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Capillary Electrophoresis pp 131–153Cite as

Ionic Liquids in Capillary Electrophoresis

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Part of the book series: Methods in Molecular Biology ((MIMB,volume 1483))

Abstract

Recently, a great interest was drawn toward ionic liquids (ILs) in analytical separation techniques. ILs possess many properties making them excellent additives in capillary electrophoresis (CE) background electrolytes (BGE). The most important property is the charge of the dissolved ions in BGE enabling the cations to interact with deprotonated silanol groups on the capillary surface and thereby modifying the electroosmotic flow (EOF). Ionic and/or proton donor–acceptor interactions between analyte and IL are possible interactions facilitating new kinds of separation mechanisms in CE. Further advantages of ILs are the high conductivity, the environmentally friendliness, and the good solubility for organic and inorganic compounds. The most commonly used ILs in capillary electrophoresis are dialkylimidazolium-based ILs, whereas for enantioseparation a lot of innovative chiral cations and anions were investigated.

ILs are reported to be additives to a normal CE background electrolyte or the sole electrolyte in CE, nonaqueous CE (NACE), micellar electrokinetic chromatography (MEKC), and in enantioseparation. An overview of applications and separation mechanisms reported in the literature is given here, in addition to the enantioseparation of pseudoephedrine using tetrabutylammonium chloride (TBAC) as IL additive to an ammonium formate buffer containing β-cyclodextrin (β-CD).

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References

  1. Rocha MA, Coutinho JA, Santos LM (2012) Cation symmetry effect on the volatility of ionic liquids. J Phys Chem B 116:10922–10927

    Article  CAS  PubMed  Google Scholar 

  2. Krossing I, Slattery JM, Daguenet C, Dyson PJ, Oleinkova A, Weingärtner H (2006) Why are ionic liquids liquid? A simple explanation based on lattice and solvation energies. J Am Chem Soc 128:13427–13434

    Article  CAS  PubMed  Google Scholar 

  3. Fuller J, Carlin RT, De Long HC, Haworth D (1994) Structure of 1-ethyl-3-methylimidazolium hexafluorophosphate: model for room temperature molten salts. J Chem Soc Chem Commun 299–300

    Google Scholar 

  4. Katritzky AR, Jain R, Lomaka A, Petrukhin R, Karelson M, Visser AE, Rogers RD (2002) Correlation of the melting points of potential ionic liquids (imidazolium bromides and benzimidazolium bromides) using the CODESSA program. J Chem Inf Comput Sci 42:225–231

    Article  CAS  PubMed  Google Scholar 

  5. Walden P (1914) Über die Molekulargrösse und elektrische Leitfähigkeit einiger geschmolzenen Salze. Bulletin de l‘Académie Impériale des Sciences de St-Pétersbourg 1–11:405–422

    Google Scholar 

  6. Bonhôte P, Dias A, Papageorgiou N, Kalyanasundaram K, Grätzel M (1996) Hydrophobic, highly conductive ambient-temperature molten salts. Inorg Chem 35:1168–1178

    Article  PubMed  Google Scholar 

  7. O'Mahony AM, Silvester DS, Aldous L, Hardacre C, Compton RG (2008) Effect of water on the electrochemical window and potential limits of room-temperature ionic liquids. J Chem Eng Data 53:2884–2891

    Article  Google Scholar 

  8. Tietze AA, Heimer P, Stark A, Imhof D (2012) Ionic liquid applications in peptide chemistry: synthesis, purification and analytical characterization processes. Molecules 17:4158–4185

    Article  CAS  PubMed  Google Scholar 

  9. Galan MC, Jones RA, Tran AT (2013) Recent developments of ionic liquids in oligosaccharide synthesis: the sweet side of ionic liquids. Carbohydr Res 375:35–46

    Article  CAS  PubMed  Google Scholar 

  10. Moniruzzaman M, Kamiya N, Goto M (2010) Ionic liquid based microemulsion with pharmaceutically accepted components: formulation and potential applications. J Colloid Interface Sci 352:136–142

    Article  CAS  PubMed  Google Scholar 

  11. Yao C, Anderson JL (2009) Retention characteristics of organic compounds on molten salt and ionic liquid-based gas chromatography stationary phases. J Chromatogr A 1216:1658–1712

    Article  CAS  PubMed  Google Scholar 

  12. Poole CF, Lenca N (2014) Gas chromatography on wall-coated open-tubular columns with ionic liquid stationary phases. J Chromatogr A 1357:87–109

