Using elementary reactions to model growth processes of polyaromatic hydrocarbons under pyrolysis conditions of light feedstocks

Molecular Simulation

Volumn 34, Issue 2, 2008, Pages 193-199

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

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Bond dissociation enthalpy; Carbon centered radicals; DFT calculations; Hydrogen abstraction; Polyaromatic hydrocarbons

Indexed keywords

ABSTRACTING; AROMATIC COMPOUNDS; CHEMICAL BONDS; CHEMICAL REACTIONS; COKE; CRACKING (CHEMICAL); DENSITY FUNCTIONAL THEORY; HYDROCARBONS; HYDROGEN; HYDROGEN BONDS; NONMETALS; ORGANIC COMPOUNDS; PROBABILITY DENSITY FUNCTION; RATE CONSTANTS; RAW MATERIALS; TOLUENE;

AROMATIC MOLECULES; BOND DISSOCIATION ENTHALPY; CARBON-CENTERED RADICALS; CARBON-HYDROGEN BOND; COKE FORMATION; COKE GROWTH; COKE PRECURSORS; DFT CALCULATIONS; ELEMENTARY REACTIONS; ELEMENTARY STEPS; FIRST ORDERS; GROWTH PROCESSES; HYDROGEN ABSTRACTION; HYDROGEN ABSTRACTION REACTIONS; METHYL NAPHTHALENE; METHYL RADICALS; POLYAROMATIC HYDROCARBONS; POLYAROMATICS; RATE COEFFICIENTS; RATE-DETERMINING STEP;

STEAM CRACKING;

EID: 46049091545     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020801930588     Document Type: Conference Paper

References (33)

1. L. Vereecken et al., Reaction of phenyl radicals with propyne, J. Am. Chem. Soc. 124 (2002), p. 2781.
2. T.J.M. de Bruin et al., Reaction kinetics of a selected number of elementary processes involved in the thermal decomposition of 9-methylphenanthrene using density functional theory, J. Phys. Chem. A 108 (2004), p. 10302.
3. J. Appel, H. Bockhorn, and M. Frenklach, Kinetic modelling of soot formation with detailed chemistry and physics: laminar premixed flames of C-2 hydrocarbons, Comb. Flame 121 (2000), p. 122.
4. V.V. Kislov and A.M. Mebel, The formation of naphthalene, azulene, and fulvalene from cyclic C-5 species in combustion: an ab initio/RRKM study of 9-h-fulvalenyl (C5H5-C5H4) radical rearrangements, J. Phys. Chem. A 111 (2007), p. 9532.
5. C. Cavallotti, S. Mancarella, R. Rota, and S. Carra, Conversion of C5 into C6 cyclic species through the formation of C7 intermediates, J. Phys. Chem. A 111 (2007), p. 3959.
6. V. Van Speybroeck, M.F. Reyniers, G.B. Marin, and M. Waroquier, The kinetics of cyclization reactions on polyaromatic from first principles, Chem. Phys. Chem. 3 (2002), p. 863.
7. M. Saeys et al., Ab initio group contribution method for activation energies for radical additions, AIChE J. 50 (2004), p. 426.
8. _ et al., Ab initio group contribution method for activation energies of hydrogen abstraction reactions, Chem. Phys. Chem. 7 (2006), p. 188.
9. (a) V. Van Speybroeck, G.B. Marin, and M. Waroquier, Hydrocarbon bond dissocation enthalpies: From substituted aromatics to polyaromatics, Chem. Phys. Chem. 7 (2006), p. 2205.
10. K. Hemelsoet et al., Thermochemistry and kinetics of hydrogen abstraction by methyl radical from polycyclic aromatic hydrocarbons, J. Phys. Chem. A 110 (2006), p. 13624.
11. V. Van Speybroeck et al., Modeling elementary reactions in coke formation from first principles, Mol. Sim. 33 (2007), p. 879.
12. S. Wauters and G.B. Marin, Kinetic modeling of coke formation during steam cracking, Ind. Eng. Chem. Res. 41 (2002), p. 2379.
13. _, Computer generation of a network of elementary steps for coke formation during the thermal cracking of hydrocarbons, Chem. Eng. J. 82 (2001), p. 267.
14. K.M. Van Geem, G.J. Heynderickx, and G.B. Marin, Effect of radial temperature profiles on yields in steam cracking, AIChE J. 50 (2004), p. 173.
15. L.J. Allamandola, Benzenoid hydrocarbons in space - the evidence and implications, Top. Curr. Chem. 153 (1990), p. 1.
16. A. Léger, L. d'Hendecourt, and N. Boccara, Polycyclic Aromatic Hydrocarbons and Astrophysics., in NATO ASI Series C ed.191, Reidel, Dordrecht, The Netherlands, 1987.
17. R.G. Harvey, Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, UK, 1991.
18. M.F. Denissenko et al., Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in P53, Science 274 (1996), p. 430.
19. M.L. Coote, Reliable theoretical procedures for the calculation of electronic-structure information in hydrogen abstraction reactions, J. Phys. Chem. A 108 (2004), p. 3865.
20. K. Hemelsoet et al., An assessment of theoretical procedures for predicting the thermochemistry and kinetics of hydrogen abstraction by methyl radical from benzene, J. Phys. Chem. A 110 (2006), p. 8942.
21. J.P. Leininger et al., Density functional theory investigation of competitive free-radical processes during the thermal cracking of methylated polyaromatics: Estimation of kinetic parameters, J. Phys. Chem. A 111 (2007), p. 3082.
22. D.A. Hrovat and W.T. Borden, Ab initio calculations of the relative resonance stabilization energies of allyl and benzyl radicals, J. Phys. Chem. 98 (1994), p. 10460.
23. M.J. Frisch et al., GAUSSIAN03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004
24. A.D. Becke, Density-functional thermochemistry. 3. The role of exact exchange, J. Chem. Phys. 98 (1993), p. 5648.
25. C. Lee, W. Yang, and R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density, Phys. Rev. B 37 (1988), p. 785.
26. A.P. Scott and L. Radom, Harmonic vibrational frequencies: An evaluation of Hartree - Fock Moller - Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors, J. Phys. Chem. 100 (1996), p. 16502.
27. A.D. Boese and J.M.L. Martin, Development of density functionals for thermochemical kinetics, J. Chem. Phys. 121 (2004), p. 3405.
28. A.G. Vandeputte et al., Theoretical study of the thermodynamics and kinetics of hydrogen abstractions from hydrocarbons, J. Phys. Chem. A 111 (2007), p. 11771.
29. (a) V. Van Speybroeck et al., Ab initio study on elementary radical reactions in coke formation, Int. J. Quantum Chem. 91 (2003), p. 384,
30. (b) P. Vansteenkiste, V. Van Speybroeck, G.B. Marin, M. Waroquier, Ab initio calculation of entropy and heat capacity of gas-phase n-alkanes using internal rotations, J. Phys. Chem. A 107 (2003), 3139.
31. (c) P. Vansteenkiste, D. Van Neck, V. Van Speybroeck and M. Waroquier, An extended hindered-rotor model with incorporation of Coriolis and vibrational - rotational coupling for calculating partition functions and derived quantities, J. Chem. Phys. 125 (2006), 049902.
32. C. Eckart, The penetration of a potential barrier by electrons, Phys. Rev. 35 (1930), p. 1303.
33. 3, OH, F): A surprising shortcoming of density functional theory, J. Phys. Chem. A 109 (2005), p. 7558.