Physical properties and CO2 reaction pathway of 1-ethyl-3-methylimidazolium ionic liquids with aprotic heterocyclic anions

Journal of Physical Chemistry B

Volumn 118, Issue 51, 2014, Pages 14870-14879

  Seo, Samuel ^a   Desilva, M Aruni ^a   Brennecke, Joan F ^a  

^a University of Notre Dame   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; IONIC LIQUIDS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; PHYSICAL PROPERTIES; POSITIVE IONS;

CARBAMATE SPECIES; HETEROCYCLIC ANIONS; IMIDAZOLIUM CATION; INHIBITING EFFECT; IONIC LIQUID (ILS); PRESENCE OF WATER; PROTON EXCHANGE PROCESS; VOLUMETRIC METHODS;

CARBON DIOXIDE;

EID: 84919934586     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp509583c     Document Type: Article

References (54)

1. 2 Capture Science 2009, 325, 1652-1654
2. 2) in Monoethanolamine (MEA) and 2-(Aminoethyl)ethanolamine (AEEA) Solutions Ind. Eng. Chem. Res. 2007, 46, 5803-5809
3. 2 Capture J. Phys. Chem. Lett. 2010, 1, 3494-3499
4. 2-Reacted Ionic Liquid Tetrabutylphosphonium 2-Cyanopyrrolide Ind. Eng. Chem. Res. 2011, 50, 8983-8993
5. 2 Capture by a Task-Specific Ionic Liquid J. Am. Chem. Soc. 2002, 124, 926-927
6. 2 Capture Chem.-Eur. J. 2009, 15, 3003-3011
7. 2 by Tetrabutylphosphonium Amino Acid Ionic Liquids Chem.-Eur. J. 2006, 12, 4021-4026
8. Goodrich, B. F.; de la Fuente, J. C.; Gurkan, B. E.; Zadigian, D. J.; Price, E. A.; Huang, Y.; Brennecke, J. F. Experimental Measurements of Amine-Functionalized Anion-Tethered Ionic Liquids with Carbon Dioxide Ind. Eng. Chem. Res. 2011, 50, 111-118
9. 2 Absorption by Anion-Functionalized Ionic Liquids J. Am. Chem. Soc. 2010, 132, 2116-2117
10. 2 Capture J. Phys. Chem. B 2014, 118, 5740-5751
11. 2 Absorption in to Phosphonium Based Anion-Functionalized Ionic Liquids Phys. Chem. Chem. Phys. 2013, 15, 7796-7811
12. 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
13. Sánchez, L. G.; Espel, J. R.; Onink, F.; Meindersma, G. W.; Haan, A. B. de. Density, Viscosity, and Surface Tension of Synthesis Grade Imidazolium, Pyridinium, and Pyrrolidinium Based Room Temperature Ionic Liquids J. Chem. Eng. Data 2009, 54, 2803-2812
14. Shi, C.; Quiroz-Guzman, M.; DeSilva, A.; Brennecke, J. F. Physicochemical and Electrochemical Properties of Ionic Liquids Containing Aprotic Heterocyclic Anions Doped with Lithium Salts J. Electrochem. Soc. 2013, 160, A1604-A1610
15. Dong, K.; Zhang, S.; Wang, D.; Yao, X. Hydrogen Bonds in Imidazolium Ionic Liquids J. Phys. Chem. A 2006, 110, 9775-9782
16. Tsuzuki, S.; Tokuda, H.; Mikami, M. Theoretical Analysis of the Hydrogen Bond of Imidazolium C2-H with Anions Phys. Chem. Chem. Phys. 2007, 9, 4780-4784
17. Gao, Y.; Zhang, L.; Wang, Y.; Li, H. Probing Electron Density of H-Bonding Between Cation-Anion of Imidazolium-Based Ionic Liquids with Different Anions by Vibrational Spectroscopy J. Phys. Chem. B 2010, 114, 2828-2833
