Stability of the reaction intermediates of ethylbenzene disproportionation over medium-pore zeolites with different framework topologies: A theoretical investigation

Journal of Physical Chemistry C

Volumn 117, Issue 45, 2013, Pages 23626-23637

  Yi, Xianfeng ^a   Byun, Youngchul ^b   Chu, Yueying ^a   Zheng, Anmin ^a   Hong, Suk Bong ^b   Deng, Feng ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLINE CATALYSTS; DISPROPORTIONATIONS; MICROPOROUS; SIZE AND SHAPE; THEORETICAL INVESTIGATIONS; VOID SPACE; ZEOLITE-Y;

ETHYLBENZENE; REACTION INTERMEDIATES; STRAIN ENERGY; TOPOLOGY;

ZEOLITES;

EID: 84887970196     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp4089386     Document Type: Article

References (42)

1. J. Phys. Chem. C 2010, 115, 16124
2. Al-Khattaf, S.; Tukur, N.; Rabiu, S. Ethylbenzene transformation over a ZSM-5-Based catalyst in a riser simulator Ind. Eng. Chem. Res. 2009, 48, 2836-2843
3. Karge, H.; Ladebeck, J.; Sarbak, Z.; Hatada, K. Conversion of alkylbenzenes over zeolite catalysts. I. Dealkylation and disproportionation of ethylbenzene over mordenites Zeolites 1982, 2, 94-102
4. Karge, H.; Hatada, K.; Zheng, Y.; Fiedorow, R. Conversion of alkylbenzenes over zeolite catalysts II. Disproportionation of ethylbenzene over faujasite-type zeolites Zeolites 1983, 3, 13-21
5. De Vos, D.; Ernst, S.; Perego, C.; O'connor, C.; Stöcker, M. Standard reaction of the International Zeolite Association for acidity characterization: Ethylbenzene disproportionation over LaNaY Microporous Mesoporous Mater. 2002, 56, 185-192
6. International Zeolite Association, CatalysisCommission: http://www.iza-online.org/catalysis/.
7. Weiß, U.; Weihe, M.; Hunger, M.; Karge, H.; Weitkamp, J. The induction period in ethylbenzene disproportionation over large pore zeolites Stud. Surf. Sci. Catal. 1997, 105, 973-980
8. Arsenova, N.; Haag, W.; Karge, H. Kinetics study of ethylbenzene disproportionation with medium and large pore zeolites Stud. Surf. Sci. Catal. 1997, 105, 1293-1300
9. Arsenova-Hätel, N.; Bludau, H.; Haag, W.; Karge, H. Influence of the zeolite pore structure on the kinetics of the disproportionation of ethylbenzene Microporous Mesoporous Mater. 2000, 35-36, 113-119
10. Arsenova-Hätel, N.; Bludau, H.; Schumacher, R.; Haag, W.; Karge, H.; Brunner, E.; Wild, U. Catalytic and sorption studies related to the para selectivity in the ethylbenzene disproportionation over H-ZSM-5 catalysts J. Catal. 2000, 191, 326-331
11. Min, H.; Hong, S. Mechanistic investigations of ethylbenzene disproportionation over medium-pore zeolites with different framework topologies J. Phys. Chem. C 2011, 115, 16124-16133
12. McCaulay, D.; Lien, A. Disproportionation of alkylbenzenes. II. Mechanism of alkyl-group transfer J. Am. Chem. Soc. 1953, 75, 2411-2413
13. Brown, H.; Smoot, C. Disproportionation of the alkylbenzenes under the influence of hydrogen bromide and aluminum bromide; the Nature of the transition state in disproportionation reactions J. Am. Chem. Soc. 1956, 78, 2176-2181
14. Streitwieser, A.; Reif, L. Mechanism of transalkylation of ethylbenzene J. Am. Chem. Soc. 1960, 82, 5003-5005
15. Huang, J.; Jiang, Y.; Marthala, V.; Hunger, M. Insight into the mechanisms of the ethylbenzene disproportionation: Transition state shape selectivity on zeolites J. Am. Chem. Soc. 2008, 130, 12642-12644
16. Min, H.; Chidambaram, V.; Hong, S. Diethylated diphenylethane species: Main reaction intermediates of ethylbenzene disproportionation over large-pore zeolites J. Phys. Chem. C 2010, 114, 1190-1193
17. Clark, L.; Sierka, M.; Sauer, J. Computational elucidation of the transition state shape selectivity phenomenon J. Am. Chem. Soc. 2004, 126, 936-947
18. Zheng, A.; Chen, L.; Yang, J.; Zhang, M.; Su, Y.; Yue, Y.; Ye, C.; Deng, F. Combined DFT theoretical calculation and solid-state NMR studies of Al substitution and acid sites in zeolite MCM-22 J. Phys. Chem. B 2005, 109, 24273-24279
19. Rungsirisakun, R.; Nanok, T.; Probst, M.; Limtrakul, J. Adsorption and diffusion of benzene in the nanoporous catalysts FAU, ZSM-5 and MCM-22: A molecular dynamics study J. Mol. Graph. Model. 2006, 24, 373-382
