Skip to main content

Synthesis, Purification and Characterization of Ionic Liquids

  • Chapter
  • First Online:
Ionic Liquids

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 290))

Abstract

The synthesis, purification and characterization of ionic liquids is reviewed. The major synthetic routes to low melting ionic salts are described in detail. The intrinsic properties of ionic liquids make purification difficult and therefore a special emphasis is placed on currently employed purification methodologies. Synthetic methods which are designed to avoid specific impurities are also discussed. For the same reasons highlighted above characterization of ionic liquids presents unique challenges; the available methods and some of the issues of their use are also reviewed.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. MacFarlane DR, Seddon KR (2007) Aust J Chem 60:3

    Article  CAS  Google Scholar 

  2. Seddon KR (1996) Kinet Catal 37:693

    CAS  Google Scholar 

  3. Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M (1996) Inorg Chem 35:1168

    Article  CAS  Google Scholar 

  4. Huddleston JG, Willauer HD, Swatloski RP, Visser AE, Rogers RD (1998) Chem Commun 1765

    Google Scholar 

  5. Dzyuba SV, Bartsch RA (2001) Chem Commun 1466

    Google Scholar 

  6. Gordon CM, Holbrey JD, Kennedy AR, Seddon KR (1998) J Mater Chem 8:2627

    Article  CAS  Google Scholar 

  7. Forsyth SA, Pringle JM, MacFarlane DR (2004) Aust J Chem 57:113

    Article  CAS  Google Scholar 

  8. Handy ST (2005) Curr Org Chem 9:959

    Article  CAS  Google Scholar 

  9. Bradaric CJ, Downard A, Kennedy C, Robertson AJ, Zhou YH (2003) Green Chem 5:143

    Article  CAS  Google Scholar 

  10. Degiorgi M, Landini D, Maia A, Penso M (1987) Synth Commun 17:521

    Article  CAS  Google Scholar 

  11. Bradaric CJ, Downard A, Kennedy C, Robertson AJ, Zhou YH (2002) Abstracts of Papers of the Am Chem Soc 224:U611

    Google Scholar 

  12. Ding J, Welton T, Armstrong DW (2004) Anal Chem 76:6819

    Article  CAS  Google Scholar 

  13. Ding J, Armstrong DW (2005) Chirality 17:281

    Article  CAS  Google Scholar 

  14. Chiappe C, Pieraccini D (2005) J Phys Org Chem 18:275

    Article  CAS  Google Scholar 

  15. Wasserscheid P, Hilgers C, Boesmann A. Solvent Innovation Gmbh, EP1182196-A1

    Google Scholar 

  16. Holbrey JD, Seddon KR (1999) J Chem Soc-Dalton Trans 2133

    Google Scholar 

  17. Forsyth S, Golding J, MacFarlane DR, Forsyth M (2001) Electrochim Acta 46:1753

    Article  CAS  Google Scholar 

  18. MacFarlane DR, Meakin P, Sun J, Amini N, Forsyth M (1999) J Phys Chem B 103:4164

    Article  CAS  Google Scholar 

  19. Goldman JL, McEwen AB (1999) Electrochem Solid State Lett 2:501

    Article  CAS  Google Scholar 

  20. Visser AE, Holbrey JD, Rogers RD (2001) Chem Commun 2484

    Google Scholar 

  21. Holbrey JD, Reichert WM, Swatloski RP, Broker GA, Pitner WR, Seddon KR, Rogers RD (2002) Green Chem 4:407

    Article  CAS  Google Scholar 

  22. Brinchi L, Germani R, Savelli G (2003) Tetrahedron Lett 44:2027

    Article  CAS  Google Scholar 

  23. Kitazume T, Tanaka G (2000) J Fluorine Chem 106:211

    Article  CAS  Google Scholar 

  24. Golding J, Forsyth S, MacFarlane DR, Forsyth M, Deacon GB (2002) Green Chem 4:223

    Article  CAS  Google Scholar 

  25. Pringle JM, Golding J, Forsyth CM, Deacon GB, Forsyth M, MacFarlane DR (2002) J Mater Chem 12:3475

    Article  CAS  Google Scholar 

  26. Leveque JM, Luche JL, Petrier C, Roux R, Bonrath W (2002) Green Chem 4:357

    Article  CAS  Google Scholar 

  27. MacFarlane DR, Golding J, Forsyth S, Forsyth M, Deacon GB (2001) Chem Commun 1430

    Google Scholar 

  28. MacFarlane DR, Forsyth SA, Golding J, Deacon GB (2002) Green Chem 4:444

    Article  CAS  Google Scholar 

  29. Xu W, Wang LM, Nieman RA, Angell CA (2003) J Phys Chem B 107:11749

    Article  CAS  Google Scholar 

  30. Larsen AS, Holbrey JD, Tham FS, Reed CA (2000) J Am Chem Soc 122:7264

    Article  CAS  Google Scholar 

  31. Fuller J, Carlin RT, Osteryoung RA (1997) J Electrochem Soc 144:3881

    Article  CAS  Google Scholar 

  32. Cammarata L, Kazarian SG, Salter PA, Welton T (2001) Phys Chem Chem Phys 3:5192

    Article  CAS  Google Scholar 

  33. Wilkes JS, Zaworotko MJ (1992) J Chem Soc-Chem Commun 965

    Google Scholar 

  34. Helfferich F (1962) Ion Exchange. New York: McGraw-Hill

    Google Scholar 

  35. Lall SI, Mancheno D, Castro S, Behaj V, Cohen JI, Engel R (2000) Chem Commun (Cambridge): 2413

    Google Scholar 

  36. Mizuta K, Kasahara T, Hashimoto H, Arimoto Y (2006) PCT/JP2006/322693

    Google Scholar 

  37. Seddon KR, Stark A, Torres MJ (2000) Pure Appl Chem 72:2275

    Article  CAS  Google Scholar 

  38. Chauvin Y, Olivierbourbigou H (1995) Chemtech 25:26

    CAS  Google Scholar 

  39. de Souza RF, Rech V, Dupont J (2002) Adv Synth Catal 344:153

    Article  Google Scholar 

  40. Siriwardana AI, Crossley IR, Torriero AAJ, Burgar IM, Dunlop NF, Bond AM, Deacon GB, MacFarlane DR (2008) J Org Chem 73:4676

