Influence of some structural characteristics of the ionic liquids on homogeneous and heterogeneous characteristics of their mixtures with water and alcohols.
Abstract
The article presents a study of influence of the structural characteristics of ionic liquids, such as length of alkyl chain of the cation, cation's symmetry, type of the cation, type of the anion and some others, on the homogeneous and heterogeneous characteristics of the mixtures of ionic liquids with water and alcohol.
About the Authors
S. A. Reshetov
Moscow Technological University (Institute of Fine Chemical Technologies), 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
A. K. Frolkova
Moscow Technological University (Institute of Fine Chemical Technologies), 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
A. A. Muzyka
Moscow Technological University (Institute of Fine Chemical Technologies), 86, Vernadskogo pr., Moscow 119571
Russian Federation
Russian Federation
References
1. Experimental measurement of the hydroscopic grade on eight imidazolium based ionic liquids / S. Cuadrado-Prado [et al.] // Fluid Phase Equilibria. - 2009. - Vol. 278. - P. 36-40.
2. Liquid-Liquid Equilibria of Room-Temperature Ionic Liquids and Butan-1-ol / C.-T. Wu [et al.] // J. Chem. Eng. Data. - 2003. - Vol. 48, № 3. - P.486-491.
3. Meindersma, G. W. Ternary Liquid-Liquid Equilibria for Mixtures of an Aromatic + an Aliphatic Hydrocarbon + 4-Methyl-N-butylpyridinium Tetrafluoroborate / G. W. Meindersma, A. Podt, A. B. de Haan // J. Chem. Eng. Data. - 2006. - Vol. 51, № 5. - P. 1814-1819.
4. Pereiro, A. B. Ternary Liquid-Liquid Equilibria Ethanol + 2-Butanone + 1-Butyl-3-methylimidazolium Hexafluorophosphate, 2-Propanol + 2-Butanone + 1-Butyl-3-methylimidazolium Hexafluorophosphate, and 2-Butanone + 2-Propanol + 1,3-Dimethylimidazolium Methyl Sulfate at 298.15 K. / A. B. Pereiro, A. Rodriguez // J. Chem. Eng. Data. - 2007. - Vol. 52, № 6. - P. 2138-2142.
5. Vapor-Liquid Equilibria for the Ternary System Ethanol + Water + 1-Butyl-1-methylimidazolium Chloride and the Corresponding Binary Systems at 101.3 kPa / N. Calvar [et al.] // J. Chem. Eng. Data. - 2006. - Vol. 51, № 6. - P. 2178-2181.
6. Study of the behavior of the azeotropic mixture ethanol-water with imidazolium-based ionic liquids / N. Calvar [et al.] // Fluid Phase Equilibria. - 2007. - Vol. 259. - P. 51-56.
7. Isobaric vapor-liquid equilibria for ethanol-water system containing different ionic liquids at atmospheric pressure / J. Zhao [et al.] // Fluid Phase Equilibria. - 2006. - Vol. 242. - P. 147-153.
8. Selection of ionic liquids as entrainers for separation of (water + ethanol) / Y. Ge [et al.] // J. Chem. Thermodyn. - 2008. - Vol. 40. - P. 1248-1252.
9. Effect of ionic liquids on (vaper + liquid) equilibrium behavior of (water + 2-methyl-2-propanol) / L. Zhang [et al.] // J. Chem. Thermodyn. - 2009. - Vol. 41. - P. 138-143.
10. Vapor Pressures of the 1-Butyl-3-methylimidazolium Bromide + Water, 1-Butyl-3-methylimidazolium Tetrafluoroborate + Water, and 1-(2-hydroxyethyl)-3-methylimidazolium Tetrafluoroborate + Water Systems / K.-S. Kim [et al.] // J. Chem. Eng. Data. - 2004. - Vol. 49, № 6. - P. 1550-1553.
11. Isobaric Vapor-Liquid Equilibria for Isopropanol + Water + 1-Ethyl-3-methylimidazolium Tetrafluoroborate / Q. Li [et al.] // J. Chem. Eng. Data. - 2008. - Vol. 53, № 1. - P. 275-279.
