Science China Chemistry

, Volume 59, Issue 5, pp 517–525 | Cite as

Recent progress in studies on polarity of ionic liquids

Reviews SPECIAL TOPIC · Ionic Liquids: Energy, Materials & Environment
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Abstract

Although many ionic liquids have been reported, their polarity is not completely understood. Different empirical polarity scales for molecular solvents always lead to different polarity orders when they are applied on ionic liquids. Based on a literature survey, this review summarizes the recent polarity scales of ionic liquids according to the following 4 classes: (1) equilibrium and kinetic rate constants of chemical reactions; (2) empirical polar parameters of ionic liquids; (3) spectral properties of probe molecules; (4) multiparameter approaches. In addition, their interrelations are presented. A systematic understanding of the relationship between different polarity parameters of ionic liquids is of great importance for finding a universal set of parameters that can be used to predict the polarities of ionic liquids quantitatively. The potential utilization of the electron paramagnetic resonance in this field is also addressed.

Keywords

ionic liquids polarity interrelations 
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References

  1. 1.
    Reichardt C. Solvents and Solvent Effects in Organic Chemistry. Weinheim: Wiley-VCH, 2003Google Scholar
  2. 2.
    Katritzky AR, Fara DC, Yang HF, Tamm K, Tamm T, Karelson M. Chem Rev, 2004, 104: 175–198CrossRefGoogle Scholar
  3. 3.
    Chiappe C, Pieraccini D. J Phys Org Chem, 2005, 18: 275–297CrossRefGoogle Scholar
  4. 4.
    Hallett JP, Welton T. Chem Rev, 2011, 111: 3508–3576CrossRefGoogle Scholar
  5. 5.
    Shukla SK, Kumar A. Clean Technol Envir, 2015, 17: 1111–1116CrossRefGoogle Scholar
  6. 6.
    Weingaertner H. Angew Chem Int Ed, 2008, 47: 654–670CrossRefGoogle Scholar
  7. 7.
    Xu YJ, Zhu X, Li HR. Sci Sinica Chim, 2014, 44: 877–888CrossRefGoogle Scholar
  8. 8.
    Angelini G, Chiappe C, De Maria P, Fontana A, Gasparrini F, Pieraccini D, Pierini M, Siani G. J Org Chem, 2005, 70: 8193–8196CrossRefGoogle Scholar
  9. 9.
    Zappacosta R, Di Crescenzo A, Di Profio P, Fontana A, Siani G. J Org Chem, 2015, 80: 2333–2338CrossRefGoogle Scholar
  10. 10.
    Kirkwood JG. J Chem Phys, 1934, 2: 351–361CrossRefGoogle Scholar
  11. 11.
    Onsager L. J Am Chem Soc, 1936, 58: 1486–1493CrossRefGoogle Scholar
  12. 12.
    Kamlet MJ, Taft RW. J Am Chem Soc, 1976, 98: 377–383CrossRefGoogle Scholar
  13. 13.
    Taft RW, Kamlet MJ. J Am Chem Soc, 1976, 98: 2886–2894CrossRefGoogle Scholar
  14. 14.
    Yokoyama T, Taft RW, Kamlet MJ. J Am Chem Soc, 1976, 98: 3233–3237CrossRefGoogle Scholar
  15. 15.
    Kamlet MJ, Abboud JL, Taft RW. J Am Chem Soc, 1977, 99: 6027–6038CrossRefGoogle Scholar
  16. 16.
    Byrne R, Coleman S, Gallagher S, Diamond D. Phys Chem Chem Phys, 2010, 12: 1895–1904CrossRefGoogle Scholar
  17. 17.
