Formation of polycyclic aromatic hydrocarbons and their growth to soot-a review of chemical reaction pathways

Progress in Energy and Combustion Science

Volumn 26, Issue 4, 2000, Pages 565-608

  Richter, H ^a   Howard, J B ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AROMATIC HYDROCARBONS; CARBONIZATION; COAGULATION; FULLERENES; NUCLEATION; REACTION KINETICS; SOOT;

CHEMICAL REACTION PATHWAYS; CYCLOPENTADIENYL; POLYCYCLIC AROMATIC HYDROCARBONS; PROPARGYL;

COMBUSTION;

EID: 0033721554     PISSN: 03601285     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0360-1285(00)00009-5     Document Type: Review

References (257)

1. Dockery DW, Pope CA, Xu X, Spengler JD, Ware JH, Fay ME, Ferris BG, Speizer FE. New Engl J Med 1993;329: 1753-9.
2. Siegmann K, Siegmann HC. Molecular precursor of soot and quantification of the associated health risk. In: Morán-López, editor. Current problems in condensed matter. New York: Plenum Press, 1998. p. 143-60.
3. Miller FJ, Gardner DE, Graham JA, Lee Jr RE, Wilson WE, Bachmann JD. Size considerations for establishing a standard for inhalable particles. J Air Pollut Control Assoc 1979;29:610-5.
4. Allen JO, Dookeran NM, Smith KA, Sarofim AF, Taghizadeh K, Lafleur AL. Measurement of polycyclic aromatic hydrocarbons associated with size-segregated atmospheric aerosols in Massachusetts. Environ Sci Technol 1996;30:1023-31.
5. Kaden DA, Hites RA, Thilly WG. Mutagenicity of soot and associated polycyclic aromatic hydrocarbons to Salmonella typhimurium. Cancer Res 1979;39:4152-9.
6. Wood AW, Levin W, Chang RL, Huang M-T, Ryan DE, Thomas PE, Lehr RE, Kumar S, Koreeda M, Akagi H, Utah Y, Dansette P, Yagi H, Jerina DM, Conney AH. Mutagenicity and tumor-initiating activity of cyclopenta[c,d]pyrene and structurally related compounds. Cancer Res 1980;40:642-9.
7. Fu PP, Beland FA, Yang SK. Cyclopenta-polycyclic aromatic hydrocarbons: potential carcinogens and mutagens. Carcinogenesis 1980;1:725-7.
8. Busby WF, Stevens EK, Kellenbach ER, Cornelisse J, Lugtenburg J. Dose-response relationships of the tumorigenicity of cyclopenta[c,d]pyrene, benzo[a]pyrene and 6 nitrochrysene in a newborn mouse lung adenoma bioassay. Carcinogenesis 1988;9:741-6.
9. Lafleur AL, Longwell JP, Shirnamé-Moré L, Monchamp PA, Peters WA, Plummer EF. Chemical characterization and bacterial mutagenicity testing of ethylene combustion products from a jet-stirred/plug-flow reactor. Energy & Fuels 1990;4:307-19.
10. Durant JL, Busby WF, Lafleur AL, Penman BW, Crespi CL. Human cell mutagenicity of oxygenated, nitrated and unsubstituted polycyclic aromatic hydrocarbons associated with urban aerosols. Mutation Res 1996;371:123-57.
11. Denissenko MF, Pao A, Tang M-S, Pfeifer GP. Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in P53. Science 1996;274:430-2.
12. Lahaye J, Prado G, editors. Soot in combustion systems and its toxic properties. New York: Plenum Press, 1981.
13. Siegla DC, Smith GW, editors. Particulate carbon formation during combustion. New York: Plenum Press, 1981.
14. Jander H, Wagner HGg, editors. Soot formation in combustion. Göttingen: Vandenhoeck & Ruprecht, 1990.
15. Bockhorn H, editor. Soot formation in combustion: mechanisms and models. Berlin: Springer, 1994.
16. Clarke AE, Hunter TC, Garner FH. The tendency to smoke of organic substances on burning, Part I. J Inst Petrol 1946;32: 627-42.
17. Schug KP, Manheimer-Timnat Y, Yaccarino P, Glassman I. Sooting behaviour of gaseous hydrocarbon diffusion flames and the influence of additives. Combust Sci Technol 1980;22:235-50.
18. Haynes BS, Wagner HGg. Soot formation. Prog Energy Combust Sci 1981;7:229-73.
19. Street JC, Thomas A. Carbon formation in pre-mixed flames. Fuel 1955;34:4-36.
20. Palmer HB, Cullis CF. The formation of carbon from gases. In: Walker PL, editor. Chemistry and physics of carbon, vol. 1. New York: Marcel Dekker, 1965. p. 265-325.
21. Homann KH. Carbon formation in premixed flames. Combust Flame 1967;11:265-87.
22. Homann KH, Wagner HGg. Chemistry of carbon formation in flames. Proc Roy Soc A 1968;307:141-52.
23. Wagner HGg. Soot formation in combustion. Seventeenth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1979. p. 3-19.
24. Glassman I. Soot formation in combustion processes, Twenty-second Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1988. p. 295-311.
