Formation mechanism of polycyclic aromatic hydrocarbons beyond the second aromatic ring

Journal of Physical Chemistry A

Volumn 117, Issue 23, 2013, Pages 4794-4816

  Kislov, V V ^a   Sadovnikov, A I ^b   Mebel, A M ^a  

^a FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^b IVANOVO STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ABSTRACTING; ACETYLENE; ANTHRACENE; AROMATIZATION; ATOMS; CALCULATIONS; CARBON; COMBUSTION; HYDROGEN; KINETICS; LIGHTING; MOLECULES; RATE CONSTANTS;

ACETYLENE MOLECULES; DOMINANT REACTION PRODUCT; ENVIRONMENTAL MIXTURES; FORMATION MECHANISM; FUSED AROMATIC RINGS; HYDROGEN ABSTRACTION; INTERMOLECULAR HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON (PAH);

NAPHTHALENE;

EID: 84879054781     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp402481y     Document Type: Article

References (87)

1. Richter, H.; Howard, J. B. Formation of Polycyclic Aromatic Hydrocarbons and Their Growth to Soot-a Review of Chemical Reaction Pathways Prog. Energy Combust. Sci. 2000, 26, 565-608
2. Grimmer, G. Environmental Carcinogens: Polycyclic Aromatic Hydrocarbons: Chemistry, Occurrence, Biochemistry, Carcinogenity; CRC Press: Boca Raton, FL, 1983.
3. Ramdahl, T.; Bjorseth, J. Handbook of Polycyclic Aromatic Hydrocarbons, 2 nd ed.; Marcel Dekker: New York, 1985; pp 1-20.
4. Dias, J. R. Handbook of Polycyclic Hydrocarbons; Elsevier: Amsterdam, The Netherlands, 1987.
5. U.S. EPA (Environmental Protection Agency). Provisional Guidance for Quantitative Risk Assessment of Polycyclic Aromatic Hydrocarbons; Environmental Criteria and Assessment Office, Office of Health and Environmental Assessment: Cincinnati, OH, 1993.
6. Clement Associates. Development of Relative Potency Estimates for PAHs and Hydrocarbon Combustion Product Fractions Compared to Benzo[a]pyrene and Their Use in Carcinogenic Risk Assessments; ICF Clement Associates: Fairfax, VA, 1990.
7. Report on Carcinogens, 12 th ed.; Department of Health and Human Services, Public Health Service, National Toxicology Program: 2011. http://ntp.niehs.nih.gov/ntp/roc/twelfth/roc12.pdf.
8. U.S. Environmental Protection Agency: IntegratedRisk InformationSystem. http://www.epa.gov/NCEA/iris/.
9. ATSDR (Agency for Toxic Substances and Disease Registry). Toxicological Profile for Polycyclic Aromatic Hydrocarbons; U.S. Department of Health and Human Services, Public Health Service: Atlanta, GA, 1995. Available at: http://www.atsdr.cdc.gov/toxprofiles/tp69.pdf.
10. IARC (InternationalAgency for Research on Cancer). Printing Processes and Printing Inks, Carbon Black and Some Nitro Compounds. In: IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Vol. 65. Lyon, France, 1996.
11. IPCS/WHO (International Programme on Chemical Safety/World Health Organization). Selected Non-Heterocyclic Polycyclic Aromatic Hydrocarbons. Environmental Health Criteria 202; International Programme on Chemical Safety: 1998.
12. Bostrom, C.-E.; Gerde, P.; Hanberg, A.; Jernstrom, B.; Johansson, C.; Kyrklund, T.; Rannug, A.; Tornqvist, M.; Victorin, K.; Westerholm, R. Cancer Risk Assessment, Indicators, and Guidelines for Polycyclic Aromatic Hydrocarbons in the Ambient Air Environ. Health Perspect. 2002, 110, 451-488 (Pubitemid 34669811)
13. Larsen, J. C.; Larsen, P. B. Chemical Carcinogens. In Air pollution and health, Issues in Environmental Sciences and Technology, 10; Hester, R. E.; Harrison, R. M., Eds.; The Royal Society of Chemistry: Cambridge, U.K., 1998; pp 33-56.