    Creary X, Willis ED, Gagnon M. J Am Chem Soc, 2005, 127: 18114–18120CrossRefGoogle Scholar
  18. 18.
    Lancaster NL, Welton T, Young GB. J Chem Soc Perk T 2, 2001, 12: 2267–2270CrossRefGoogle Scholar
  19. 19.
    Lancaster NL, Salter PA, Welton T, Young GB. J Org Chem, 2002, 67: 8855–8861CrossRefGoogle Scholar
  20. 20.
    Lancaster NL, Welton T. J Org Chem, 2004, 69: 5986–5992CrossRefGoogle Scholar
  21. 21.
    Crowhurst L, Falcone R, Lancaster NL, Llopis-Mestre V, Welton T. J Org Chem, 2006, 71: 8847–8853CrossRefGoogle Scholar
  22. 22.
    Weingartner H, Knocks A, Schrader W, Kaatze U. J Phys Chem A, 2001, 105: 8646–8650CrossRefGoogle Scholar
  23. 23.
    Weingartner H. J Mol Liq, 2014, 192: 185–190CrossRefGoogle Scholar
  24. 24.
    Wakai C, Oleinikova A, Ott M, Weingartner H. J Phys Chem B, 2005, 109: 17028–17030CrossRefGoogle Scholar
  25. 25.
    Daguenet C, Dyson PJ, Krossing I, Oleinikova A, Slattery J, Wakai C, Weingartner H. J Phys Chem B, 2006, 110: 12682–12688CrossRefGoogle Scholar
  26. 26.
    Weingartner H. Z Phys Chem, 2006, 220: 1395–1405CrossRefGoogle Scholar
  27. 27.
    Huang MM, Weingartner H. ChemPhysChem, 2008, 9: 2172–2173CrossRefGoogle Scholar
  28. 28.
    Huang MM, Jiang YP, Sasisanker P, Driver GW, Weingartner H. J Chem Eng Data, 2011, 56: 1494–1499CrossRefGoogle Scholar
  29. 29.
    Bulut S, Klose P, Huang MM, Weingartner H, Dyson PJ, Laurenczy G, Friedrich C, Menz J, Kummerer K, Krossing I. Chem-Eur J, 2010, 16: 13139–13154CrossRefGoogle Scholar
  30. 30.
    Ekimova M, Frohlich D, Stalke S, Lenzer T, Oum K. Chem- PhysChem, 2012, 13: 1854–1859Google Scholar
  31. 31.
    Jin H, Baker GA, Arzhantsev S, Dong J, Maroncelli M. J Phys Chem B, 2007, 111: 7291–7302CrossRefGoogle Scholar
  32. 32.
    Luo HM, Baker GA, Dai S. J Phys Chem B, 2008, 112: 10077–10081CrossRefGoogle Scholar
  33. 33.
    Jin H, O’Hare B, Dong J, Arzhantsev S, Baker GA, Wishart JF, Benesi AJ, Maroncelli M. J Phys Chem B, 2008, 112: 81–92CrossRefGoogle Scholar
  34. 34.
    Deng LS, Wang Q, Chen YL, Zhang ZF, Tang J. J Mol Liq, 2013, 187: 246–251CrossRefGoogle Scholar
  35. 35.
    Chen YL, Wang Q, Zhang ZF, Tang J. Ind Eng Chem Res, 2012, 51: 15293–15298CrossRefGoogle Scholar
  36. 36.
    Zhang ZH, Wei J, Ma XX, Xu WG, Tong J, Guan W, Yang JZ. Sci Sinica Chim, 2014, 44: 1005–1013CrossRefGoogle Scholar
  37. 37.
    Wei J, Bu XX, Guan W, Xing NN, Fang DW, Wu Y. Rsc Adv, 2015, 5: 70333–70338CrossRefGoogle Scholar
  38. 38.
    Zaitsau DH, Yermalayeu VA, Emel’yanenko VN, Verevkin SP, Welz-biermann U, Schubert T. Sci China Chem, 2012, 55: 1525–1531CrossRefGoogle Scholar
  39. 39.
    Wei J, Ma TY, Ma XX, Guan W, Liu QS, Yang JZ. Rsc Adv, 2014, 4: 30725–30732CrossRefGoogle Scholar
  40. 40.
    Hong M, Liu RJ, Yang HX, Guan W, Tong J, Yang JZ. J Chem Thermodyn, 2014, 70: 214–218CrossRefGoogle Scholar
  41. 41.
    Jarvas G, Quellet C, Dallos A. Fluid Phase Equilibr, 2011, 309: 8–14CrossRefGoogle Scholar
  42. 42.
    Reichardt C. ACS Sym Ser, 2005, 7: 339–351Google Scholar
