson, M.A. Petrie, H.H. Michels, J.C. Bottaro, and R. Gilardi Inorg. Chem. 35 1996 5068 5071
31. M.A. Petrie, J.A. Sheehy, J.A. Boatz, G. Rasul, G.K. Surya Prakash, G.A. Olah, and K.O. Christe J. Am. Chem. Soc. 119 1997 8802 8808
32. J.C. Bottaro, P.E. Penwell, and R.J. Schmitt J. Am. Chem. Soc. 119 1997 9405 9410
33. R. Gilardi, J. Flippen-Anderson, C. George, and R.J. Butcher J. Am. Chem. Soc. 119 1997 9411 9416
34. T.M. Klapötke, P. Mayer, A. Schulz, and J.J. Weigand J. Am. Chem. Soc. 127 2005 2032 2033
35. D.E.G. Jones, Q.S.M. Kwok, M. Vachon, C. Badeen, and W. Ridley Propellants, Explosives Pyrotechnics 30 2 2005 140 147
36. J.C. Gálvez-Ruiz, G. Holl, K. Karaghiosoff, T.M. Klapötke, K. Löhnwitz, P. Mayer, H. Nöth, K. Polborn, C.J. Rohbogner, M. Suter, and J.J. Weigand Inorg. Chem. 44 12 2005 4237 4253
37. M.W. Schmidt, M.S. Gordon, and J.A. Boatz J. Phys. Chem. A 109 32 2005 7285 7295
38. H. Xue, Y. Gao, B. Twamley, and J.M. Shreeve Inorg. Chem. 44 2005 5068 5072
39. H. Xue, B. Twamley, and J.M. Shreeve J. Mater. Chem. 15 2005 3459 3465
40. C.F. Ye, and J.M. Shreeve Chem. Commun. 2005 2570 2572
41. C.M. Jin, C.F. Ye, C. Piekarski, B. Twamley, and J.M. Shreeve Eur. J. Inorg. Chem. 18 2005 3760 3767
42. A. Hammerl, M.A. Hiskey, G. Holl, T.M. Klapötke, K. Polborn, J. Stierstorfer, and J.J. Weigand Chem. Mater. 17 14 2005 3784 3793
43. W. Ogihara, M. Yoshizawa, and H. Ohno Chem. Lett. 33 8 2004 1022 1023
44. A.R. Katritzky, S. Singh, K. Kirichenko, J.D. Holbrey, M. Smiglak, W.M. Reichert, and R.D. Rogers Chem. Commun. 7 2005 868 870
45. J. Pernak, and I. Goc Polish J. Chem. 77 2003 975 984
46. Z.B. Zhou, M. Takeda, and M. Ue J. Fluorine Chem. 123 2003 127 131
47. Z.B. Zhou, H. Matsumoto, and K. Tatsumi Chem. Lett. 33 6 2004 680 681
48. Z.B. Zhou, H. Matsumoto, and K. Tatsumi Chem. Lett. 33 7 2004 886 887
49. Z.B. Zhou, H. Matsumoto, and K. Tatsumi Chem. Lett. 33 12 2004 1636 1637
50. Z.B. Zhou, M. Takeda, and M. Ue J. Fluorine Chem. 125 2004 471 476
51. Z.B. Zhou, H. Matsumoto, and K. Tatsumi Chem. Eur. J. 10 24 2004 6581 6591
52. Z.B. Zhou, H. Matsumoto, and K. Tatsumi Chem. Eur. J. 11 2 2005 752 766
53. Z.B. Zhou, H. Matsumoto, and K. Tatsumi Chem. Phys. Chem. 6 7 2005 1324 1332
54. O.D. Gupta, B. Twamley, and J.M. Shreeve Tetrahedron Lett. 45 8 2004 1733 1736
55. O.D. Gupta, B. Twamley, and J.M. Shreeve J. Fluorine Chem. 126 8 2005 1222 1229
56. O.D. Gupta, P.D. Armstrong, and J.M. Shreeve Tetrahedron Lett. 44 2003 9367 9370
57. O.D. Gupta, B. Twamley, and J.M. Shreeve J. Fluorine. Chem. 127 2006 0000
58. R. Hagiwara, T. Hirashige, T. Tsuda, and Y. Ito J. Fluorine Chem. 99 1999 1 3
59. K. Matsumoto, R. Hagiwara, and Y. Ito J. Fluorine Chem. 115 2 2002 133 135
60. R. Hagiwara, T. Hirashige, T. Tsuda, and Y. Ito J. Electrochem. Soc. 149 1 2002 D1 D6
61. R. Hagiwara, K. Matsumoto, Y. Nakamori, T. Tsuda, Y. Ito, H. Matsumoto, and K. Momota J. Electrochem. Soc. 150 12 2003 D195 D199
62. K. Matsumoto, R. Hagiwara, R. Yoshida, Y. Ito, Z. Mazej, P. Benkic, B. Zemva, O. Tamada, H. Yoshino, and S. Matsubara Dalton Trans. 1 2004 144 149
63. K. Matsumoto, and R. Hagiwara Electrochemistry 73 8 2005 730 732 (Tokyo, Japan)
64. R. Hagiwara, Y. Nakamori, K. Matsumoto, and Y. Ito J. Phys. Chem. B 109 12 2005 5445 5449
65. K. Matsumoto, and R. Hagiwara J. Fluorine Chem. 126 7 2005 1095 1100
66. J.V.D. Broeke, F. Winter, B.J. Deelman, and G.V. Koten Org. Lett. 22 4 2002 3851 3854
67. N.V. Ignat'ev, W.R. Pitner, U. Welz-Biermann, M. Weiden, O. Sheppard, C. Hardacre, Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, United States, ORGN-546, American Chemical Society, Washington, DC, August 22-26, 2004.
