Liquid-liquid phase behavior of solutions of 1-Octyl- and 1-Decyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide (C 8,10mimNTf2) in n -alkyl alcohols

Journal of Chemical and Engineering Data

Volumn 55, Issue 5, 2010, Pages 2030-2038

  Vale, Vlad R ^a   Rathke, Bernd ^a   Will, Stefan ^a   Schroer W ^a  

^a UNIVERSITY OF BREMEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1-DECANOL; 1-DODECANOL; 1-NONANOL; 1-OCTADECANOL; 1-OCTANOL; ALKYL ALCOHOLS; CLOUD POINT METHOD; COEXISTENCE CURVE; CRITICAL POINTS; EICOSANOL; HEXADECANOL; LIQUID LIQUID PHASE DIAGRAMS; LIQUID-LIQUID PHASE; PARAMETERS CHARACTERIZING; TEMPERATURE RANGE;

ALKYLATION; ATMOSPHERIC PRESSURE; BINARY MIXTURES; EQUATIONS OF STATE; HYDROCARBONS; IONIC LIQUIDS; PHASE DIAGRAMS; PHASE EQUILIBRIA; PIPE FLOW;

IONIZATION OF LIQUIDS;

EID: 77952366293     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je900988a     Document Type: Article

References (57)

1. Ionic Liquids in Synthesis, 2 nd ed.; Wasserscheid, P. and Welton, T., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
2. Holbrey, J. D.; Seddon, K. R. The phase behavior of 1-alkyl-3- methylimidazolium tetrafluoroborates, ionic liquids and ionic liquid crystals J. Chem. Soc., Dalton Trans. 1999, 2133-2139
3. Weingärtner, H. Understanding ionic liquids at the molecular level: Facts, problems, and controversies Angew. Chem., Int. Ed. 2008, 47, 654-670
4. Heintz, A. Recent developments in thermodynamics and thermophysics of non-aqueous mixtures containing ionic liquids. A review J. Chem. Thermodyn. 2005, 37, 525-535
5. Rebelo, L. P. N.; Canongia Lopes, J. N.; Esperanca, J. M. S. S.; Guedes, H. J. R.; Łachwa, J.; Najdanovic-Visak, V.; Visak, Z. P. Accounting for the unique, doubly dual nature of ionic liquids from a molecular thermodynamic and modeling standpoint Acc. Chem. Res. 2007, 40, 1114-1121
6. Zaitsau, D. H.; Kabo, G. J.; Strechan, A. A.; Paulechka, Y. U.; Tschersich, A.; Verevkin, S. P.; Heintz, A. Experimental vapor pressures of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and a correlation scheme for estimation of vaporization enthalpies of ionic liquids J. Phys. Chem. A 2006, 110, 7303-7306
7. Rebelo, L. P. N.; Canongia- Lopes, J. N.; Esperanca, J. M. S. S.; Filipe, E. On the critical temperature, normal boiling point, and vapor pressure of ionic liquids J. Phys. Chem. B 2005, 109, 6040-6043
8. Zaitsau, D. H.; Paulechka, Y. U.; Kabo, G. J. The kinetics of thermal decomposition of 1-butyl-3-methylimidazolium hexafluorophosphate J. Phys. Chem. A 2006, 110, 11602-11604
9. Fredlake, C. B.; Crosthwaite, J. M.; Hert, D. G.; Aki, S. N. V. K.; Brennecke, J. F. Thermophysical properties of Imidazolium-Based Ionic Liquids J. Chem. Eng. Data 2004, 49, 954-964
10. Brennecke, J. F.; Maginn, E. J. Ionic liquids: Innovative fluids for chemical processing AIChE J. 2001, 47, 2384-2389
11. Anthony, J. L.; Maginn, E. J.; Brennecke, J. F. Solution Thermodynamics of Imidazolium-Based Ionic Liquids and Water J. Phys. Chem. B 2001, 105, 10942-10949
12. Wagner, M.; Stanga, O.; Schröer, W. Corresponding states analysis of the critical points in binary solutions of room temperature ionic liquids Phys. Chem. Chem. Phys. 2003, 5, 3943-3950
13. 4] + Water System ACS Symp. Ser. 2005, 901, 175-186
14. Saracsan, D.; Rybarsch, C.; Schröer, W. Phase separation in solutions of room temperature ionic liquids in hydrocarbons Z. Phys. Chem. 2006, 220, 1417-1437
15. Lachwa, J.; Szydlowski, J.; Makowska, A.; Seddon, K. R.; Esperanca, J. M. S. S.; Guedes, H. J. R.; Rebelo, L. P. N. Changing from an unusual high-temperature demixing to a UCST-type in mixtures of 1-alkyl-3- methylimidazolium bis{(trifluoromethyl)sulfonyl}amide and arenes Green Chem. 2006, 8, 262-267
