Molecular interactions in 1-butanol + IL solutions by measuring and modeling activity coefficients

Journal of Physical Chemistry B

Volumn 117, Issue 11, 2013, Pages 3173-3185

  Nann, Alexander ^a   Mündges, Jan ^a   Held, Christoph ^a   Verevkin, Sergey P ^b   Sadowski, Gabriele ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BINARY MIXTURES; GAS CHROMATOGRAPHY; IONIC LIQUIDS; MOLECULAR INTERACTIONS; MOLECULAR STRUCTURE;

1-BUTANOL; BINARY SOLUTIONS; CONCENTRATION RANGES; EXPERIMENTAL DATUM; GAS-LIQUID CHROMATOGRAPHY; OSMOMETRY; PC-SAFT; PERTURBED-CHAIN STATISTICAL ASSOCIATING FLUID THEORIES;

ACTIVITY COEFFICIENTS;

EID: 84875436778     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp307276y     Document Type: Article

References (53)

1. Brennecke, J. F.; Maginn, E. J. Ionic Liquids: Innovative Fluids for Chemical Processing AIChE J. 2001, 47 (11) 2384-2389
2. Seddon, K. R. Ionic Liquids: A Taste of the Future Nat. Mater. 2003, 2 (6) 363-365
3. Fredlake, C. P.; 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 (4) 954-964
4. Roosen, C.; Mueller, P.; Greiner, L. Ionic Liquids in Biotechnology: Applications and Perspectives for Biotransformations Appl. Microbiol. Biotechnol. 2008, 81 (4) 607-614
5. Oppermann, S.; Stein, F.; Kragl, U. Ionic Liquids for Two-phase Systems and Their Application for Purification, Extraction and Biocatalysis Appl. Microbiol. Biotechnol. 2011, 89 (3) 493-499
6. Armand, M.; Endres, F.; MacFarlane, D. R.; Ohno, H.; Scrosati, B. Ionic-liquid Materials for the Electrochemical Challenges of the Future Nat. Mater. 2009, 8 (8) 621-629
7. Plechkova, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry Chem. Soc. Rev. 2008, 37 (1) 123-150
8. Fadeev, A. G.; Meagher, M. M. Opportunities for Ionic Liquids in Recovery of Biofuels Chem. Commun. 2001, 3, 295-296
9. Han, X.; Armstrong, D. W. Ionic Liquids in Separations Acc. Chem. Res. 2007, 40 (11) 1079-1086
10. Poole, C. F.; Poole, S. K. Extraction of Organic Compounds with Room Temperature Ionic Liquids J. Chromatogr., A 2009, 1217 (16) 2268-2286
11. Heintz, A. Recent Developments in Thermodynamics and Thermophysics of Non-Aqueous Mixtures Containing Ionic Liquids. A Review J. Chem. Thermodyn. 2005, 37 (6) 525-535
12. Calvar, N.; Gonzalez, B.; Dominguez, A.; Macedo, E. A. Osmotic Coefficients of Binary Mixtures of Four Ionic Liquids with Ethanol or Water at T = (313.15 and 333.15) K J. Chem. Thermodyn. 2009, 41 (1) 11-16
13. Calvar, N.; Gonzalez, B.; Dominguez, A.; Macedo, E. A. Osmotic Coefficients of Binary Mixtures of 1-Butyl-3-methylimidazolium Methylsulfate and 1,3-Dimethylimidazolium Methylsulfate with Alcohols at T=323.15 K J. Chem. Thermodyn. 2009, 41 (5) 617-622
14. Calvar, N.; Gomez, E.; Dominguez, A.; Macedo, E. A. Vapour Pressures, Osmotic and Activity Coefficients for Binary Mixtures Containing (1-Ethylpyridinium Ethylsulfate plus Several Alcohols) at T=323.15 K J. Chem. Thermodyn. 2010, 42, 625-630
15. Calvar, N.; Gonzalez, B.; Dominguez, A.; Macedo, E. A. Vapour Pressures and Osmotic Coefficients of Binary Mixtures of 1-Ethyl-3-methylimidazolium Ethylsulfate and 1-Ethyl-3-methylpyridinium Ethylsulfate with Alcohols at T=323.15 K J. Chem. Thermodyn. 2009, 41 (12) 1439-1445
16. Calvar, N.; Gómez, E.; Domínguez, Á.; Macedo, E. A. Determination and Modelling of Osmotic Coefficients and Vapour Pressures of Binary Systems 1-and 2-Propanol with CnMimNTf2 Ionic Liquids (n = 2, 3, and 4) at T = 323.15 K J. Chem. Thermodyn. 2011, 43 (8) 1256-1262
17. Gomez, E.; Calvar, N.; Dominguez, A.; Macedo, E. A. Measurement and Modeling of Osmotic Coefficients of Binary Mixtures (Alcohol+1,3- Dimethylpyridinium Methylsulfate) at T=323.15 K J. Chem. Thermodyn. 2011, 43, 908-913