18. Izgorodina, E. I.; MacFarlane, D. R. Nature of Hydrogen Bonding in Charged Hydrogen-Bonded Complexes and Imidazolium-Based Ionic Liquids J. Phys. Chem. B 2011, 115, 14659-14667
19. Dong, K.; Song, Y.; Liu, X.; Cheng, W.; Yao, X.; Zhang, S. Understanding Structures and Hydrogen Bonds of Ionic Liquids at the Electronic Level J. Phys. Chem. B 2012, 116, 1007-1017
20. Cremer, T.; Kolbeck, C.; Lovelock, K. R. J.; Paape, N.; Wölfel, R.; Schulz, P. S.; Wasserscheid, P.; Weber, H.; Thar, J.; Kirchner, B. Towards a Molecular Understanding of Cation-Anion Interactions-Probing the Electronic Structure of Imidazolium Ionic Liquids by NMR Spectroscopy, X-Ray Photoelectron Spectroscopy and Theoretical Calculations Chem.-Eur. J. 2010, 16, 9018-9033
21. Hollóczki, O.; Kelemen, Z.; Könczöl, L.; Szieberth, D.; Nyulászi, L.; Stark, A.; Kirchner, B. Significant Cation Effects in Carbon Dioxide-Ionic Liquid Systems ChemPhysChem 2013, 14, 315-320
22. Shiflett, M. B.; Kasprzak, D. J.; Junk, C. P.; Yokozeki, A. Phase Behavior of {Carbon Dioxide+[Bmim][Ac]} Mixtures J. Chem. Thermodyn. 2008, 40, 25-31
23. 2 In Room-Temperature Ionic Liquid 1-Ethyl-3-Ethylimidazolium Acetate ChemPhysChem 2012, 13, 1806-1817
24. 2 Absorbents. Quarterly Technical Report to DOE; DOE Office of Scientific and Technical Information: Springfield, VA, 2007.
25. Cabaço, M. I.; Besnard, M.; Danten, Y.; Coutinho, J. A. P. Carbon Dioxide in 1-Butyl-3-Methylimidazolium Acetate. I. Unusual Solubility Investigated by Raman Spectroscopy and DFT Calculations J. Phys. Chem. A 2012, 116, 1605-1620
26. 2 In 1-Butyl-3-Methylimidazolium Acetate. 2. NMR Investigation of Chemical Reactions J. Phys. Chem. A 2012, 116, 4890-4901
27. Gurau, G.; Rodríguez, H.; Kelley, S. P.; Janiczek, P.; Kalb, R. S.; Rogers, R. D. Demonstration of Chemisorption of Carbon Dioxide in 1,3-Dialkylimidazolium Acetate Ionic Liquids Angew. Chem., Int. Ed. 2011, 50, 12024-12026
28. Besnard, M.; Cabaço, M. I.; Chávez, F. V.; Pinaud, N. On the Spontaneous Carboxylation of 1-Butyl-3-Methylimidazolium Acetate by Carbon Dioxide Chem. Commun. 2012, 48, 1245-1247
29. Hollóczki, O.; Gerhard, D.; Massone, K.; Szarvas, L.; Németh, B.; Veszprémi, T.; Nyulászi, L. Carbenes in Ionic Liquids New J. Chem. 2010, 34, 3004-3009
30. Bordwell, F. G.; Algrim, D. Nitrogen Acids. 1. Carboxamides and Sulfonamides J. Org. Chem. 1976, 41, 2507-2508
31. Bordwell, F. G. Equilibrium Acidities in Dimethyl Sulfoxide Solution Acc. Chem. Res. 1988, 21, 456-463
32. 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
33. Yokozeki, A.; Shiflett, M. B.; Junk, C. P.; Grieco, L. M.; Foo, T. Physical and Chemical Absorptions of Carbon Dioxide in Room-Temperature Ionic Liquids J. Phys. Chem. B 2008, 112, 16654-16663
34. 4] Ind. Eng. Chem. Res. 2005, 44, 4453-4464
35. Barthel, J.; Feuerlein, F.; Neueder, R.; Wachter, R. Calibration of Conductance Cells at Various Temperatures J. Solution Chem. 1980, 9, 209-219
36. Lee, B. I.; Kesler, M. G. A Generalized Thermodynamic Correlation Based on Three-Parameter Corresponding States AIChE J. 1975, 21, 510-527