25. Smith OI. Fundamentals of soot formation in flames with application to diesel engine particulate emissions. Prog Energy Combust Sci 1981;7:275-91.
26. Warnatz J. Calculation of the structure of laminar flat flames I: flame velocity of freely propagating ozone decomposition flames. Ber Bunsenges Phys Chem 1978;82:193-200.
27. 2 system. Ber Bunsenges Phys Chem 1979;83:950-7.
28. Warnatz J. The structure of laminar alkane-, alkene-, and acetylene flames, Eighteenth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1981. p. 369-84.
29. Kee RJ, Rupley FM, Miller JA. CHEMKIN-II: a Fortran chemical kinetics package for the analysis of gas-phase chemical kinetics. Sandia Report SAND89-8009, Sandia National Laboratory, Livermore, CA, 1989.
30. Kee RJ, Grcar JF, Smooke MD, Miller JA. a Fortran program for modeling steady laminar one-dimensional premixed flames. Sandia Report SAND85-8240, 1985.
31. Glarborg P, Kee RJ, Grcar JF, Miller JA. PSR: a Fortran program for modeling well-stirred reactors. Sandia Report SAND86-8209, 1986.
32. Lutz AE, Kee RJ, Miller JA. SENKIN: a Fortran program for predicting homogeneous gas phase chemical kinetics with sensitivity analysis. Sandia Report SAND87-8248, 1988.
33. Mitchell RE, Kee RJ. A general-purpose computer code for predicting chemical behavior behind incident and reflected shocks. Sandia Report SAND82-8205, 1982.
34. Westbrook CK, Dryer FL. Chemical kinetics and modeling of combustion processes. Eighteenth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1981. p. 749-67.
35. 2-Ar flame. Twenty-third Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1990. p. 1567-72.
36. Lindstedt P. Modeling of the chemical complexities of flames. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 269-85.
37. Gerhardt Ph, Löffler KH, Homann KH. Polyhedral carbon ions in hydrocarbon flames. Chem Phys Lett 1987;137:306-9.
38. 70 in flames. Nature 1991;352:139-41.
39. Howard JB, Das Chowdhury K, Vander Sande JB. Carbon shells in flames. Nature 1994;370:603.
40. Arnott N. Elements of physics or natural philosophy. 5th ed., vol. 2. London: Longman, Rees, Orme, Brown and Green, 1833. p. 146-8.
41. Berthelot M. Sur la Formation des Carbures Pyrogénés. Ann Chim Phys 4ème Série 1869;16:143-8.
42. Lewes VB. The action of heat upon ethylene. Proc Roy Soc 1894;55:90-107.
43. Gaydon AG. Spectroscopy and combustion theory. London: Chapman and Hall, 1948.
44. Rummel K, Veh P-O. Die Strahlung leuchtender Flammen. Erster Teil: Schrifttumsgrundlagen, Arbeitshypothesen und Vorversuche. Arch Eisenhüttenw 1941;14:489-99.
45. Bradley JN, Kistiakowsky GB. Shock wave studies by mass spectrometry. II. Polymerization and oxidation of acetylene. J Chem Phys 1961;35:264-70.
46. Homann KH, Wagner HGg. Untersuchung des Reaktionsablaufs in fetten Kohlenwasserstoff-Sauerstoff-Flammen II. Versuche an rußenden Acetylen-Sauerstoff-Flammen bei niedrigem Druck. Ber Bunsenges Phys Chem 1965;69:20-35.
47. Bonne U, Homann KH, Wagner HGg. Carbon formation in premixed flames. Tenth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1965. p. 503-12.
48. Bonne U, Wagner HGg. Untersuchung des Reaktionsablaufs in fetten Kohlenwasserstoff-Sauerstoff-Flammen III. Optische Untersuchungen an rußenden Flammen. Ber Bunsenges Phys Chem 1965;69:35-48.
49. Homann KH, Wagner HGg. Some new aspects of the mechanism of carbon formation in premixed flames. Eleventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1967. p. 371-9.
50. Crittenden BD, Long R. Formation of polycyclic aromatics in rich premixed acetylene and ethylene flames. Combust Flame 1973;20:359-68.
51. Stehling FC, Frazee JD, Anderson RC. Mechanisms of nucleation in carbon formation. Eighth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1962. p. 774-84.
52. Berthelot MPE. Les carbures d'hydrogène. Paris: Gauthier- Villars, 1901.
53. Fenimore CP, Jones GW, Moore GE. Carbon formation in quenched flat flames at 1600 K. Sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1957. p. 242-7.
54. Berthelot M. Théorie des corps pyrogénés. Ann Chim Phys 4ème Série 1866;9:469-80.
55. Bone WA, Coward HF. The thermal decomposition of hydrocarbons. Part I. [Methane, ethane, ehtylene, and acetylene]. J Chem Soc 1908;93:1197-225.
