Ionic Liquids and Relative Process Design

  • S. Zhang
  • X. Lu
  • Y. Zhang
  • Q. Zhou
  • J. Sun
  • L. Han
  • G. Yue
  • X. Liu
  • W. Cheng
  • S. Li
Part of the Structure and Bonding book series (STRUCTURE, volume 131)

Abstract

Ionic liquids have gained increasing attention in recent years due to their significant advantages, not only as alternative solvents but also as new materials and catalysts. Until now, most research work on ionic liquids has been at the laboratory or pilot scale. In view of the multifarious applications of ionic liquids, more new knowledge is needed and more systematic work on ionic liquids should be carried out deeply and broadly in order to meet the future needs of process design. For example, knowledge of the physicochemical properties is indispensable for the design of new ionic liquids and for the development of novel processes. The synthesis and application of ionic liquids are fundamental parts of engineering science, and the toxicity and environmental assessment of ionic liquids is critical importance for their large scale applications, especially for process design. These research aspects are closely correlated to the industrial applications of ionic liquids and to sustainable processes. However, material process design in the industrial applications of ionic liquids has hardly been implemented. Therefore, this chapter reviews several essential issues that are closely related to process design, such as the synthesis, structure-property relationships, important applications, and toxicity of ionic liquids.

Keywords

Ionic liquids Process design Synthesis Properties Applications Toxicity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Han X, Armstrong DW (2007) Acc Chem Res 40:1079Google Scholar
  2. 2.
    Alkire RC, Braatz RD (2004) AIChE J 50:2000Google Scholar
  3. 3.
    El Seoud OA, Koschella A, Fidale LC, Dorn S, Heinze T (2007) Biomacromolecules 8:2629Google Scholar
  4. 4.
    Ranke J, Stolte S, Stormann R, Arning J, Jastorff B (2007) Chem Rev 107:2183Google Scholar
  5. 5.
    van Rantwijk F, Sheldon RA (2007) Chem Rev 107:2757Google Scholar
  6. 6.
    Fellay C (2007) Chimia 61:172Google Scholar
  7. 7.
    Weyershausen B, Hell K, Hesse U (2005) Green Chem 7:283Google Scholar
  8. 8.
    Chemical industry vision 2020 technology partnership. Ionic liquids. http://www. chemicalvision2020.org/ionicliquids.html
  9. 9.
    Rogers RD, Seddon KR (2003) Science 302:792Google Scholar
  10. 10.
    Broch SC, Berthod A, Armstrong DW (2003) Anal Bioanal Chem 375:191Google Scholar
  11. 11.
    Zhang Q-G, Yang J-Z, Lu X-M, Gui LS, Huang M (2004) Fluid Phase Equilibria 226:207Google Scholar
  12. 12.
    Hanz KR, Riechel TL (1997) Inorg Chem 36:4024Google Scholar
  13. 13.
    Holbrey JD, Seddon KR (1999) J Chem Soc Dalton Trans 13:2133Google Scholar
  14. 14.
    Souza RFd, Rech V, Dupont J (2002) Adv Synth Catal 344:153Google Scholar
  15. 15.
    Tao G-H, He L, Sun N, Kou Y (2005) Chem Commun 28:3562Google Scholar
  16. 16.
    Holbrey JD, Reichert WM, Swatloski RP, Broker GA, Pitner WR, Seddon KR, Rogers RD (2002) Green Chem 4:407Google Scholar
  17. 17.
    Holbrey JD, Turner MB, Reichert WM, Rogers RD (2003) Green Chem 5:731Google Scholar
  18. 18.
    Tao G-H, He L, Liu W-S, Xu L, Xiong W, Wang T, Kou Y (2006) Green Chem 8:639Google Scholar
  19. 19.
    Allen CR, Richard PL, Ward AJ, van de Water LGA, Masters AF, Maschmeyer T (2006) Tetrahedron Lett 47:7367Google Scholar
  20. 20.
    Del Pópolo MG, Voth GA (2004) J Phys Chem B 108:1744Google Scholar
  21. 21.
    Wasserscheid P, Keim W (2000) Angew Chem 39:3772Google Scholar
  22. 22.
    Wang P, Zakeeruddin SM, Grätzel M, Kantlehner W, Mezger J, Stoyanov EV, Scherr O (2004) Appl Phys A: Mater Sci Process 79:73Google Scholar
  23. 23.
    Welton T (1999) Chem Rev 99:2071Google Scholar
  24. 24.
    Morrow TI, Maginn EJ (2002) J Phys Chem B 106:12807Google Scholar
  25. 25.
    Brennecke JF, Maginn EJ (2001) AIChE J 47:2384Google Scholar
  26. 26.
    Sheldon R (2001) Chem Commun 23:2399Google Scholar
  27. 27.