    Article  CAS  Google Scholar 

  41. Kuhn N, Steimann M, Weyers G (1999) Zeitschrift Fur Naturforschung Sect B J Chem Sci 54:427

    CAS  Google Scholar 

  42. Tommasi I, Sorrentino F (2005) Tetrahedron Lett 46:2141

    Article  CAS  Google Scholar 

  43. Holbrey JD, Reichert WM, Tkatchenko I, Bouajila E, Walter O, Tommasi I, Rogers RD (2003) Chem Commun 28

    Google Scholar 

  44. Moulton SE, Minett AI, Murphy R, Ryan KP, McCarthy D, Coleman JN, Blau WJ, Wallace GG (2005) Carbon 43:1879

    Article  CAS  Google Scholar 

  45. Kuhlmann E, Himmler S, Giebelhaus H, Wasserscheid P (2007) Green Chem 9:233

    Article  CAS  Google Scholar 

  46. Modro AM, Modro TA (1989) J Phys Org Chem 2:377

    Article  CAS  Google Scholar 

  47. Burns JA, Butler JC, Moran J, Whitesides GM (1991) J Org Chem 56:2648

    Article  CAS  Google Scholar 

  48. Cassol CC, Ebeling G, Ferrera B, Dupont J (2006) Adv Synth Catal 348:243

    Article  CAS  Google Scholar 

  49. Jodry JJ, Mikami K (2004) Tetrahedron Lett 45:4429

    Article  CAS  Google Scholar 

  50. Himmler S, Hormann S, van Hal R, Schulz PS, Wasserscheid P (2006) Green Chem 8:887

    Article  CAS  Google Scholar 

  51. Yoshizawa M, Xu W, Angell CA (2003) J Am Chem Soc 125:15411

    Article  CAS  Google Scholar 

  52. Yoshizawa M, Belieres JP, Xu W, Angell CA (2003) Abst Pap Am Chem Soc 226:U627

    Google Scholar 

  53. Ohno H, Yoshizawa M (2002) Solid State Ionics 154:303

    Article  Google Scholar 

  54. Greaves TL, Drummond CJ (2008) Chem Rev 108:206

    Article  CAS  Google Scholar 

  55. Nuthakki B, Greaves TL, Krodkiewska I, Weerawardena A, Burgar MI, Mulder RJ, Drummond CJ (2007) Aust J Chem 60:21

    Article  CAS  Google Scholar 

  56. MacFarlane DR, Pringle JM, Johansson KM, Forsyth SA, Forsyth M (2006) Chem Commun 1905

    Google Scholar 

  57. Johansson KM, Izgorodina EI, Forsyth M, MacFarlane DR, Seddon KR (2008) Phys Chem Chem Phys 10:2972

    Article  CAS  Google Scholar 

  58. Janus E, Goc-Maciejewska I, Lozynski M, Pernak J (2006) Tetrahedron Lett 47:4079

    Article  CAS  Google Scholar 

  59. MacFarlane DR, Pringle JM, Johansson KM, Forsyth SA, Forsyth M (2006) Chem Commun 1905

    Google Scholar 

  60. Abbott AP, Capper G, Davies DL, Rasheed R (2004) Inorg Chem 43:3447

    Article  CAS  Google Scholar 

  61. Lin IJB, Vasam CS (2005) J Organomet Chem 690:3498

    Article  CAS  Google Scholar 

  62. Hitchcock PB, Seddon KR, Welton T (1993) J Chem Soc-Dalton Trans 2639

    Google Scholar 

  63. Dent AJ, Lees A, Lewis RJ, Welton T (1996) J Chem Soc-Dalton Trans 2787

    Google Scholar 

  64. Gao Y, Twamley B, Shreeve JM (2004) Inorg Chem 43:3406