56. Davidson JG. The formation of aromatic hydrocarbons from natural gas condensate. Ind Engng Chem 1918;10:901-10.
57. Hague EN, Wheeler RV. The mechanism of thermal decomposition of normal paraffins. J Chem Soc (London) 1929:378-93.
58. Hurd CD, Spence LU. The pyrolysis of hydrocarbons: isobutylene. J Am Chem Soc 1929;51:3561-72.
59. Bockhorn H, Fetting F, Wenz HW. Investigation of the formation of high molecular hydrocarbons and soot in premixed hydrocarbon-oxygen flames. Ber Bunsenges Phys Chem 1983;87:1067-73.
60. Cole JA, Bittner JD, Longwell JP, Howard JB. Formation mechanisms of aromatic compounds in aliphatic flames. Combust Flame 1984;56:51-70.
61. Ebert KH, Ederer HJ, Stabel U. Modeling studies of the homogeneous formation of aromatic compounds in the thermal composition of n-hexane. Ber Bunsenges Phys Chem 1983;87:1036-9.
62. Weissman M, Benson SW. Pyrolysis of methyl chloride: a pathway in the chlorine-catalyzed polymerization of methane. Int J Chem Kinet 1984;16:307-33.
63. Frenklach M, Warnatz J. Detailed modeling of PAH profiles in a sooting low-pressure acetylene flame. Combust Sci Technol 1987;51:265-83.
64. Frenklach M, Clary DW, Yuan T, Gardiner Jr WC, Stein SE. Mechanism of soot formation in acetylene-oxygen mixtures. Combust Sci Technol 1986;50:79-115.
65. Colket MB. The pyrolysis of acetylene and vinylacetylene in a single-pulse shock tube. Twenty-first Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1986. p. 851-64.
66. Frenklach, M., Clary, D.W., Gardiner, W.C., Stein, S.E., Detailed kinetic modeling of soot formation in shock-tube pyrolysis of acetylene. Twentieth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1984. p. 887-901.
67. Harris SJ, Weiner AM, Blint RJ. Formation of small aromatic molecules in a sooting ethylene flame. Combust Flame 1988;72:91-109.
68. Warnatz J. Chemistry of high temperature combustion of alkanes up to octane. Twentieth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1984. p. 845-56.
69. Bittner JD, Howard JB. Composition profiles and reaction mechanisms in a near-sooting premixed benzene/oxygen/argon flame. Eighteenth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1981. p. 1105-16.
70. Kiefer JH, Kapsalis SA, Al-Alami MZ, Budach KA. The very high temperature pyrolysis of ethylene and the subsequent reactions of product acetylene. Combust Flame 1983;51:79-93.
71. 6 and chlorobenzene behind shock waves. J Phys Chem 1984;88:5990-5.
72. Westmoreland PR, Dean AM, Howard JB, Longwell JP. Forming benzene in flames by chemically activated isomerization. J Phys Chem 1989;93:8171-80.
73. Westmoreland PR, Howard JB, Longwell JP. Tests of published mechanisms by comparison with measured laminar flame structure in fuel-rich acetylene combustion. Twenty-first Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1986. p. 773-82.
74. Dean AM. Predictions of pressure and temperature effects upon radical addition and recombination reactions. J Phys Chem 1985;89:4600-8.
75. 2-Ar flame. Twenty-second Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1988. p. 313-22.
76. Westmoreland PR. Comment to Bastin et al. (Ref. [75]). Twenty-second Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1988. p. 321.
77. Miller JA, Melius CF. Kinetic and thermodynamic issues in the formation of aromatic compounds in flames of aliphatic fuels. Combust Flame 1992;91:21-39.
78. 2/Ar flames. Twenty-third Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1990. p. 187-94.
79. Kee RJ, Rupley FM, Miller JA. The CHEMKIN thermodynamic data base. Sandia Technical Report SAND87-8215, Sandia National Laboratories, Livermore, CA, April 1987.
80. Hurd CD, Macon AR, Simon JI, Levetan RV. Pyrolytic formation of arenes. I. Survey of general principles and findings. J Am Chem Soc 1962;84:4509-15.
81. Wu CH, Kern RD. Shock tube study of allene pyrolysis. J Phys Chem 1987;91:6291-6.
82. Hidaka Y, Nakamura T, Miyauchi A, Shiraishi T, Kawano H. Thermal decomposition of propyne and allene in shock waves. Int J Chem Kinet 1989;21:643-66.
83. Kern RD, Singh HJ, Wu CH. Thermal decomposition of 1,2-butadiene. Int J Chem Kinet 1988;20:731-47.
84. Henry TJ, Bergman RG. Independent mechanisms in the thermal rearrangement of mono- and bicyclic 3,4-bismethylenecyclobutene derivatives. J Am Chem Soc 1972;94: 5103-5.
85. Farmer JB, Lossing FP. Free radicals by mass spectrometry VII. The ionization potentials of ethyl, isopropyl, and propargyl radicals and the appearance potentials of the radical ions in some derivatives. Can J Chem 1955;33:861-9.
86. 6 isomers by recombination of propynyl in the system sodium vapour/propynylhalide. Z Phys Chem (Neue Folge) 1989;161:19-34.
87. 6 hydrocarbon species. Twenty-fourth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1992. p. 621-8.
88. 2 reaction. J Chem Phys 1994;101:3923-7.