18. Shekaari, H.; Zafarani-Moattar, M. T. Osmotic Coefficients of some Imidazolium Based Ionic Liquids in Water and Acetonitrile at Temperature 318.15 K Fluid Phase Equilib. 2007, 254 (1-2) 198-203
19. Shekaari, H.; Mousavi, S. S. Measurement and Modeling of Osmotic Coefficients of Aqueous Solution of Ionic Liquids Using Vapor Pressure Osmometry Method Fluid Phase Equilib. 2009, 279 (1) 73-79
20. Shekaari, H.; Mousavi, S. S.; Mansoori, Y. Thermophysical Properties of Ionic Liquid, 1-Pentyl-3-methylimidazolium Chloride in Water at Different Temperatures Int. J. Thermophys. 2009, 30 (2) 499-514
21. Shekaari, H.; Armanfar, E. Physical Properties of Aqueous Solutions of Ionic Liquid, 1-Propyl-3-methylimidazolium Methyl Sulfate, at T = (298.15 to 328.15) K J. Chem. Eng. Data 2010, 55 (2) 765-772
22. Gardas, R. L.; Dagade, D. H.; Coutinho, J. A. P.; Patil, K. J. Thermodynamic Studies of Ionic Interactions in Aqueous Solutions of Imidazolium-based Ionic Liquids [Emim][Br] and [Bmim][Cl] J. Phys. Chem. B 2008, 112 (11) 3380-3389
23. Sadr, M. H.; Sardroodi, J. J. Vapor Pressures and Osmotic Coefficients of the Acetone Solutions of Three Bis(tetraalkylammonium)tetrathiomolybdates at 298.15 K Measured by Head-Space Gas chromatography Fluid Phase Equilib. 2006, 250 (1-2) 53-58
24. Solie, T. N.; Hirs, C. H. W.; Timasheff, S. N. Vapor Pressure Osmometry. In Methods in Enzymology; Academic Press: New York, 1972; Vol. 26, pp 50-73.
25. Kim, H.-D.; Hwang, I.-C.; Park, S.-J. Isothermal Vapor-Liquid Equilibrium Data at T = 333.15 K and Excess Molar Volumes and Refractive Indices at T = 298.15 K for the Dimethyl Carbonate + Methanol and Isopropanol + Water with Ionic Liquids J. Chem. Eng. Data 2010, 55 (7) 2474-2481
26. Heintz, A.; Kulikov, D. V.; Verevkin, S. P. Thermodynamic Properties of Mixtures Containing Ionic Liquids. 1. Activity coefficients at Infinite Dilution of Alkanes, Alkenes, and Alkylbenzenes in 4-Methyl-n-butylpyridinium Tetrafluoroborate Using Gas-Liquid Chromatography J. Chem. Eng. Data 2001, 46 (6) 1526-1529
27. Heintz, A.; Kulikov, D. V.; Verevkin, S. P. Thermodynamic Properties of Mixtures Containing Ionic Liquids. 2. Activity Coefficients at Infinite Dilution of Hydrocarbons and Polar Solutes in 1-Methyl-3-ethyl-imidazolium Bis(trifluoromethyl-sulfonyl) Amide and in 1,2-Dimethyl-3-ethyl-imidazolium Bis(trifluoromethyl-sulfonyl) Amide Using Gas-Liquid Chromatography J. Chem. Eng. Data 2002, 47 (4) 894-899
28. Shimizu, K.; Tariq, M.; Gomes, M. F. C.; Rebelo, L. P. N.; Lopes, J. N. C. Assessing the Dispersive and Electrostatic Components of the Cohesive Energy of Ionic Liquids Using Molecular Dynamics Simulations and Molar Refraction Data J. Phys. Chem. B 2010, 114 (17) 5831-5834
29. Koddermann, T.; Wertz, C.; Heintz, A.; Ludwig, R. Ion-pair Formation in the Ionic Liquid 1-Ethyl-3-methylimidazolium Bis(triflyl)imide as a Function of Temperature and Concentration ChemPhysChem 2006, 7 (9) 1944-1949
30. Dorbritz, S.; Ruth, W.; Kragl, U. Investigation on Aggregate Formation of Ionic Liquids Adv. Synth. Catal. 2005, 347 (9) 1273-1279
31. Vega, L. F.; Vilaseca, O.; Llovell, F.; Andreu, J. S. Modeling Ionic Liquids and the Solubility of Gases in Them: Recent Advances and Perspectives Fluid Phase Equilib. 2010, 294 (1-2) 15-30
32. Paduszyński, K.; Domańska, U. Solubility of Aliphatic Hydrocarbons in Piperidinium Ionic Liquids: Measurements and Modeling in Terms of Perturbed-Chain Statistical Associating Fluid Theory and Nonrandom Hydrogen-Bonding Theory J. Phys. Chem. B 2011, 115 (43) 12537-12548
33. Gross, J.; Sadowski, G. Perturbed-Chain SAFT: An Equation of State Based on a Perturbation Theory for Chain Molecules Ind. Eng. Chem. Res. 2001, 40 (4) 1244-1260
34. Gross, J.; Sadowski, G. Application of the Perturbed-chain SAFT Equation of State to Associating Systems Ind. Eng. Chem. Res. 2002, 41 (22) 5510-5515
