Modeling elementary reactions in coke formation from first principles

Molecular Simulation

Volumn 33, Issue 9-10, 2007, Pages 879-887

  Van Speybroeck, V ^a   Hemelsoet, K ^a   Minner, B ^a   Marin, G B ^a   Waroquier, M ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Bond dissocation enthalpy; Coke; Density functional calculations; Hydrogen abstraction; Polyaromatic hydrocarbons; Radical reactions

Indexed keywords

AROMATIC HYDROCARBONS; BOND STRENGTH (CHEMICAL); CRACKING (CHEMICAL); DENSITY FUNCTIONAL THEORY; FREE RADICALS; REACTION RATES;

BOND DISSOCATION ENTHALPY; HYDROGEN ABSTRACTION; POLYAROMATIC HYDROCARBONS; RADICAL REACTIONS;

COKE;

EID: 34548316121     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020701308315     Document Type: Conference Paper

References (39)

1. S. Wauters, G.B. Marin. Kinetic modeling of coke formation during steam, cracking. Ind. Eng. Chem. Res., 41, 2379 (2002).
2. S. Wauters, G.B. Marin. Computer generation of a network of elementary steps for coke formation during the thermal cracking of hydrocarbons. Chem. Eng. J., 82, 267 (2001).
3. S. Wauters. Kinetics of coke formation during thermal cracking of hydrocarbons based on elementary reactions, PhD Thesis. Ghent University (2001).
4. M.F.S.G. Reyniers, G.F. Froment. Influence of metal-surface and sulfur addition on coke deposition in the thermal-cracking of hydrocarbons. Ind. Eng. Chem. Res., 34, 773 (1995).
5. M.J. Frisch, G.W. Tracks, 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. Kiene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, 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., Wallingford CT (2004).
6. R.G. Parr, W. Yang. Density-Functional Theory of Atoms and Molecules, Oxford University Press, an example of a reference work (1989).
7. A.D. Becke. Density-functional thermochemistry. 3. The role of exact exchange. J. Chem. Phys., 98, 5648 (1993).
8. K. Hemelsoet, D. Moran, V. Van Speybroeck, M. Waroquier, L. Radom. An assessment of theoretical procedures for predicting the thermochemistry and kinetics of hydrogen abstraction by methyl radical from benzene. J. Phys. Chem. A, 110, 8942 (2006).
9. L.A. Curtiss, K. Raghavachari, P.C. Redfern, J.A. Pople. Assessment of Gaussian-2 and density functional, theories for the computation of enthalpies of formation. J. Chem. Phys., 106, 1063 (1997).
10. M.L. Coote. Reliable theoretical procedures for the calculation of electronic-structure information in hydrogen abstraction reactions. J. Phys. Chem. A, 108, 3865 (2004).
11. B.J. Lynch, D.G. Truhlar. How well can hybrid density functional methods predict transition state geometries and barrier heights? J. Phys. Chem. A, 105, 2936 (2001).
12. A.P. Scott, L. Radom. Harmonic vibrational frequencies: An evaluation of Hartree-Fock, Moller-Plesset, quadratic configuration interaction, density functional theory, and semiempirieal scale factors. J. Phys. Chem., 100, 16502 (1996).
13. A.D. Boese, J.M.L, Martin. Development of density functional for thermochemical kinetics. J. Chem. Phys., 121, 3405 (2004).
14. H. Eyring. J. Chem. Phys., A more comprehensive treatment can be found in W.F.K. Wynne-Jones, H. Eyring, J. Chem. Phys. 3, 492.
15. This article is reproduced in full in M. H. Back, K. L. Laidler, Selected readings in chemical kinetics; Pergamon Oxford, 1967 1935(107).
16. K.J. Laidler. Chemical Kinetics, HarperCollins Publishers, Inc., (1987).
17. D.A. Mc Quarrie, J.D Simon. Physical Chemlstry-A Molecular Approach, University Science Books, Sausalito, California (1997).
