Measurements and correlation of high-pressure densities of phosphonium based ionic liquids

Journal of Chemical and Engineering Data

Volumn 56, Issue 5, 2011, Pages 2205-2217

  Tomé, Luciana I N ^a   Gardas, Ramesh L ^b   Carvalho, Pedro J ^a   Pastoriza Gallego, Maria José ^c   Piñeiro, Manuel M ^c   Coutinho, João A P ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

^c UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CELL MODEL; DENSITY MEASUREMENTS; DICYANAMIDE; EQUATION OF STATE; ISOBARIC EXPANSIVITY; ISOTHERMAL COMPRESSIBILITY; PREDICTIVE METHODS; PRESSURE RANGES; RELATIVE DEVIATIONS; SANCHEZ-LACOMBE; TAIT EQUATION; TEMPERATURE RANGE; THERMAL PRESSURE COEFFICIENT;

BROMINE COMPOUNDS; CHLORINE COMPOUNDS; COMPRESSIBILITY OF LIQUIDS; DENSITY OF LIQUIDS; EQUATIONS OF STATE; HIGH PRESSURE EFFECTS; IONS;

IONIC LIQUIDS;

EID: 79956138214     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je101232g     Document Type: Article

References (69)

1. Marsh, K. N.; Boxall, J. A.; Lichtenthaler, R. Room temperature ionic liquids and their mixtures-a review Fluid Phase Equilib. 2004, 219, 93-98 (Pubitemid 38507666)
2. Pletchkova, N. V.; Seddon, K. R. Applications of ionic liquids in the chemical industry Chem. Soc. Rev. 2008, 37, 123-150
3. Joglekar, H. G.; Rahman, I.; Kulkarni, B. D. The path ahead for ionic liquids Chem. Eng. Technol. 2007, 30, 819-828 (Pubitemid 47104075)
4. Zhao, H. Innovative applications of ionic liquids as 'green' engineering liquids Chem. Eng. Commun. 2006, 193, 1660-1677 (Pubitemid 44264054)
5. Freemantle, M. New frontiers for ionic liquids Chem. Eng. News 2007, 85, 23-26 (Pubitemid 46102324)
6. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room temperature ionic liquids as novel media for clean liquid-liquid extraction Chem. Commun. 1998, 1765, 1765-1766 (Pubitemid 128675787)
7. Poole, C. F.; Poole, S. K. Extraction of organic compounds with room temperature ionic liquids J. Chromatogr. A 2010, 1217, 2268-2286
8. Zhao, H.; Xia, S.; Ma, P. Use of ionic liquids as 'green' solvents for extractions J. Chem. Technol. Biotechnol. 2005, 80, 1089-1096 (Pubitemid 41419384)
9. Wang, J.; Pei, Y.; Zhao, Y.; Hu, Z. Recovery of amino acids by imidazolium-based ionic liquids from aqueous media Green Chem. 2005, 7, 196-202 (Pubitemid 40592195)
10. Tomé, L. I. N.; Catambas, V. R.; Teles, A. R. R.; Freire, M. G.; Marrucho, I. M.; Coutinho, J. A. P. Tryptophan extraction using hydrophobic ionic liquids Sep. Purif. Technol. 2010, 72, 167-173
11. Domínguez-Pérez, M.; Tomé, L. I. N.; Freire, M. G.; Marrucho, I. M.; Cabeza, O.; Coutinho, J. A. P. (Extraction of biomolecules using) aqueous biphasic systems formed by ionic liquids and amino acids Sep. Purif. Technol. 2010, 72, 85-91
12. Louros, C. L. S.; Cláudio, A. F. M.; Neves, C. M. S. S.; Freire, M. G.; Marrucho, I. M.; Pauly, J.; Coutinho, J. A. P. Extraction of biomolecules using phosphonium-based ionic liquids+K3PO4 aqueous biphasic systems Int. J. Mol. Sci. 2010, 11, 1777-1791
13. Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Chemical and biochemical transformations in ionic liquids Tetrahedron 2005, 61, 1015-1060 (Pubitemid 40126710)
14. Welton, T. Room temperature ionic liquids. Solvents for synthesis and catalysis Chem. Rev. 1999, 99, 2071-2083 (Pubitemid 129585179)
15. Kragel, U.; Eckstein, M.; Kaftzik, N. Enzyme catalysis in ionic liquids Curr. Opin. Biotechnol. 2002, 13, 565-571 (Pubitemid 35448057)
16. Zhao, H.; Luo, R. G.; Malhotra, S. V. Kinetic study on the enzymatic resolution of homophenylalanine ester using ionic liquids Biotechnol. Prog. 2003, 19, 1016-1018 (Pubitemid 36715151)