    Dupont J, de Souza RF, Suarez PAZ (2002) Chem Rev 102:3667Google Scholar
  28. 28.
    Smit B, Krishna R (2003) Chem Eng Sci 58:557Google Scholar
  29. 29.
    Rogers RD, Seddon KR (2003) Ionic liquids as green solvents: progress and prospects. American Chemical Society, Washington, DCGoogle Scholar
  30. 30.
    de Andrade J, Boes ES, Stassen H (2002) J Phys Chem B 106:13344Google Scholar
  31. 31.
    Liu Z, Huang S, Wang W (2004) J Phys Chem B 108:12978Google Scholar
  32. 32.
    Lopes JNC, Padua AAH (2004) J Phys Chem B 108:16893Google Scholar
  33. 33.
    Yu G, Zhang S, Yao X, Zhang J, Dong K, Dai W, Mori R (2006) Ind Eng Chem Res 45:2875Google Scholar
  34. 34.
    Yu G, Zhang S, Zhou G, Liu X, Chen X (2007) AIChE J 53:3210Google Scholar
  35. 35.
    Yu G, Zhang S (2007) Fluid Phase Equilib 255:86Google Scholar
  36. 36.
    Dong K, Zhang S, Wang D, Yao X (2006) J Phys Chem A 110:9775Google Scholar
  37. 37.
    Zhang S, Yuan X, Chen Y, Zhang X (2005) J Chem Eng Data 50:1582Google Scholar
  38. 38.
    Liu X, Zhang S, Zhou G, Wu G, Yuan X, Yao X (2006) J Phys Chem B 110:12062Google Scholar
  39. 39.
    Liu X, Zhou G, Zhang S, Wu G, Yu G (2007) J Phys Chem B 111:5658Google Scholar
  40. 40.
    Zhou G, Liu X, Zhang S, Yu G, He H (2007) J Phys Chem B 111:7078Google Scholar
  41. 41.
    Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD (2001) Green Chem 3:156Google Scholar
  42. 42.
    Wilkes JS, Zaworotko MJ (1992) J Chem Soc Chem Commun 13:965Google Scholar
  43. 43.
    Gordon CM, Holbrey JD, Kennedy AR, Seddon KR (1998) J Mater Chem 8:2627Google Scholar
  44. 44.
    Ngo HL, LeCompte K, Hargens L, McEwen AB (2000) Thermochim Acta 357–358:97Google Scholar
  45. 45.
    Matsumoto H, Kageyama H, Miyazaki Y (2002) Chem Commun 16:1726Google Scholar
  46. 46.
    Zhou Z-B, Matsumoto H, Tatsumi K (2004) Chem Lett 33:680Google Scholar
  47. 47.
    Larsen AS, Holbrey JD, Tham FS, Reed CA (2000) J Am Chem Soc 122:7264Google Scholar
  48. 48.
    Branco LC, Rosa JN, Ramos JJM, Alfonso CAM (2002) Chem Eur J 8:3671Google Scholar
  49. 49.
    Omotowa BA, Shreeve JM (2004) Organometallics 23:783Google Scholar
  50. 50.
    Suarez PAZ, Einloft S, Dullius JEL, Souza Red, Dupont L (1998) J Chim Phys 95:1626Google Scholar
  51. 51.
    Crosthwaite JM, Muldoon MJ, Dixon JK, Anderson LL, Brennecke JE (2005) J Chem Ther-modyn 37:559Google Scholar
  52. 52.
    Nishida T, Tashiro Y, Yamamoto M (2003) J Fluorine Chem 120:135Google Scholar
  53. 53.
    Law G, Watson PR (2001) Langmuir 17:6138Google Scholar
  54. 54.
    Dzyuba SV, Bartsch RA (2002) Chem Phys Chem 3:161Google Scholar
  55. 55.
    Perry RL, Jones KM, Scott WD, Liao Q, Hussey CL (1995) J Chem Eng Data 40:615Google Scholar
  56. 56.
    Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M (1996) Inorg Chem 35:1168Google Scholar
  57. 57.
    Gu Z, Brennecke JF (2002) J Chem Eng Data 47:339Google Scholar
  58. 58.
    Widegren JA, Laesecke A, Magee JW (2005) Chem Commun 12:1610Google Scholar
  59. 59.
    Seddon KR, Stark A, Torres M-J (2000) Pure Appl Chem 72:2275Google Scholar
  60. 60.
    Holbrey JD, Seddon KR (1999) Clean Prod Process 1:223Google Scholar
  61. 61.
    Parvulescu VI, Hardacre C (2007) Chem Rev 107:2615Google Scholar
  62. 62.
    Zhao D, Wu M, Kou Y, Min E (2002) Catal Today 74:157Google Scholar
  63. 63.
    Gibson DH (1996) Chem Rev 96:2063Google Scholar
  64. 64.