68. N.V. Ignat'ev, and U. Welz-Biermann Chim. Oggi 22 9 2004 42 43
69. N.V. Ignat'ev, U. Welz-Biermann, A. Kucheryna, G. Bissky, and H. Willner J. Fluorine Chem. 126 2005 1150 1159
70. N.V. Ignat'ev, U. Welz-Biermann, G. Bissky, H. Willner, Abstracts of Papers, 14th European Symposium on Fluorine Chemistry, Poznań, Poland, July 11-16, 2004, C-P-29.
71. N.V. Ignat'ev, U. Welz-Biermann, A. Miller, G. Bissky, A. I. Kucheryna, H. Willner, Abstracts of Papers, 17th Winter Fluorine Conference, St. Petersburg, FL, 107, American Chemical Society, Washington, DC, January 9-14, 2005.
72. N.V. Ignat'ev, U. Welz-Biermann, M. Heckmeieer, A. Kucheryna, P. Sartori, H. Willner, Abstracts of Papers, 17th International Symposium on Fluorine Chemistry, Shanghai, China, July 24-29, 2005, B-0-08.
73. N.V. Ignat'ev, U. Welz-Biermann, and H. Willner Rossiiskii Khimicheskii Zhurnal 48 6 2004 36 39
74. D.B. Zhao, Z.F. Fei, C.A. Ohlin, G. Laurenczy, and P.J. Dyson Chem. Commun. 2004 2500 2501
75. P. Dyson, D. Zhao, Z.F. Fei, PCT Int. Appl. WO 2,005,019,185, March 3, 2005.
76. H. Matsumoto, H. Kageyama, and Y. Miyazaki Chem. Commun. 2002 1726 1727
77. T. Sato, G. Masuda, and K. Takagi Electrochim. Acta 49 2004 3603 3611
78. M. Egashira, S. Okada, J.I. Yamaki, D.A. Dri, F. Bonadies, and B. Scrosati J. Power Sources 138 2004 240 244
79. M. Egashira, S. Okada, J.I. Yamaki, N. Yoshimoto, and M. Morita Electrochim. Acta 50 2005 3708 3712
80. J. Pernak, and J. Feder-Kubis Chem. Eur. J. 11 5 2005 4441 4449
81. H. Martinez, H. Walker, V. Hernandez, R. Engel, S. Lall-Ramnarine, Abstracts, 37th Middle Atlantic Regional Meeting of the American Chemical Society, New Brunswick, NJ, United States, GENE-190, May 22-25, 2005.
82. C.J. Bradaric, A. Downard, C. Kennedy, A.J. Robertson, and Y.H. Zhou Green Chem. 5 2003 143 152
83. M.R. Netherton, and G.C. Fu Org. Lett. 26 3 2001 4295 4298
84. M.O. Wolff, K.M. Alexander, G. Belder, Chim. Oggi (2000) 29-32.
85. T. Ramnial, D.D. Ino, and J.A.C. Clyburne Chem. Commun. 2005 325 327
86. ® IL 109) and Strem Chemicals.