17. Vaher, M.; Borissova, M.; Koel, M.; Kaljurand, M. Ionic liquids as background electrolyte additives and coating materials in capillary electrophoresis Proc. Estonian Acad. Sci. Chem. 2007, 56, 187-198
18. Zhao, H.; Malhotra, S. V. Applications of ionic liquids in organic synthesis Aldrichim. Acta 2002, 35, 75-83 (Pubitemid 36232714)
19. Branco, L. C.; Crespo, J. G.; Afonso, C. A. M. Studies on the selective transport of organic compounds by using ionic liquids as novel supported liquid membranes Chem.-Eur. J. 2002, 8, 3865-3871 (Pubitemid 35024132)
20. Scovazzo, P.; Kieft, J.; Finan, D. A.; Koval, C.; DuBois, D.; Noble, R. Gas separations using non-hexafluorophosphate [PF6]- anion supported ionic liquid membranes J. Membr. Sci. 2004, 238, 57-63 (Pubitemid 38739498)
21. Buzzeo, M. C.; Evans, R. G.; Compton, R. G. Non-haloaluminate room temperature ionic liquids in electrochemistry-a review Chem. Phys. Chem. 2004, 5, 1106-1120
22. Gan, Q.; Rooney, D.; Xue, M.; Thompson, G.; Zou, Y. An experimental study of gas transport and separation properties of ionic liquids supported on nano filtration membranes J. Membr. Sci. 2006, 280, 948-956
23. 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, 954-964
24. Zhang, S.; Sun, N.; He, X.; Lu, X.; Zhang, X. Physical properties of ionic liquids: database and evaluation J. Phys. Chem. Ref. Data 2006, 35, 1475-1517 (Pubitemid 44920183)
25. http://ilthermo.boulder.nist.gov/ILThermo/mainmenu.uix.
26. Azevedo, R. G.; Esperança, J. M. S. S.; Najdanovic-Visak, V.; Visak, Z. P.; Guedes, H. J. R.; Nunes da Ponte, M.; Rebelo, L. P. N. Thermophysical and thermodynamic properties of 1-butyl-3-methylimidazolium tetrafluoroborate and 1-butyl-3-methylimidazoliumhexafluorophosphate over an extended pressure range J. Chem. Eng. Data 2005, 50, 997-1088
27. Azevedo, R. G.; Esperança, J. M. S. S.; Szydlowski, J.; Visak, Z. P.; Pires, P. F.; Guedes, H. J. R.; Rebelo, L. P. N. Thermophysical and thermodynamic properties of ionic liquids over an extended pressure range: [bmim][NTf2] and [hmim][NTf2] J. Chem. Thermodyn. 2005, 37, 888-899 (Pubitemid 41013996)
28. Esperança, J. M. S. S.; Guedes, H. J. R.; Blesic, M.; Rebelo, L. P. N. Densities and derived thermodynamic properties of ionic liquids. 3. Phosphonium-based ionic liquids over an extended pressure range J. Chem. Eng. Data 2006, 51, 237-242 (Pubitemid 43151895)
29. Esperança, J. M. S. S.; Visak, Z. P.; Pletchkova, N. V.; Seddon, K. R.; Guedes, H. J. R.; Rebelo, L. P. N. Densities and derived thermodynamic properties of ionic liquids. 3. [C3mim][NTf2] and [C5mim][NTf2] J. Chem. Eng. Data 2006, 51, 2009-2015
30. Pereiro, A. B.; Verdia, P.; Tojo, E.; Rodriguez, A. Physical properties of 1-butyl-3-methylimidazolium methyl sulfate as a function of temperature J. Chem. Eng. Data 2007, 52, 377-380 (Pubitemid 46480674)
31. Gardas, R. L.; Freire, M. G.; Carvalho, P. J.; Marrucho, I. M.; Fonseca, I. M. A.; Ferreira, A. G. M.; Coutinho, J. A. P. High-pressure densities and derived thermodynamic properties of imidazolium-based ionic liquids J. Chem. Eng. Data 2007, 52, 80-88
32. Gardas, R. L.; Freire, M. G.; Carvalho, P. J.; Marrucho, I. M.; Fonseca, I. M. A.; Ferreira, A. G. M.; Coutinho, J. A. P. PρT measurements of imidazolium-based ionic liquids J. Chem. Eng. Data 2007, 52, 1881-1888
33. Tomé, L. I. N.; Carvalho, P. J.; Freire, M. G.; Marrucho, I. M.; Fonseca, I. M. A.; Ferreira, A. G. M.; Coutinho, J. A. P.; Gardas, R. L. Measurements and correlation of high-pressure densities of imidazolium-based ionic liquids J. Chem. Eng. Data 2008, 53, 1914-1921
34. Gardas, R. L.; Costa, H. F.; Freire, M. G.; Carvalho, P. J.; Marrucho, I. M.; Fonseca, I. M. A.; Ferreira, A. G. M.; Coutinho, J. A. P. Densities and derived thermodynamic properties of imidazolium-, pyridinium-, pyrrolidinium- and piperidinium-based ionic liquids J. Chem. Eng. Data 2008, 53, 805-811