    Leitner W (1996) Coord Chem Rev 153:257Google Scholar
  65. 65.
    Darensbourg DJ, Holtcamp MW (1996) Coord Chem Rev 153:155Google Scholar
  66. 66.
    Yin X, Moss JR (1999) Coord Chem Rev 181:27Google Scholar
  67. 67.
    Shi M, Shen YM (2003) Curr Org Chem 7:737Google Scholar
  68. 68.
    White CM, Strazisar BR, Granite EJ, Hoffman JS, Pennline HW (2003) J Air Waste Manage Assoc 53:645Google Scholar
  69. 69.
    Pez GP, Carlin RT, Laciak DV, Sorensen JC (1988) US Patent 4761,164Google Scholar
  70. 70.
    Blanchard LA, Hancu D, Beckman EJ, Brennecke JF (1999) Nature 399:28Google Scholar
  71. 71.
    Anthony JL, Maginn EJ, Brennecke JF (2002) J Phys Chem B 106:7315Google Scholar
  72. 72.
    Blanchard LA, Gu Z, Brennecke JF (2001) J Phys Chem B 105:2437Google Scholar
  73. 73.
    Aki SNVK, Mellein BR, Saurer EM, Brenneke JF (2004) J Phys Chem B 108:20355Google Scholar
  74. 74.
    Cadena C, Anthony JL, Shah JK, Morrow TI, Brennecke JF, Maginn EJ (2004) J Am Chem Soc 126:5300Google Scholar
  75. 75.
    Shariati A, Peters CJ (2005) J Supercrit Fluids 34:171Google Scholar
  76. 76.
    Camper D, Scovazzo P, Koval C, Noble R (2004) Ind Eng Chem Res 43:3049Google Scholar
  77. 77.
    Kazarian SG, Briscoe BJ, Welton T (2000) Chem Commun 20:2047Google Scholar
  78. 78.
    Anthony JL, Anderson JL, Maginn EJ, Brennecke JF (2005) J Phys Chem B 109:6366Google Scholar
  79. 79.
    Zhang S, Chen Y, Ren RXF, Zhang Y, Zhang J, Zhang X (2005) J Chem Eng Data 50:230Google Scholar
  80. 80.
    Zhang J, Zhang S, Dong K, Zhang Y, Shen Y, Lu X (2006) Chem Eur J 12:4021Google Scholar
  81. 81.
    Yuan X, Zhang S, Chen Y, Lu X, Dai W, Mori R (2006) J Chem Eng Data 51:645Google Scholar
  82. 82.
    Dupont J, Suarez PAZ (2006) Phys Chem Chem Phys 8:244Google Scholar
  83. 83.
    Migowski P, Dupont J (2007) Chem Eur J 13:32Google Scholar
  84. 84.
    Dupont J, Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR (2002) J Am Chem Soc 124:4228Google Scholar
  85. 85.
    Huang J, Jiang T, Han B, Gao H, Chang Y, Zhao G, Wu W (2003) Chem Commun 14:1654Google Scholar
  86. 86.
    Huang J, Jiang T, Gao H, Han B, Liu Z, Wu W, Chang Y, Zhao G (2004) Angew Chem Int Edn 43:1397Google Scholar
  87. 87.
    Zhao C, Wang H-Z, Yan N, Xiao CX, Mu XD, Dyson PJ, Kou Y (2007) J Catal 250:33Google Scholar
  88. 88.
    Riisager A, Wasserscheid P, Hal RV, Fehrmann R (2003) J Catal 219:452Google Scholar
  89. 89.
    Chauvin Y, Mussmann L, Olivier H (1996) Angew Chem Int Edn 34:2698Google Scholar
  90. 90.
    Zulfiqar F, Kitazume T (2000) Green Chem 2:296Google Scholar
  91. 91.
    Adams CJ, Earle MJ, Seddon KR (2000) Green Chem 2:21Google Scholar
  92. 92.
    Green L, Hemeon I, Singer RD (2000) Tetrahedron Lett 41:1343Google Scholar
  93. 93.
    Freemantle M (2000) Chem Eng News 15:20Google Scholar
  94. 94.
    Song CE, Oh CR, Roh EJ, Choo DJ (2000) Chem Commun 18:1743Google Scholar
  95. 95.
    Hardacre C, Katdare SP, Milroy D, Nancarrow P, Rooney DW, Thompson JM (2004) J Catal 227:44Google Scholar
  96. 96.
    Boon JA, Levisky JA, Pflug JL, Wilkes JS (1986) J Org Chem 51:480Google Scholar
  97. 97.
    Stark A, MacLean BL, Singer RD (1999) J Chem Soc Dalton Trans 1:63Google Scholar
  98. 98.
    Song CE, Roh EJ, Shim WH, Choi JH (2000) Chem Commun 17:1695Google Scholar
  99. 99.