87. E. Frackowiak, G. Lota, and J. Pernak Appl. Phys. Lett. 86 2005 1 3 164104
88. M.D. Baumann, A.J. Daugulis, and P.G. Jessop Appl. Microbiol. Biotechnol. 67 2005 131 137
89. D.Q. Xu, B.Y. Liu, S.P. Luo, Z.Y. Xu, and Y.C. Shen Synthesis 17 2003 2626 2628
90. V.V. Namboodiri, and R.S. Varma Tetrahedron Lett. 43 2002 5381 5383
91. J.D. Holbrey, W.M. Reichert, and R.D. Rogers Dalton Trans. 15 2004 2267 2271
92. P. Kölle, and R. Dronskowski Eur. J. Inorg. Chem. 2004 2313 2320
93. H.L. Ngo, K. LeCompte, L. Hargens, and A.B. McEwen Thermochim. Acta 357-358 2000 97 102
94. A. Paul, P.K. Mandal, and A. Samanta Chem. Phys. Lett. 402 2005 4 6
95. M.T. Garcia, N. Gathergood, and P.J. Scammells Green Chem. 7 2005 9 14
96. S.V. Dzyuba, and R.A. Bartsch Chem. Commun. 2001 1466 1467
97. S.V. Dzyuba, and R.A. Bartsch Chem. Phys. Chem. 3 2002 161 166
98. L.C. Branco, J.N. Rosa, J.J.M. Ramos, and C.A.M. Afonso Chem. Eur. J. 8 16 2002 3671 3677
99. J. Pernak, A. Olszowka, and R. Olszewski Polish J. Chem. 77 2 2003 179 187
100. J.D. Holbrey, A.E. Visser, S.K. Spear, W.M. Reichert, R.P. Swatloski, G.A. Broker, and R.D. Rogers Green Chem. 5 2003 129 135
101. D. Demberelnyamba, S.J. Yoon, and H. Lee Chem. Lett. 33 5 2004 560 561
102. H. Liu, H.Z. Wang, G.H. Tao, and Y. Kou Chem. Lett. 34 8 2005 1184 1185
103. D.B. Zhao, Z.F. Fei, R. Scopelliti, and P.J. Dyson Inorg. Chem. 43 2004 2197 2205
104. P.A. Fox, S.T. Griffin, W.M. Reichert, E.A. Salter, A.B. Smith, M.D. Tickell, B.F. Wicker, E.A. Cioffi, J.H. Davis Jr., R.D. Rogers, and A. Wierzbicki Chem. Commun. 2005 3679 3681
105. Z.G. Mu, F. Zhou, S.X. Zhang, Y.M. Liang, and W.M. Liu Helvetica Chim. Acta 87 2004 2549 2555
106. D.J. Zhang, J.M. Chen, Y.M. Liang, and H.D. Zhou Synth. Commun. 35 4 2005 521 526
107. C.F. Ye, and J.M. Shreeve J. Org. Chem. 69 2004 6511 6513
108. P. Wasserscheid, A. Boesmann, and C. Bolm Chem. Commun. 2002 200 201
109. Y. Ishida, H. Miyauchi, and K. Saigo Chem. Commun. 2002 2240 2241
110. Y. Ishida, D. Sasaki, H. Miyauchi, and K. Saigo Tetrahedron Lett. 45 2004 9455 9459
111. J.J. Jodry, and K. Mikami Tetrahedron Lett. 45 2004 4429 4431
112. M. Tosoni, S. Laschat, and A. Baro Helvetica Chim. Acta 87 2004 2742 2749
113. P.J. Dyson Appl. Organomet. Chem. 16 2002 495 500 and references therein
114. M. Hassan, I.V. Kozhevnikov, M.R.H. Siddiqui, A. Steiner, and N. Winterton Inorg. Chem. 38 1999 5637 5641
115. M. Deetlefs, H.G. Raubenheimer, and Esterhuysen Catal. Today 72 2002 29 41
116. C.J. Bowlas, D.W. Bruce, and K.R. Seddon Chem. Commun. 1996 1625 1626
117. R.J.C. Brown, P.J. Dyson, D.J. Ellis, and T. Welton Chem. Commun. 2001 1862 1863
118. P.J. Dyson, J.S. McIndoe, and D. Zhao Chem. Commun. 2003 508 509
119. C.K. Lee, H.H. Peng, and I.J.B. Lin Chem. Mater. 16 2004 530 536
120. H. Schottenberger, K. Wurst, U.E.I. Horvath, S. Cronje, J. Lukasser, J. Polin, J.M. McKenzie, and H.G. Raubenheimer Dalton Trans. 2003 4275 4281