89. 4 flame. Combust Sci Technol 1995;110/111:249-76.
90. 2/Ar flame. Combust Flame 1996;105:451-61.
91. Stein SE, Walker JA, Suryan MM, Fahr A. A new pathway to benzene in flames. Twenty-third Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1990. p. 85-90.
92. Marinov NM, Pitz WJ, Westbrook CK, Castaldi MJ, Senkan SM. Modeling of aromatic and polycyclic aromatic hydrocarbon formation in premixed methane and ethane flames. Combust Sci Technol 1996;116/117:211.
93. 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.
94. 4 hydrocarbons. Combust Flame 1998;113:620-3.
95. Lindstedt RP, Skevis G. Benzene formation chemistry in premixed 1,3-butadiene flames. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 703-9.
96. Dente M, Ranzi E, Goossens AG. Detailed prediction of olefin yields from hydrocarbon pyrolysis through a fundamental simulation model (SPYRO). Computer Chem. Engng 1979;3:61-75.
97. Faravelli T, Goldaniga A, Ranzi E. The kinetic modeling of soot precursors in ethylene flames. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1489-95.
98. 5 cyclopentadienyl moiety. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 685-92.
99. 5 reaction: a potential source of benzene at high temperatures. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 521-6.
100. Miller JA. Theory and modeling in combustion chemistry. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 461-80.
101. Atkinson DB, Hudgens JW. Rate coefficients for the propargyl radical self-reaction and oxygen addition reaction measured using ultraviolet cavity ring-down spectroscopy. J Phys Chem A 1999;103:4242-52.
102. 3. J Phys Chem 1994;98:7029-35.
103. Dean AM. Detailed kinetic modeling of autocatalysis in methane pyrolysis. J Phys Chem 1990;94:1432-9.
104. Castaldi MJ, Marinov NM, Melius CF, Huang J, Senkan SM, Pitz WJ, Westbrook CK. Experimental and modeling investigation of aromatic and polycyclic aromatic hydrocarbon formation in a premixed ethylene flame. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 693-702.
105. Marinov NM, Pitz WJ, Westbrook CK, Vincitore AM, Castaldi MJ, Senkan SM, Melius CF. Aromatic and polycyclic aromatic hydrocarbon formation in a laminar premixed n-butane flame. Combust Flame 1998;114:192-213.
106. Richter H, Grieco WJ, Howard JB. Formation mechanism of polycyclic aromatic hydrocarbons and fullerenes in premixed benzene flames. Combust Flame 1999;119:1-22.
107. Olivella S, Solé A, García-Raso A. Ab initio calculations of the potential surface for the thermal decomposition of the phenoxyl radical. J Phys Chem 1995;99:10549-56.
108. Liu R, Morokuma K, Mebel AM, Lin MC. Ab initio study of the mechanism for the thermal decomposition of the phenoxy radical. J Phys Chem 1996;100:9314-22.
109. Frank P, Herzler J, Just Th, Wahl C. High-temperature reactions of phenyl oxidation. Twenty-fifth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1994. p. 833-40.
110. Buth R, Hoyermann K, Seeba J. Reactions of phenoxy radicals in the gas phase. Twenty-fifth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1994. p. 841-9.
111. Horn C, Roy K, Frank P, Just Th. Shock-tube study on the high-temperature pyrolysis of phenol. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 321-8.
112. Alzueta MU, Oliva M, Glarborg P. Parabenzoquinone pyrolysis and oxidation in a flow reactor. Int J Chem Kinet 1998;30:683-97.
113. Roy K, Horn C, Frank P, Slutsky VG, Just Th. High-temperature investigations on the pyrolysis of cyclopentadiene, Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 329-36.
114. Homann KH. Formation of large molecules, particulates and ions in premixed hydrocarbon flames: progress and unresolved questions. Twentieth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1984. p. 857-70.
115. Howard JB. Carbon addition and oxidation reactions in heterogeneous combustion and soot formation. Twenty-third Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1990. p. 1107-27.
116. Jensen DE. Prediction of soot formation rates: a new approach. Proc Roy Soc London A 1974;338:375-396.
117. 4-air flames. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 2319-26.
118. Kazakov A, Frenklach M. On the relative contribution of acetylene and aromatics to soot particle surface growth. Combust Flame 1998;112:270-4.
119. Levy M, Szwarc M. Reactivities of aromatic hydrocarbons toward methyl radicals. J Am Chem Soc 1955;77:1949-55.
120. Prado GP, Lee ML, Hites RA, Hoult DP, Howard JB. Soot and hydrocarbon formation in a turbulent diffusion flame. Sixteenth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1977. p. 649-61.
121. 160 polycyclic aromatic hydrocarbons by atmospheric-pressure chemical ionization mass spectrometry with liquid introduction via heated nebulizer interface. J Am Soc Mass Spectrom 1996;7:276-86.
122. Lafleur AL, Howard JB, Plummer E, Taghizadeh K, Necula A, Scott LT, Swallow KC. Identification of some novel cyclopenta-fused polycyclic aromatic hydrocarbons in ethylene flames. Polycyc Arom Compound 1998;12:223-37.