12. Isobaric Vapor-Liquid Equilibria for Water + 2-Propanol + 1-Butyl-3-methylimidazolium Tetrafluoroborate / L. Z. Zhang [et al.] // J. Chem. Eng. Data. - 2007. - Vol. 52, № 1. - P. 199-205.
13. Isobaric Vapor-Liquid Equilibria for Three Ternary Systems: Water + 2-Propanol + 1-Ethyl-3-methylimidazolium Tetrafluoroborate, Water + 1-Propanol + 1-Ethyl-3-methylimidazolium Tetrafluoroborate, Water + 1-Propanol + 1-Butyl-3-methylimidazolium Tetrafluoroborate / L. Zhang [et al.] // J. Chem. Eng. Data. - 2007. - Vol. 52, № 4. - P. 1401-1407.
14. Aqueous biphasic composed of ionic liquids and fructose / Y. Zhang [et al.] // Fluid Phase Equilibria. - 2007. - Vol. 257. - P. 173-176
15. Liquid Phase Behavior of Ionic Liquids with Water and 1-Octanol and Modeling of 1-Octanol/Water Partition Coefficients / A. Chapeaux [et al.] // J. Chem. Eng. Data. - 2007. - Vol. 52, № 6. - P. 2462-2467.
16. Wu, B. Aqueous Biphasic Systems of Hydrophilic Ionic Liquids + Sucrose for Separation / B. Wu, Y. M. Zhang, H. P. Wang // J. Chem. Eng. Data. - 2008. - Vol. 53, № 4. - P. 983-985.
17. Influence of Ionic Liquids on the Phase Behavior of Aqueous Azeotropic Systems / C. York [et al.] // J. Chem. Eng. Data. - 2004. - Vol. 49, № 4. - P. 852-857.
18. Vapor pressure measurement for binary and ternary systems containing a phosphoric ionic liquid / J. Zhao [et al.] // Fluid Phase Equilibria. - 2006. - Vol. 247. - P. 190-198.
19. Vapor pressure measurement for water, methanol, ethanol, and their mixtures in the presence of an ionic liquid 1-Ethyl-3-methylimidazolium dimethylphosphate / J.-F. Wang [et al.] // Fluid Phase Equilibria. - 2007. - Vol. 255. - P. 186-192.
20. Boiling temperature measurement for water, methanol, ethanol, and their binary mixtures in the presence of a hydrochloric or acetic salt of mono-, di-, or tri-ethanolamine at 101,3 kPa / J.-F. Wang [et al.] // J. Chem. Thermodyn. - 2009. - Vol .41. - P. 167-170.
21. Vapor Pressures for 1,4-Dioxane + Tetrabutylammonium Nitrate, Water + Tetrabutylammonium Nitrate, and 1,4-Dioxane + Water + Tetrabutylammonium Nitrate / A.V. Kurzin [et al.] // J. Chem. Eng. Data. - 2008. - Vol. 53, № 1. - P. 207-210.
22. Viscosities, Vapor Pressures, and Excess Enthalpies of Choline Lactate + Water, Choline Glycolate + Water, and Choline Methanesulfonate + Water Systems / D. Constantinescu [et al.] // J. Chem. Eng. Data. - 2007. - Vol. 52, № 4. - P. 1280-1285.
23. Vapor-Liquid Equilibria for the Ternary System Ethanol + Water + 1-Ethyl-1-methylimidazolium Ethylsulfata and the Corresponding Binary Systems Containing the Ionic Liquids at 101.3 kPa / N. Calvar [et al.] // J. Chem. Eng. Data. - 2008. - Vol. 53, № 3. - P. 820-825.
24. Vapour pressure measurement for binary and ternary systems containing water methanol ethanol and an ionic liquid 1-ethyl-1-ethylimidazolium diethylphosphate / X.-C. Jiang [et al.] // Fluid Phase Equilibria. - 2007. - Vol. 39. - P. 841-846.
25. Wang, J. F. Measurement and Prediction of Vapor Pressure of Binary and Ternary Systems Containing 1-Ethyl-3-methylimidazolium Ethyl Sulfate / J. F. Wang, C. X. Li, Z. H. Wang // J. Chem. Eng. Data. - 2007. - Vol. 52, № 4. - P. 1307-1312.