16. Domanska, U.; Casas, L. M. Solubility of phosphonium ionic liquid in alcohols, benzene, and alkylbenzenes J. Phys. Chem. B 2007, 111, 4109-4115
17. Domanska, U.; Paduszynski, K. Phase equilibria study in binary systems (tetra- n -butylphosphonium tosylate ionic liquid + 1-alcohol, or benzene, or n -alkylbenzene) J. Phys. Chem. B 2008, 112, 11054-11059
18. Ionic Liquids: Industrial Applications for Green Chemistry; Rogers, R. D.; Seddon, K. R., Eds.; ACS Symposium Series 818; American Chemical Society: Washington, DC, 2002.
19. Ionic Liquids as Green Solvents: Progress and Prospects; Rogers, R. D.; Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003.
20. 2] with cyclohexanol and 1,2-hexanediol including studies of the influence of small amounts of water J. Chem. Eng. Data 2005, 50, 956-960
21. Wertz, Ch.; Tschersich, A.; Lehmann, J. K.; Heintz, A. Liquid-liquid equilibria and liquid-liquid interfacial tension measurements of mixtures containing ionic liquids J. Mol. Liq. 2007, 131-132, 2-6
22. Heintz, A.; Lehmann, J.; Wertz, C. Thermodynamic properties of mixtures containing ionic liquids. 3. Liquid-liquid equilibria of binary mixtures of 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide with propan-1-ol, butan-1-ol, and pentan-1-ol J. Chem. Eng. Data 2003, 48, 472-474
23. Wu, C. T.; Marsh, K. N.; Deev, A. V.; Boxall, J. A. Liquid-liquid equilibria of room-temperature ionic liquids and butan-1-ol J. Chem. Eng. Data 2003, 48, 486-491
24. Marsh, K. N.; Deev, A.; Wu, C. T.; Tran, E.; Klamt, A. K. Room temperature ionic liquids as replacements for conventional solvents-A review Korean J. Chem. Eng. 2002, 19, 357-362
25. Crosthwaite, J. M.; Aki, S. N. V. K.; Maginn, E. J.; Brennecke, J. F. Liquid phase behavior of imidazolium-based ionic liquids with alcohols J. Phys. Chem. B 2004, 108, 5113-5119
26. Crosthwaite, J. M.; Aki, S. N. V. K.; Maginn, E. J.; Brennecke, J. F. Liquid phase behavior of imidazolium-based ionic liquids with alcohols: effect of hydrogen bonding and non-polar interactions Fluid Phase Equilib. 2005, 228-229, 303-309
27. Butka, A.; Vale, V. R.; Saracsan, D.; Rybarsch, C.; Weiss, V. C.; Schröer, W. The Liquid- Liquid Phase Transition in Solutions of Ionic Liquids with Halide Anions: Criticality and Corresponding States Pure Appl. Chem. 2008, 80, 1613-1630
28. Sahandzhieva, K.; Tuma, D.; Breyer, S.; Kamps, A.; Maurer, G. Liquid-liquid equilibrium in mixtures of the ionic liquid 1- n -butyl-3-methylimidazolium hexafluorophosphate and an alkanol J. Chem. Eng. Data 2006, 51, 1516-1525
29. 8 n -Alcohol} Mixtures: Liquid-Liquid Equilibrium and Excess Volumes J. Chem. Eng. Data 2006, 51, 2215-2221
30. Lachwa, J.; Szydlowski, J.; Najdanovic-Visak, V.; Rebelo, L. P. N.; Seddon, K. R.; da Ponte, M. N.; Esperanca, J. M. S. S.; Guedes, H. J. R. Evidence for Lower Critical Solution Behavior in Ionic Liquid Solutions J. Am. Chem. Soc. 2005, 127, 6542-6543
31. Ferreira, R.; Blesic, M.; Trindade, J.; Marrucho, I.; Canongia-Lopes, J. N.; Rebelo, L. P. N. Solubility of fluorinated compounds in a range of ionic liquids. Cloud-point temperature dependence on composition and pressure Green Chem. 2008, 10, 918-928
32. Schröer, W.; Vale, V. R. Liquid-liquid phase separation in solutions of ionic liquids: phase diagrams, corresponding state analysis and comparison with simulations of the primitive model J. Phys.: Condens. Matter. 2009, 21 424119
33. Swatloski, R. P.; Holbrey, J. D.; Rogers, R. D. Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate Green Chem. 2003, 5, 361-363
34. Triolo, A.; Russina, O.; Bleif, H.-J.; Di Cola, E. Nanoscale Segregation in Room Temperature Ionic Liquids J. Phys. Chem. B 2007, 111, 4641-4644