35. Curras, M. R.; Vijande, J.; Pineiro, M. M.; Lugo, L.; Salgado, J.; Garcia, J. Behavior of the Environmentally Compatible Absorbent 1-Butyl-3-methylimidazolium Tetrafluoroborate with 2,2,2-Trifluoroethanol: Experimental Densities at High Pressures and Modeling of PVT and Phase Equilibria Behavior with PC-SAFT EoS Ind. Eng. Chem. Res. 2011, 50 (7) 4065-4076
36. Ji, X.; Held, C.; Sadowski, G. Modeling Imidazolium-Based Ionic Liquids with ePC-SAFT Fluid Phase Equilib. 2012, 335 (0) 64-73
37. Paduszyński, K.; Chiyen, J.; Ramjugernath, D.; Letcher, T. M.; Domańska, U. Liquid-Liquid Phase Equilibrium of (Piperidinium-based Ionic Liquid + an Alcohol) Binary Systems and Modelling with NRHB and PCP-SAFT Fluid Phase Equilib. 2011, 305 (1) 43-52
38. Wagner, W.; Pruss, A. The IAPWS Formulation 1995 for the Thermodynamic Properties of Ordinary Water Substance for General and Scientific Use J. Phys. Chem. Ref. Data 2002, 31 (2) 387-535
39. Nasirzadeh, K.; Papaiconomou, N.; Neueder, R.; Kunz, W. Vapor Pressures, Osmotic and Activity coefficients of Electrolytes in Protic Solvents at Different Temperatures. 1. Lithium Bromide in Methanol J. Solution Chem. 2004, 33 (3) 227-245
40. Everett, D. H. Effect of Gas Imperfection on Glc Measurements-A Refined Method for Determining Activity Coefficients and 2 Virial Coefficients Trans. Faraday Soc. 1965, 61, 1637-1645
41. Cruickshank, A. J. B.; Windsor, M. L.; Young, C. L. The Use of Gas-Liquid Chromatography to Determine Activity Coefficients and Second Virial Coefficients of Mixtures. I. Theory and Verification of Method of Data Analysis Proc. R. Soc. London, Ser. A 1966, 295, 259-270
42. Grant, D. W. Gas-Liquid Chromatography; Van Nostrand Reinhold Co: London, NY, 1971.
43. Tsonopoulos, C. Empirical Correlation of Second Virial-Coefficients AIChE J. 1974, 20, 263-272
44. Poling, B. E.; Prausnitz, J. M.; O'Connell, J. P. The Properties of Gases and Liquids; McGraw-Hill: New York, 2001.
45. Kemme, H. R.; Kreps, S. I. Vapor Pressure of Primary n-Alkyl Chlorides and Alcohols J. Chem. Eng. Data 1969, 14 (1) 98-102
46. Wolbach, J. P.; Sandler, S. I. Using Molecular Orbital Calculations to Describe the Phase Behavior of Cross-associating Mixtures Ind. Eng. Chem. Res. 1998, 37 (8) 2917-2928
47. Held, C.; Neuhaus, T.; Sadowski, G. Compatible Solutes: Thermodynamic Properties and Biological Impact of Ectoines and Prolines Biophys. Chem. 2010, 152 (1-3) 28-39
48. Domańska, U.; Marciniak, A. Physicochemical Properties and Activity Coefficients at Infinite Dilution for Organic Solutes and Water in the Ionic Liquid 1-Decyl-3-methylimidazolium Tetracyanoborate J. Phys. Chem. B 2010, 114 (49) 16542-16547
49. Luckas, M.; Krissmann, J. Thermodynamik der Elektrolytlösungen: Eine Einheitliche Darstellung der Berechnung Komplexer Gleichgewichte; Springer: Berlin, 2001.
50. Heintz, A.; Verevkin, S. P.; Lehmann, J. K.; Vasiltsova, T. V.; Ondo, D. Activity Coefficients at Infinite Dilution and Enthalpies of Solution of Methanol, 1-Butanol, and 1-Hexanol in 1-Hexyl-3-methyl-imidazolium Bis(trifluoromethyl-sulfonyl) Imide J. Chem. Thermodyn. 2007, 39 (2) 268-274
51. Reschke, T.; Naeem, S.; Sadowski, G. Osmotic Coefficients of Aqueous Weak Electrolyte Solutions: Influence of Dissociation on Data Reduction and Modeling J. Phys. Chem. B 2012, 116 (25) 7479-7491
52. Nasirzadeh, K.; Neueder, R.; Kunz, W. Vapor Pressures, Osmotic and Activity Coefficients of Electrolytes in Protic Solvents at Different Temperatures. 3. Lithium Bromide in 2-Propanol J. Solution Chem. 2005, 34 (1) 9-24
53. Tsioptsias, C.; Tsivintzelis, I.; Panayiotou, C. Equation-of-State Modeling of Mixtures with Ionic Liquids Phys. Chem. Chem. Phys. 2010, 12 (18) 4843-4851