20. Boekfa, B.; Choomwattana, S.; Khongpracha, P.; Limtrakul, J. Effects of the zeolite framework on the adsorptions and hydrogen-exchange reactions of unsaturated aliphatic, aromatic, and heterocyclic compounds in ZSM-5 zeolite: A combination of perturbation theory (MP2) and a newly developed density functional theory (M06-2X) in ONIOM scheme Langmuir 2009, 25, 12990-12999
21. Dominguez-Soria, V.; Calaminici, P.; Goursot, A. Theoretical study of host-guest interactions in the large and small cavities of MOR zeolite models J. Phys. Chem. C 2011, 115, 6508-6512
22. Fang, H.; Zheng, A.; Xu, J.; Li, S.; Chu, Y.; Chen, L.; Deng, F. Theoretical investigation of the effects of the zeolite framework on the stability of carbenium ions J. Phys. Chem. C 2011, 115, 7429-7439
23. Tranca, D.; Hansen, N.; Swisher, J.; Smit, B.; Keil, F. Combined density functional theory and Monte Carlo analysis of monomolecular cracking of light alkanes over H-ZSM-5 J. Phys. Chem. C 2012, 116, 23408-23417
24. Mazar, M.; Al-Hashimi, S.; Bhan, A.; Cococcioni, M. Methylation of ethene by surface methoxides: A periodic PBE+D study across zeolites J. Phys. Chem. C 2012, 116, 19385-19395
25. Kassab, E.; Castella-Ventura, M.; Akacem, Y. Theoretical study of 4,4′-bipyridine adsorption on the Brønsted acid sites of H-ZSM-5 zeolite J. Phys. Chem. C 2009, 113, 20388-20395
26. 2+ complexes in ZSM-5 zeolite J. Phys. Chem. C 2011, 115, 9668-9680
27. Sauer, J. Quantum mechanical studies of zeolites. In Modelling of Structure and Reactivity in Zeolites; Catlow, C., Ed.; Academic Press: London, 1992.
28. Wannakao, S.; Warakulwit, C.; Kongpatpanich, K.; Probst, M.; Limtrakul, J. Methane activation in gold cation-exchanged zeolites: A DFT study ACS Catal. 2012, 2, 986-992
29. Clark, L.; Sierka, M.; Sauer, J. Stable mechanistically-relevant aromatic-based carbenium ions in zeolite catalysts J. Am. Chem. Soc. 2003, 125, 2136-2141
30. McCann, D.; Lesthaeghe, D.; Kletnieks, P.; Guenther, D.; Hayman, M.; Van Speybroeck, V.; Waroquier, M.; Haw, J. A complete catalytic cycle for supramolecular methanol-to-olefins conversion by linking theory with experiment Angew. Chem., Int. Ed. 2008, 47, 5179-5182
31. Hemelsoet, K.; Nollet, A.; Vandichel, M.; Lesthaeghe, D.; Van Speybroeck, V.; Waroquier, M. The effect of confined space on the growth of naphthalenic species in a chabazite-type catalyst: A molecular modeling study ChemCatChem 2009, 1, 373-378
32. Hemelsoet, K.; Nollet, A.; Van Speybroeck, V.; Waroquier, M. Theoretical simulations elucidate the role of naphthalenic species during methanol conversion within H-SAPO-34 Chem.-Eur. J. 2011, 17, 9083-9093
33. Chai, J.; Head-Gordon, M. Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
34. Frisch, M. Gaussian 09, Revision B.01; Gaussian Inc.: Wallingford, CT, 2010.
35. Van der Mynsbrugge, J.; Hemelsoet, K.; Vandichel, M.; Waroquier, M.; Speybroeck, V. Efficient approach for the computational study of alcohol and nitrile adsorption in H-ZSM-5 J. Phys. Chem. C 2012, 116, 5499-5508
36. Katada, N.; Suzuki, K.; Noda, T.; Sastre, G.; Niwa, M. Correlation between Brønsted acid strength and local structure in zeolites J. Phys. Chem. C 2009, 113, 19208-19217
37. Baerlocher, Ch.; McCusker, L. Database of Zeolite Structures: http://www.iza-structure.org/databases/.
38. Wade, L. Structure and Stereochemistry of Alkanes in Organic Chemistry, 6 th ed.; Pearson Prentice Hall: Upper Saddle River, NJ, 2006, 103-122.
39. Greenberg, A.; Liebman, J. Strained Organic Molecules; Academic Press: New York, 1978.
40. Smith, M.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6 th ed.; John Wiley & Sons: New York, 2007, 216-217.
41. Kasuriya, S.; Namuangruk, S.; Treesukol, P.; Tirtowidjojo, M.; Limtrakul, J. Adsorption of ethylene, benzene, and ethylbenzene over faujasite zeolites investigated by the ONIOM method J. Catal. 2003, 219, 320-328
42. Kondo, J.; Nishioka, D.; Yamazaki, H.; Kubota, J.; Domen, K.; Tatsumi, T. Activation Energies for the Reaction of Ethoxy Species to Ethene over Zeolites J. Phys. Chem. C 2010, 114, 20107-201130