26. Isobaric Vapor-Liquid Equilibria for 1-Propanol + Water + 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate at 100 kPa / A. V. Orhilles [et al.] // J. Chem. Eng. Data. - 2008. - Vol. 53, № 10. - P. 2426-431.
27. Liquid Phase Behavior of Imidazolium-Based Ionic Liquids with Alcohols / J.M. Crosthwaite [et al.] // J. Phys. Chem. B. - 2004. - Vol. 108, № 16. - P. 5113-5119.
28. Anthony, J. L. Solution Thermodynamics of Imidazolium-Based Ionic Liquids and Water / J. L. Anthony, E. J. Maginn, J. F. Brennecke // J. Phys. Chem. B. - 2001. - Vol. 105, № 44. - P. 1094-10949.
29. Domanska, U. Solubility of 1-alkyl-3-ethylimidazolium-Based Ionic Liquids in Water and 1-Octanol / U. Domanska, A. Rekawek, A. Marciniak // J. Chem. Eng. Data. - 2008. - Vol. 53, № 5. - P. 1126-1132.
30. Physicochemical properties and toxicities of hydrophobic piperidinium and pyrrolidinium ionic liquids / J. Salminen [et al.] // Fluid Phase Equilibria. - 2007. - Vol. 261. - P. 421-426.
31. Domanska, U. Phase behavior of 1-hexyloxymethyl-3-methyl-imidazolium and 1,3-dihexyloxymethyl-imidazolium based ionic liquids with alcohols, water, ketones and hydrocarbons: The effect of cation and anion on solubility / U. Domanska, A. Marciniak // Fluid Phase Equilibria. - 2007. - V. 260. - P. 9-18
32. Solubility of Water in Tetradecyltrihexylphosphonium-Based Ionic Liquids / M.G. Freire [et al.] // J. Chem. Eng. Data. - 2008. - Vol. 53, № 10. - P. 2378-2382.
33. Huo, Y. Solubility of Alcohols and Aromatic Compounds in Imidazolium-Based Ionic Liquids / Y. Huo, S. Xia, P. Ma // J. Chem. Eng. Data. - 2008. - Vol. 53, № 11. - P. 2535-2539.
34. Kato, R. Systems with ionic liquids: Measurements of VLE and γ∞ data and prediction of their thermodynamic behavior using original UNIFAC, mod. UNIFAC(Do) and COSMO-RS(Ol) / R. Kato, J. Gmehling // J. Chem. Thermodyn. - 2005. - Vol. 37. - P. 603-619.
35. Thermodynamic Properties of Mixtures Containing Ionic Liquids. 4. LLE of Binary Mixtures of [C2MIM][NTf2] with Propan-1-ol, butan-1-ol, and pentan-1ol and [C4MIM][NTf2] with Cyclohexanol, and1,2-Hexanediol Including Studies of the Influence of Small Amounts of Water / A. Heintz [et al.] // J. Chem. Eng. Data. - 2005. - Vol. 5, № 3. - P. 956-960.
36. Heintz, A. 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-1ol / A. Heintz, J. K. Lehmann, C. Wertz // J. Chem. Eng. Data. - 2003. - Vol. 48, № 3. - P. 472-474.
37. Liquid phase behavior of imidazolium-based ionic liquids with alcohols: effect of hydrogen bonding and non-polar interactions / J.M. Crosthwaite [et al.] // Fluid Phase Equilibria. - 2005. - Vol. 228-229. - P. 303-309.
38. Liquid-Liquid Equilibria in Mixtures of the Ionic Liquid 1-n-Butyl-3-methylimidazolium Hexafluorophosphate and an Alkanol / K. Sahandzhieva [et al.] // J. Chem. Eng. Data. - 2006. - Vol. 51, № 5. - P. 1516-1525.