    Article  CAS  Google Scholar 

  65. Kolle P, Dronskowski R (2004) Inorg Chem 43:2803

    Article  CAS  Google Scholar 

  66. Sun XG, Angell CA (2005) Electrochem Commun 7:261

    Article  CAS  Google Scholar 

  67. Palgunadi J, Kwon OS, Lee H, Bae JY, Ahn BS, Min NY, Kim HS (2004) Catal Today 98:511

    Article  CAS  Google Scholar 

  68. Dullius JEL, Suarez PAZ, Einloft S, de Souza RF, Dupont J, Fischer J, De Cian A (1998) Organometallics 17:815

    Article  CAS  Google Scholar 

  69. Zhao DB, Fei ZF, Scopelliti R, Dyson PJ (2004) Inorg Chem 43:2197

    Article  CAS  Google Scholar 

  70. Xiao JC, Twamley B, Shreeve JM (2004) Org Lett 6:3845

    Article  CAS  Google Scholar 

  71. Hasan M, Kozhevnikov IV, Siddiqui MRH, Femoni C, Steiner A, Winterton N (2001) Inorg Chem 40:795

    Article  CAS  Google Scholar 

  72. Chen J, Burrell AK, Collis GE, Officer DL, Swiegers GF, Too CO, Wallace GG (2002) Electrochim Acta 47:2715

    Article  CAS  Google Scholar 

  73. Matsumoto K, Tsuda T, Nohira T, Hagiwara R, Ito Y, Tamada O (2002) Acta Crystallogr Sect C Cryst Struct Commun 58:m186

    Article  CAS  Google Scholar 

  74. Sentman AC, Csihony S, Waymouth RM, Hedrick JL (2005) J Org Chem 70:2391

    Article  Google Scholar 

  75. Deetlefs M, Raubenheimer HG, Esterhuysen MW (2002) Catal Today 72:29

    Article  CAS  Google Scholar 

  76. Dyson PJ, McIndoe JS, Zhao DB (2003) Chem Commun: 508

    Google Scholar 

  77. Wasserscheid P, Waffenschmidt H (2000) J Mol Catal A: Chem 164:61

    Article  CAS  Google Scholar 

  78. Earle MJ, Hakala U, Hardacre C, Karkkainen J, McAuley BJ, Rooney DW, Seddon KR, Thompson JM, Wahala K (2005) Chem Commun: 903

    Google Scholar 

  79. Edgar A, Williams GVM, Sagar PKD, Secu M, Schweizer S, Spaeth JM, Hu X, Newman PJ, Macfarlane DR (2003) J Non-Cryst Solids 326:489

    Article  CAS  Google Scholar 

  80. Hitchcock PB, Mohammed TJ, Seddon KR, Zora JA, Hussey CL, Ward EH (1986) Inorg Chim Acta 113:L25

    Article  CAS  Google Scholar 

  81. Nockemann P, Thijs B, Postelmans N, Van Hecke K, Van Meervelt L, Binnemans K (2006) J Am Chem Soc 128:13658

    Article  CAS  Google Scholar 

  82. Lee SG (2006) Chem Commun: 1049

    Google Scholar 

  83. Davis JH (2004) Chem Lett 33:1072

    Article  CAS  Google Scholar 

  84. Visser AE, Swatloski RP, Reichert WM, Mayton R, Sheff S, Wierzbicki A, Davis JH, Rogers RD (2002) Environ Sci Technol 36:2523

    Article  CAS  Google Scholar 

  85. Visser AE, Swatloski RP, Reichert WM, Mayton R, Sheff S, Wierzbicki A, Davis JH, Rogers RD (2001) Chem Commun 135

    Google Scholar 

  86. Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC, Davis JH (2002) J Am Chem Soc 124:5962