14. Bartoszek, A. Chemical and Functional Properties of Food Components, 2 nd ed.; CRC Press: Boca Raton, FL, 2002; p 307.
15. Baek, S. O.; Field, R. A.; Goldstone, M. E.; Kirk, P. W.; Lester, J. N.; Perry, R. A Review of Atmospheric Polycyclic Aromatic Hydrocarbons: Sources, Fate and Behavior Water, Air, Soil Pollut. 1991, 60, 279-300
16. Harvey, G. R. In The Handbook of Environmental Chemistry; Neilson, A. H., Ed.; Springer: Berlin, 1998; Vol. 3-I, pp 1-54.
17. Howsam, M.; Jones, K. C. In The Handbook of Environmental Chemistry; Neilson, A. H., Ed.; Springer: Berlin, 1998; Vol. 3-I, pp 138-174.
18. NRC (National Research Council). Polycyclic Aromatic Hydrocarbons: Evaluation of Sources and Effects, Committee on Pyrene and Selected Analogues, Board on Toxicology and Environmental Health Hazard, Commission on Life Sciences; National Academy Press: Washington, DC, 1983.
19. Jemal, A.; Bray, F.; Center, M. M.; Ferlay, J.; Ward, E.; Forman, D. Global Cancer Statistics Ca-Cancer J. Clin. 2011, 61, 69-90
20. Frenklach, M.; Wang, H. Detailed Modeling of Soot Particle Nucleation and Growth Proc. Combust. Inst. 1991, 23, 1559-1566
21. Frenklach, M.; Clary, D. W.; Gardiner, W. C.; Stein, S. E. Detailed Kinetic Modeling of Soot Formation on Shock-Tube Pyrolysis of Acetylene Proc. Int. Symp. Combust. 1985, 20, 887-901
22. Wang, H.; Frenklach, M. Calculations of Rate Coefficients for the Chemically Activated Reactions of Acetylene with Vinylic and Aromatic Radicals J. Phys. Chem. 1994, 98, 11465-11489
23. Appel, J.; Bockhorn, H.; Frenklach, M. Kinetic Modeling of Soot Formation with Detailed Chemistry and Physics: Laminar Premixed Flames of C-2 Hydrocarbons Combust. Flame 2000, 121, 122-136
24. Frenklach, M. Reaction Mechanism of Soot Formation in Flames Phys. Chem. Chem. Phys. 2002, 4, 2028-2037
25. Bittner, J. D.; Howard, J. B. Composition Profiles and Reaction Mechanisms in a near-Sooting Premixed Benzene/Oxygen/Argon Flame Proc. Int. Symp. Combust. 1981, 18, 1105-1116 (Pubitemid 12466313)
26. Kislov, V. V.; Islamova, N. I.; Kolker, A. M.; Lin, S. H.; Mebel, A. M. Hydrogen Abstraction Acetylene Addition and Diels-Alder Mechanisms of PAH Formation: A Detailed Study Using First Principles Calculations J. Chem. Theory Comput. 2005, 1, 908-924
27. Tokmakov, I. V.; Lin, M. C. Reaction of Phenyl Radicals with Acetylene: Quantum Chemical Investigation of the Mechanism and Master Equation Analysis of the Kinetics J. Am. Chem. Soc. 2003, 125, 11397-11408 (Pubitemid 37108077)
28. Bauschlicher, C. W.; Ricca, A. Mechanisms for Polycyclic Aromatic Hydrocarbon (PAH) Growth Chem. Phys. Lett. 2000, 326, 283-287
29. Moriarty, N. W.; Brown, N. J.; Frenklach, M. Hydrogen Migration in the Phenylethen-2-yl Radical J. Phys. Chem. A 1999, 103, 7127-7135 (Pubitemid 129579387)
30. Roesler, J. F.; Martinot, S.; McEnally, C. S.; Pfefferle, L. D.; Delfau, J. -L.; Vovelle, C. Investigating the Role of Methane on the Growth of Aromatic Hydrocarbons and Soot in Fundamental Combustion Processes Combust. Flame 2003, 134, 249-260 (Pubitemid 37025922)
31. Melton, T. R.; Inal, F.; Senkan, S. M. The Effects of Equivalence Ratio on the Formation of Polycyclic Aromatic Hydrocarbons and Soot in Premixed Ethane Flames Combust. Flame 2000, 121, 671-678
