Mechanism of thermal toluene autoxidation

ChemPhysChem

Volumn 8, Issue 18, 2007, Pages 2678-2688

  Hermans, Ive ^a,b   Peeters, Jozef ^a   Vereecken, Luc ^a   Jacobs, Pierre A ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b ETH ZURICH   (Switzerland)

Author keywords

Autoxidation; Density functional calculations; Kinetics; Radical reactions; Reaction mechanisms

Indexed keywords

ATOMS; BENZOIC ACID; DENSITY FUNCTIONAL THEORY; ENZYME KINETICS; REACTION KINETICS; TOLUENE;

AEROBIC OXIDATIONS; AUTOXIDATION; EQUIMOLAR AMOUNT; HYDROGEN TRANSFER; OXIDATION RATES; RADICAL CHAIN REACTIONS; RADICAL REACTIONS; REACTION MECHANISM;

OXIDATION;

EID: 38049035350     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.200700563     Document Type: Article

References (37)

1. R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981.
2. Oxidation, G. Franz, R. A. Sheldon, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.
3. C. A. Tolman, J. D. Druliner, M. J. Nappa, N. Herron in Activation and Functionalization of Alkanes (Ed.: C. L. Hill), Wiley, New York, 1989, p. 303.
4. S. Bhaduri, D. Mukesh, Homogeneous Catalysis, Mechanisms and Industrial Applications, Wiley, New York, 2000.
5. I. Hermans, T. L. Nguyen, P. A. Jacobs, J. Peeters, ChemPhysChem 2005, 6, 637.
6. I. Hermans, P. A. Jacobs, J. Peeters, J. Mol. Catal. A 2006, 251, 221.
7. I. Hermans, J. Peeters, P. Jacobs, J. Org. Chem. 2007, 72, 3057.
8. I. Hermans, P. A. Jacobs, J. Peeters, Chem. Eur. J. 2006, 12, 4229.
9. L. Vereecken, T. L. Nguyen, I. Hermans, J. Peeters, Chem. Phys. Lett. 2004, 393, 432.
10. I. Hermans, P. A. Jacobs, J. Peeters, Chem. Eur. J. 2007, 13, 754.
11. I. Hermans, J.-F. Müller, T. L. Nguyen, P. A. Jacobs, J. Peeters, J. Phys. Chem. A 2005, 109, 4303.
12. D. M. Rowley, R. Lesclaux, P. D. Lightfoot, B. Nozière, T. J. Wallington, M. D. Hurley, J. Phys. Chem. 1992, 96, 4889.
13. 2OH] increased from 20 to 28 mM, which suggests that the propagation of PhCHO also produces alcohol.
14. [15].
15. See, for example: a) B. S. Jursic, J. Phys. Chem. A 1997, 101, 2345;
16. b) D. S. Y. Hsu, W. M. Shaub, T. Creamer, D. Gutman, M. C. Lin, Ber. Bunsen-Ges. 1983, 87, 909;
17. c) Y. Abashkin, N. Russo, E. Sicilia, M. Toscano in Modern Density Functional Theory. A Tool for Chemistry (Eds.: J. M. Seminario, P. Politzer), Elsevier, Amsterdam, 1995, pp. 255.
18. 2OOH (8.54 and 8.53 eV, respectively).
19. D. R. Lide, Handbook of Chemistry and Physics, CRC, Boca Raton, 2001.
20. J. A. A. Hoorn, P. L. Alsters, G. F. Versteeg, Int. J. Chem. React. Eng. 2005, 3, A6.
21. 2.
22. -1.
23. M. C. Lin, A. M. Mebel, J. Phys. Org. Chem. 1995, 8, 407.
24. I. V. Tokmakov, G.-S. Kim, V. V. Kislov, A. M. Mebel, M. C. Lin, J. Phys. Chem. A 2005, 109, 6114.
25. B. Bohn, J. Phys. Chem. A 2001, 105, 6092.
26. [23]
27. C. Bloss, V. Wagner, M. E. Jenkin, R. Volkamer, W. J. Bloss, J. D. Lee, D. E. Heard, K. Wirtz, M. Martin-Reviejo, G. Rea, J. C. Wenger, M. J. Pilling, Atmos. Chem. Phys. 2005, 5, 641.
28. a) D. A. S. Ravens, Trans. Faraday Soc. 1959, 55, 1768;
29. b) W. Partenheimer, Catal. Today 1995, 23, 69.
30. [3]
31. 2 solution will also cause other (secondary) effects, induced by the solvent.
32. M. Goethals, B. Vanderstraeten, J. Berghmans, G. De Smedt, S. Vliegen, E. Van't Oost, J. Hazard. Mater. 1999, 70, 93.
33. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, GAUSSIAN 03 (Revision B.03), Gaussian, Inc., Pittsburgh PA, 2003.
34. a) A. D. Becke, J. Chem. Phys. 1992, 96, 2115;
35. A. D. Becke, J. Chem. Phys. 1992, 97, 9173;
36. A. D. Becke, J. Chem. Phys. 1993, 98, 5648;
37. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.