Estimation of extraction properties of new imidazolide anion based ionic liquids on the basis of activity coefficient at infinite dilution measurements

Separation and Purification Technology

Volumn 118, Issue , 2013, Pages 242-254

  Zawadzki, Maciej ^a   Niedzicki, Leszek ^a   Wieczorek, Władysław ^a   Domańska, Urszula ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

1 Butyl 3 methylimidazolium 4,5 dicyano 2 (trifluoromethyl)imidazolide, BMIM TDI ; 1 Butyl 3 methylpyridinium 4,5 dicyano 2 (trifluoromethyl) imidazolide, BM3PY TDI ; Activity coefficients at infinite dilution; Extraction of sulfur compounds from aliphatics; Ionic liquids; Separation of aromatics from aliphatics

Indexed keywords

ABRAHAM SOLVATION PARAMETER MODEL; ACTIVITY COEFFICIENT AT INFINITE DILUTION; ACTIVITY COEFFICIENTS AT INFINITE DILUTION; GAS-LIQUID CHROMATOGRAPHY; GAS-LIQUID PARTITION COEFFICIENTS; SCANNING MICROCALORIMETRY; SECOND-ORDER POLYNOMIAL; TRIFLUOROMETHYL;

ACTIVITY COEFFICIENTS; ATMOSPHERIC PRESSURE; DILUTION; ENTHALPY; ENTROPY; EXTRACTION; GAS CHROMATOGRAPHY; GLASS; GLASS TRANSITION; HYDROCARBONS; KETONES; SURFACE TENSION; THIOPHENE; VISCOSITY;

IONIC LIQUIDS;

EID: 84881093979     PISSN: 13835866     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.seppur.2013.07.006     Document Type: Article

References (62)

