Aggregation in systems of ionic liquids

Structure and Bonding

Volumn 151, Issue , 2013, Pages 39-77

  Wang, Jianji ^a   Wang, Huiyong ^a  

^a HENAN NORMAL UNIVERSITY   (China)

Author keywords

Aggregate microstructure; Aggregation in solution; Ionic liquids; Potential applications

Indexed keywords

EID: 84958552254     PISSN: 00815993     EISSN: 16168550     Source Type: Book Series    
DOI: 10.1007/978-3-642-38619-0_2     Document Type: Article

References (89)

1. Welton T (1996) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071-2084
2. Swatloski RP, Holbrey JD, Rogers RD (2003) Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate. Green Chem 5:361-363
3. Docherty KM, Kulpa J, Charles F (2005) Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem 7:185-189
4. Wasserschein P, Welton T (2003) Ionic liquids in syntheses. VCH-Wiley, Weinhein
5. Rantwijk F, Lau RM, Sheldon RA (2003) Biocatalytic transformations in ionic liquids. Trends Biotechnol 21:131-138
6. Jain N, Kumar A, Chauhan S, Chauhan SMS (2005) Chemical and biochemical transformations in ionic liquids. Tetrahedron 61:1015-1060
7. Buzzeo MC, Evans RG, Compton RG (2004) Non-haloaluminate room-temperature ionic liquids in electrochemistry-a review. Chemphyschem 5:1106-1120
8. Endres F, Abedin SZE (2006) Air and water stable ionic liquids in physical chemistry. Phys Chem Chem Phys 8:2101-2116
9. Liu J, Jonsson JA, Jing G (2005) Application of ionic liquids in analytical chemistry. Trends Anal Chem 24:20-27
10. Zhao H, Xia S, Ma P (2005) Use of ionic liquids as 'green' solvents for extractions. J Chem Technol Biotechnol 80:1089-1096
11. Seddon KR (2003) Ionic liquids: a taste of the future. Nat Mater 2:363-365
12. Visser A, Swaltowski RP, Reichert RM, Mayton R, Sheff S, Wierzbicki A, Davis JH, Rogers RD (2002) Task-specific ionic liquids incorporating novel cations for the coordination and extraction of Hg2+ and Cd2+: synthesis, characterization, and extraction studies. Environ Sci Technol 36:2523-2529
13. Zhang J, Yang C, Hou Z (2003) Effect of dissolved CO2 on the conductivity of the ionic liquid [bmim][PF6]. New J Chem 27:333-336
14. Ianchard LA, Gu Z, Brennecke JF (2001) High-pressure phase behavior of ionic liquid/CO2 systems. J Phys Chem B 105:2437-2444
15. Armstrong W, Anderson JL (2003) High-stability ionic liquids: a new class of stationary phases for gas chromatography. Anal Chem 75:4851-4858
16. Bowers JP, Butts CJ, Martin PC, Vergara-Gutierrez M (2004) Aggregation behaviour of aqueous solutions in ionic liquids. Langmuir 20:2191-2198
17. Miskolczy Z, Sebok-Nagy K, Biczok L, Gokturk S (2004) Aggregation and micelle formation of ionic liquids in aqueous solution. Chem Phys Lett 400:296-300
18. Vanyur R, Biczok L, Miskolczy Z (2007) Micelle formation of 1-alkyl-3-methylimidazolium bromide ionic liquids in aqueous solution. Colloids Surf A Physicochem Eng Aspects 299:256-261
19. Blesic M, Marques MH, Plechkova NV, Seddon KR, Rebelo LPN, Lopes A (2007) Selfaggregation of ionic liquids: micelle formation in aqueous solution. Green Chem 9:481-490
20. Huddleston JG, Visser AE, Reichert MW, Willauer HD, Broker GA, Rogers RD (2001) Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem 3:156-164
21. Stepnowski P, Mrozik W, Nichthauser J (2007) Adsorption of alkylimidazolium and alkylpyridinium ionic liquids onto natural soils. Environ Sci Technol 41:511-516
22. Jungnickel C, Łuczak J, Ranke J, Fernández JF, Müller A, Thöing J (2008) Micelle formation of imidazolium ionic liquids in aqueous solution. Colloids Surf A Physicochem Eng Aspects 316:278-284
23. Modaressi A, Sifaoui H, Mielcarz M, Domanska U, Rogalski M (2007) Influence of the molecular structure on the aggregation of imidazolium ionic liquids in aqueous solutions. Colloids Surf A Physicochem Eng Aspects 302:181-185
24. El Seoud OA, Pires PAR, Abdel-Moghny T, Bastos EL (2007) Synthesis and micellar properties of surface-active ionic liquids: 1-alkyl-3-methylimidazolium chlorides. J Colloid Interface Sci 313:296-304