    Article  CAS  Google Scholar 

  87. Xing HB, Wang T, Zhou ZH, Dai YY (2005) Ind Eng Chem Res 44:4147

    Article  CAS  Google Scholar 

  88. Fukumoto K, Yoshizawa M, Ohno H (2005) J Am Chem Soc 127:2398

    Article  CAS  Google Scholar 

  89. Kim S, Lee JK, Kang SO, Ko J, Yum JH, Fantacci S, De Angelis F, Di Censo D, Nazeeruddin MK, Gratzel M (2006) J Am Chem Soc 128:16701

    Article  CAS  Google Scholar 

  90. Lombardo M, Pasi F, Trombini C, Seddon KR, Pitner WR (2007) Green Chem 9:321

    Article  CAS  Google Scholar 

  91. Kottsieper KW, Stelzer O, Wasserscheid P (2001) J Mol Catal A Chem 175:285

    Article  CAS  Google Scholar 

  92. Brauer DJ, Kottsieper KW, Liek C, Stelzer O, Waffenschmidt H, Wasserscheid P (2001) J Organomet Chem 630:177

    Article  CAS  Google Scholar 

  93. Branco LC, Rosa JN, Ramos JJM, Afonso CAM (2002) Chem Eur J 8:3671

    Article  CAS  Google Scholar 

  94. Ouadi A, Gadenne B, Hesemann P, Moreau JJE, Billard I, Gaillard C, Mekki S, Moutiers G (2006) Chem Eur J 12:3074

    Article  CAS  Google Scholar 

  95. Siyutkin DE, Kucherenko AS, Struchkova MI, Zlotin SG (2008) Tetrahedron Lett 49:1212

    Article  CAS  Google Scholar 

  96. Fraga-Dubreuil J, Bazureau JP (2001) Tetrahedron Lett 42:6097

    Article  CAS  Google Scholar 

  97. Fraga-Dubreuil J, Famelart MH, Bazureau JP (2002) Org Process Res Dev 6:374

    Article  CAS  Google Scholar 

  98. Bates ED, Mayton RD, Ntai I, Davis JH (2002) J Am Chem Soc 124:926

    Article  CAS  Google Scholar 

  99. Rickert PG, Antonio MR, Firestone MA, Kubatko KA, Szreder T, Wishart JF, Dietz ML (2007) Dalton Trans: 529

    Google Scholar 

  100. Yoshizawa M, Hirao M, Ito-Akita K, Ohno H (2001) J Mater Chem 11:1057

    Article  CAS  Google Scholar 

  101. Holbrey JD, Turner MB, Reichert WM, Rogers RD (2003) Green Chem 5:731

    Article  CAS  Google Scholar 

  102. Bao WL, Wang ZM, Li YX (2003) J Org Chem 68:591

    Article  CAS  Google Scholar 

  103. Leitner W, Seddon KR, Wasserscheid P (2003) Green Chem 5:G28

    Article  Google Scholar 

  104. Habermann J, Ponzi S, Ley SV (2005) Mini-Reviews in Org Chem 2:125

    Article  CAS  Google Scholar 

  105. Varma RS, Namboodiri VV (2001) Pure Appl Chem 73:1309

    Article  CAS  Google Scholar 

  106. Varma RS, Namboodiri VV (2001) Chem Commun 643

    Google Scholar 

  107. Thanh GV, Pegot B, Loupy A (2004) European Journal of Organic Chemistry 2004:1112

    Article  CAS  Google Scholar 

  108. Law MC, Wong KY, Chan TH (2002) Green Chem 4:328

    Article  CAS  Google Scholar 

  109. Khadilkar BM, Rebeiro GL (2002) Org Process Res Dev 6:826

    Article  CAS  Google Scholar 

  110. Deetlefs M, Seddon KR (2003) Green Chem 5:181

    Article  CAS  Google Scholar 

  111. Cravotto G, Boffa L, L’Eveque JM, Estager J, Draye M, Bonrath W (2007) Aust J Chem 60:946

    Article  CAS  Google Scholar 

  112. Namboodiri VV, Varma RS (2002) Chem Commun 342

    Google Scholar 

  113. Kim YJ, Varma RS (2005) Tetrahedron Lett 46:1467

    Article  CAS  Google Scholar 

  114. Rong H, Li W, Chen ZY, Wu XM (2008) J Phys Chem B 112:1451

    Article  CAS  Google Scholar 

  115. Clare BR, Bayley PM, Best AS, Forsyth M, MacFarlane DR (2008) Chem Commun (Cambridge, UK) 2689

    Google Scholar 

  116. Scammells PJ, Scott JL, Singer RD (2005) Aust J Chem 58:155

    Article  CAS  Google Scholar 

  117. Appetecchi GB, Scaccia S, Tizzani C, Alessandrini F, Passerini S (2006) J Electrochem Soc 153:A1685