    Article  CAS  PubMed  Google Scholar 

  13. Tsunashima K, Niwa E, Kodama S, Sugiya M, Ono Y (2009) Thermal and transport properties of ionic liquids based on benzyl-substituted phosphonium cation. J Phys Chem B 113:15870–15874

    Article  CAS  PubMed  Google Scholar 

  14. Ding J, Welton T, Armstrong DW (2004) Chiral ionic liquids as stationary phases in gas chromatography. Anal Chem 76:6819–6822

    Article  CAS  PubMed  Google Scholar 

  15. Poole CF, Kersten BR, Ho SSJ, Coddens ME, Furton KG (1986) Organic salts, liquid at room temperature, as mobile phase in liquid chromatography. J Chromatogr A 352:407–425

    Article  CAS  Google Scholar 

  16. Sun Y, Stalcup AM (2006) Mobile phase effects on retention on a new butylimidazolium-based high-performance liquid chromatographic stationary phase. J Chromatogr A 1126:276–282

    Article  CAS  PubMed  Google Scholar 

  17. Armstrong DW, Zhang L, He L, Gross M (2001) Ionic liquids as matrixes for matrix-assisted laser desorption/ionization mass spectrometry. Anal Chem 73:3679–3686

    Article  CAS  PubMed  Google Scholar 

  18. Martinelango PK, Anderson JL, Dasgupta PK, Armstrong DW, Al-Horr RS, Slingdby RW (2005) Gas-phase ion association provides increased selectivity and sensitivity for measuring perchlorate by mass spectrometry. Anal Chem 77:4829–4835

    Article  CAS  PubMed  Google Scholar 

  19. Tsuda T (1987) Modification of electroosmotic flow with cetyltrimethylammonium bromide in capillary zone electrophoresis. J High Resolut Chromatogr 10:622–624

    Article  CAS  Google Scholar 

  20. Huang X, Luckey JA, Gordon MJ, Zare RN (1989) Quantitative analysis of low molecular weight carboxylic acids by capillary electrophoresis/conductivity detection. Anal Chem 61:766–770

    Article  CAS  Google Scholar 

  21. Garner TW, Yeung ES (1993) Increased selectivity for electrochromatography by dynamic ion exchange. J Chromatogr A 640:397–402

    Article  CAS  Google Scholar 

  22. Iskandarani Z, Pietrzyk J (1982) Ion interaction chromatography of organic anions on a poly(styrene-divinylbenzene) adsorbent in the presence of tetraalkylammonium salts. Anal Chem 54:1065–1071

    Article  CAS  Google Scholar 

  23. Pfeffer WD, Yeung ES (1990) Open-tubular liquid chromatography with surfactant-enhanced electroosmotic flow. Anal Chem 62:2178–2182

    Article  CAS  Google Scholar 

  24. Liu C, Ho Y, Pai Y (2000) Preparation and evaluation of an imidazole-coated capillary column for the electrophoretic separation of aromatic acids. J Chromatogr A 897:383–392

    Article  CAS  PubMed  Google Scholar 

  25. Qin W, Li SFY (2002) An ionic liquid coating for determination of sildenafil and UK-103,320 in human serum by capillary zone electrophoresis-ion trap mass spectrometry. Electrophoresis 23:4110–4116

    Article  CAS  PubMed  Google Scholar 

  26. Qin W, Wei H, Li SFY (2003) 1,3-Dialkylimidazolium-based room-temperature ionic liquids as background electrolyte and coating material in aqueous capillary electrophoresis. J Chromatogr A 985:447–454

    Article  CAS  PubMed  Google Scholar 

  27. Qin W, Li SFY (2003) Electrophoresis of DNA in ionic liquid coated capillary. Analyst 128:37–41

    Article  CAS  PubMed  Google Scholar 

  28. Yanes EG, Gratz SR, Baldwin MJ, Robison SE, Stalcup AM (2001) Capillary electrophoretic application of 1-alkyl-3-methylimidazolium-based ionic liquids. Anal Chem 73:3838–3844

    Article  CAS  PubMed  Google Scholar 

  29. Gao Y, Xu Y, Han B, Li J, Xiang Q (2009) Sensitive determination of verticine and verticinone in Bulbus Fritillariae by ionic liquid assisted capillary electrophoresis-electrochemiluminescence system. Talanta 80:448–453

    Article  CAS  PubMed  Google Scholar 

  30. Vaher M, Koel M, Kazarjan J, Kaljurand M (2011) Capillary electrophoretic analysis of neutral carbohydrates using ionic liquids as background electrolytes. Electrophoresis 32:1068–1073

