Influence of an oxygen functionalization on the physicochemical properties of ionic liquids: Density, viscosity, and carbon dioxide solubility as a function of temperature

Journal of Chemical and Engineering Data

Volumn 56, Issue 11, 2011, Pages 4194-4202

  Deng, Yun ^a,b   Husson, Pascale ^a   Delort, Anne Marie ^b   Besse Hoggan, Pascale ^b   Sancelme, Martine ^a   Costa Gomes, Margarida F ^a,b  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM CATIONS; ENTROPIC CONTRIBUTIONS; ESTER GROUPS; FUNCTIONALIZATIONS; HYDROXYL GROUPS; IN-MOLE-FRACTION; OXYGEN FUNCTIONAL GROUPS; OXYGEN GROUPS; PHYSICOCHEMICAL PROPERTY; PYRIDINIUM; PYRROLIDINIUM;

AMMONIUM COMPOUNDS; ATMOSPHERIC PRESSURE; CARBON DIOXIDE; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; IONIC LIQUIDS; OXYGEN; POSITIVE IONS; SOLUBILITY; VISCOSITY;

DENSITY OF LIQUIDS;

EID: 80955163972     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je2006743     Document Type: Article

References (50)

1. Pham, T. P. T.; Cho, C.-W.; Yun, Y.-S. Environmental Fate and Toxicity of Ionic Liquids: a Review Water Res. 2010, 44, 352-72
2. Wells, A. S.; Coombe, V. T. On the freshwater ecotoxicity and biodegradation properties of some common ionic liquids Org. Process Res. Dev. 2006, 10, 794-798 (Pubitemid 44196612)
3. Cho, C. W.; Pham, T. P. T.; Jeon, Y. C.; Vijayaraghavan, K.; Choe, W. S.; Yun, Y. S. Toxicity of imidazolium salt with anion bromide to a phytoplankton Selenastrum capricornutum: Effect of alkyl-chain length Chemosphere 2007, 69, 1003-1007 (Pubitemid 47410266)
4. Docherty, K. M.; Kulpa, C. F. Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids Green Chem. 2005, 7, 185-189 (Pubitemid 40592193)
5. Kulacki, K. J.; Lamberti, G. A. Toxicity of imidazolium ionic liquids to freshwater algae Green Chem. 2008, 10, 104-110
6. Latala, A.; Nedzi, M.; Stepnowski, P. Toxicity of imidazolium and pyridinium based ionic liquids towards algae. Chlorella vulgaris, Oocystis submarina (green algae) and Cyclotella meneghiniana, Skeletonema marinoi (diatoms) Green Chem. 2009, 11, 580-588
7. Pretti, C.; Chiappe, C.; Baldetti, I.; Brunini, S.; Monni, G.; Intorre, L. Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio Ecotoxicol. Environ. Safety 2009, 72, 1170-1176
8. Bernot, R. J.; Brueseke, M. A.; Evans-White, M. A.; Lamberti, G. A. Acute and chronic toxicity of imidazolium-based ionic liquids on Daphnia magna Environ. Toxicol. Chem. 2005, 24, 87-92 (Pubitemid 39658146)
9. Coleman, D.; Gathergood, N. Biodegradation Studies of Ionic Liquids Chem. Soc. Rev. 2010, 39, 600-637
10. Romero, A.; Santos, A.; Tojo, J.; Rodriguez, A. Toxicity and biodegradability of imidazolium ionic liquids J. Hazard. Mater. 2008, 151, 268-273
11. Stolte, S.; Abdulkarim, S.; Arning, J.; Blomeyer-Nienstedt, A. K.; Bottin-Weber, U.; Matzke, M.; Ranke, J.; Jastorff, B.; Thoming, J. Primary biodegradation of ionic liquid cations, identification of degradation products of 1-methyl-3-octylimidazolium chloride and electrochemical wastewater treatment of poorly biodegradable compounds Green Chem. 2008, 10, 214-224 (Pubitemid 351199055)
12. Docherty, K. M.; Dixon, J. K.; Kulpa, C. F. Biodegradability of imidazolium and pyridinium ionic liquids by an activated sludge microbial community Biodegradation 2007, 18, 481-493 (Pubitemid 47030027)
13. Himmler, S.; Hormann, S.; Hal, R. V.; Schulz, P. S.; Wasserscheid, P. Transesterification of Methylsulfate and Ethylsulfate Ionic Liquids-an Environmentally Benign Way to Synthesize Long-chain and Functionalized Alkylsulfate Ionic Liquids Green Chem. 2006, 8, 887-894 (Pubitemid 44527093)