    Rideout DC, Breslow R (1980) J Am Chem Soc 102:7816Google Scholar
  100. 100.
    Olivier H (1999) J Mol Catal A: Chem 146:285Google Scholar
  101. 101.
    Olivier H, Hirschauer A (1962) French patent application 96:1996Google Scholar
  102. 102.
    Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2002) Green Chem 4:24Google Scholar
  103. 103.
    Meracz I, Oh T (2003) Tetrahedron Lett 44:6465Google Scholar
  104. 104.
    Doherty S, Goodrich P, Hardacre C, Luo HK, Rooney DW, Seddon KR, Styring P (2004) Green Chem 6:63Google Scholar
  105. 105.
    Mathews CJ, Smith PJ, Welton T (2003) J Mol Catal A: Chem 206:77Google Scholar
  106. 106.
    Mathews CJ, Smith PJ, Welton T (2004) J Mol Catal A: Chem 214:27Google Scholar
  107. 107.
    McLachlan F, Mathews CJ, Smith PJ, Welton T (2003) Organometallics 22:5350Google Scholar
  108. 108.
    Wang R, Twamley B, Shreeve JM (2006) J Org Chem 71:426Google Scholar
  109. 109.
    Jin CM, Twamley B, Shreeve JM (2005) Organometallics 24:3020Google Scholar
  110. 110.
    Xiao JC, Twamley B, Shreeve JM (2004) Org Lett 6:3845Google Scholar
  111. 111.
    Zou G, Wang Z, Zhu J, Tang J, He MY (2003) J Mol Catal A: Chem 206:193Google Scholar
  112. 112.
    Corma A, Garcia H, Leyva A (2004) Tetrahedron 60:8553Google Scholar
  113. 113.
    Hamill NA, Hardacre C, McMath SEJ (2002) Green Chem 4:139Google Scholar
  114. 114.
    Deshmukh RR, Rajagopal R, Srinivasan KV (2001) Chem Commun 17:1544Google Scholar
  115. 115.
    Cassol CC, Umpierre AP, Machado G, Wolke SI, Dupont J (2005) J Am Chem Soc 127:3298Google Scholar
  116. 116.
    Reetz MT, Westermann E (2000) Angew Chem Int Edn 39:165Google Scholar
  117. 117.
    Vallin KSA, Emilsson P, Larhed M, Hallberg A (2002) J Org Chem 67:6243Google Scholar
  118. 118.
    Xie X, Lu J, Chen B, Han J, She X, Pan X (2004) Tetrahedron Lett 45:809Google Scholar
  119. 119.
    Hagiwara H, Shimizu Y, Hoshi T, Suzuki T, Ando M, Ohkubo K, Yokoyama C (2001) Tetrahedron Lett 42:4349Google Scholar
  120. 120.
    Okubo K, Shirai M, Yokoyama C (2002) Tetrahedron Lett 43:7115Google Scholar
  121. 121.
    Forsyth SA, Gunaratne HQN, Hardacre C,McKeown A, Rooney DW, Seddon K (2005) J Mol Catal A: Chem 231:61Google Scholar
  122. 122.
    Hagiwara H, Sugawara Y, Hoshi T, Suzuki T (2005) Chem Commun, 23:2942Google Scholar
  123. 123.
    Wang L, Zhang Y, Xie C, Wang Y (2005) Synlett 12:1861Google Scholar
  124. 124.
    de Bellefon C, Pollet E, Grenouillet P (1999) J Mol Catal A: Chem 145:121Google Scholar
  125. 125.
    Chen W, Xu L, Chatterton C, Xiao J (1999) Chem Commun 13:1247Google Scholar
  126. 126.
    Zevenhoven R, Eloneva S, Teir S (2006) Catal Today 115:73Google Scholar
  127. 127.
    Jessop PG, Ikariya T, Noyori R (1999) Chem Rev 99:475Google Scholar
  128. 128.
    Zhang S, Chen Y, Li F et al (2006) Catal Today 115:61Google Scholar
  129. 129.
    Peng J, Deng Y (2001) New J Chem 25:639Google Scholar
  130. 130.
    Sun J, Fujita SI, Arai MJ (2005) Organomet Chem 690:3490Google Scholar
  131. 131.
    Bhanage BM, Fujita S-I, Ikushima Y, Arai M (2001) Appl Catal A: General 219:259Google Scholar
  132. 132.
    Kawanami H, Sasaki A, Matsui K, Ikushima Y (2003) Chem Commun 7:896Google Scholar
  133. 133.
    Calo V, Nacci A, Monopoli A, Fanizzi A (2002) Org Lett 4:2561Google Scholar
  134. 134.
    Kim HS, Kim JJ, Kim H, Jang HG (2003) J Catal 220:44Google Scholar
  135. 135.