    Article  CAS  PubMed  Google Scholar 

  31. Laamanen P, Busi S, Lahtinen M, Matilainen R (2005) A new ionic liquid dimethyldinonylammonium bromide as a flow modifier for the simultaneous determination of eight carboxylates by capillary electrophoresis. J Chromatogr A 1095:164–171

    Article  CAS  PubMed  Google Scholar 

  32. Marszall MP, Markuszewski MJ, Kaliszan R (2006) Separation of nicotinic acid and its structural isomers using 1-ethyl-3-methylimidazolium ionic liquid as a buffer additive by capillary electrophoresis. J Pharm Biomed Anal 41:329–332

    Article  CAS  PubMed  Google Scholar 

  33. Yu L, Qin W, Li SFY (2005) Ionic liquids as additives for separation of benzoic acid and chlorophenoxy acid herbicides by capillary electrophoresis. Anal Chim Acta 547:165–171

    Article  CAS  Google Scholar 

  34. Mo H, Zhu L, Xu W (2008) Use of 1-alkyl-3-methylimidazolium-based ionic liquids as background electrolytes in capillary electrophoresis for the analysis of inorganic anions. J Sep Sci 31:2470–2475

    Article  CAS  PubMed  Google Scholar 

  35. Krizek T, Breitbach ZS, Armstrong DW, Tesarova E, Coufal P (2009) Separation of inorganic and small organic anions by CE using phosphonium-based mono- and dicationic reagents. Electrophoresis 30:3955–3963

    Article  CAS  PubMed  Google Scholar 

  36. Li J, Wang Q, Han H, Liu X, Jiang S (2010) Polymeric ionic liquid as additive for the high speed and efficient separation of aromatic acids by co-electroosmotic capillary electrophoresis. Talanta 82:56–60

    Article  CAS  PubMed  Google Scholar 

  37. Li J, Han H, Wang Q, Liu X, Jiang S (2011) Polymeric ionic liquid-coated capillary for capillary electrophoresis. J Sep Sci 34:1555–1560

    Article  CAS  PubMed  Google Scholar 

  38. Li J, Han H, Wang Q, Liu X, Jiang S (2010) Polymeric ionic liquid as a dynamic coating additive for separation of basic proteins by capillary electrophoresis. Anal Chim Acta 674:243–248

    Article  CAS  PubMed  Google Scholar 

  39. Yue M-E, Shi Y-P (2006) Application of 1-alkyl-3-methylimidazolium-based ionic liquids in separation of bioactive flavonoids by capillary zone electrophoresis. J Sep Sci 29:272–276

    Article  CAS  PubMed  Google Scholar 

  40. Jiang TF, Wang YH, Lv ZH (2006) Dynamic coating of a capillary with room-temperature ionic liquids for the separation of amino acids and acid drugs by capillary electrophoresis. J Anal Chem 61:1108–1112

    Article  CAS  Google Scholar 

  41. Lu Y, Jia C, Yao Q, Zhong H, Breadmore MC (2013) Analysis of flavonoids by non-aqueous capillary electrophoresis with 1-ethyl-3-methylimidazolium ionic-liquids as background electrolytes. J Chromatogr A 1319:160–165

    Article  CAS  PubMed  Google Scholar 

  42. Cabovska B, Kreishman GP, Wassell DF, Stalcup AM (2003) Capillary electrophoretic and nuclear magnetic resonance studies of interactions between halophenols and ionic liquid or tetraalkylammonium cations. J Chromatogr A 1007:179–187

    Article  CAS  PubMed  Google Scholar 

  43. Borissova M, Gorbatsova J, Ebber A, Kaljurand M, Koel M, Vaher M (2007) Nonaqueous CE using contactless conductivity detection and ionic liquids as BGEs in ACN. Electrophoresis 28:3600–3605

    Article  CAS  PubMed  Google Scholar 

  44. Seiman A, Vaher M, Kaljurand M (2008) Monitoring of the electroosmotic flow of ionic liquid solutions in non-aqueous media using thermal marks. J Chromatogr A 1189:266–273

    Article  CAS  PubMed  Google Scholar 

  45. Bao Y, Yang F, Yang X (2011) CE-electrochemiluminescence with ionic liquid for the facile separation and determination of diester-diterpenoid aconitum alkaloids in traditional Chinese herbal medicine. Electrophoresis 32:1515–1521

    Article  CAS  PubMed  Google Scholar 

  46. Gao Y, Xiang Q, Xu Y, Tian Y, Wang E (2006) The use of CE-electrochemiluminescence with ionic liquid for the determination of bioactive constituents in Chinese traditional medicine. Electrophoresis 27:4842–4848