123. Wornat MJ, Vernaglia BA, Lafleur AL, Plummer EF, Taghizadeh K, Nelson PF, Li C-Z, Necula A, Scott LT. Cyclopenta-fused polycyclic aromatic hydrocarbons from brown coal pyrolysis. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1677-86.
124. Frenklach M, Ramachandra MK, Matula RA. Soot formation in shock-tube oxidation of hydrocarbons. Twentieth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1984. p. 871-8.
125. Frenklach M, Clary DW, Gardiner WC, Stein SE. Effect of fuel structure on pathways to soot. Twenty-first Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1986. p. 1067-76.
126. Frenklach M, Wang H. Detailed modeling of soot particle nucleation and growth. Twenty-third Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1990. p. 1559-66.
127. Kazakov A, Wang H, Frenklach M. Detailed modeling of soot formation in laminar premixed ethylene flames at a pressure of 10 bar. Combust Flame 1995;100:111-20.
128. 4 flat flames at elevated pressure. Twenty-third Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1990. p. 1581-7.
129. Krestinin AV. Polyyne model of soot formation. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1557-63.
130. Miller JH, Smyth KC, Mallard WG. Calculations of the dimerization of aromatic hydrocarbons: implications for soot formation. Twentieth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1984. p. 1139-47.
131. Brown NJ, Revzan KL, Frenklach M. Detailed kinetic modeling of soot formation in ethylene/air mixtures reacting in a perfectly stirred reactor. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1573-80.
132. Pope CJ, Howard JB. Simultaneous particle and molecule modeling (SPAMM): an approach for combining sectional aerosol equations and elementary gas-phase reactions. Aerosol Sci Technol 1997;27:73-94.
133. Kiefer JH, Mizerka LJ, Patel MR, Wei H-C. A shock tube study of major pathways in the high-temperature pyrolysis of benzene. J Phys Chem 1985;89:2013-9.
134. Nicovich JM, Ravishankara AR. Reaction of hydrogen atom with benzene: kinetics and mechanism. J Phys Chem 1984;88:2534-41.
135. 6 + H reactions. J Phys Chem A 1997;101:3189-96.
136. Sauer MC, Mani I. Rate constants and transient spectra in the gas-phase reactions of hydrogen atoms. Substituents effects in monosubstituted benzenes. J Phys Chem 1970;74:59-63.
137. Cioslowski J, Liu G, Martinov M, Piskorz P, Moncrieff D. Energetics and site specificity of the homolytic C-H bond cleavage in benzenoid hydrocarbons: an ab initio electronic structure study. J Am Chem Soc 1996;118:5261-4.
138. 3P) and benzene at high temperatures. Z Phys Chem (Neue Folge) 1989;165:1-7.
139. 6 reaction over a wide temperature range. J Phys Chem 1991;95:8745-8.
140. 6 over 790-1410 K. J Phys Chem 1985;89:3556-61.
141. Fahr A, Stein SE. Reactions of vinyl and phenyl radicals with ethyne, ethene and benzene. Twenty-second Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1988. p. 1023-9.
142. Heckmann E, Hippler H, Troe J. High-temperature reactions and thermodynamic properties of phenyl radicals. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 543-50.
143. Yu T, Lin MC, Melius CF. Absolute rate constant for the reaction of phenyl radical with acetylene. Int J Chem Kinet 1994;26:1095-104.
144. Wang H, Frenklach M. Calculations of rate coefficients for the chemically activated reactions of acetylene with vinylic and aromatic radicals. J Phys Chem 1994;98:11465-89.
145. D'Anna A, Violi A. A kinetic model for the formation of aromatic hydrocarbons in premixed laminar flames. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 425-33.
146. Braun-Unkhoff M, Chrysostomou A, Frank P, Gutheil E, Lückerath R, Stricker W. Experimental and numerical study on soot formation in laminar high-pressure flames. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1565-72.
147. Böhm H, Jander H, Tanke D. PAH growth and soot formation in the pyrolysis of acetylene and benzene at high temperatures and pressures: modeling and experiment. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1605-12.
148. 6 reaction. J Phys Chem A 1999;103:9036-41.
149. Park J, Lin MC. Kinetics of the recombination of phenyl radicals. J Phys Chem A 1997;101:14-18.
150. 14C]naphthalene. Aust J Chem 1964;17:771-7.
151. Sarofim AF, Longwell JP, Wornat MJ, Mukherjee J. The role of biaryl reactions in PAH and soot formation. In: Bockhorn H, editor. Soot formation in combustion: mechanisms and models. Berlin: Springer, 1994. p. 485-96.
152. Masonjones MC, Lafleur AL, Sarofim AF. Biarene formation during pyrolysis of a mixture of anthracene and naphthalene. Combust Sci Technol 1995;109:273-85.
153. Badger GM, Donnelly JK, Spotswood TM. The formation of aromatic hydrocarbons at high temperatures XXII. The pyrolysis of phenanthrene. Aust J Chem 1964;17:1138-46.
154. Badger GM, Donnelly JK, Spotswood TM. The formation of aromatic hydrocarbons at high temperatures XXIII. The pyrolysis of anthracene. Aust J Chem 1964;17:1147-56.