121. Y. Gao, B. Twamley, and J.M. Shreeve Inorg. Chem. 43 2004 3406 3412
122. R.P. Singh, S. Manandhar, and J.M. Shreeve Tetrahedron Lett. 43 2002 9497 9499
123. R.P. Singh, S. Manandhar, and J.M. Shreeve Synthesis 10 2003 1579 1585
124. J.C. Xiao, and J.M. Shreeve J. Org. Chem. 70 2005 3072 3078
125. J.C. Xiao, C.F. Ye, and J.M. Shreeve Org. Lett. 7 2005 1963 1965
126. C.M. Jin, B. Twamley, and J.M. Shreeve Organometallics 24 2005 3020 3023
127. B.A. Omotowa, and J.M. Shreeve Organometallics 23 2004 783 791
128. R.P. Singh, and J.M. Shreeve Chem. Commun. 2003 1366 1367
129. R.P. Singh, and J.M. Shreeve Inorg. Chem. 42 2003 7416 7421
130. J. Kim, R.P. Singh, and J.M. Shreeve Inorg. Chem. 43 2004 2960 2966
131. Y. Gao, and J.M. Shreeve Synthesis 7 2004 1072 1082
132. Y.L. Yagupolskii, T.M. Sokolenko, K.I. Petko, and L.M. Yagupolskii J. Fluorine Chem. 126 2005 669 672
133. S.A. Forsyth, and D.R. MacFarlane J. Mater. Chem. 13 2003 2451 2456
134. Y.R. Mirzaei, B. Twamley, and J.M. Shreeve J. Org. Chem. 67 2002 9340 9345
135. Y.R. Mirzaei, and J.M. Shreeve Synthesis 1 2003 24 26
136. H. Xue, and J.M. Shreeve J. Org. Chem. 69 2004 1397 1400
137. Y.R. Mirzaei, H. Xue, and J.M. Shreeve Inorg. Chem. 43 2004 361 367
138. Y. Xiao, and S.V. Malhotra J. Mol. Catal. A: Chem. 230 2005 129 133
139. Y. Xiao, and S.V. Malhotra Tetrahedron Lett. 45 45 2004 8339 8342
140. C. Patrascu, C. Sugisaki, C. Mingotaud, J.D. Marty, Y. Génisson, and N.L. de Viguerie Heterocycles 63 9 2004 2033 2041
141. D.B. Zhao, Z.F. Fei, T.J. Geldbach, R. Scopelliti, and P.J. Dyson J. Am. Chem. Soc. 126 2004 15876 15882
142. J.M. Crosthwaite, M.J. Muldoon, J.K. Dixon, J.L. Anderson, and J.F. Brennecke J. Chem. Thermodyn. 37 2005 559 568
143. R.P. Swatloski, J.D. Holbrey, and R.D. Rogers Green Chem. 5 4 2003 361 363
144. T. Kitazume J. Fluorine Chem. 105 2 2000 265 278
145. T. Fuchigami, and T. Tajima J. Fluorine Chem. 126 2005 181 187
146. D.W. Kim, C.E. Song, and D.Y. Chi J. Am. Chem. Soc. 124 2002 10278 10279
147. D.W. Kim, and D.Y. Chi Angew. Chem. Int. Ed. 43 2004 483 485
148. C.B. Murray, G. Sandford, and S.R. Korn J. Fluorine Chem. 123 2003 81 84
149. T. Kitazume, and T. Ebata J. Fluorine Chem. 125 2004 1509 1511
150. J.W. Kim, and J.M. Shreeve Org. Biomol. Chem. 2 2004 2728 2734
151. H. Yoshino, S. Matsubara, K. Oshima, K. Matsumoto, R. Hagiwara, and Y. Ito J. Fluorine Chem. 125 2004 455 458
152. H. Yoshino, K. Nomura, S. Matsubara, K. Oshima, K. Matsumoto, R. Hagiwara, and Y. Ito J. Fluorine Chem. 125 2004 1127 1129
153. H. Yoshino, S. Matsubara, K. Oshima, K. Matsumoto, R. Hagiwara, and Y. Ito J. Fluorine Chem. 126 2005 121 123
154. K.K. Laali, and G.I. Borodkin J. Chem. Soc. Perkin Trans. 2 2002 953 957
155. J. Baudoux, A.F. Salit, D. Cahard, and J.C. Plaquevent Tetrahedron Lett. 43 2002 6573 6574