    Article  CAS  PubMed  Google Scholar 

  47. Jiang T-F, Gu Y-L, Liang B, Li J-B, Shi Y-P, Ou Q-Y (2003) Dynamically coating the capillary with 1-alkyl-3-methylimidazolium-based ionic liquids for separation of basic proteins by capillary electrophoresis. Anal Chim Acta 479:249–254

    Article  CAS  Google Scholar 

  48. Corradini D, Nicoletti I, Bonn GK (2009) Co-electroosmotic capillary electrophoresis of basic proteins with 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids as non-covalent coating agents of the fused-silica capillary and additives of the electrolyte solution. Electrophoresis 30:1869–1876

    Article  CAS  PubMed  Google Scholar 

  49. Mwongela SM, Numan A, Gill NL, Agbaria RA, Warner IM (2003) Separation of achiral and chiral analytes using polymeric surfactants with ionic liquids as modifiers in micellar electrokinetic chromatography. Anal Chem 75:6089–6096

    Article  CAS  PubMed  Google Scholar 

  50. Rizvi SAA, Shamsi SA (2006) Synthesis, characterization, and application of chiral ionic liquids and their polymers in micellar electrokinetic chromatography. Anal Chem 78:7061–7069

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  51. Wang B, He J, Bianchi V, Shamsi SA (2009) Combined use of chiral ionic liquid and cyclodextrin for MEKC: part I. Simultaneous enantioseparation of anionic profens. Electrophoresis 30:2812–2819

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. Tian K, Qi S, Cheng Y, Chen X, Hu Z (2005) Separation and determination of lignans from seeds of Schisandra species by micellar electrokinetic capillary chromatography using ionic liquid as modifier. J Chromatogr A 1078:181–187

    Article  CAS  PubMed  Google Scholar 

  53. Borissova M, Palk K, Koel M (2008) Micellar electrophoresis using ionic liquids. J Chromatogr A 1183:192–195

    Article  CAS  PubMed  Google Scholar 

  54. Cao J, Qu H, Cheng Y (2010) The use of novel ionic liquid-in-water microemulsion without the addition of organic solvents in a capillary electrophoretic system. Electrophoresis 31:3492–3498

    Article  CAS  PubMed  Google Scholar 

  55. Mwongela SM, Siminialayi N, Fletcher KA, Warner IM (2007) A comparison of ionic liquids to molecular organic solvents as additives for chiral separations in micellar electrokinetic chromatography. J Sep Sci 30:1334–1342

    Article  CAS  PubMed  Google Scholar 

  56. Francois Y, Varenne A, Juillerat E, Villemin D, Gareil P (2007) Evaluation of chiral ionic liquids as additives to cyclodextrins for enantiomeric separations by capillary electrophoresis. J Chromatogr A 1155:134–141

    Article  CAS  PubMed  Google Scholar 

  57. Mofaddel N, Krajian H, Villemin D, Desbene PL (2008) Enantioseparation of binaphthol and its mono derivatives by cyclodextrin-modified capillary zone electrophoresis. J Chromatogr A 1211:142–150

    Article  CAS  PubMed  Google Scholar 

  58. Tran CD, Mejac I (2008) Chiral ionic liquids for enantioseparation of pharmaceutical products by capillary electrophoresis. J Chromatogr A 1204:204–209

    Article  CAS  PubMed  Google Scholar 

  59. Huang L, Lin JM, Yu L, Xu L, Chen G (2009) Improved simultaneous enantioseparation of beta-agonists in CE using beta-CD and ionic liquids. Electrophoresis 30:1030–1036

    Article  CAS  PubMed  Google Scholar 

  60. Wang B, He J, Bianchi V, Shamsi SA (2009) Combined use of chiral ionic liquid and CD for MEKC: part II. Determination of binding constants. Electrophoresis 30:2820–2828

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  61. Zhao M, Cui Y, Yu J, Xu S, Guo X (2014) Combined use of hydroxypropyl-beta-cyclodextrin and ionic liquids for the simultaneous enantioseparation of four azole antifungals by CE and a study of the synergistic effect. J Sep Sci 37:151–157

    Article  CAS  PubMed  Google Scholar 

  62. Liu Q, Wu K, Tang F, Yao L, Yang F, Nie Z, Yao S (2009) Amino acid ionic liquids as chiral ligands in ligand-exchange chiral separations. Chemistry 15:9889–9896