    Sun J, Wang L, Zhang S, Li Z, Zhang X, Dai W, Mori R (2006) J Mol Catal A: Chem 256:295Google Scholar
  136. 136.
    Sun J, Fujita S-i, Zhao F, Arai M (2004) Green Chem 6:613Google Scholar
  137. 137.
    Alvaro M, Baleizao C, Das D, Carbonell E, Garcia H (2004) J Catal 228:254Google Scholar
  138. 138.
    Zhu YJ, Wang WW, Qi RJ, Hu XL (2004) Angew Chem Int Edn 43:1410Google Scholar
  139. 139.
    Endres F, Abedin SZE (2002) Chem Commun 8:892Google Scholar
  140. 140.
    Nakashima T, Kimizuka N (2003) J Am Chem Soc 125:6386Google Scholar
  141. 141.
    Zhou Y, Antonietti M (2003) J Am Chem Soc 125:14960Google Scholar
  142. 142.
    Li Z, Zhang J, Du J, Gao H, Gao Y, Mu T, Han B (2005) Mater Lett 59:963Google Scholar
  143. 143.
    Wang Y, Yang H (2005) J Am Chem Soc 127:5316Google Scholar
  144. 144.
    Jiang Y, Zhu YJ (2005) J Phys Chem B 109:4361Google Scholar
  145. 145.
    Li Z, Liu Z, Zhang J, Han B, Du J, Gao Y, Jiang T (2005) J Phys Chem B 109:14445Google Scholar
  146. 146.
    Cao J, Wang J, Fang B, Chang X, Zheng M, Wang H (2004) Chem Lett 33:1332Google Scholar
  147. 147.
    Wang W-W, Zhu Y-J, Cheng G-F, Huang YH (2006) Mater Lett 60:609Google Scholar
  148. 148.
    Yang LX, Zhu YJ, Wang WW, Tong H, Ruan ML (2006) J Phys Chem B 110:6609Google Scholar
  149. 149.
    Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR, Dupont J (2003) Chem Eur J 9:3263Google Scholar
  150. 150.
    Fonseca GS, Scholten JD, Dupont J (2004) Synlett 9:1525Google Scholar
  151. 151.
    Miao S, Miao Z, Liu Z, Han B, Zhang H, Zhang J (2006) Microporous Mesoporous Mater 95:26Google Scholar
  152. 152.
    Biswas K, Rao CNR (2007) Chem Eur J 13:6123Google Scholar
  153. 153.
    Jin K, Huang X, Pang L, Li J, Appel A, Wherland S (2002) Chem Commun 23:2872Google Scholar
  154. 154.
    Sakamoto H, Watanabe Y, Saito T (2006) Inorg Chem 45:4578Google Scholar
  155. 155.
    Wang T, Kaper H, Antonietti M, Smarsly B (2007) Langmuir 23:1489Google Scholar
  156. 156.
    Cooper ER, Andrews CD, Wheatley PS, Webb PB, Wormald P, Morris RE (2004) Nature 430:1012Google Scholar
  157. 157.
    Parnham ER, Drylie EA, Wheatley PS, Slawin AMZ, Morris RE (2006) Angew Chem Int Edn 45:4962Google Scholar
  158. 158.
    Parnham ER, Wheatley PS, Morris RE (2006) Chem Commun 4:380Google Scholar
  159. 159.
    Parnham ER, Morris RE (2006) Chem Mater 18:4882Google Scholar
  160. 160.
    Parnham ER, Morris RE (2006) J Am Chem Soc 128:2204Google Scholar
  161. 161.
    Parnham ER, Morris RE (2006) J Mater Chem 16:3682Google Scholar
  162. 162.
    Cooper ER, Andrews CD, Wheatley PS, Webb PB, Wormald P, Morris RE (2005) Studies Surf Sci Catal 158:247Google Scholar
  163. 163.
    Tang M-F, Liu Y-H, Chang P-C, Liao YC, Kao HM, Lii KH (2007) Dalton Trans 40:4523Google Scholar
  164. 164.
    Sheu CY, Lee SF, Lii KH (2006) Inorg Chem 45:1891Google Scholar
  165. 165.
    Tsao CP, Sheu CY, Nguyen N, Lii KH (2006) Inorg Chem 45:6361Google Scholar
  166. 166.
    Dybtsev DN, Chun H, Kim K (2004) Chem Commun 14:1594Google Scholar
  167. 167.
    Liao J-H, Huang W-C (2006) Inorg Chem Commun 9:1227Google Scholar
  168. 168.
    Lin Z, Slawin AMZ, Morris RE (2007) J Am Chem Soc 129:4880Google Scholar
  169. 169.
    Lin Z, Wragg DS, Warren JE, Morris RE (2007) J Am Chem Soc 129:10334Google Scholar
  170. 170.