35. - anion J. Mol. Liq. 2006, 125, 164-173
36. Anisimov, M. A. Critical Phenomena in Liquids and Liquid Crystals; Gordon and Breach: Philadelphia, 1991.
37. Guggenheim, E. A. The Principle of Corresponding States J. Chem. Phys. 1945, 13, 253-261
38. Pitzer, K. S. Critical Phenomena in Ionic Fluids Acc. Chem. Res. 1990, 23, 333-338
39. Fisher, M. E. The Story of Coulombic Criticality J. Stat. Phys. 1994, 75, 1-36
40. Weingärtner, H.; Schröer, W. Criticality of Ionic Fluids Adv. Chem. Phys. 2001, 116, 1-66
41. Singh, R. R.; Pitzer, K. S. Near-Critical Coexistence Curve and Critical Exponent of an Ionic Fluid J. Chem. Phys. 1990, 92, 6775-6778
42. Zhang, K. C.; Briggs, M. E.; Gammon, R. W.; Levelt Sengers, J. M. H. The susceptibility critical exponent for a nonaqueous ionic binary mixture near a consolute point J. Chem. Phys. 1992, 97, 8692-8697
43. Wiegand, S.; Briggs, M. E.; Levelt Sengers, J. M. H.; Kleemeier, M.; Schröer, W. Turbidity, light scattering, and coexistence curve data for the ionic binary mixture triethyl- n -hexylammonium triethyl- n -hexylborate in diphenyl ether J. Chem. Phys. 1998, 109, 9038-9051
44. Caillol, J. M.; Levesque, D.; Weiss, J. J. Critical behavior of the restricted primitive model revisited J. Chem. Phys. 2002, 116, 10794-10800
45. Orkoulas, G.; Panagiotopoulos, A. Z. Phase behavior of the restricted primitive model and square-well fluids from Monte Carlo simulations in the grand canonical ensemble J. Chem. Phys. 1999, 110, 1581-1590
46. Yan, Q. L.; de Pablo, J. J. Hyper-parallel tempering Monte Carlo: Application to the Lennard-Jones fluid and the restricted primitive model J. Chem. Phys. 1999, 111, 9509-9515
47. Lee, B. P.; Fisher, M. E. Ginzburg criterion for Coulombic criticality Phys. Rev. Lett. 1996, 77, 3561-3564
48. Schröer, W.; Weiss, V. C. Ginzburg criterion for the crossover behavior of model fluids J. Chem. Phys. 1998, 109, 8504-8513
49. Kleemeier, M.; Wiegand, S.; Schröer, W.; Weingärtner, H. The liquid-liquid phase transition in ionic solution: Coexistence curves of tetra- n -butylammonium picrate in alkylalcohols J. Chem. Phys. 1999, 110, 3085-3099
50. Oleinikova, A.; Bonetti, M. Coexistence curve of the ionic binary mixture tetra- n -butylammonium picrate in 1-dodecanol Chem. Phys. Lett. 1999, 299, 417-422
51. Wagner, M.; Stanga, O.; Schröer, W. The liquid-liquid coexistence of binary mixtures of the room temperature ionic liquid 1-methyl-3- hexylimidazolium tetrafluoroborate with alcohols Phys. Chem. Chem. Phys. 2004, 6, 4421-4431
52. Schröer, W.; Wiegand, S.; Weingärtner, H. The effect of short-range hydrogen-bonded interactions on the nature of the critical point of ionic fluids. Part II: Static and dynamic light scattering on solutions of ethylammonium nitrate in n -octanol Ber. Bunsen.-Ges. Phys. Chem. 1993, 97, 975-982
53. Barthel, J.; Carl, E.; Gores, H. J. Coulombic liquid-liquid phase separation of dilithium hexafluoropropane-1,3- bis[sulfonylbis(trifluoromethylsulfonyl)methanide] solutions in diethylcarbonate Electrochem. Solid State Lett. 1999, 2, 218-221
54. Schröer, W.; Wagner, M.; Stanga, O. Apparent Mean-Field Criticality of Liquid-Liquid Phase Transitions in Ionic Solutions J. Mol. Liq. 2006, 127, 2-9
55. Wang, J.; Cenderina, C. A.; Anisimov, M. A.; Sengers, J. V. Principle of isomorphism and complete scaling for binary-fluid criticality Phys. Rev. E 2008, 77 031127
56. Gutkowski, K.; Anisimov, M. A.; Sengers, J. V. Crossover criticality in ionic solutions J. Chem. Phys. 2001, 114, 3133-3148
57. Handbook of Chemistry and Physics, 76 th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995.