1. J.P. Hallet, and T. Welton Room-temperature ionic liquids: solvents for synthesis and catalysis. 2 Chem. Rev. 111 2011 3508 3576
2. A. Arce, M. Earle, S. Katdare, H. Rodríguez, and K.S. Seddon Application of mutually immiscible ionic liquids to the separation of aromatic and aliphatic hydrocarbons by liquid extraction: a preliminary approach Phys. Chem. Chem. Phys. 10 2008 2538 2542
3. U. Domańska Ionic liquids in chemical analysis General Review of Ionic Liquids and their Properties 2008 CRC Press, Taylor & Francis Group Abingdon, UK (Chapter 1)
4. G.W. Meindersma, A.R. Hansmeier, and A.B. de Haan Ionic liquids for aromatic extraction. Present status and future outlook Ind. Eng. Chem. Res. 49 2010 7530 7540
5. A.R. Hansmeier, G.W. Meindersma, and A.B. de Haan Desulfurization and denitrogenation of gasoline and diesel fuels by means of ionic liquids Green Chem. 13 2011 1907 1913
6. I. Zhang, Q. Zhang, B. Qjao, and J. Deng Solubilities of the gaseous and liquid solutes and their thermodynamics of solubilization in the novel room-temperature ionic liquids at infinite dilution by gas chromatography J. Chem. Eng. Data 52 2007 2277 2283 (Pubitemid 350229764)
7. U. Domańska, and A. Marciniak Measurements of activity coefficients at infinite dilution of aromatic and aliphatic hydrocarbons, alcohols, and water in the new ionic liquid [EMIM][SCN] using GLC Chem. Thermodyn. 40 2008 860 866
8. U. Domańska, M. Laskowska, and A. Pobudkowska Phase equilibria study of the binary system (1-butyl-3-methylimidazolium thiocyanate ionic liquid + organic solvent, or water) J. Phys. Chem. B 113 2009 6397 6404
9. U. Domańska, M. Królikowska, and M. Arasimowicz Phase equilibria of (1-hexyl-3-methylimidazolium thiocyanate + water, or hydrocarbon) binary system J. Chem. Eng. Data 55 2010 773 777
10. U. Domańska, M. Królikowska, and M. Królikowski Thermodynamic phase behaviour and physico-chemical properties of the binary systems {(1-ethyl-3-methylimidazolium thiocyanate, or 1-ethyl-3- methylimidazolium tosylate + water, or + an alcohol) Fluid Phase Equilib. 294 2010 72 83
11. U. Domańska, M. Królikowski, and K. Ślesińska Phase equilibria study of the binary system (ionic liquid + thiophene): desulfurization process J. Chem. Thermodyn. 41 2009 1303 1311
12. U. Domańska, and M. Laskowska Measurements of activity coefficients at infinite dilution of measurements of activity coefficients at infinite dilution of aliphatic hydrocarbons and aromatic hydrocarbons, alcohols, thiophene, tetrahydrofurane, MTBE and water in ionic liquid [BMIM][SCN] using GLC J. Chem. Thermodyn. 41 2009 645 650
13. U. Domańska, A. Marciniak, M. Królikowska, and M. Arasimowicz Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-hexyl-3-methylimidazolium thiocyanate J. Chem. Eng. Data 55 2010 2532 2536
14. L. Niedzicki, G.Z. Åukowska, M. Bukowska, P. Szczeciński, S. Grugeon, S. Laruelle, M. Armand, S. Panero, B. Scrosati, M. Marcinek, and W. Wieczorek New type of imidazole based salt designed specifically for lithium batteries Electrochim. Acta 55 2010 1450 1454
15. M. Bukowska, J. Prejzner, and P. Szczeciński Synthesis of 4,5-dicyanoimidazoles Pol. J. Chem. 78 2004 417 422 (Pubitemid 38407464)
16. L. Niedzicki, E. Karpierz, M. Zawadzki, M. Dranka, M. Kasprzyk, A. Zalewska, M. Marcinek, J. Zachara, U. Domańska, W. Wieczorek, 2013, Tailored ionic liquids for modern battery applications, Energy Environ. Sci. submitted for publication.
17. 2, (sulfolane) at the temperature 303.15 K J. Chem. Thermodyn. 27 1995 867 872
18. W.C. Moollan, The Determination of Activity Coefficients at Infinite Dilution, PhD Thesis, University of Natal, Durban, 1993.
19. F. Mutelet, and J.-N. Jaubert Accurate measurements of thermodynamic properties of solutes in ionic liquids using inverse gas chromatography J. Chromatogr. A 1102 2006 256 267 (Pubitemid 41790356)
20. F. Mutelet, J.-N. Jaubert, M. Rogalski, J. Harmand, M. Sindt, and J.-L. Mieloszynski Activity coefficients at infinite dilution of organic compounds in 1-(meth)acryloyloxyalkyl-3-methylimidazolium bromide using inverse gas chromatography J. Phys. Chem. B 112 2008 3773 3785
21. D. Tiegs, J. Gmehling, A. Medina, M. Soares, J. Bastos, P. Alessi, and I. Kikic Activity coefficients at infinite dilution Chem. Data Ser. IX Part 1 1986 586