    Jiang J, Yu SH, Yao WT, Ge H, Zhang GZ (2005) Chem Mater 17:6094Google Scholar
  171. 171.
    Fonseca GS, Machado G, Teixeira SR, Fecher GH, Morais J, Alves MCM, Dupont J (2006) J Colloid Interf Sci 301:193Google Scholar
  172. 172.
    Wang WW, Zhu YJ (2005) Cryst Growth Des 5:505Google Scholar
  173. 173.
    Gao S, Zhang H, Wang X, Mai W, Peng C, Ge L (2005) Nanotechnology 16:1234Google Scholar
  174. 174.
    Ding K, Miao Z, Liu Z, Zhang Z, Han B, An G, Miao S, Xie Y (2007) J Am Chem Soc 129:6362Google Scholar
  175. 175.
    Wang L, Xu Y, Wei Y, Duan J, Chen A, Wang B, Ma H, Tian Z, Lin L (2006) J Am Chem Soc 128:7432Google Scholar
  176. 176.
    Xu Y-P, Tian Z-J, Wang S-J, Hu Y, Wang L, Wang BC, Ma YC, Hou L, Yu JY, Lin LW (2006) Angew Chem Int Edn 45:3965Google Scholar
  177. 177.
    Han L, Wang Y, Li C, Zhang S, Lu X, Cao M (2008) AIChE J 54:280Google Scholar
  178. 178.
    Parnham ER, Morris RE (2007) Acc Chem Res 40:1005Google Scholar
  179. 179.
    Fuller J, Carlin RT, Osteryoung RA (1997) J Electrochem Soc 144:3881Google Scholar
  180. 180.
    Nanjundiah C, McDevitt SF, Koch VR (1997) J Electrochem Soc 144:3392Google Scholar
  181. 181.
    Suarez PAZ, Selbach VM, Dullius JEL, Einloft S, Piatnicki CMS, Azambuja DS, de Souza RF, Dupont J (1997) Electrochim Acta 42:2533Google Scholar
  182. 182.
    Koch VR, Dominey LA, Nanjundiah C, Ondrechen MJ (1996) J Electrochem Soc 143:798Google Scholar
  183. 183.
    Trulove PC, Mantz RA (2003) Ionic liquids in synthesis. Wiley-VCH, New YorkGoogle Scholar
  184. 184.
    Buzzeo MC, Evans RG, Compton RG (2004) Chem Phys Chem 5:1106Google Scholar
  185. 185.
    Ito Y, Nohira T (2000) Electrochim Acta 45:2611Google Scholar
  186. 186.
    Ohno H (2005) Electrochemical aspects of ionic liquids. Wiley, HobokenGoogle Scholar
  187. 187.
    Endres F (2002) Chem Phys Chem 3:144Google Scholar
  188. 188.
    Abbott AP, McKenzie KJ (2006) Phys Chem Chem Phys 8:4265Google Scholar
  189. 189.
    Abbott AP, Capper G, McKenzie KJ, Ryder KS (2006) Electrochim Acta 51:4420Google Scholar
  190. 190.
    Christopher S (2005) Engineer 293:36Google Scholar
  191. 191.
    Abbott AP, Capper G, Swain BG, Wheeler DA (2005) Trans Inst Metal Finish 83:51Google Scholar
  192. 192.
    Barhdadi R, Courtinard C, Nédélec JY, Troupel M (2003) Chem Commun 12:1434Google Scholar
  193. 193.
    Martiz B, Keyrouz R, Gmouh S, Vaultier M, Jouikov V (2004) Chem Commun 6:674Google Scholar
  194. 194.
    Doherty AP, Brooks CA (2004) Electrochim Acta 49:3821Google Scholar
  195. 195.
    Naudin E, Ho HA, Branchaud S, Breau L, Belanger D (2002) J Phys Chem B 106:10585Google Scholar
  196. 196.
    Koo YK, Kim BH, Park DH, Joo J (2004) Mol Crystals Liquid Crystals 425:55Google Scholar
  197. 197.
    Pringle JM, Efthimiadis J, Howlett PC, Efthimiadis J, MacFarlane DR, Chaplin AB, Hall SB, Officer L, Wallace G G, Forsyth M (2004) Polymer 45:1447Google Scholar
  198. 198.
    Webber A, Blomgren GE (2002) Advances in lithium-ion batteries. Springer, Berlin Heidelberg New YorkGoogle Scholar
  199. 199.
    Tobishima S-I (2002) Electrochemistry 70:198Google Scholar
  200. 200.
    Garcia B, Lavallee S, Perron G, Michot C, Armand M (2004) Electrochim Acta 49:4583Google Scholar
  201. 201.
    Rogers RD, Seddon KR, Volkov S (2003) Green industrial applications of ionic liquids. Kluwer, DordrechtGoogle Scholar
  202. 202.