    Article  CAS  PubMed  Google Scholar 

  63. Mu X, Qi L, Zhang H, Shen Y, Qiao J, Ma H (2012) Ionic liquids with amino acids as cations: novel chiral ligands in chiral ligand-exchange capillary electrophoresis. Talanta 97:349–354

    Article  CAS  PubMed  Google Scholar 

  64. Ma Z, Zhang L, Lin L, Ji P, Guo X (2010) Enantioseparation of rabeprazole and omeprazole by nonaqueous capillary electrophoresis with an ephedrine-based ionic liquid as the chiral selector. Biomed Chromatogr 24:1332–1337

    Article  CAS  PubMed  Google Scholar 

  65. Stavrou IJ, Kapnissi-Christodoulou CP (2013) Use of chiral amino acid ester-based ionic liquids as chiral selectors in CE. Electrophoresis 34:524–530

    Article  CAS  PubMed  Google Scholar 

  66. Yu J, Zuo L, Liu H, Zhang L, Guo X (2013) Synthesis and application of a chiral ionic liquid functionalized beta-cyclodextrin as a chiral selector in capillary electrophoresis. Biomed Chromatogr 27:1027–1033

    Article  CAS  PubMed  Google Scholar 

  67. Zhang J, Du Y, Zhang Q, Lei Y (2014) Evaluation of vancomycin-based synergistic system with amino acid ester chiral ionic liquids as additives for enantioseparation of non-steroidal anti-inflammatory drugs by capillary electrophoresis. Talanta 119:193–201

    Article  CAS  PubMed  Google Scholar 

  68. Zhang Q, Du Y (2013) Evaluation of the enantioselectivity of glycogen-based synergistic system with amino acid chiral ionic liquids as additives in capillary electrophoresis. J Chromatogr A 1306:97–103

    Article  CAS  PubMed  Google Scholar 

  69. Vaher M, Koel M, Kaljurand M (2001) Non-aqueous capillary electrophoresis in acetonitril using ionic-liquid buffer electrolytes. Chromatographia 53:302–306

    Article  Google Scholar 

  70. Vaher M, Koel M, Kaljurand M (2002) Ionic liquids as electrolytes for nonaqueous capillary electrophoresis. Electrophoresis 23:426–430

    Article  CAS  PubMed  Google Scholar 

  71. Vaher M, Koel M, Kaljurand M (2002) Application of 1-alkyl-3-methylimidazloium-based ionic liquids in non-aqueous capillary electrophoresis. J Chromatogr A 979:27–32

    Article  CAS  PubMed  Google Scholar 

  72. Kuldvee R, Vaher M, Koel M, Kaljurand M (2003) Heteroconjugation-based capillary electrophoretic separation of phenolic compounds in acetonitrile and propylene carbonate. Electrophoresis 24:1627–1634

    Article  CAS  PubMed  Google Scholar 

  73. Francois Y, Varenne A, Juillerat E, Servais AC, Chiap P, Gareil P (2007) Nonaqueous capillary electrophoretic behavior of 2-aryl propionic acids in the presence of an achiral ionic liquid. A chemometric approach. J Chromatogr A 1138:268–275

    Article  CAS  PubMed  Google Scholar 

  74. Wedig M, Holzgrabe U (1999) Resolution of ephedrine derivatives by means of neutral and sulfated heptakis(2,3-di-O-acetyl)beta-cyclodextrins using capillary electrophoresis and nuclear magnetic resonance spectroscopy. Electrophoresis 20:2698–2704

    Article  CAS  PubMed  Google Scholar 

  75. Borst C, Holzgrabe U (2010) Comparison of chiral electrophoretic separation methods for phenethylamines and application on impurity analysis. J Pharm Biomed Anal 53:1201–1209

    Article  CAS  PubMed  Google Scholar 

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  1. Institut für Pharmazie und Lebensmittelchemie, Universität Würzburg, Am Hubland, Würzburg, 97074, Germany

    Ulrike Holzgrabe & Joachim Wahl

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  1. Ulrike Holzgrabe
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  2. Joachim Wahl
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Correspondence to Ulrike Holzgrabe .

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  1. Helmholtz Zentrum Munchen, Neuherberg, Germany

    Philippe Schmitt-Kopplin

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Holzgrabe, U., Wahl, J. (2016). Ionic Liquids in Capillary Electrophoresis. In: Schmitt-Kopplin, P. (eds) Capillary Electrophoresis. Methods in Molecular Biology, vol 1483. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4939-6403-1_8

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  • DOI: https://doi.org/10.1007/978-1-4939-6403-1_8

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