25. Thomaier S, Werner K (2007) Aggregates in mixtures of ionic liquids. J Mol Liq 130:104-107
26. Goodchild I, Collier L, Millar SL, Prokěs I, Lord JCD, Butts CPB, Bowers J, Webster JRP, Heenan RK (2007) Structural studies of the phase, aggregation and surface behaviour of 1-alkyl-3-methylimidazolium halide + water mixtures. J Colloid Interface Sci 307:455-468
27. Sirieix-Plénet J, Gaillon L, Letellier P (2004) Behaviour of a binary solvent mixture constituted by an amphiphilic ionic liquid, 1-decyl-3-methylimidazolium bromide and water: potentiometric and conductimetric studies. Talanta 63:979-986
28. Baltazar QQ, Chandawalla J, Sawyer K, Anderson JL (2007) Interfacial and micellar properties of imidazolium-based monocationic and dicationic ionic liquids. Colloids Surf A Physicochem Eng Aspects 302:150-156
29. Dong B, Li N, Zheng L, Yu L, Inoue T (2007) Surface adsorption and micelle formation of surface active ionic liquids in aqueous solution. Langmuir 23:4178-4182
30. Inoue T, Ebina H, Dong B, Zheng L (2007) Electrical conductivity study on micelle formation of long-chain imidazoliium ionic liquids in aqueous solution. J Colloid Interface Sci 314:236-241
31. Wang J, Wang H, Zhang S, Zhang H, Zhao Y (2007) Conductivities, volumes, fluorescence, and aggregation behavior of ionic liquids [C4mim][BF4] and [Cnmim]Br (n = 4, 6, 8, 10, 12) in aqueous solutions. J Phys Chem B 111:6181-6188
32. Zhao Y, Gao S, Wang J, Tang J (2008) Aggregation of ionic liquids [Cnmim]Br (n = 4, 6, 8, 10, 12) in D2O: a NMR study. J Phys Chem B 112:2031-2039
33. Lianos P, Zana R (1981) Fluorescence probe studies of the effect of concentration on the state of aggregation of surfactants in aqueous solution. J Colloid Interface Sci 84:100-107
34. Li XW, Gao YA, Liu J, Zheng LQ, Chen B, Wu LZ, Tung CH (2010) Aggregation behavior of a chiral long-chain ionic liquid in aqueous solution. J Colloid Interface Sci 343:94-101
35. Zhang H, Li K, Liang H, Wang J (2008) Spectroscopic studies of the aggregation of imidazolium-based ionic liquids. Colloids Surf A Physicochem Eng Aspects 329:75-81
36. Bai G, Lopes A, Bastos M (2008) Thermodynamics of micellization of alkylimidazolium surfactants in aqueous solution. J Chem Thermodyn 40:1509-1516
37. Geng F, Liu J, Zheng L, Yu L, Li Z, Li G, Tung C (2010) Micelle formation of long-chain imidazolium ionic liquids in aqueous solution measured by isothermal titration microcalorimetry. J Chem Eng Data 55:147-151
38. Cornellas A, Perez L, Comelles F, Ribosa I, Manresa A, Garcia MT (2011) Self-aggregation and antimicrobial activity of imidazolium and pyridinium based ionic liquids in aqueous solution. J Colloid Interface Sci 355:164-171
39. Singh T, Kumar A (2008) Self-aggregation of ionic liquids in aqueous media: a thermodynamic study. Colloids Surf A Physicochem Eng Aspects 318:263-268
40. Łuczak J, Hupka J, Thoeming J, Jungnickel C (2007) In: Wilk KA (ed) International scientific conference, surfactants and dispersed systems in theory and practice. PALMA Press, Wrocław/Ksiaz Castle
41. Rodriguez JR, Gonzalez-Perez A, Del Castillo JL, Czapkiewicz J (2005) Thermodynamics of micellization of alkyldimethylbenzylammonium chlorides in aqueous solutions. J Colloid Interface Sci 250:438-443
42. Chen L, Shi-Yow L, Chiung-Chang H, En-Ming C (1998) Temperature dependence of critical micelle concentration of polyoxyethylenated non-ionic surfactants. Colloids Surf A Physicochem Eng Aspects 135:175-181
43. Mehta SK, Bhasin KK, Chauhan R, Dham S (2005) Effect of temperature on critical micelle concentration and thermodynamic behavior of dodecyldimethylethylammonium bromide and dodecyltrimethylammonium chloride in aqueous media. Colloids Surf A Physicochem Eng Aspects 255:153-157
44. Muller N (1993) Temperature dependence of critical micelle concentrations and heat capacities of micellization for ionic surfactants. Langmuir 9:96-100