    Li Z, Liu H, Liu Y, He P, Li J (2004) J Phys Chem B 108:17512Google Scholar
  203. 203.
    Sato T, Maruo T, Marukane S, Takagi K (2004) J Power Sources 138:253Google Scholar
  204. 204.
    Lee JS, Bae JY, Lee H, Quan N D, Kim H S, Kim H (2004) J Ind Eng Chem 10:1086Google Scholar
  205. 205.
    Shibata Y, Kato T, Kado T, Shiratuchi R, Takashima W, Kaneto K, Hayase S (2003) Chem Commun 21:2730Google Scholar
  206. 206.
    Wang P, Zakeeruddin SM, Exnar I, Gratzel M (2002) Chem Commun 24:2972Google Scholar
  207. 207.
    Stathatos E, Lianos P, Zakeeruddin SM, Liska P, Gratzel M (2003) Chem Mater 15:1825Google Scholar
  208. 208.
    Mikoshiba S, Murai S, Sumino H, Kado T, Kosugi D, Hayase S (2005) Curr Appl Phys 5:152Google Scholar
  209. 209.
    Kang MG, Ryu KS, Chang SH, Park NG (2004) ETRI J 26:647Google Scholar
  210. 210.
    Wang P, Zakeeruddin SM, Comte P, Exnar I, Gratzel M (2003) J Am Chem Soc 125:1166Google Scholar
  211. 211.
    Wang P, Zakeeruddin SM, Moser JE, Gratzel M (2003) J Phys Chem B 107:13280Google Scholar
  212. 212.
    Kawano R, Matsui H, Matsuyama C Sato A, Susan MABH, Tanabe N, Watanabe M (2004) J Photochem Photobiol A: Chem 164:87Google Scholar
  213. 213.
    Xue B, Wang H, Hu Y, Li H, Wang Z, Meng Q, Huang X, Sato O, Chen L, Fujishima A (2004) Photochem Photobiol Sci 3:918Google Scholar
  214. 214.
    Angell CA, Xu W, Belieres J-P, Yoshizawa M (2004) International patent WO2004114445Google Scholar
  215. 215.
    Susan MABH, Noda A, Mitsushima S, Watanabe M (2003) Chem Commun 8:938Google Scholar
  216. 216.
    Susan MABH, Yoo M, Nakamoto H, Watanabe M (2003) Chem Lett 32:836Google Scholar
  217. 217.
    Hagiwara R, Nohira T, Matsumoto K, Tamba Y (2005) Electrochem Solid-State Lett 8:A231Google Scholar
  218. 218.
    de Souza RF, Padilha JC, Goncalves RS, Dupont J (2003) Electrochem Commun 5:728Google Scholar
  219. 219.
    Balducci A, Henderson WA, Mastragostino M, Passerini S, Simon P, Soavi F (2005) Elec-trochim Acta 50:2233Google Scholar
  220. 220.
    Sato T, Masuda G, Takagi K (2004) Electrochim Acta 49:3603Google Scholar
  221. 221.
    Ue M, Takeda M, Toriumi A, Kominato A, Hagiwara R, Ito Y (2003) J Electrochem Soc 150:A499Google Scholar
  222. 222.
    Ue M (2003) Mater Integration 16:40Google Scholar
  223. 223.
    Lewandowski AAS (2004) Polish J Chem 78:1371Google Scholar
  224. 224.
    Lewandowski A, Swiderska A (2003) Solid State Ionics 161:243Google Scholar
  225. 225.
    Buzzeo MC, Hardacre C, Compton RG (2004) Anal Chem 76:4583Google Scholar
  226. 226.
    Lee YG, Chou T-C (2004) Biosens Bioelectron 20:33Google Scholar
  227. 227.
    Wang R, Hoyano S, Ohsaka T (2004) Chem Lett 33:6Google Scholar
  228. 228.
    Wang R, Okajima T, Kitamura F, Obsaka T (2004) Electroanalysis 16:66Google Scholar
  229. 229.
    Brinz T, Simon U (2002) German patent DE 2002-10245337Google Scholar
  230. 230.
    Pernak J, Feder K (2005) Chem Eur J 11:4441Google Scholar
  231. 231.
    Ding J, Zhou D, Spinks G, Wallace G, Forsyth S, Forsyth M, MacFarlane D (2003) Chem Mater 15:2392Google Scholar
  232. 232.
    Zhou D, Spinks GM, Wallace GG, Tiyapiboonchaiya C, MacFarlane DR, Forsyth M, Sun J (2003) Electrochim Acta 48:2355Google Scholar
  233. 233.
    Vidal F, Plesse C, Teyssie D, Chevrot C (2004) Synth Metals 142:287Google Scholar
  234. 234.
    Zhao F, Wu X, Wang M, Liu Y, Gao L, Dong S (2004) Anal Chem 76:4960Google Scholar
  235. 235.