32. Vincitore, A. M.; Senkan, S. M. Polycyclic Aromatic Hydrocarbon Formation in Opposed Flow Diffusion Flames of Ethane Combust. Flame 1998, 114, 259-266 (Pubitemid 28211285)
33. Slavinskaya, N. A.; Riedel, U.; Dworkin, S. B.; Thomson, M. J. Detailed Numerical Modeling of PAH Formation and Growth in Non-Premixed Ethylene and Ethane Flames Combust. Flame 2012, 159, 979-995
34. Olten, N.; Senkan, S. Formation of Polycyclic Aromatic Hydrocarbons in an Atmospheric Pressure Ethylene Diffusion Flame Combust. Flame 1999, 118, 500-507 (Pubitemid 29275225)
35. Wang, H.; Frenklach, M. A Detailed Kinetic Modeling Study of Aromatics Formation in Laminar Premixed Acetylene and Ethylene Flames Combust. Flame 1997, 110, 173-221 (Pubitemid 27273036)
36. Granata, S.; Faravelli, T.; Ranzi, E.; Olten, N.; Senkan, S. Kinetic Modeling of Counterflow Diffusion Flames of Butadiene Combust. Flame 2002, 131, 273-284 (Pubitemid 35341759)
37. Marinov, N. M.; Pitz, W. J.; Westbrook, C. K.; Vincitore, A. M.; Castaldi, M. J.; Senkan, S. M.; Melius, C. F. Aromatic and Polycyclic Aromatic Hydrocarbon Formation in a Laminar Premixed n-Butane Flame Combust. Flame 1998, 114, 192-213 (Pubitemid 28211281)
38. Inal, F.; Senkan, S. M. Effects of Equivalence Ratio on Species and Soot Concentrations in Premixed n-Heptane Flames Combust. Flame 2002, 131, 16-28 (Pubitemid 35333296)
39. Richter, H.; Grieco, W. J.; Howard, J.-B. Formation Mechanism of Polycyclic Aromatic Hydrocarbons and Fullerenes in Premixed Benzene Flames Combust. Flame 1999, 119, 1-22 (Pubitemid 29398490)
40. Golea, D.; Rezgui, Y.; Guemini, M.; Hamdane, S. Reduction of PAH and Soot Precursors in Benzene Flames by Addition of Ethanol J. Phys. Chem. A 2012, 116, 3625-3642
41. Tian, Z.; Pitz, W. J.; Fournet, R.; Glaude, P.-A.; Battin-Leclerc, F. A Detailed Kinetic Modeling Study of Toluene Oxidation in a Premixed Laminar Flame Proc. Combust. Inst. 2011, 33, 233-241
42. Raj, A.; Prada, I. D. C.; Amer, A. A.; Chung, S. H. A Reaction Mechanism for Gasoline Surrogate Fuels for Large Polycyclic Aromatic Hydrocarbons Combust. Flame 2012, 159, 500-515
43. Wang, Z.; Wang, J.; Richter, H.; Howard, J.-B.; Carlson, J.; Levendis, Y. A. Comparative Study on Polycyclic Aromatic Hydrocarbons, Light Hydrocarbons, Carbon Monoxide, and Particulate Emissions from the Combustion of Polyethylene, Polystyrene, and Poly(vinyl chloride) Energy Fuels 2003, 17, 999-1013
44. Castro, D.; Slezakova, K.; Delerue-Matos, C.; Alvim-Ferraz, M.; Morais, S.; Pereira, M. Polycyclic Aromatic Hydrocarbons in Gas and Particulate Phases of Indoor Environments Influenced by Tobacco Smoke: Levels, Phase Distributions, and Health Risks Atmos. Environ. 2011, 45, 1799-1808
45. Hoh, E.; Hunt, R. N.; Quintana, P. J. E.; Zakarian, J. M.; Chatfield, D. A.; Wittry, B. C.; Rodriguez, E.; Matt, G. E. Environmental Tobacco Smoke as a Source of Polycyclic Aromatic Hydrocarbons in Settled Household Dust Environ. Sci. Technol. 2012, 46, 4174-4183
46. Bradley, L. J. N.; Magee, B. H.; Allen, S. L. Background Levels of Polycyclic Aromatic Hydrocarbons (PAH) and Selected Metals in New England Urban Soils J. Soil Contam. 1994, 4, 349-361
47. Jensen, H.; Reimann, C.; Finne, T. E.; Ottesen, R. T.; Arnoldussen, A. PAH Concentrations and Compositions in the Top 2 cm of Forest Soils along a 120 km Long Transect through Agricultural Areas, Forests and the City of Oslo, Norway Environ. Pollut. 2007, 145, 829-838 (Pubitemid 46149159)