  43. 43.
    Reichardt C. Angew Chem Int Ed, 1965, 4: 29–40CrossRefGoogle Scholar
  44. 44.
    Carmichael AJ, Seddon KR. J Phys Org Chem, 2000, 13: 591–595CrossRefGoogle Scholar
  45. 45.
    Zhang SG, Qi XJ, Ma XY, Lu LJ, Deng YQ. J Phys Chem B, 2010, 114: 3912–3920CrossRefGoogle Scholar
  46. 46.
    Muldoon MJ, Gordon CM, Dunkin IR. J Chem Soc Perk T 2, 2001, 4: 433–435CrossRefGoogle Scholar
  47. 47.
    Akdogan Y, Heller J, Zimmermann H, Hinderberger D. Phys Chem Chem Phys, 2010, 12: 7874–7882CrossRefGoogle Scholar
  48. 48.
    Mladenova BY, Kattnig DR, Grampp G. J Phys Chem B, 2011, 115: 8183–8198CrossRefGoogle Scholar
  49. 49.
    Kawai A, Hidemori T, Shibuya K. Chem Lett, 2004, 33: 1464–1465CrossRefGoogle Scholar
  50. 50.
    Strehmel V, Lungwitz R, Rexhausen H, Spange S. New J Chem, 2010, 34: 2125–2131CrossRefGoogle Scholar
  51. 51.
    Strehmel V, Laschewsky A, Stoesser R, Zehl A, Herrmann W. J Phys Org Chem, 2006, 19: 318–325CrossRefGoogle Scholar
  52. 52.
    Strehmel V. Macromol Symp, 2007, 254: 25–33CrossRefGoogle Scholar
  53. 53.
    Nunes P, Nagy NV, Alegria E, Pombeiro AJL, Correia I. Inorg Chim Acta, 2014, 409: 465–471CrossRefGoogle Scholar
  54. 54.
    Nunes P, Nagy NV, Alegria E, Pombeiro AJL, Correia I. J Mol Struct, 2014, 1060: 142–149CrossRefGoogle Scholar
  55. 55.
    Strehmel V, Berdzinski S, Rexhausen H. J Mol Liq, 2014, 192: 153–170CrossRefGoogle Scholar
  56. 56.
    Fujisawa T, Fukuda M, Terazima M, Kimura Y. J Phys Chem A, 2006, 110: 6164–6172CrossRefGoogle Scholar
  57. 57.
    Kimura Y, Fukuda M, Fujisawa T, Terazima M. Chem Lett, 2005, 34: 338–339CrossRefGoogle Scholar
  58. 58.
    Cha DK, Kloss AA, Tikanen AC, Fawcett WR. Phys Chem Chem Phys, 1999, 1: 4785–4790CrossRefGoogle Scholar
  59. 59.
    Fletcher KA, Storey IA, Hendricks AE, Pandey S, Pandey S. ACS Sym Ser, 2001, 3: 210–215Google Scholar
  60. 60.
    Karmakar R, Samanta A. J Phys Chem A, 2002, 106: 6670–6675CrossRefGoogle Scholar
  61. 61.
    Karmakar R, Samanta A. J Phys Chem A, 2003, 107: 7340–7346CrossRefGoogle Scholar
  62. 62.
    Mandal PK, Samanta A. J Phys Chem B, 2005, 109: 15172–15177CrossRefGoogle Scholar
  63. 63.
    Kashyap HK, Biswas R. J Phys Chem B, 2010, 114: 16811–16823CrossRefGoogle Scholar
  64. 64.
    Zech O, Hunger J, Sangoro JR, Iacob C, Kremer F, Kunz W, Buchner R. Phys Chem Chem Phys, 2010, 12: 14341–14350CrossRefGoogle Scholar
  65. 65.
    Contreras R, Aizman A, Tapia RA, Cerda-Monje A. J Phys Chem B, 2013, 117: 1911–1920CrossRefGoogle Scholar
  66. 66.
    Klein R, Zech O, Maurer E, Kellermeier M, Kunz W. J Phys Chem B, 2011, 115: 8961–8969CrossRefGoogle Scholar
  67. 67.
    Kurnia KA, Lima F, Claudio AFM, Coutinho JAP, Freire MG. Phys Chem Chem Phys, 2015, 17: 18980–18990CrossRefGoogle Scholar
  68. 68.
    Crowhurst L, Mawdsley PR, Perez-Arlandis JM, Salter PA, Welton T. Phys Chem Chem Phys, 2003, 5: 2790–2794CrossRefGoogle Scholar
  69. 69.
    Wu YS, Sasaki T, Kazushi K, Seo T, Sakurai K. J Phys Chem B, 2008, 112: 7530–7536CrossRefGoogle Scholar