    Pappenfus TM, Henderson WA, Owens BB, Mann KR, Smyrl WH (2003) Polym Mater Sci Eng Prepr 88:302Google Scholar
  236. 236.
    Tiyapiboonchaiya C, MacFarlane DR, Sun J, Forsyth M (2002) Macromol Chem Phys 203:1906Google Scholar
  237. 237.
    Barisci JN, Wallace GG, MacFarlane DR, Baughman RH (2004) Electrochem Commun 6:22Google Scholar
  238. 238.
    Fukushima T, Kosaka A, Ishimura Y, Yamamoto T, Takigawa T, Ishii N, Aida T (2003) Science 300:2072Google Scholar
  239. 239.
    Fukushima T, Aida T (2004) Polym Prepr 45:306Google Scholar
  240. 240.
    Balczewski P, Bachowska B, Bialas T, Biczak R, Wieczorek WM, Balinska A (2007) J Agric Food Chem 55:1881Google Scholar
  241. 241.
    Cho CW, Pham TPT, Jeon YC, Vijayaraghavan K, Choe WS, Yun YS (2007) Chemosphere 69:1003Google Scholar
  242. 242.
    Matzke M, Stolte S, Thiele K, Juffernholz T, Arning J, Ranke J, Welz-Biermann U, Jastorff B (2007) Green Chem 9:1198Google Scholar
  243. 243.
    Jastorff B, Störmann R, Ranke J Mölter K, Stock F, Oberheitmann B, Hoffmann W, Hoffmann J, Nüchter M, Ondruschka B, Filser J (2003) Green Chem 5:136Google Scholar
  244. 244.
    Ranke J, Molter K, Stock F, Bottin Weber U, Poczobutt J, Hoffmann J, Ondruschka B, Filser J, Jastorff B (2004) Ecotoxicol Environ Saf 58:396Google Scholar
  245. 245.
    Pernak J, Smiglak M, Griffin ST, Hough WL, Wilson TB, Pernak A, Matejuk JZ, Fojutowski A, Kita K, Rogers RD (2006) Green Chem 8:798Google Scholar
  246. 246.
    Jastorff B, Mölter K, Behrend P, Weber UB, Filser J, Heimers A, Ondruschka B, RankeJ, Schaefer M, Schröder H, Stark A, Stepnowski P, Stock F, Störmann R, Stolte S, Biermann UW, Ziegert S, Thöming J (2005) Green Chem 7:362Google Scholar
  247. 247.
    Frade RFM, Matias A, Branco LC, Afonso CAM, Duarte CMM (2007) Green Chem 9:873Google Scholar
  248. 248.
    Nockemann P, Thijs B, Driesen K, Janssen CR, VanHecke K, VanMeervelt L, Kossmann S, Kirchner B, Binnemans K (2007) J Phys Chem B 111:5254Google Scholar
  249. 249.
    Bernot RJ, Brueseke MA, Evans-White MAE, Lamberti GA (2005) Environ Toxicol Chem 24:87Google Scholar
  250. 250.
    Samorì C, Pasteris A, Galletti P, Tagliavini E (2007) Environ Toxicol Chem 26:2379Google Scholar
  251. 251.
    Garcia MT, Gathergood N, Scammells PJ (2005) Green Chem 7:9Google Scholar
  252. 252.
    Stock F, Hoffmann J, Ranke J, Störmann R, Ondruschka B, Jastorff B (2004) Green Chem 6:286Google Scholar
  253. 253.
    Stolte S, Arning J, Bottin-Weber U, Müller A, Pitner WR, Biermann UW, Jastorff B, Ranke J (2007) Green Chem 9:760Google Scholar
  254. 254.
    Ranke J, Muller A, Bottin-Weber U, Stock F, Stolte S, Arning J, Stormann R, Jastorff B (2007) Ecotoxicol Environ Safety 67:430Google Scholar
  255. 255.
    Stolte S, Arning J, Weber UB, Matzke M, Stock F, Thiele K, Uerdingen M, Biermann UW, Jastorff B, Ranke J (2006) Green Chem 8:621Google Scholar
  256. 256.
    Stepnowski P, Skladanowski AC, Ludwiczak A, Laczynska E (2004) Hum Exp Toxicol 23:513Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  • S. Zhang
    • 1
  • X. Lu
    • 1
  • Y. Zhang
    • 1
  • Q. Zhou
    • 1
  • J. Sun
    • 1
  • L. Han
    • 1
  • G. Yue
    • 1
  • X. Liu
    • 1
  • W. Cheng
    • 1
  • S. Li
    • 1
  1. 1.Key Laboratory of Green Process and EngineeringInstitute of Process Engineering, Chinese Academy of SciencesBeijingPeople's Republic of China

Personalised recommendations