35. Gu, Z.; Brennecke, J. F. Volume expansivities and isothermal compressibilities of imidazolium and pyridinium-based ionic liquids J. Chem. Eng. Data 2002, 47, 339-345 (Pubitemid 34255049)
36. Harris, K. R.; Woolf, L. A.; Kanakubo, M. Temperature and pressure dependence of the viscosity of the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate J. Chem. Eng. Data 2005, 50, 1777-1782 (Pubitemid 41381071)
37. Harris, K. R.; Kanakubo, M.; Woolf, L. A. Temperature and pressure dependence of the viscosity of the ionic liquids 1-methyl-3-octylimidazolium hexafluorophosphate and 1-methyl-3-octylimidazolium tetrafluoroborate J. Chem. Eng. Data 2006, 51, 1161-1167 (Pubitemid 43798552)
38. Paulechka, Y. U.; Kabo, G. J.; Blokhin, A. V.; Shaplov, A. S.; Lozinskaya, E. I.; Vygodskii, Y. S. Thermodynamic properties of 1-alkyl-3-methylimidazolium bromide ionic liquids J. Chem. Thermodyn. 2007, 39, 158-166 (Pubitemid 46123150)
39. Papaiconomou, N.; Salminen, J.; Lee, J.-M.; Prausnitz, J. M. Physicochemical properties of hydrophobic ionic liquids containing 1-octylpyridinium, 1-octyl-2-methylpyridinium or 1-octyl-4-methylpyridinium cations J. Chem. Eng. Data 2007, 52, 833-840 (Pubitemid 46848236)
40. Castro, C. A. N.; Langa, E.; Morais, A. L.; Lopes, M. L. M.; Lourenço, M. J. V.; Santos, F. J. V.; Santos, M. S. C. S.; Canongia Lopes, J. N.; Veiga, H. I. M.; Macatrão, M.; Esperança, J. M. S. S.; Marques, C. S.; Rebelo, L. P. N.; Afeonso, C. A. M. Studies on the density, heat capacity, surface tension and infinite dilution diffusion with the ionic liquids [C4mim][NTf2], [C4mim][dca], [C2mim][EtOSO3] and [Aliquat][dca] Fluid Phase Equilib. 2010, 294, 157-179
41. Sesto, R. E. D.; Corley, C.; Robertson, A. J.; Wilkes, J. S. Tetraalkylphosphonium-based ionic liquids J. Org. Chem. 2005, 690, 2536-2542 (Pubitemid 40597291)
42. Bradaric, C. J.; Downard, A.; Kennedy, C.; Robertson, A. J.; Zhou, Y. H. Industrial preparation of phosphonium ionic liquids Green Chem. 2003, 5, 143-152 (Pubitemid 37487470)
43. Atefi, F.; Garcia, M. T.; Singer, R. D.; Scammels, P. J. Phosphonium ionic liquids: design, synthesis and evaluation of biodegrability Green Chem. 2009, 11, 1595-1604
44. Marták, J.; Schlosser, S. Extraction of lactic acid by phosphonium ionic liquids Sep. Purif. Technol. 2007, 57, 483-494 (Pubitemid 47489824)
45. Carvalho, P. J.; Regueira, T.; Santos, L. M. N. B. F.; Fernandez, J.; Coutinho, J. A. P. Effect of water on the viscosities and densities of 1-butyl-3-methylimidazolium dicyanamide and 1-butyl-3-methylimidazolium tricyanomethane at atmospheric pressure J. Chem. Eng. Data 2010, 55, 645-652
46. Carvalho, P. J.; Álvarez, V. H.; Marrucho, I. M.; Aznar, M.; Coutinho, J. A. P. High carbon dioxide solubilities in trihexyltetradecylphosphonium-based ionic liquids Supercrit. Fluids 2010, 52, 258-265
47. Carvalho, P. J.; Coutinho, J. A. P. On the nonideality of CO2 solutions in ionic liquids and other low volatile solvents J. Phys. Chem. Lett. 2010, 1, 774-780
48. Ventura, S. P. M.; Pauly, J.; Daridon, J. L.; Lopes da Silva, J. A.; Marrucho, I. M.; Dias, A. M. A.; Coutinho, J. A. P. High pressure solubility data of carbon dioxide in tri-iso-butyl(metyl)phosphonium tosylate-water systems J. Chem. Thermodyn. 2008, 40, 1187-1192
49. Cornmell, R. J.; Winder, C. L.; Schuler, S.; Goodacre, R.; Stephens, G. Using a biphasic ionic liquid/water reaction system to improve oxygenase-catalysed biotransformatio with whole cells Green Chem. 2008, 10, 685-691 (Pubitemid 351782890)