39. Pereiro, A. B. Ternary (liquid-liquid) equilibria of the azeotrope (ethyl acetate + 2-propanol) with different ionic liquids at T = 298.15 K / A. B. Pereiro, A. Rodriguez // J. Chem. Thermodyn. - 2007. - Vol. 39. - P. 1608-1613.
40. Pereiro, A. B. Experimental Liquid-Liquid Equilibria of 1-Alkyl-3-methylimidazolium Hexafluorophosphate with 1-Alcohols / A. B. Pereiro, A. Rodriguez // J. Chem. Eng. Data. - 2007. - V. 52, № 4. - P. 1408-1412.
41. Pereiro, A. B. A study on the liquid-liquid equilibria 1-alkyl-3-methylimidazolium hexafluorophosphate with ethnol and alkanes / A. B. Pereiro, A. Rodriguez // Fluid Phase Equilibria. - 2008. - Vol. 270. - P. 23-29.
42. Pressure, Isotope, and Water Co-solvent Effects in Liquid-Liquid Equilibria of (Ionic Liquid + Alcohol) Systems / V. Najdanovic-Visak [et al.] // J. Phys. Chem. B. - 2003. - Vol. 107, № 46. - P. 12797-12807.
43. Domanska, U. Solubility of Ionic Liquid [emim][PF6] in Alcohols / U. Domanska, A. Marciniak // J. Phys. Chem. B. - 2004. - Vol. 108, № 7. - P. 2376-2382.
44. Ternary Liquid-Liquid Equilibria for mixtures of 1-Methyl-3-octylimidazolium Chloride + an Alcanol + an Alcane at 298.2 K and 1 bar / T.M. Letcher [et al.] // J. Chem. Eng. Data. - 2003. - Vol. 48, № 4. - P. 904-907.
45. Arce, A. Experimental Determination of Liquid-Liquid Equilibrium Using Ionic Liquids: tert-Amyl Ethyl Ether + Ethanol + 1-octyl-3-Methylimidazolium Cloride System at 298.15 K / A. Arce, O. Rodriguez, A. Soto // J. Chem. Eng. Data. - 2004. - Vol. 49, № 3. - P. 514-517.
46. Ionic Liquids as Entrainers in Extractive Distillation: Isobaric Vapor-Liquid Equilibria for Acetone + Methanol + 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate / A.V. Orchilles [et al.] // J. Chem. Eng. Data. - 2007. - Vol. 52, № 1. - P. 141-147.
47. Isobaric Vapor-Liquid Equilibria for Methyl Acetate + Methanol + 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate / A. V. Orchilles [et al.] // J. Chem. Eng. Data. - 2007. - Vol. 52, № 3. - P. 915-920.
48. Isobaric Vapor-Liquid Equilibria for Ethyl Acetate + Ethanol + 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate at 100 kPa / A. V. Orchilles [et al.] // J. Chem. Eng. Data. - 2007. - Vol. 52, № 6. - P. 2325-2330.
49. Isobaric Vapor-Liquid and Liquid-Liquid Equilibria for Chloroform + Ethanol + 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate at 100 kPa / A. V. Orchilles [et al.] // J. Chem. Eng. Data. - 2008. - Vol. 53, № 11. - P. 2642-2648.
50. Naydenov, D. Ternary Liquid-Liquid Equilibria for Systems Containing Alcohol or Acetic Acid + Ester + 1-Ethyl-3-methylimidazolium Hydrogen Sulfate at 313.2 K Using Headspace Gas Chromatography / D. Naydenov, H.-J. Bart // J. Chem. Eng. Data. - 2009. - Vol. 54, № 1. - P. 43-47.
51. Domanska, U. Liquid phase behavior of 1-hexyloxymethyl-3-methyl-imidazolium-based ionic liquids with hydrocarbons: The influence of anion / U. Domanska, A. Marciniak // J. Chem. Thermodyn. - 2005. - Vol. 37. - P. 577-585.
For citation:
Reshetov S.A., Frolkova A.K., Muzyka A.A. Influence of some structural characteristics of the ionic liquids on homogeneous and heterogeneous characteristics of their mixtures with water and alcohols. Fine Chemical Technologies. 2009;4(6):33-39. (In Russ.)
Views: 150
Email this article 