37. Yu, Y.; Lu, X.; Zhou, Q.; Dong, K.; Yao, H.; Zhang, S. Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure-Biodegradation Relationship Chem.-Eur. J. 2008, 14, 11174-11182
38. Xu, W.; Cooper, E. I.; Angell, C. A. Ionic Liquids: Ion Mobilities, Glass Temperatures, and Fragilities J. Phys. Chem. B 2003, 107, 6170-6178
39. MacFarlane, D. R.; Forsyth, M.; Izgorodina, E. I.; Abbott, A. P.; Annat, G.; Fraser, K. On the Concept of Ionicity in Ionic Liquids Phys. Chem. Chem. Phys. 2009, 11, 4962-4967
40. Johansson, K. M.; Izgorodina, E. I.; Forsyth, M.; MacFarlane, D. R.; Seddon, K. R. Protic Ionic Liquids Based on the Dimeric and Oligomeric Anions: [(AcO)xHx-1]- Phys. Chem. Chem. Phys. 2008, 10, 2972-2978
41. Rodríguez, H.; Gurau, G.; Holbrey, J. D.; Rogers, R. D. Reaction of Elemental Chalcogens with Imidazolium Acetates to Yield Imidazole-2-Chalcogenones: Direct Evidence for Ionic Liquids as Proto-Carbenes Chem. Commun. 2011, 47, 3222-3224
42. Alder, R. W.; Allen, P. R.; Williams, S. J. Stable Carbenes as Strong Bases J. Chem. Soc., Chem. Commun. 1995, 1267-1268
43. Chen, H.; Justes, D. R.; Cooks, R. G. Proton Affinities of N-Heterocyclic Carbene Super Bases Org. Lett. 2005, 7, 3949-3952
44. Magill, A. M.; Cavell, K. J.; Yates, B. F. Basicity of Nucleophilic Carbenes in Aqueous and Nonaqueous SolventsTheoretical Predictions J. Am. Chem. Soc. 2004, 126, 8717-8724
45. 2 by Using N-Heterocyclic Carbenes Chem.-Eur. J. 2013, 19, 11134-11138
46. 2 Chem. Commun. 2013, 49, 11527-11529
47. Van Ausdall, B. R.; Glass, J. L.; Wiggins, K. M.; Aarif, A. M.; Louie, J. A Systematic Investigation of Factors Influencing the Decarboxylation of Imidazolium Carboxylates J. Org. Chem. 2009, 74, 7935-7942
48. Duong, H. A.; Tekavec, T. N.; Arif, A. M.; Louie, J. Reversible Carboxylation of N-Heterocyclic Carbenes Chem. Commun. 2004, 112-113
49. Seddon, K. R.; Stark, A.; Torres, M. J. Influence of Chloride, Water, and Organic Solvents on the Physical Properties of Ionic Liquids Pure Appl. Chem. 2000, 72, 2275-2287
50. 2 By Amine-Functionalized Anion-Tethered Ionic Liquids J. Phys. Chem. B 2011, 115, 9140-9150
51. 2 Capture by Amino Acid Ionic Liquids Environ. Chem. Lett. 2013, 12, 201-208
52. Stevanovic, S.; Podgorsek, A.; Padua, A. A. H.; Gomes, M. F. C. Effect of Water on the Carbon Dioxide Absorption by 1-Alkyl-3-Methylimidazolium Acetate Ionic Liquids J. Phys. Chem. B 2012, 116, 14416-14425
53. Brehm, M.; Weber, H.; Pensado, A. S.; Stark, A.; Kirchner, B. Proton Transfer and Polarity Changes in Ionic Liquid-Water Mixtures: a Perspective on Hydrogen Bonds From Ab Initio Molecular Dynamics at the Example of 1-Ethyl-3-Methylimidazolium Acetate-Water Mixtures-Part 1 Phys. Chem. Chem. Phys. 2012, 14, 5030-5044
54. Bertini, I.; Luchinat, C.; Messori, L.; Scozzafava, A.; Pellacani, G.; Sola, M. Carbon-13 NMR Study of the Synergistic Anion in Transferrins Inorg. Chem. 1986, 25, 1782-1786