48. Harman, K.; Thomas, K. V.; Tollefsen, K. E.; Meier, S.; Boyum, O.; Grung, M. Monitoring the Freely Dissolved Concentrations of Polycyclic Aromatic Hydrocarbons (PAH) and Alkylphenols (AP) around a Norwegian Oil Platform by Holistic Passive Sampling Mar. Pollut. Bull. 2009, 58, 1671-1679
49. Kim, D.; Young, T. M. Significance of Indirect Deposition on Wintertime PAH Concentrations in an Urban Northern California Creek Environ. Eng. Sci. 2009, 26, 269-277
50. Anyakora, C.; Ogbeche, A.; Palmer, P.; Coker, H. Determination of Polynuclear Aromatic Hydrocarbons in Marine Samples of Siokolo Fishing Settlement J. Chromatogr., A 2005, 1073, 323-330 (Pubitemid 40544506)
51. Watts, A. W.; Ballestero, T. P.; Gardner, K. H. Soil and Atmospheric Inputs to PAH Concentrations in Salt Marsh Plants Water, Air, Soil Pollut. 2008, 189, 253-263
52. Gmeiner, G.; Stehlik, G.; Tausch, H. Determination of Seventeen Polycyclic Aromatic Hydrocarbons in Tobacco Smoke Condensate J. Chromatogr., A 1997, 767, 163-169 (Pubitemid 27199254)
53. Sepetdjian, E.; Shihadeh, A.; Saliba, N. A. Measurement of 16 Polycyclic Aromatic Hydrocarbons in Narghile Waterpipe Tobacco Smoke Food Chem. Toxicol. 2008, 46, 1582-1590
54. Martorell, I.; Perello, G.; Marti-Cid, R.; Castell, V.; Llobet, J.-M.; Domingo, J. L. Polycyclic Aromatic Hydrocarbons (PAH) in Foods and Estimated PAH Intake by the Population of Catalonia, Spain: Temporal Trend Environ. Int. 2010, 36, 424-432
55. Perello, G.; Marti-Cid, R.; Castell, V.; Llobet, J.-M.; Domingo, J. L. Concentrations of Polybrominated Diphenyl Ethers, Hexachlorobenzene and Polycyclic Aromatic Hydrocarbons in Various Foodstuffs before and after Cooking Food Chem. Toxicol. 2009, 47, 709-715
56. Stumpe-Viksna, I.; Bartkevics, V.; Kukare, A.; Morozovs, A. Polycyclic Aromatic Hydrocarbons in Meat Smoked with Different Types of Wood Food Chem. 2008, 110, 794-797
57. Lin, G.-F.; Weigel, S.; Tang, B.; Schulz, C.; Shen, J.-H. The Occurrence of Polycyclic Aromatic Hydrocarbons in Peking Duck: Relevance to Food Safety Assessment Food Chem. 2011, 129, 524-527
58. Suchanova, M.; Hajslova, J.; Tomaniova, M.; Kocourek, V.; Babicka, L. Polycyclic Aromatic Hydrocarbons in Smoked Cheese J. Sci. Food Agric. 2008, 88, 1307-1317 (Pubitemid 351752296)
59. Moret, S.; Purcaro, G.; Conte, L. S. Polycyclic Aromatic Hydrocarbons in Vegetable Oils from Canned Foods Eur. J. Lipid Sci. Technol. 2005, 107, 488-496 (Pubitemid 41188573)
60. Orecchio, S.; Papuzza, V. Levels, Fingerprint and Daily Intake of Polycyclic Aromatic Hydrocarbons (PAHs) in Bread Baked Using Wood as Fuel J. Hazard. Mater. 2009, 164, 876-883
61. Orecchio, S.; Ciotti, V. P.; Culotta, L. Polycyclic Aromatic Hydrocarbons (PAHs) in Coffee Brew Samples: Analytical Method by GC-MS, Profile, Levels and Sources Food Chem. Toxicol. 2009, 47, 819-826
62. Chatonnet, P.; Escobessa, J. Impact of Toasting Oak Barrels on the Presence of Polycyclic Aromatic Hydrocarbons in Wine J. Agric. Food Chem. 2007, 55, 10351-10358
63. Becke, A. D. Density-Functional Thermochemistry. I. The Effect of the Exchange-Only Gradient Correction J. Chem. Phys. 1992, 96, 2155-2160
64. Becke, A. D. Density-Functional Thermochemistry. II. The Effect of the Perdew-Wang Generalized-Gradient Correlation Correction J. Chem. Phys. 1992, 97, 9173-9177
65. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
66. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
67. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-3 Theory Using Density Functional Geometries and Zero-Point Energies J. Chem. Phys. 1999, 110, 7650-7657
68. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Baboul, A. G.; Pople, J. A. Gaussian-3 Theory Using Coupled Cluster Energies Chem. Phys. Lett. 1999, 314, 101-107 (Pubitemid 129556745)
69. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. Gaussian-3 (G3) Theory for Molecules Containing First and Second-Row Atoms J. Chem. Phys. 1998, 109, 7764-7776 (Pubitemid 128678347)
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
71. Werner, H.-J.; Knowles, P. J.; Amos, R. D.; Bernhardsson, A.; Berning, A.; Celani, P.; Cooper, D. L.; Deegan, M. J. O.; Dobbyn, A. J.; Eckert, F.; Hampel, C.; Hetzer, G.; MOLPRO, a package of ab initio programs, version 2002.1.
72. Kislov, V. V.; Mebel, A. M. Ab Initio/RRKM-ME Study on the Mechanism and Kinetics of the Reaction of Phenyl Radical with 1,2-Butadiene J. Phys. Chem. A 2010, 114, 7682-7692
73. Kislov, V. V.; Mebel, A. M.; Aguilera-Iparraguirre, J.; Green, W. H. The Reaction of Phenyl Radical with Propylene as a Possible source of indene and other polycyclic aromatic hydrocarbons: An Ab Initio/RRKM-ME Study J. Phys. Chem. A 2012, 116, 4176-4191
74. Glasstone, S.; Laidler, K. J.; Eyring, H. The Theory of Rate Processes; McGraw-Hill: New York, 1941.
75. Steinfield, J.; Francisco, J.; Hase, W. Chemical Kinetics and Dynamics; Prentice-Hall: Englewood Cliffs, NJ, 1989.
76. Eyring, H.; Lin, S. H.; Lin, S. M. Basic Chemical Kinetics; Wiley: New York, 1980.
77. Robinson, P. J.; Holbrook, K. A. Unimolecular Reactions; Wiley: New York, 1972.
78. Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; Blackwell Science: Malden, MA; 1990; ISBN 9780632027491.
79. Hairer, E.; Nørsett, S. P.; Wanner, G. Solving Ordinary Differential Equations I: Nonstiff Problems, 2 nd ed.; Springer-Verlag: Berlin, 1993. Hairer, E.; Wanner, G. Solving Ordinary Differential Equations II: Stiff and Differential-Algebraic Problems, 2 nd ed.; Springer-Verlag: Berlin, 1996.
80. Subroutines for solving differential equations using linear multistep methods. http://www.netlib.org/ode/.
81. Frenklach, M.; Moriarty, N. W.; Brown, N. J. Hydrogen Migration in Polyaromatic Growth Proc. Combust. Inst. 1998, 27, 1655-1661
82. Frenklach, M.; Ping, J. On the Role of Surface Migration in the Growth and Structure of Graphene Layers Carbon 2004, 42, 1209-1212
83. Frenklach, M.; Schuetz, C. A.; Ping, J. Migration Mechanism of Aromatic-Edge Growth Proc. Combust. Inst. 2005, 30, 1389-1396
84. Whitesides, R.; Kollias, A. C.; Domin, D.; Lester, W. A., Jr.; Frenklach, M. Graphene Layer Growth: Collision of Migrating Five-Member Rings Proc. Combust. Inst. 2007, 31, 539-546 (Pubitemid 47424426)
85. Whitesides, R.; Domin, D.; Salomon-Ferrer, R.; Lester, W. A., Jr.; Frenklach, M. Graphene Layer Growth Chemistry: Five- and Six-Member Ring Flip Reaction J. Phys. Chem. A 2008, 112, 2125-2130
86. Whitesides, R.; Domin, D.; Salomon-Ferrer, R.; Lester, W. A., Jr.; Frenklach, M. Embedded-Ring Migration on Graphene Zigzag Edge Proc. Combust. Inst. 2009, 32, 577-583
87. Whitesides, R.; Frenklach, M. Detailed Kinetic Monte Carlo Simulations of Graphene-Edge Growth J. Phys. Chem. A 2010, 114, 689-703