Synthesis and characterization of thiazolium-based room temperature ionic liquids for gas separations

Industrial and Engineering Chemistry Research

Volumn 51, Issue 35, 2012, Pages 11530-11537

  Hillesheim, Patrick C ^a   Mahurin, Shannon M ^a   Fulvio, Pasquale F ^a   Yeary, Joshua S ^a   Oyola, Yatsandra ^a   Jiang, De En ^a   Dai, Sheng ^a,b  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE ABSORPTION; GAS SEPARATIONS; INFRARED SPECTRUM; PHYSICOCHEMICAL PROPERTY; ROOM TEMPERATURE IONIC LIQUIDS;

CARBON DIOXIDE; LIQUID MEMBRANES; SEPARATION;

IONIC LIQUIDS;

EID: 84865847880     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie3015632     Document Type: Article

References (44)

1. Wilkes, J. S. A short history of ionic liquids-from molten salts to neoteric solvents Green Chem. 2002, 4, 73-80
2. Wilkes, J. S. Properties of ionic liquid solvents for catalysis J. Mol. Catal. A: Chem. 2004, 214, 11-17
3. Wang, H.; Gurau, G.; Rogers, R. D. Ionic liquid processing of cellulose Chem. Soc. Rev. 2012, 41, 1519-1537
4. 2 capture and comparisons to imidazolium-based ionic liquids Ind. Eng. Chem. Res. 2011, 50, 8665-8677
5. Sun, X. Q.; Luo, H. M.; Dai, S. Ionic liquids-based extraction: A promising strategy for the advanced nuclear fuel cycle Chem. Rev. 2012, 112, 2100-2128
6. Smiglak, M.; Metlen, A.; Rogers, R. D. The second evolution of ionic liquids: From solvents and separations to advanced materials-energetic examples from the ionic liquid cookbook Acc. Chem. Res. 2007, 40, 1182-1192
7. Davis, J. H. Task-specific ionic liquids Chem. Lett. 2004, 33, 1072-1077
8. 2 separation J. Membr. Sci. 2010, 353, 177-183
9. 2 in room-temperature ionic liquids using a transient thin-liquid-film method Ind. Eng. Chem. Res. 2007, 46, 8166-8175
10. 2 separation Ind. Eng. Chem. Res. 2011, 50, 14061-14069
11. 4 separation Chem. Eng. J. 2011, 166, 401-406
12. Hu, Y. F.; Liu, Z. C.; Xu, C. M.; Zhang, X. M. The molecular characteristics dominating the solubility of gases in ionic liquids Chem. Soc. Rev. 2011, 40, 3802-3823
13. Davis, J. H.; Forrester, K. J. Thiazolium-ion based organic ionic liquids (oils). Novel oils which promote the benzoin condensation Tetrahedron Lett. 1999, 40, 1621-1622
14. Yu, F. L.; Zhang, R. L.; Xie, C. X.; Yu, S. T. Polyether-substituted thiazolium ionic liquid catalysts-a thermoregulated phase-separable catalysis system for the stetter reaction Green Chem. 2010, 12, 1196-1200
15. Normand, A. T.; Yen, S. K.; Huynh, H. V.; Hor, T. S. A.; Cavell, K. J. Catalytic annulation of heterocycles via a novel redox process involving the imidazolium salt n-heterocyclic carbene couple Organometallics 2008, 27, 3153-3160
16. Wolfe, D. M.; Schreiner, P. R. Oxidative desulfurization of azole-2-thiones with benzoyl peroxide: Syntheses of ionic liquids and other azolium salts Eur. J. Org. Chem. 2007, 2825-2838
17. Ford, L.; Harjani, J. R.; Atefi, F.; Garcia, M. T.; Singer, R. D.; Scammells, P. J. Further studies on the biodegradation of ionic liquids Green Chem. 2010, 12, 1783-1789
18. Leclercq, L.; Suisse, I.; Roussel, P.; Agbossou-Niedercorn, F. Inclusion of tetrabutylammonium cations in a chiral thiazolium/triflate network: Solid state and solution structural investigation J. Mol. Struct. 2012, 1010, 152-157
19. Orsini, M.; Chiarotto, I.; Sotgiu, G.; Inesi, A. Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The stetter reaction Electrochim. Acta 2010, 55, 3511-3517
20. Stander-Grobler, E.; Schuster, O.; Strasser, C. E.; Albrecht, M.; Cronje, S.; Raubenheimer, H. G. Normal and abnormal carbene complexes derived from thiazole: Preparation and a preliminary investigation of their relative catalytic performance Polyhedron 2011, 30, 2776-2782
21. Hallett, J. P.; Welton, T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. 2 Chem. Rev. 2011, 111, 3508-3576
22. 2 separation: A molecular simulation study Langmuir 2011, 27, 3451-3460