14. Deng, Y.; Morrissey, S.; Gathergood, N.; Delort, A.-M.; Husson, P.; Costa Gomes, M. F. The Presence of Functional Groups Key for Biodegradation in Ionic Liquids: Effect on Gas Solubility ChemSusChem 2010, 3, 377-385
15. Muldoon, M. J.; Aki, S. N. V. K.; Anderson, J. L.; Dixon, J. K.; Brennecke, J. F. Improving Carbon Dioxide Solubility in Ionic Liquids J. Phys. Chem. B 2007, 111, 9001-9009 (Pubitemid 47317479)
16. Pensado, A.; Pádua, A. A. H.; Costa Gomes, M. F. Influence of Ester Functional Groups on the Liquid-Phase Structure and Solvation Properties of Imidazolium-Based Ionic Liquids J. Phys. Chem. B 2011, 115, 3942-3948
17. Beckman, E. J. A Challenge for Green Chemistry: Designing Molecules that Readily Dissolve in Carbon Dioxide Chem. Commun. 2004, 1885-1888 (Pubitemid 39335991)
18. Jacquemin, J.; Husson, P.; Pádua, A. A. H.; Majer, V. Density and Viscosity of Several Pure and Water-saturated Ionic Liquids Green Chem. 2006, 8, 172-180 (Pubitemid 43490361)
19. Anthony, J. L.; Anderson, J. L.; Maginn, E. J.; Brennecke, J. F. Anion Effects on Gas Solubility in Ionic Liquids J. Phys. Chem. B 2005, 109, 6366-6374
20. Almantariotis, D.; Gefflaut, T.; Pádua, A. A. H.; Coxam, J.-Y.; Costa Gomes, M. F. Effect of Fluorination and Size of the Alkyl Side-Chain on the Solubility of Carbon Dioxide in 1-Alkyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)amide Ionic Liquids J. Phys. Chem. B 2010, 114, 3608-3617
21. Davila, M. A. J.; Aparicio, S.; Alcalde, R.; García, B.; Leal, J. M. On the Properties of 1-butyl-3-methylimidazolium Octylsulfate Ionic Liquid Green Chem. 2007, 9, 221-232
22. Fandino, O.; Pensado, A. S.; Lugo, L.; Comunas, M. J. P.; Fernandez, J. J. Chem. Eng. Data 2005, 50, 939-946
23. 2] and a Molecular Component J. Phys. Chem. B 2011, 115, 6088-6099
24. Jacquemin, J.; Costa Gomes, M. F.; Husson, P.; Majer, V. Solubility of Carbon Dioxide, Ethane, Methane, Oxygen, Nitrogen, Hydrogen, Argon, and Carbon Monoxide in 1-butyl-3-methylimidazolium tetrafluoroborate between Temperatures 283 and 343 K and at Pressures Close to Atmospheric J. Chem. Thermodyn. 2006, 38, 490-502
25. 2 in Ionic Liquids Based on the Bis(trifluoromethylsulfonyl)imide Anion J. Solution Chem. 2007, 36, 967-979
26. Kilaru, P.; Baker, G. A.; Scovazzo, P. Density and Surface Tension Measurements of Imidazolium-, Quaternary Phosphonium-, and Ammonium-Based Room-Temperature Ionic Liquids: Data and Correlations J. Chem. Eng. Data 2007, 52, 2306-2314 (Pubitemid 350229769)
27. Tokuda, H.; Ishii, K.; Susan, M.; Tsuzuki, S.; Hayamizu, K.; Watanabe, M. Physicochemical Properties and Structures of Room-temperature Ionic Liquids. 3. Variation of Cationic Structures J. Phys. Chem. B 2006, 110, 2833-2839 (Pubitemid 43342878)
28. Kato, R.; Gmehling, J. Systems with ionic liquids: Measurement of VLE and gamma(infinity) data and prediction of their thermodynamic behavior using original UNIFAC, mod. UNIFAC(Do) and COSMO-RS(O1) J. Chem. Thermodyn. 2005, 37, 603-619
29. 2N] J. Chem. Eng. Data 2010, 55, 165-172
30. Hong, G.; Jacquemin, J.; Deetlefs, M.; Hardacre, C.; Husson, P.; Costa Gomes, M. F. Solubility of Carbon Dioxide and Ethane in Three Ionic Liquids Based on the Bis {(trifluoromethyl)sulfonyl}imide Anion Fluid Phase Equilib. 2007, 257, 27-37
31. Jacquemin, J.; Ge, R.; Nancarrow, P.; Rooney, D. W.; Costa Gomes, M. F.; Pádua, A. A. H.; Hardacre, C. Prediction of Ionic Liquid Properties. I. Volumetric Properties as a Function of Temperature at 0.1 MPa J. Chem. Eng. Data 2008, 53, 716-726
32. Jacquemin, J.; Nancarrow, P.; Rooney, D. W.; Costa Gomes, M. F.; Husson, P.; Majer, V.; Pádua, A. A. H.; Hardacre, C. Prediction of Ionic Liquid Properties. II. Volumetric Properties as a Function of Temperature and Pressure J. Chem. Eng. Data 2008, 53, 2133-2143