50. Neves, C. M. S. S.; Freire, M. G.; Robertson, A. J.; Coutinho, J. A. P., Separation of ethanol-water mixtures using phosphonium ionic liquids. 2010, submitted for publication.
51. Liu, Y.; Guo, L.; Zhu, L.; Sun, X.; Chen, J. Removal of Cr(III,VI) by quaternary ammonium and quaternary phosphonium ionic liquids functionalized silica materials Chem. Eng. J. 2010, 158, 108-114
52. Mokhodoeva, O. B.; Myasoedova, G. V.; Kubrakova, I. V.; Nikulin, O. I.; Artyushin, O. I.; Odinets, I. L. New solid extractants forpreconcentrating noble metals J. Anal. Chem. 2010, 65, 12-16
53. Stojanovic, A.; Kogelnig, D.; Fischer, L.; Hann, S.; Galanski, M.; Groessl, M.; Krachler, R.; Keppler, B. K. Phosphonium and ammonium ionic liquids with aromatic anions: sysnthesis, properties and platinum extraction Aust. J. Chem. 2010, 63, 511-524
54. Oliveira, F. S.; Freire, M. G.; Pratas, M. J.; Pauly, J.; Daridon, J. L.; Marrucho, I. M.; Coutinho, J. A. P. Solubility of adamantane in phosphonium-based ionic liquids J. Chem. Eng. Data 2010, 55, 662-665
55. Kilaru, P. K.; Scovazzo, S. Correlations of low-pressure carbon dioxide and hydrocarbon solubilities in imidazolium-, phosphonium- and ammonium-based room temperature ionic liquids. Part 2. Using activation energy of viscosity Ind. Eng. Chem. Res. 2008, 47, 910-919 (Pubitemid 351269534)
56. Dymond, J. H.; Malhotra, R. The Tait equation: 100 years on Int. J. Thermophys. 1988, 9, 941-951
57. Sanchez, I. C.; Lacombe, R. H. Statistical thermodynamics of polymer solutions Macromolecules 1978, 11, 1145-1156
58. Dee, G. T.; Walsh, D. J. Equation of state for polymer liquids Macromolecules 1988, 21, 811-815
59. Dee, G. T.; Walsh, D. J. A modified cell model equation of state for polymer liquids Macromolecules 1988, 815-817 (Pubitemid 18618611)
60. Gardas, R. L.; Coutinho, J. A. P. Extension of the Ye and Shreeve group contribution method for density estimation of ionic liquids in a wide range of temperatures and pressures Fluid Phase Equilib. 2008, 263, 26-32 (Pubitemid 350216956)
61. Kilaru, P. K.; 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)
62. Neves, C. M. S. S.; Carvalho, P. J.; Freire, M. G.; Coutinho, J. A. P., Thermophysical Properties of Neat and Water Saturated Tetradecyltrihexylphosphonium-based Ionic Liquids. J. Chem. Thermodyn. 2010, DOI: 10.1016/j.jct.2011.01.016.
63. Piñeiro, M. M.; Bessières, D.; Saint-Guirons, H.; Legido, J. L. Measurements of Nonafluorobutyl Methyl Ether and Nonafluorobutyl Ethyl Ether between 283.15 and 323.15 K at Pressures up to 40 MPa Int. J. Thermophys. 2003, 24, 1265-1276
64. Piñeiro, M. M.; Bessières, D.; Gacio, J. M.; Saint-Guirons, H.; Legido, J. L. Determination of high-pressure liquid density for n-perfluorohexane and n-perfluorononane Fluid Phase Equilib. 2004, 220, 127-136 (Pubitemid 38739230)
65. Huddleston, J. G.; Visser, A. E. R., W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation Green Chem. 2001, 3, 156-164 (Pubitemid 33319370)
66. Machida, H.; Sato, Y.; Smith, R. L. J. Pressure-volume-temperature (PVT) measurements of ionic liquids ([bmim+][PF6-], [bmim+][BF4-], [bmim+][OcSO4-]) and analysis with the Sanchez-Lacombe equation of state Fluid Phase Equilib. 2008, 264, 147-155
67. Sato, Y.; Hashiguchi, H.; Takishima, S.; Masuoka, H. Prediction of PVT properties of polymer melts with a new group-contribution equation of state Fluid Phase Equilib. 1998, 144, 427-440 (Pubitemid 128718330)
68. Ye, C.; Shreeve, J. M. Rapid and accurate estimation of densities of room-temperature ionic liquids and salts J. Phys. Chem. A 2007, 111, 1456-1461 (Pubitemid 46456173)
69. Machida, H.; Taguchi, R.; Sato, Y.; Smith, R. L. J. Analysis of ionic liquid PVT behavior with a Modified Cell Model Fluid Phase Equilib. 2009, 281, 127-132