45. Richard CR, Wildin JL, Rapp AL, Moyna GM (2007) Hydrogen bonds in ionic liquids revisited: (35/37)Cl NMR studies of deuterium isotope effects in 1-n-butyl-3-methylimidazolium chloride. J Phys Chem B 111:11619-11621
46. Stepnowski P, Nichthauser J, Mrozik W, Buszewski B (2006) Usefulness of φ. . .φ aromatic interactions in the selective separation and analysis of imidazolium and pyridinium ionic liquid cations. Anal Bioanal Chem 385:1483-1491
47. Gonzalez-Perez A, Ruso JM, Prieto G, Sarmiento F (2004) Self-assembly of sodium heptafluorobutyrate in aqueous solution. Colloids Surf A Physicochem Eng Aspects 249:41-44
48. Zhao M, Zheng L (2011) Micelle formation by N-alkyl-N-methylpyrrolidinium bromide in aqueous solution. Phys Chem Chem Phys 13:1332-1337
49. Klevens HB (1953) Structure and aggregation in dilate solution of surface active agents. J Am Oil Chem Soc 30:74-80
50. Huibers PDT, Lobanov VS, Katritzky AR, Shah DO, Karelson M (1997) Prediction of critical micelle concentration using a quantitative structure-property relationship approach. J Colloid Interface Sci 187:113-120
51. Baker GA, Pandey S, Pandey S, Baker SN (2004) A new class of cationic surfactants inspired by N-alkyl-N-methyl pyrrolidinium ionic liquids. Analyst 12:890-892
52. Łuczaka J, Hupkaa J, Thöing J, Jungnickel C (2008) Self-organization of imidazolium ionic liquids in aqueous solution. Colloids Surf A Physicochem Eng Aspects 329:125-133
53. Wang H, Wang J, Zhang S, Xuan X (2008) Structural effects of anions and cations on the aggregation behavior of ionic liquids in aqueous solutions. J Phys Chem B 112:16682-16689
54. Freire MG, Neves CMSS, Carvalho PJ, Gardas RL, Fernandes AM, Marrucho IM, Santos LMNBF, Coutinho JAP (2007) Mutual solubilities of water and hydrophobic ionic liquids. J Phys Chem B 111:13082-13089
55. Tokuda H, Ishii K, Suan MABH, Tauzuki S, Hayamizu K, Watanabe M (2006) Physicochemical properties and structures of room-temperature ionic liquids. 3. Variation of cationic structures. J Phys Chem B 110:2833-2839
56. Bini R, Bortolini O, Chiappe C, Pieraccini D, Siciiano T (2007) Development of cation/anion "interaction" scales for ionic liquids through ESI-MS measurements. J Phys Chem B 111:598-604
57. Blesic M, Lopes A, Melo E, Petrovski Z, Plechkova NV, Canongia Lopes JN, Seddon KR, Rebelo LPN (2008) On the self-aggregation and fluorescence quenching aptitude of surfactant ionic liquids. J Phys Chem B 112:8645-8650
58. Pino V, Baltazar QQ, Anderson JL (2007) Examination of analyte partitioning to monocationic and dicationic imidazolium-based ionic liquid aggregates using solid-phase microextractiongas chromatography. J Chromatogr A 1148:92-99
59. Zana R (1996) Critical micellization concentration of surfactants in aqueous solution and free energy of micellization. Langmuir 12:1208-1211
60. Sepúlveda L, Cortés J (1985) Ionization degrees and critical micelle concentrations of hexadecyltrimethylammonium and tetradecyltrimethylammonium micelles with different counterions. J Phys Chem 89:5322-5324
61. Marcus Y (1991) Thermodynamics of solvation of ions. Part 5.-Gibbs free energy of hydration at 298.15 K. J Chem Soc Faraday Trans 87:2995-2999
62. Bunton CA, Cowell C (1988) The binding of phenols and phenoxide ions to cationic micelles. J Colloid Interface Sci 122:154-162
63. Abdel-Rahem R (2008) The influence of hydrophobic counterions on micellar growth of ionic surfactants. Adv Colloid Interface Sci 141:24-36
64. Shaw DJ (1992) Introduction to colloid and surface chemistry. Butterworth, Heinemann, Oxford
65. Dong B, Zhao X, Zheng L, Zhang J, Li N, Inoue T (2008) Aggregation behavior of long-chain imidazolium ionic liquids in aqueous solution: micellization and characterization of micelle microenvironment. Colloids Surf A Physicochem Eng Aspects 317:666-672
66. Vaghela NM, Sastry NV, Aswal VK (2011) Effect of additives on the surface active and morphological features of 1-octyl-3-methylimidazolium halide aggregates in aqueous media. Colloids Surf A Physicochem Eng Aspects 373:101