33. Canongia Lopes, J. N.; Cordeiro, T. C.; Esperança, J. M. S. S.; Guedes, H. J. R.; Huq, S.; Rebelo, L. P. N.; Seddon, K. R. Deviations from Ideality in Mixtures of Two Ionic Liquids Containing a Common Ion J. Phys. Chem. B 2005, 109, 3519-3525 (Pubitemid 40352321)
34. Okoturo, O. O.; VanderNoot, T. J. Temperature Dependence of Viscosity for Room Temperature Ionic Liquids J. Electroanal. Chem. 2004, 568, 167-181
35. Pereiro, A. B.; Veiga, H. I. M.; Esperança, J. M. S. S.; Rodriguez, A. Effect of temperature on the physical properties of two ionic liquids J. Chem. Thermodyn. 2009, 41, 1419-1423
36. Tokuda, H.; Tsuzuki, S.; Hasan Susan, A. B.; Hayamizu, K.; Watanabe, M. How Ionic Are Room-Temperature Ionic Liquids? An Indicator of the Physicochemical Properties J. Phys. Chem. B 2006, 110, 19593-19600 (Pubitemid 44626443)
37. Branco, L. C.; Rosa, J. N.; Ramos, J. J. M.; Afonso, C. A. M. Preparation and Characterization of New Room Temperature Ionic Liquids Chem.-Eur. J. 2002, 8, 3671-3677 (Pubitemid 34951455)
38. Crosthwaite, J. M.; Muldoon, M. J.; Dixon, J. K.; Anderson, J. L.; Brennecke, J. F. Phase Transition and Decomposition Temperatures, Heat Capacities and Viscosities of Pyridinium Ionic Liquids J. Chem. Thermodyn. 2005, 37, 559-568 (Pubitemid 40750633)
39. Olivier-Bourbigou, H.; Magna, L.; Morvan, D. Ionic Liquids and Catalysis: Recent Progress from Knowledge to Applications Appl. Catal. A: Gen. 2010, 373, 1-56
40. Kanakubo, M.; Nanjo, H.; Nishida, T.; Takano, J. Density, viscosity, and electrical conductivity of N-methoxymethyl-N-methylpyrrolidinium bis(trifluoromethanesulfonyl)- amide Fluid Phase Equilib. 2011, 302, 10-13
41. Liu, K.; Zhou, Y. X.; Han, H. B.; Zhou, S. S.; Feng, W. F.; Nie, J.; Li, H.; Huang, X. J.; Armand, M.; Zhou, Z. B. Ionic Liquids Based on (Fluorosulfonyl)- (pentafluoroethanesulfonyl)imide with Various Oniums Electrochim. Acta 2010, 55, 7145-7151
42. MacFarlane, D. R.; Meakin, P.; Sun, J.; Amini, N.; Forsyth, M. Pyrrolidinium Imides A New Family of Molten Salts and Conductive Plastic Crystal Phases J. Phys. Chem. B 1999, 103, 4164-4170 (Pubitemid 129702544)
43. Dymond, J. H.; Smith, E. B. The Virial Coefficients of Pure Gases, Mixtures; Clarendon Press: Oxford, 1980.
44. Kilaru, P. K.; Condemarin, R. A.; Scovazzo, P. Correlations of low-pressure carbon dioxide and hydrocarbon solubilities in imidazolium-, phosphonium-, and ammonium-based room-temperature ionic liquids. Part 1. Using Surface Tension Ind. Eng. Chem. Res. 2008, 47, 900-909 (Pubitemid 351269533)
45. Costa Gomes, M. F. Low-Pressure Solubility and Thermodynamics of Solvation of Carbon Dioxide, Ethane, and Hydrogen in 1-Hexyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)-amide between Temperatures of 283 and 343 K J. Chem. Eng. Data 2007, 52, 472-475
46. 2 in Room-Temperature Ionic Liquids Using a Transient Thin-Liquid-Film Method Ind. Eng. Chem. Res. 2007, 46, 8166-8175 (Pubitemid 350208026)
47. 2 in 1-Hexyl-3-methylpyridinium Bis(trifluoromethylsulfonyl)imide: Comparison to Other Ionic Liquids Acc. Chem. Res. 2007, 40, 1208-1216
48. 2 in the Ionic Liquid 1-(2-Hydroxyethyl)-3-methylimidazolium Tetrafluoroborate J. Chem. Eng. Data 2010, 55, 1663-1668
49. 2 in 1-(2-hydroxyethyl)-3-methylimidazolium Ionic Liquids with Different Anions J. Chem. Thermodyn. 2010, 42, 787-791
50. Mazille, F.; Fei, Z.; Kuang, D.; Zhao, D.; Zakeeruddin, S. M.; Gratzel, M.; Dyson, P. J. Influence of Ionic Liquids Bearing Functional Groups in Dye-Sensitized Solar Cells Inorg. Chem. 2006, 45, 1585-1590