155. Stein SE, Griffith LL, Billmers R, Chen RH. Pyrocondensation of anthracene. J Org Chem 1987;52:1582-91.
156. Mukherjee J, Sarofim AF, Longwell JP. Polycyclic aromatic hydrocarbons from the high-temperature pyrolysis of pyrene. Combust Flame 1994;96:191-200.
157. Griesheimer J, Homann K-H. Large molecules, radicals ions, and small soot particles in fuel-rich hydrocarbon flames Part II. Aromatic radicals and intermediate PAHs in a premixed low-pressure naphthalene/oxygen/argon flame. Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1753-9.
158. Siegmann K, Hepp H, Sattler K. Reactive dimerization: a new pah growth mechanism in flames. Combust Sci Technol 1995;109:165-81.
159. Hepp H, Siegmann K, Sattler K. New aspects of growth mechanisms for polycyclic aromatic hydrocarbons in diffusion flames. Chem Phys Lett 1995;233:16-22.
160. Cioslowski J, Piskorz P, Moncrieff D. Thermally induced cyclodehydrogenation of biaryls: a simple radical reaction or a sequence of rearrangements? J Org Chem 1998;63:4051-4.
161. Orlow NA. Über die pyrogenetische Dissoziation von Phenanthren in Gegenwart von Wasserstoff unter Druck. Ber Deutsch Chem Ges 1927;60:1950-6.
162. Brouwer L, Troe J. Thermal isomerization of azulene to naphthalene in shock waves. Int J Chem Kinet 1988;20:379-86.
163. Scott LT, Roelofs NH. Benzene ring contractions at high temperatures. Evidence from the thermal interconversions of aceanthrylene, acephenanthrylene, and fluoranthene. J Am Chem Soc 1987;109:5461-5.
164. Visser T, Sarobe M, Jenneskens LW, Wesseling JW. Identification of isomeric polycyclic aromatic hydrocarbons (PAH) in pyrolysates from ethynylated PAH by gas chromatography-Fourier infrared spectroscopy. Their relevance for the understanding of PAH rearrangement and interconversion processes during combustion. Fuel 1998;77:913-20.
165. Colket MB, Seery DJ. Reaction mechanisms for toluene pyrolysis. Twenty-fifth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1994. p. 883-91.
166. Howard JB, Longwell JP, Marr JA, Pope CJ, Busby WF, Lafleur AL, Taghizadeh K. Effects of PAH isomerizations on mutagenicity of combustion products. Combust Flame 1995;101:262-70.
167. Gerhardt P, Löffler S, Homann KH. Polyhedral carbon ions in hydrocarbon flames. Chem Phys Lett 1987;137:306-10.
168. Gerhardt P, Löffler S, Homann KH. The formation of polyhedral carbon ions in fuel-rich acetylene and benzene flames. Twenty-second Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1988. p. 395-401.
169. 70 in flames. Nature 1991;352:139-41.
170. 70 fullerenes in benzene-oxygen flames. J Phys Chem 1992;96:6657-62.
171. Howard JB. Fullerenes formation in flames. Twenty-fourth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1992. p. 933-46.
172. Howard JB, Lafleur AL, Makarovsky Y, Mitra S, Pope CJ, Yadav TK. Fullerenes synthesis in combustion. Carbon 1992;30:1183-201.
173. Richter H, Fonseca A, Emberson SC, Gilles J-M, Nagy BJ, Thiry PA, Caudano R, Lucas AA. Fabrication of fullerenes in benzene/oxygen/argon and benzene/acetylene/oxygen/argon flames. J Chim Phys 1995;92:1272-85.
174. Richter H, Labrocca AJ, Grieco WJ, Taghizadeh K, Lafleur AL, Howard JB. Generation of higher fullerenes in flames. J Phys Chem B 1997;101:1556-60.
175. Zhang QL, O'Brien SC, Heath JR, Liu Y, Curl RF, Kroto HW, Smalley RE. Reactivity of large carbon clusters: spheroidal carbon shells and their possible relevance to the formation and morphology of soot. J Phys Chem 1990;90: 525-8.
176. 60: Buckminsterfullerene. Nature 1985;318:162-3.
177. Howard JB, Chowdhury KD, Vander Sande JB. Carbon shells in flames. Nature 1994;370:603.
178. Chowdhury KD, Howard JB, Vander Sande JB. Fullerenic nanostructures in flames. J Mater Res 1996;11:341-7.
179. Grieco WJ, Howard JB, Rainey LC, Vander Sande JB. Fullerenic carbon in combustion-generated soot. Carbon 2000;38:597-614.
180. Grieco WJ, Lafleur AL, Swallow KC, Richter H, Taghizadeh K, Howard JB. Fullerences and PAH in low-pressure premixed benzene/oxygen flames, Twenty-seventh Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1998. p. 1669-75.
181. Ugarte D. High-temperature behaviour of fullerene black. Carbon 1994;32:1245-8.
182. Frenklach M, Ebert LB. Comment on the proposed role of spheroidal carbon clusters in soot formation. J Phys Chem 1988;92:561-3.