23. Teague, C. M.; Dai, S.; Jiang, D.-E. Computational investigation of reactive to nonreactive capture of carbon dioxide by oxygen-containing lewis bases J. Phys. Chem. A 2010, 114, 11761-11767
24. Jin, H.; O'Hare, B.; Dong, J.; Arzhantsev, S.; Baker, G. A.; Wishart, J. F.; Benesi, A. J.; Maroncelli, M. Physical properties of ionic liquids consisting of the 1-butyl-3-methylimidazolium cation with various anions and the bis(trifluoromethylsulfonyl)imide anion with various cations J. Phys. Chem. B 2008, 112, 81-92
25. Fujimori, T.; Fujii, K.; Kanzaki, R.; Chiba, K.; Yamamoto, H.; Umebayashi, Y.; Ishiguro, S. I. Conformational structure of room temperature ionic liquid n-butyl-n-methyl-pyrrolidinium bis(trifluoromethanesulfonyl) imide-raman spectroscopic study and dft calculations J. Mol. Liq. 2007, 131, 216-224
26. Campbell, J. L. E.; Johnson, K. E.; Torkelson, J. R. Infrared and variable-temperature 1H-NMR investigations of ambient-temperature ionic liquids prepared by reaction of HCl with 1-ethyl-3-methyl-1H-imidazolium chloride Inorg. Chem. 1994, 33, 3340-3345
27. - anions J. Phys. Chem. A 2009, 113, 2873-2889
28. Dieter, K. M.; Dymek, C. J.; Heimer, N. E.; Rovang, J. W.; Wilkes, J. S. Ionic structure and interactions in 1-methyl-3-ethylimidazolium chloride-alcl3 molten-salts J. Am. Chem. Soc. 1988, 110, 2722-2726
29. Erdmenger, T.; Vitz, J.; Wiesbrock, F.; Schubert, U. S. Influence of different branched alkyl side chains on the properties of imidazolium-based ionic liquids J. Mater. Chem. 2008, 18, 5267-5273
30. Heimer, N. E.; Del Sesto, R. E.; Meng, Z. Z.; Wilkes, J. S.; Carper, W. R. Vibrational spectra of imidazolium tetrafluoroborate ionic liquids J. Mol. Liq. 2006, 124, 84-95
31. Katsyuba, S. A.; Dyson, P. J.; Vandyukova, E. E.; Chernova, A. V.; Vidis, A. Molecular structure, vibrational spectra, and hydrogen bonding of the ionic liquid 1-ethyl-3methyl-1h-imidazolium tetrafluoroborate Helv. Chim. Acta 2004, 87, 2556-2565
32. Matsumoto, K.; Hagiwara, R.; Yoshida, R.; Ito, Y.; Mazej, Z.; Benkic, P.; Zemva, B.; Tamada, O.; Yoshino, H.; Matsubara, S. Syntheses, structures and properties of 1-ethyl-3-methylimidazolium salts of fluorocomplex anions Dalton Trans. 2004, 144-149
33. Huddleston, J. G.; Visser, A. E.; Reichert, 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
34. 2] and a molecular component J. Phys. Chem. B 2011, 115, 6088-6099
35. 6] anion supported ionic liquid membranes J. Membr. Sci. 2004, 238, 57-63
36. Kilaru, P. K.; Condemarin, P. 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
37. Scovazzo, P. Determination of the upper limits, benchmarks, and critical properties for gas separations using stabilized room temperature ionic liquid membranes (silms) for the purpose of guiding future research J. Membr. Sci. 2009, 343, 199-211
38. Muldoon, M. J.; Aki, S.; Anderson, J. L.; Dixon, J. K.; Brennecke, J. F. Improving carbon dioxide solubility in ionic liquids J. Phys. Chem. B 2007, 111, 9001-9009
39. Zheng, W.; Mohammed, A.; Hines, L. G.; Xiao, D.; Martinez, O. J.; Bartsch, R. A.; Simon, S. L.; Russina, O.; Triolo, A.; Quitevis, E. L. Effect of cation symmetry on the morphology and physicochemical properties of imidazolium ionic liquids J. Phys. Chem. B 2011, 115, 6572-6584
40. Zhou, Z. B.; Matsumoto, H.; Tatsumi, K. Cyclic quaternary ammonium ionic liquids with perfluoroalkyltrifluoroborates: Synthesis, characterization, and properties Chem.Eur. J. 2006, 12, 2196-2212
41. Tokuda, H.; Tsuzuki, S.; Susan, M.; 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
42. O'Mahony, A. M.; Silvester, D. S.; Aldous, L.; Hardacre, C.; Compton, R. G. Effect of water on the electrochemical window and potential limits of room-temperature ionic liquids J. Chem. Eng. Data 2008, 53, 2884-2891
43. 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
44. Mahurin, S. M.; Yeary, J. S.; Baker, S. N.; Jiang, D. E.; Dai, S.; Baker, G. A. Ring-opened heterocycles: Promising ionic liquids for gas separation and capture J. Membr. Sci. 2012, 401, 61-67