Thermal decomposition mechanism of 1-ethyl-3-methylimidazolium bromide ionic liquid

Journal of Physical Chemistry A

Volumn 116, Issue 24, 2012, Pages 5867-5876

  Chambreau, Steven D ^a   Boatz, Jerry A ^b   Vaghjiani, Ghanshyam L ^b   Koh, Christine ^c   Kostko, Oleg ^d   Golan, Amir ^d   Leone, Stephen R ^c,d  

^a AIR FORCE RESEARCH LABORATORY   (United States)

^b AIR FORCE RESEARCH LABORATORY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1-BUTYL-3-METHYLIMIDAZOLIUM BROMIDE; AB INITIO THERMODYNAMICS; ACTIVATION ENTHALPIES; ALKYL BROMIDES; CALCULATED VALUES; CARBENES; ENTHALPIES OF FORMATION; ENTHALPY OF VAPORIZATION; GASPHASE; ION PAIRS; LIQUID PHASE; LITERATURE DATA; MOLECULAR DYNAMICS CALCULATION; THERMAL DECOMPOSITION MECHANISM; TIME OF FLIGHT MASS SPECTROMETRY; VACUUM ULTRAVIOLET PHOTOIONIZATION; VOLATILIZATION PROCESS;

BROMINE COMPOUNDS; CALCULATIONS; DECOMPOSITION; ENTHALPY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; PHOTOIONIZATION; REACTION KINETICS; THERMODYNAMICS; THERMOGRAVIMETRIC ANALYSIS; VAPORIZATION; VAPORS;

IONIC LIQUIDS;

1 ETHYL 3 METHYLIMIDAZOLIUM BROMIDE; 1-ETHYL-3-METHYLIMIDAZOLIUM BROMIDE; IMIDAZOLE DERIVATIVE; IONIC LIQUID;

ARTICLE; CHEMISTRY; MOLECULAR DYNAMICS; THERMODYNAMICS;

IMIDAZOLES; IONIC LIQUIDS; MOLECULAR DYNAMICS SIMULATION; THERMODYNAMICS;

EID: 84859622063     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp209389d     Document Type: Article

References (67)