22. D.H. Everett Effects of gas imperfections on GLC measurements Trans. Faraday Soc. 61 1965 1637 1639
23. A.J.B. Cruickshank, B.W. Gainey, C.P. Hicks, T.M. Letcher, R.W. Moody, and C.L. Young Gas-liquid chromatographic determination of cross-term second virial coefficients using glycerol Trans. Faraday Soc. 65 1969 1014 1031
24. Design Institute for Physical Properties, Sponsored by AIChE (2005, 2008, 2009, 2010). DIPPR Project 801 - Full Version, Design Institute for Physical Property Research/AIChE. < http://knovel.com/web/portal/browse/display?-EXT- KNOVEL-DISPLAY-bookid=1187&VerticalID=0 >.
25. B.E. Poling, and J.M. Prausnitz Properties of Gases and Liquids 2001 McGraw-Hill Publishing < http://lib.myilibrary.com?ID=91317 >
26. U. Domańska, and M. Królikowska Measurements of activity coefficients at infinite dilution in solvent mixtures with thiocyanate-based ionic liquids using GLC technique J. Phys. Chem. B 114 2010 8460 8466
27. H. Vogel The law of the relationship between viscosity of liquids and the temperature Phys. Z. 22 1921 645 646
28. G.S. Fulcher Analysis of recent measurements of the viscosity of glasses J. Am. Ceram. Soc. 8 1925 339 355
29. G. Tammann, and W. Hesse Die Abhängigkeit der Viscosität von der Temperatur bie Unterkühlten Flüssigkeiten Z. Anorg. Allg. Chem. 156 1926 245 257
30. U. Domańska, and A. Marciniak Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate J. Phys. Chem. B 112 2008 11100 11105
31. Ming-Lan Ge, Li-Sheng Wang, Mi-Yi Li, and Jun-Sheng Wu Activity coefficients at infinite dilution of alkanes, alkenes, and alkyl benzenes in 1-butyl-3-methylimidazolium trifluoromethanesulfonate using gas-liquid chromatography J. Chem. Eng. Data 52 2007 2257 2260 (Pubitemid 350229760)
32. A. Heintz, L.M. Casas, I.A. Nesterov, V.N. Emel'yaneko, and S.P. Verevkin Thermodynamic properties of mixtures containing ionic liquids. 5. Activity coefficients at infinite dilution of hydrocarbons, alcohols, esters, and aldehydes in 1-methyl-3-butyl-imidazolium bis(trifluoromethyl-sulfonyl) imide using gas-liquid chromatography J. Chem. Eng. Data 50 2005 1510 1514
33. M. Krummen, P. Wasserscheid, and J. Gmehling Measurement of activity coefficients at infinite dilution in ionic liquids using the dilutor technique J. Chem. Eng. Data 47 2002 1411 1417 (Pubitemid 35458133)
34. J.C. Moise, F. Mutulet, J.N. Jaubet, L.M. Grubbs, W.E. Acree, and G.A. Baker Activity coefficients at infinite dilution of organic compounds in four new imidazolium-based ionic liquids J. Chem. Eng. Data 56 2011 3106 3114
35. Y.X. Feng, L.S. Wang, and Y. Li Activity coefficients at infinite dilution of organic solutes in 1-butyl-3-methylimidazolium nitrate using gas-liquid chromatography J. Chem. Eng. Data 56 2011 2730 2736
36. M.L. Ge, X.J. Song, G.M. Li, F.Z. Liu, and H.L. Ma Activity coefficients at infinite dilution of alkanes, alkenes, and alkyl benzenes in 1-butyl-3-methylimidazolium dibutylphosphate using gas-liquid chromatography J. Chem. Eng. Data 57 2012 2109 2113
37. U. Domańska, and M. Królikowski Determination of activity coefficients at infinite dilution of 35 solutes in the ionic liquid, 1-butyl-3-methylimidazolium tosylate, using gas-liquid chromatography J. Chem. Eng. Data 55 2010 4817 4822
38. P.F. Yan, M. Yang, Ch.-P. Li, X.-M. Liu, Z.-Ch. Tan, and U. Welz-Biermann Gas-liquid chromatography measurements of activity coefficients at infinite dilution of hydrocarbons and alkanols in 1-alkyl-3-methylimidazolium bis(oxalato)borate Fluid Phase Equilib. 298 2010 287 292
39. Q. Zhou, and L.-S. Wang Activity coefficients at infinite dilution of alkanes, alkenes, and alkyl benzenes in 1-butyl-3-methylimidazolium tetrafluoroborate using gas-liquid chromatography J. Chem. Eng. Data 51 2006 1698 1701 (Pubitemid 44562520)
40. Q. Xu, B. Su, X. Luo, H. Xing, Z. Bao, Q. Yang, Y. Yang, and Q. Ren Accurate measurements of infinite dilution activity coefficients using gas chromatography with static-wall-coated open-tubular columns Anal. Chem. 84 2012 9109 9115
41. F. Mutulet, V. Butet, and J.N. Jaubert Application of inverse gas chromatography and regular solution theory for characterization of ionic liquids Ind. Eng. Chem. Res. 44 2005 4120 4127