18. P. Pechukas. Dynamics of Molecular Collisions, Part B, W.H. Miller (Ed.), Plenum Press, New York;
19. (b) K. J. Laidler, M. C. King, J. Phys. Chem. 1983, 87, 2657;
20. (c) D. G. Truhlar, W. L. Hase, J. T. Hynes, J. Phys. Chem. 1983, 87, 2664;
21. (d) R. G. Gilbert, S. C. Smith, Theory of Unimolecular and Recombination Reactions, Blackwell: Oxford, 1990 (1976).
22. V. Van Speybroeck, D. Van Neck, M. Waroquier, S. Wauters, M. Saeys, G.B. Marin. Ab initio study of radical addition reactions: Addition of a primary ethylbenzene radical to ethene (I). J. Phys. Chem. A, 104, 10939 (2000).
23. F.D. Kopinke, G. Zimmermann, S. Nowak. N the mechanism of coke formation in steam, cracking - conclusions from, results obtained by tracer experiments. Carbon, 26, 117 (1988);
24. (b) F.D. Kopinke, G. Zimmermann, G.C. Reyniers, G.F. Froment, Relative rates of coke formation from, hydrocarbons in steam, cracking of naphtha. 2. Paraffins, Naphthenes, Monoolefins, Diolefins, and Cycloolefins, and Acetylenes. Ind. Eng. Chem. Res., 32, 56 (1993);
25. (c) F.D. Kopinke, G. Zimmermann, G.C. Reyniers, G.F. Froment, Relative rates of coke formation from hydrocarbons in steam, cracking of naphtha. 3. Aromatic-hydrocarbons. Ind. Eng. Chem. Res., 32, 2620 (1993).
26. G.F. Froment. Fouling of heat transfer surfaces by coke formation in petrochemical reactors. In Fouling of Heat Transfer Equipment, E. Summerscales, J.G. Knudson (Eds.), Hemisphere Publ. Corp, (1981).
27. P.J. Clymans, G.F. Froment. Computer-generation of reaction paths and rate-equations in the thermal-cracking of normal and branched paraffins. Comput. Chem. Eng., 8, 137 (1984).
28. G.C. Reyniers, G.F. Froment, F.D. Kopinke, G. Zimmerman. Coke formation in the thermal-cracking of hydrocarbons. 4. Modeling of coke formation in naphtha cracking. Ind. Eng. Chem. Res., 33(11), 2584 (1994);
29. (b) P.M.. Plehiers, G.C. Reyniers, G.F. Froment, Simulation of the run length of an ethane cracking furnace. Ind. Eng. Chem. Res., 29, 636 (1990).
30. M.G. Evans. Discuss. Faraday Soc., 2, 271;
31. M. G. Evans, J. Gergely, E. C. Seaman, J. Polym. Sci., 1948, 3, 866;
32. M.G. Evans, M. Polanyi, Trans. Faraday Soc., 34, 11 (1938).
33. N.N. Semenov. Some Problems In Chemical Kinetics and Reactivity, Engl. Trans. pp. 29-33, Princeton Press, Princeton (1958).
34. V. Van Speybroeck, G.B. Marin, M. Waroquier. Hydrocarbon bond dissociation enthalpies: From substituted aromatics to polyaromatics. Chem. Phys. Chem., 7, 2205 (2006).
35. H. Wang, M. Frenklach. Enthalpies of formation of benzenoid aromatic-molecules and radicals. J. Phys. Chem., 97, 3867 (1993).
36. C.-C. Chen, J.W. Bozzelli. Structures, intramolecular rotation barriers, and thermochemical properties of methyl ethyl, methyl isopropyl, and methyl tert-butyl ethers and the corresponding radicals. J. Phys. Chem. A, 107, 4531 (2003).
37. J. Aihara. Theoretical evidence for the presence of linear polyacenes in the interstellar-medium. Bull. Chem. Soc. Jpn., 63, 2781 (1990).
38. J. Cioslowski, G. Liu, M. Martinov, P. Piskorz, D. Moncrieff. Energetics and site specificity of the homolytic C-H bond cleavage in benzenoid hydrocarbons: An ab initio electronic structure study. J. Am. Chem. Soc., 118, 5261 (1996).
39. K. Hemelsoet, V. Van Speybroeck, D. Moran, G.B. Marin, L. Radom, M. Waroquier. Thermochemistry and kinetics of hydrogen abstraction by methyl, radical from polycyclic aromatic hydrocarbons. J. Phys. Chem. A, 110 (50), 13624 (2006).