1. Plechkova, N. V.; Seddon, K. R. Chem. Soc. Rev. 2008, 37, 123-150
2. Friere, M. G.; Neves, C. M. S. S.; Marrucho, I. M.; Canongia Lopes, J. N.; Rebelo, L. P. N; Coutinho, J. A. P. Green Chem. 2010, 12, 1715-1718
3. Giunta, D.; Solinas, M. Curr. Org. Chem. 2009, 13, 1300-1321
4. Sheldon, R. Chem. Commun. 2001, 23, 2399-2407
5. Visser, A. E.; Swatloski, R. P.; Griffin, S. T.; Hartman, D. H.; Rogers, R. Sep. Sci. Technol. 2001, 36, 785-804
6. Di Noto, V.; Negro, E.; Sanchez, J.-Y.; Lojoiu, C. J. Am. Chem. Soc. 2010, 132, 2183-2195
7. Kim, S. Y.; Kim, S.; Park, M. J. Nature Communications 2010, 1 10.1038/ncomms1086
8. Nakamoto, H.; Noda, A.; Hayamizu, K.; Hayashi, S.; Hamaguchi, H.; Watanabe, M. J. Phys. Chem. C 2007, 111, 1541-1548
9. Yasuda, T.; Ogawa, A.; MKanno, M.; Mori, K.; Sakakibara, K.; Watanabe, M. Chem. Lett. 2009, 38, 692-693
10. Armand, M.; Endres, F.; MacFarlane, D. R.; Ohno, H.; Scrosati, B. Nat. Mater. 2009, 8, 621-629
11. Zakeeruddin, S. M.; Graetzel, M. Adv. Funct. Mater. 2009, 19, 2187-2202
12. Chambreau, S. D.; Schneider, S.; Rosander, M.; Hawkins, T.; Gallegos, C. J.; Pastewait, M. F.; Vaghjiani, G. L. J. Phys. Chem. A 2008, 112, 7816-7824
13. Gao, H.; Joo, Y.-H.; Twamley, B.; Zhou, Z.; Shreeve, J. n. M. Angew. Chem., Int. Ed. 2009, 48, 2792-2795
14. Hawkins, T.; Rosander, M.; Vaghjiani, G. L.; Chambreau, S. D.; Drake, G.; Schneider, S. Energy Fuels 2008, 22, 2871-2872
15. Bermudez, M.-D.; Jimenez, A.-E.; Sanes, J.; Carrion, F.-J. Molecules 2009, 14, 2888-2908
16. Palacio, M.; Brushan, B. Tribol. Lett. 2010, 40, 247-268
17. Van Renesselar, J. Tribol. Lubr. Technol. 2010, 66, 24-31
18. Baranyai, K. J.; Deacon, G. B.; MacFarlane, D. R.; Pringle, J. M.; Scott, J. L. Aust. J. Chem. 2004, 57, 145-147
19. Leal, J. P.; Esperança, J. M. S. S.; Minas da Piedade, M. E.; Canongia Lopes, J. N.; Rebelo, L. P. N; Seddon, K. R. J. Phys. Chem. A 2007, 111, 6176-6182
20. Chan, B. K. M.; Chang, N.-H.; Grimmett, M. R. Aust. J. Chem. 1977, 30, 2005-2013
21. Kroon, M. C.; Buijs, W.; Peters, C. J.; Witkamp, G.-J. Thermochim. Acta 2007, 465, 40-47
22. Chowdhury, A.; Thynell, S. T. Thermochim. Acta 2006, 443, 159-172
23. Fredlake, C. P.; Crosthwaite, J. M.; Hert, D. G.; Aki, S. N. V. K.; Brennecke, J. F. J. Chem. Eng. Data 2004, 49, 954-964
24. Ngo, H. L.; LeCompte, K.; Hargens, L.; McEwen, A. B. Thermochim. Acta 2000, 357-358, 97-102
25. Handy, S. T.; Okello, M. J. Org. Chem. 2005, 70, 1915-1918
26. Breslow, R. J. Am. Chem. Soc. 1957, 79, 1962-1963
27. Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363
28. Breslow, R. Chem. Ind. 1957, 26, 893-894
29. Wanzlick, H. W.; Schonherr, H. J. Liebigs Ann. Chem. 1970, 731, 176-179
30. Kan, H.-C.; Tseng, M.-C.; Chu, Y.-H. Tetrahedron 2007, 63, 1644-1653
31. Holloczki, O.; Gerhard, D.; Massone, K.; Szarvas, L.; Nemeth, B.; Veszpremi, T.; Nyulaszi, L. New J. Chem. 2010, 34, 3004-3009
32. Koppel, I. A.; Taft, R. W.; Anvia, F.; Hu, L.-Q.; Sung, K.-S.; DesMarteau, D. D.; Yagupolskii, L. M.; Yagupolskii, Y. L.; Ignat'ev, N. V.; Kondratenko, N. V.; volkonskii, A. Y.; Vlasov, V. M.; Notario, R.; Maria, P.-C. J. Am. Chem. Soc. 1994, 116, 3047-3057
33. Gross, J. H. J. Am. Soc. Mass Spectrom. 2008, 19, 1347-1352
34. Chambreau, S. D.; Vaghjiani, G. L.; Koh, C.; Golan, A.; Strasser, D.; Leone, S. R. in preparation.
35. Chambreau, S. D.; Vaghjiani, G. L.; To, A.; Koh, C.; Strasser, D.; Kostko, O.; Leone, S. R. J. Phys. Chem. B 2010, 114, 1361-1367
36. Strasser, D.; Goulay, F.; Belau, L.; Kostko, O.; Koh, C.; Chambreau, S. D.; Vaghjiani, G. L.; Ahmed, M.; Leone, S. R. J. Phys. Chem. A 2010, 114, 879-883
37. Strasser, D.; Goulay, F.; Kelkar, M. S.; Maginn, E. J.; Leone, S. R. J. Phys. Chem. A 2007, 111, 3191-3915
38. Koh, C.; Liu, C.-L.; Harmon, C.; Strasser, D.; Golan, A.; Kostko, O.; Chambreau, S. D.; Vaghjiani, G. L.; Leone, S. R. J. Phys. Chem. A 2011, 115, 4630-4635
39. Paulechka, Y. U.; Kabo, A. G.; Blokhin, A. V. J. Phys. Chem. B 2009, 113, 14742-14746
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
41. Hertwig, R. H.; Koch, W. Chem. Phys. Lett. 1997, 268, 345-351
42. Stephens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
43. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
44. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301
45. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728
46. Hariharan, P. C.; Pople, J. A. Theoret. Chim. Acta. 1973, 28, 213-222
47. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261
48. Mitin, A. V.; Baker, J.; Pulay, P. J. Chem. Phys. 2003, 118, 7775-7782
49. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023
50. Wilson, A. K.; Woon, D. E.; Peterson, K. A.; Dunning, T. H. J. J. Chem. Phys. 1999, 110, 7667-7676
51. Gordon, M. S.; Schmidt, M. W. Advances in Electronic Structure Theory: GAMESS a Decade Later. In Theory and Applications of Computational Chemistry: The First Forty Years; Dykstra, C. E.; Frenking, G.; Kim, K. S.; Scuseria, G. E., Eds.; Elsevier: Amsterdam, 2005; pp 1167-1189.
52. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363
53. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
54. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 2007, 126, 084108
55. Borodin, O.; Smith, G. D.; Kim, H. J. Phys. Chem. B 2009, 113, 4771-4774
56. Innovations Through Molecular Simulations: http://www.wasatchmolecular. com/lucretiusPage.html, accessed June 11, 2011.
57. Palmer, B. J. J. Comput. Phys. 1993, 104, 470-472
58. Martyna, G. J.; Tuckerman, M. E.; Tobias, D. J.; Klein, M. L. Mol. Phys. 1996, 87, 1117-1157
59. Paulechka, Y. U.; Kabo, G. J.; Blokhin, A. V.; Shaplov, A. S.; Lozinskaya, E. I.; Vygodskii, Y. S. J. Chem. Thermodyn. 2006, 39, 158-166
60. Baer, T.; Song, Y.; Liu, J.; Chen, W.; Ng, C. Y. Faraday Discuss. 2000, 115, 137-145
61. Locht, R.; Leyh, B.; Dahareng, D.; Hottmann, K.; Jochims, H. W.; Baumgartel, H. Chem. Phys. 2006, 323, 458-472
62. Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Neutral Thermochemical Data. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J.; Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 2005.
63. Lias, S. G. Ionization Energy Evaluation. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J.; Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 2005.
64. Yamaoka, H.; Fokkens, R. H.; Nibbering, N. M. M. Int. J. Mass. Spectrom. 1999, 188, 1-6
65. Arellano, I. H. J.; Guarino, J. G.; Paredes, F. U.; Arco, S. D. J. Therm. Anal. Calorim. 2011, 103, 725-730
66. Kabo, G. J.; Paulechka, Y. U.; Kabo, A. G.; Blokhin, A. V. J. Chem. Thermodyn. 2010, 42, 1292-1297
67. vap of Imidazolium Bromide Ionic Liquids. Private communication.