    Article  CAS  Google Scholar 

  118. Earle MJ, Gordon CM, Plechkova NV, Seddon KR, Weton T (2007) Anal Chem 79:758

    Article  CAS  Google Scholar 

  119. Davis JH Jr, Gordon CM, Hilgers C, Wasserscheid P (2003) In: Wasserscheid P, Welton T (eds) Ionic liquids in synthesis. (Wiley, Weinheim) Chap 2

    Google Scholar 

  120. Endres F, Zein El Abedin S, Borissenko N (2006) Z Phys Chem (Muenchen, Ger.) 220:1377

    CAS  Google Scholar 

  121. Nockemann P, Binnemans K, Driesen K (2005) Chem Phys Lett 415:131

    Article  CAS  Google Scholar 

  122. Kreher UP, Rosamilia AE, Raston CL (2004) Molecules 9:387

    Article  CAS  Google Scholar 

  123. Fraser KJ, Izgorodina EI, Forsyth M, Scott JL, MacFarlane DR (2007) Chem Commun 3817

    Google Scholar 

  124. Rebelo Luis PN, Canongia Lopes Jose N, Esperanca Jose MSS, Filipe E (2005) J Phys Chem B 109:6040

    Article  CAS  Google Scholar 

  125. Earle MJ, Esperanca JMSS, Gilea MA, Canongia Lopes JN, Rebelo LPN, Magee JW, Seddon KR, Widegren JA (2006) Nature (London, UK) 439:831

    Article  CAS  Google Scholar 

  126. Leal JP, Esperanca JMSS, Da Piedade MEM, Lopes JNC, Rebelo LPN, Seddon KR (2007) J Phys Chem A 111:6176

    Article  CAS  Google Scholar 

  127. Widegren JA, Wang Y-M, Henderson WA, Magee JW (2007) J Phys Chem B 111:8959

    Article  CAS  Google Scholar 

  128. Rudolph P, Fukuda T (1999) Cryst Res Technol 34:3

    Article  CAS  Google Scholar 

  129. Thalladi VR, Weiss H-C, Blaeser D, Boese R, Nangia A, Desiraju GR (1998) J Am Chem Soc 120:8702

    Article  CAS  Google Scholar 

  130. Kirchner MT, Boese R, Billups WE, Norman LR (2004) J Am Chem Soc 126:9407

    Article  CAS  Google Scholar 

  131. Choudhury AR, Winterton N, Steiner A, Cooper AI, Johnson KA (2005) J Am Chem Soc 127:16792

    Article  CAS  Google Scholar 

  132. Choudhury AR, Winterton N, Steiner A, Cooper AI, Johnson KA (2006) Cryst Eng Commun 8:742

    CAS  Google Scholar 

  133. Koenig A, Wasserscheid P (2006) Proceedings of the 13th International Workshop on Industrial Crystallization BIWIC 2006, September 13–15, 2006, Delft, the Netherlands, p 79

    Google Scholar 

  134. Burrell AK, Del Sesto RE, Baker SN, McCleskey TM, Baker GA (2007) Green Chem 9:449

    Article  CAS  Google Scholar 

  135. Armarego WLF, Chai CLL (2003) Purification of laboratory chemicals, 5th ed. (Butter­worth–Heinemann)

    Google Scholar 

  136. Ramnial T, Taylor Stephanie A, Bender Marissa L, Gorodetsky B, Lee Peter TK, Dickie Diane A, McCollum Brett M, Pye Cory C, Walsby Charles J, Clyburne Jason AC (2008) J Org Chem 73:801

    Article  CAS  Google Scholar 

  137. Mendham J et al. (2000) Vogel’s textbook of quantitative chemical analysis, 6th edn. Addison Wesley Publishing Co

    Google Scholar 

  138. Holbrey JD, Seddon KR, Wareing R (2001) Green Chem 3:33

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to ARC for salary support for BC (Linkage Project with Degussa), AS (Linkage Project with Orica) and DRM (Federation Fellowship).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Bronya Clare .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Clare, B., Sirwardana, A., MacFarlane, D.R. (2009). Synthesis, Purification and Characterization of Ionic Liquids. In: Kirchner, B. (eds) Ionic Liquids. Topics in Current Chemistry, vol 290. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2008_31

Download citation

Publish with us

Policies and ethics