183. Lafleur AL, Howard JB, Marr JA, Yadav T. Proposed fullerene precursor corannulene identified in flames both in the presence and absence of fullerene production. J Phys Chem 1993;97:13539-43.
184. 10 dicyclopentapyrenes in flames: correlation with corannulene and fullerene formation. J Phys Chem 1996;100:17421-8.
185. 70 formation in flames. J Phys Chem 1993;97:11001-13.
186. Pope CJ, Howard JB. Further testing of the fullerene formation mechanism with predictions of temperature and pressure trends. Twenty-fifth Symposium
187. Pope CJ, Howard JB. Thermodynamic limitations for fullerene formation in flames. Tetrahedron 1996;52:5161-78.
188. McKinnon JT, Howard JB. The roles of PAH and acetylene in soot nucleation and growth. Twenty-fourth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1992. p. 965-71.
189. Baum T, Löffler P, Weilmünster P, Homann K-H. Fullerene ions and their relation to PAH and soot in low-pressure hydrocarbon flames. Ber Bunsenges Phys Chem 1992;96:841-57.
190. 60 and its precursors in naphthalene flames. Chem Phys Lett 1994;223:506-10.
191. Ahrens J, Bachmann M, Baum T, Griesheimer J, Kovacs R, Weilmünster P, Homann K-H. Fullerenes and their ions in hydrocarbon flames. Int J Mass Spectrom Ion Process 1994;138:133-48.
192. Bachmann M, Wiese W, Homann K-H. PAH and aromers: precursors of fullerenes and soot. Twenty-sixth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1996. p. 2259-67.
193. Bachmann M, Wiese W, Homann K-H. Fullerenes versus soot in benzene flames. Combust Flame 1995;101:548-50.
194. Ahrens J, Kovacs R, Shafranovskii EA, Homann K-H. Online multi-photon ionization mass spectrometry applied to PAH and fullerenes in flames. Ber Bunsenges Phys Chem 1994;98:265-8.
195. 60 and some related species. Chem Phys Lett 1986;128:501-3.
196. Scott LT. Fragments of fullerenes: novel syntheses, structures, and reactions. Pure Appl Chem 1996;68:291-300.
197. Calcote HF. Mechanisms of soot nucleation in flames - a critical review. Combust Flame 1981;42:215-42.
198. Calcote HF, Gill RJ. Comparison of the ionic mechanism of soot formation with a free radical mechanism. In: Bockhorn H, editor. Soot formation in combustion: mechanisms and models, Berlin: Springer, 1994. p. 471-84.
199. Kern RD, Singh HJ, Xie K. Identification of chemi-ions formed by reactions of deuterated fuels in the reflected shock tube. J Phys Chem 1990;94:3333-5.
200. McKinnon JT, Meyer E, Howard JB. Infrared analysis of flame-generated PAH samples. Combust Flame 1995;105:161-6.
201. Benson SW, Buss JH. Additivity rules for the estimation of molecular properties. Thermodynamic properties. J Chem Phys 1958;29:546-72.
202. Benson SW, Cruickshank FR, Golden DM, Haugen GR, O'Neal HE, Rodgers AS, Shaw R, Walsh R. Additivity rules for the estimation of thermochemical properties. Chem Rev 1969;69:279-324.
203. Benson SW. Thermochemical kinetics. New York: Wiley- Interscience, 1976.
204. Stein SE, Golden DM, Benson SW. Predictive scheme for thermodynamic properties of polycyclic aromatic hydrocarbons. J Phys Chem 1977;81:314-7.
205. Ritter ER, Bozzelli JW. THERM: thermodynamic property estimation for gas phase radicals and molecules. Int J Chem Kinet 1991;23:767-78.
206. Stein SE, Barton BD. Chemical thermodynamics of polyaromatic compounds containing heteroatoms and five-membered rings. Thermochim Acta 1981;44:265-81.
207. Moiseeva NF, Dorofeeva OV. Group additivity scheme for calculating the chemical thermodynamic properties of gaseous polycyclic aromatic hydrocarbons containing five-membered rings. Thermochim Acta 1990;168:179-86.
208. Allinger NL, Yuh YH, Lu J-H. Molecular mechanics. The MM3 force field for hydrocarbons. 1. J Am Chem Soc 1989;111:8551-66.
209. Lii J-H, Allinger NL. Molecular mechanics. The MM3 force field for hydrocarbons. 2. Vibrational frequencies and thermodynamics. J Am Chem Soc 1989;111:8566-75.
210. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc 1985;107:3902-9.
211. Stewart JJP. Optimization of parameters for semiempirical methods I. Method. J Comput Chem 1989;10:209-20.
212. Stewart JJP. Optimization of parameters for semiempirical methods II. Applications. J Comput Chem 1989;10:221-64.
213. Stewart JJP. MOPAC: a semiempirical molecular orbital program. J Computer-Aided Mol Des 1990;4:1-105.
214. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Replogle ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JJP, Head-Gordon M, Gonzalez C, Pople JA. GAUSSIAN 94. Gaussian Inc., Pittsburgh, PA, 1995.