67. Wang H, Feng Q, Wang J, Zhang H (2010) Salt effect on the aggregation behavior of 1-decyl-3-methylimidazolium bromide in aqueous solutions. J Phys Chem B 114:1380-1387
68. Lin Z, Cai JJ, Scriven LE, Davis HT (1994) Spherical-to-wormlike micelle transition in CTAB solutions. J Phys Chem 98:5984-5993
69. Magid LJ, Han Z, Warr GG, Cassidy MA, Butler PD, Hamilton WA (1997) The effect of counterion competition for cetyltrimethylammonium micellar surfaces on micellar growth horizons: electrostatics and specific binding. J Phys Chem B 101:7919-7927
70. Armstrong DW, Henry SJ (1980) Use of an aqueous micellar mobile phase for separation of phenols and polynuclear aromatic hydrocarbons via HPLC. J Liq Chromatogr 3:657-662
71. Berthod A, García-álvarez-Coque C (2000) Micellar liquid chromatography. Marcel Dekker, New York
72. Esteve-Romero J, Carda-Broch S, Gil-Agustí M, Capella-Peiró ME, Bose D (2005) Micellar liquid chromatography for the determination of drug materials in pharmaceutical preparations and biological samples. Trends Anal Chem 24:75-91
73. Armstrong DW (1985) Micelles in separations: application and theory. Sep Purif Methods 14:213-304
74. Thomas DP, Foley JP (2007) Efficiency enhancements in micellar liquid chromatography through selection of stationary phase and alcohol modifier. J Chromatogr A 1149:282-293
75. Ruiz-ángel MJ, Torres-Lapasió JR, García-álvarez-Coque MC (2008) Retention mechanisms for basic drugs in the submicellar and micellar reversed-phase liquid chromatographic modes. Anal Chem 80:9705-9713
76. Pino V, Yao C, Anderson JL (2009) Micellization and interfacial behavior of imidazoliumbased ionic liquids in organic solvent-water mixtures. J Colloid Interface Sci 333:548-556
77. Wang J, Zhang L, Wang H, Wu C (2012) Aggregation behavior modulation of 1-dodecyl-3-methylimidazolium bromide by organic solvents in aqueous solution. J Phys Chem B 115:4955-4962
78. Sugihara S, Era Y, Funatsu M, Kunitake T, Lee S, Sasaki Y (1997) Micelle formation of dodecylammonium surfactant with mixed counterions: perfluorocarboxylate and alkanesulfonate ions. J Colloid Interface Sci 187:435-442
79. Beyaz A, Oh WS, Reddy VP (2004) Ionic liquids as modulators of the critical micelle concentration of sodium dodecyl sulfate. Colloids Surf B Biointerfaces 35:119
80. Dorbritz S, Ruth W, Kragl U (2005) Investigation on aggregate formation of ionic liquids. Adv Synth Catal 347:1273-1279
81. Li W, Zhang Z, Zhang J, Han B, Wang B, Hou M, Xie Y (2006) Micropolarity and aggregation behavior in ionic liquid + organic solvent solutions. Fluid Phase Equilibria 248:211-216
82. Consorti CS, Suarez PAZ, de Souza RF, Burrow RA, Farrar DH, Lough AJ, Loh W, da Silva HML, Dupont J (2005) Identification of 1,3-dialkylimidazolium salt supramolecular aggregates in solution. J Phys Chem B 109:4341-4349
83. Feng Q, Wang H, Zhang S, Wang J (2010) Aggregation behavior of 1-dodecyl-3-methylimidazolium bromide ionic liquid in non-aqueous solvents. Colloids Surf A Physicochem Eng Aspects 367:7-11
84. Singh T, Kumar A (2007) Aggregation behavior of ionic liquids in aqueous solutions: effect of alkyl chain length, cations, and anions. J Phys Chem B 111:7843-7851
85. Bhargava BL, Klein ML (2009) Molecular dynamics studies of cation aggregation in the room temperature ionic liquid [C10mim][Br] in aqueous solution. J Phys Chem A 113:1898-1904
86. Bhargava BL, Klein ML (2009) Initial stages of aggregation in aqueous solutions of ionic liquids: molecular dynamics studies. J Phys Chem B 113:9499-94505
87. Fernández JF, Waterkamp D, Thöming J (2008) Recovery of ionic liquids from wastewater: aggregation control for intensified membrane filtration. Desalination 224:52-56
88. Shen Y, Zhang Y, Kuehner D, Yang G, Yuan F, Niu L (2008) Ion-responsive behavior of ionic-liquid surfactant aggregates with applications in controlled release and emulsification. Chemphyschem 9:2198-2202
89. Pei YC, Li ZY, Liu L, Wang JJ, Wang HY (2010) Selective separation of protein and saccharides by ionic liquids aqueous two-phase systems. Sci China Chem 53:1554-1560