42. A. Marciniak, and M. Wlazło Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-3-methyl-pyridinium trifluoromethanesulfonate J. Chem. Eng. Data 55 2010 3208 3211
43. M. Krummen, D. Gruber, and J. Gmehling Measurement of activity coefficients at infinite dilution in solvent mixtures using the dilutor technique Ind. Eng. Chem. Res. 39 2000 2114 2123 (Pubitemid 30414888)
44. A. Marciniak Influence of cation and anion structure of the ionic liquid on extraction process based on activity coefficients at infinite dilution - a review Fluid Phase Equilib. 294 2010 213 233
45. M.H. Abraham Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes Chem. Soc. Rev. 22 1993 73 83
46. M.H. Abraham, A. Ibrahim, and A.M. Zissimos Determination of sets of solute descriptors from chromatographic measurements J. Chromatogr. A 1037 2004 29 47 (Pubitemid 38591335)
47. W.E. Acree Jr., and M.H. Abraham The analysis of solvation in ionic liquids and organic solvents using the abraham linear free energy relationship J. Chem. Technol. Biotechnol. 81 2006 1441 1446 (Pubitemid 44082470)
48. M.H. Abraham, and W.E. Acree Jr. Comparative analysis of solvation and selectivity in room temperature ionic liquids using the Abraham linear free energy relationship Green Chem. 8 2006 906 915 (Pubitemid 44527096)
49. M.G. Freire, P.J. Carvalho, A.M. Fernandes, I.M. Marrucho, A.J. Queimada, and J.A.P. Couthino Surface tensions of imidazolium based ionic liquids: anion, cation, temperature and water effect J. Colloid Interf. Sci. 314 2007 621 630 (Pubitemid 47285141)
50. U. Domańska, and M. Krolikowska Effect of temperature and composition on the surface tension and thermodynamic properties of binary mixtures of 1-butyl-3-methylimidazolium thiocyanate with alcohols J. Colloid Interf. Sci. 348 2010 661 667
51. P. Kilaru, G.A. Baker, and P. Scovazzo Density and surface tension measurements of imidazolium-, quaternary phosphonium-, and ammonium-based room-temperature ionic liquids: data and correlations J. Chem. Eng. Data 52 2007 2306 2314 (Pubitemid 350229769)
52. M.H. Ghatee, M. Zare, A.R. Zolghadr, and F. Moosavi Temperature dependence of viscosity and relation with the surface tension of ionic liquids Fluid Phase Equilib. 291 2010 188 194
53. J. Klomfar, M. Součková, and J. Pátek Surface tension measurements with validated accuracy for four 1-alkyl-3- methylimidazolium based ionic liquids J. Chem. Thermodyn. 42 2010 323 329
54. J. Bowers, C.P. Butts, P.J. Martin, and M.C. Vergara-Gutierrez Aggregation behavior of aqueous solutions of ionic liquids Langmuir 20 2004 2191 2198
55. A.D. McNaught, and A. Wilkinson Compendium of Chemical Terminology, IUPAC Recomendation second ed. 1997 Blackwell Sci. Cambridge
56. K.R. Harris, M. Kanakubo, and L.A. Woolf Temperature and pressure dependence of the viscosity of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate: viscosity and density relationships in ionic liquids J. Chem. Eng. Data 52 2007 2425 2430 (Pubitemid 350229788)
57. J. Troncoso, C.A. Cerdeirin, Y.A. Sanmamed, L. Romani, L. Paulo, and N. Rebelo Thermodynamic properties of imidazolium-based ionic liquids: densities, heat capacities, and enthalpies of fusion of [bmim][PF6] and [bmim][NTf2] J. Chem. Eng. Data 51 2006 1856 1859 (Pubitemid 44562549)
58. R.L. Gardas, M.G. Freire, P.J. Carvalho, I.M. Marrucho, I.M.A. Fonseca, A.G.M. Ferreira, and J.A.P. Coutinho High-pressure densities and derived thermodynamic properties of imidazolium-based ionic liquids J. Chem. Eng. Data 52 2007 80 88
59. AA. Miran Beigi, M. Abdouss, M. Yousefi, SM. Pourmortazavi, and A. Vahid Investigation on physical and electrochemical properties of three imidazolium based ionic liquids (1-hexyl-3-methylimidazolium tetrafluoroborate,1-ethyl-3- methylimidazolium bis(trifluoromethylsulfonyl) imide and 1-butyl-3- methylimidazolium methylsulfate) J. Mol. Liq. 177 2013 361 368
60. J.L. Shereshefsky Surface tension of saturated vapors and the equation of Eötvös J. Phys. Chem. 35 1931 1712 1720
61. E.A. Guggenheim The principle of corresponding states J. Chem. Phys. 13 1945 253 261
62. R. Auerbach Oberflachenspannung und Schallgeschwindigkeit Experientia 4 1948 473 474