  70. 70.
    Acree WE, Abraham MH. J Chem Technol Biot, 2006, 81: 1441–1446CrossRefGoogle Scholar
  71. 71.
    Abraham MH. Chem Soc Rev, 1993, 22: 73–83CrossRefGoogle Scholar
  72. 72.
    Poole SK, Poole CF. Analyst, 1995, 120: 289–294CrossRefGoogle Scholar
  73. 73.
    Poole CF. J Chromatogr A, 2004, 1037: 1–1CrossRefGoogle Scholar
  74. 74.
    Lee SB. J Chem Technol Biot, 2005, 80: 133–137CrossRefGoogle Scholar
  75. 75.
    Del Valle JC, Blanco FG, Catalan J. J Phys Chem B, 2015, 119: 4683–4692CrossRefGoogle Scholar
  76. 76.
    Pandey A, Rai R, Pal M, Pandey S. Phys Chem Chem Phys, 2014, 16: 1559–1568CrossRefGoogle Scholar
  77. 77.
    Kawai A, Hidemori T, Shibuya K. Chem Phys Lett, 2005, 414: 378–383CrossRefGoogle Scholar
  78. 78.
    Miyake Y, Akai N, Kawai A, Shibuya K. J Phys Chem A, 2011, 11: 6347–6356CrossRefGoogle Scholar
  79. 79.
    Baker GA, Rachford AA, Castellano FN, Baker SN. ChemPhysChem, 2013, 14: 1025–1030CrossRefGoogle Scholar
  80. 80.
    Aparicio S, Atilhan M, Khraisheh M, Alcalde R. J Phys Chem B, 2011, 115: 12473–12486CrossRefGoogle Scholar
  81. 81.
    Singh T, Rao KS, Kumar A. ChemPhysChem, 2011, 12: 836–845CrossRefGoogle Scholar
  82. 82.
    Simijonovic D, Petrovic ZD, Petrovic VP. J Mol Liq, 2013, 179: 98–103CrossRefGoogle Scholar
  83. 83.
    Ladesov AV, Kosyakov DS, Bogolitsyn KG, Gorbova NS. Russ J Phys Chem A, 2015, 89: 1814–1820CrossRefGoogle Scholar
  84. 84.
    Zhang PF, Gong YT, Lv YQ, Guo Y, Wang Y, Wang CM, Li HR. Chem Commun, 2012, 48: 2334–2336CrossRefGoogle Scholar
  85. 85.
    Funasako Y, Mochida T, Takahashi K, Sakurai T, Ohta H. Chem-Eur J, 2012, 18: 11929–11936CrossRefGoogle Scholar
  86. 86.
    Ding F, Zheng JJ, Chen YQ, Chen KH, Cui GK, Li HR, Wang CM. Ind Eng Chem Res, 2014, 53: 18568–18574CrossRefGoogle Scholar
  87. 87.
    Shen MM, Che SY, Zhang YY, Yao J, Li HR. J Chem Eng Data, 2014, 59: 3960–3968CrossRefGoogle Scholar
  88. 88.
    Ueda T, Mochida T. Organometallics, 2015, 34: 1279–1286CrossRefGoogle Scholar
  89. 89.
    Komurasaki A, Funasako Y, Mochida T. Dalton T, 2015, 44: 7595–7605CrossRefGoogle Scholar
  90. 90.
    Funasako Y, Kaneshige K, Inokuchi M, Hosokawa H, Mochida T. J Organomet Chem, 2015, 797: 120–124CrossRefGoogle Scholar
  91. 91.
    Lynden-bell RM, Del Popolo MG, Youngs TGA, Kohanoff J, Hanke CG, Harper JB, Pinilla CC. Acc Chem Res, 2007, 40: 1138–1145CrossRefGoogle Scholar
  92. 92.
    Fumino K, Ludwig R. J Mol Liq, 2014, 192: 94–102CrossRefGoogle Scholar
  93. 93.
    Derecskei B, Derecskei-Kovacs A. Mol Sim, 2008, 34: 1167–1175CrossRefGoogle Scholar

Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  1. 1.Department of Chemistry, ZJU-NHU United R&D CenterZhejiang UniversityHangzhouChina
  2. 2.State Key Laboratory of Chemical EngineeringZhejiang UniversityHangzhouChina
  3. 3.College of Chemical and Biological EngineeringZhejiang UniversityHangzhouChina

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