215. Herndon WC, Nowak PC, Connor DA, Lin P. Empirical model calculations for thermodynamic and structural properties of condensed polycyclic aromatic hydrocarbons. J Am Chem Soc 1992;114:41-47.
216. Pope CJ, Howard JB. Thermochemical properties of curved PAH and fullerenes: a group additivity method compared with MM3 (92) and MOPAC predictions. J Phys Chem 1995;99:4306-16.
217. Wang H, Frenklach M. Enthalpies of formation of benzenoid aromatic molecules and radicals. J Phys Chem 1993;97:3867-74.
218. Peck RC, Schulman JM, Disch RL. Ab initio heats of formation of medium-sized hydrocarbons 12. 6-31G studies of the benzenoid aromatics. J Phys Chem 1990;94:6637-41.
219. Stein SE. On the high temperature chemical equilibria of polycyclic aromatic hydrocarbons. J Phys Chem 1978;82:566-71.
220. Stein SE, Fahr A. High temperature stabilities of hydrocarbons. J Phys Chem 1985;82:3714-25.
221. Godleski SA, Schleyer PVR, Osawa E, Wipke WT. The systematic prediction of the most stable neutral hydrocarbon isomer. Prog Phys Org Chem 1981;13:63-117.
222. Lam FW, Howard JB, Longwell JP. The behavior of polycyclic aromatic hydrocarbons during the early stages of soot formation. Twenty-second Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1988. p. 323-32
223. Fletcher RA, Dobbins RA, Chang H-C. Mass spectrometry of particles formed in a deuterated ethene diffusion flame. Anal Chem 1998;70:2745-9.
224. Dobbins RA, Fletcher RA, Chang H-C. The evolution of soot precursor particles in a diffusion flame. Combust Flame 1998;115:285-98.
225. Alberty RA. Thermodynamics of the formation of benzene series polycyclic aromatic hydrocarbons in a benzene flame. J Phys Chem 1989;93:3299-304.
226. Alberty RA. Use of analytical expressions for the calculation of equilibrium distributions of polycyclic aromatic hydrocarbons in benzene flames. Twenty-third Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1990. p. 487-94.
227. Goeres A, Keller R, Sedlmayr E, Gail H-P. Circumstellar carbon condensation: I. Low-p, T stabilities of polyaromatic hydrocarbons. Polycycl Arom Compound 1996;8:129-65.
228. DiNaro JL. Oxidation of benzene in supercritical water: experimental measurements and development of an elementary reaction mechanism. PhD thesis, Department of Chemical Engineering, Massachusetts Institute of Technology, 1999.
229. DiNaro JL, Tester JW, Swallow KC, Howard JB. Experimental measurements of benzene oxidation in supercritical water. AIChE J 2000 (in press).
230. 3. J Phys Chem 1996;100:4111-9.
231. Tsang W. In: Martinho Simoes JA, Greenberg A, Liebman JF, editors. Heats of formation of organic free radicals by kinetic methods in energetics of organic free radicals, London: Blackie Academic and Professional, 1996. p. 22-58.
232. 3 + H. Phys Chem Chem Phys 1999;1:989-97.
233. 2 reaction. Tunneling and the shape of falloff curves. J. Phys. Chem. 1996;100:16899-911.
234. 4 reactions. J Phys Chem 1996;100:11346-54.
235. 3 cross-radical reactions. J Phys Chem A 1999;103: 8433-9.
236. Steinfield JI, Francisco JS, Hase WL. Chemical kinetics and dynamics. Upper Saddle River, NJ: Prentice-Hall, 1989.
237. Robinson PJ, Holbrook KA. Unimolecular reactions. New York: Wiley-Interscience, 1972.
238. Forst W. Theory of unimolecular reactions. New York: Academic Press, 1973.
239. Rice OK, Ramsperger HC. Theories of unimolecular gas reactions at low pressures. J Am Chem Soc 1927;49:1617-29.
240. Rice OK, Ramsperger HC. Theories of unimolecular gas reactions at low pressures II. J Am Chem Soc 1928;50:617-20.
241. Kassel LS. Studies in homogeneous gas reactions I. J Phys Chem 1928;32:225-42.
242. Warnatz J. The mechanism of high temperature combustion of propane and butane. Combust Sci Technol 1983;34:177-200.
243. Westmoreland PR, Howard JB, Longwell JP, Dean AM. Prediction of rate constants for combustion and pyrolysis reactions by bimolecular QRRK. AIChE J 1986;32:1971-9.
244. Dean AM, Bozzelli JW, Ritter ER. CHEMACT: a computer code to estimate rate constants for chemically-activated reactions. Combust Sci Technol 1991;80:63-85.
245. Bozzelli JW. Personal communication.
246. Marcus RA. Unimolecular dissociations and free radical recombination reactions. J Chem Phys 1952;20:359-64.
247. Yu T, Lin MC. Kinetics of the phenyl radical reaction with ethylene: an RRKM theoretical analysis of low and high temperature data. Combust Flame 1995;100:169-76.
248. 2 reaction at low temperatures. J Am Chem Soc 1994;116:9571-6.
249. Bedanov V, Tsang W, Zachariah MR. Master equation analysis of thermal activation reactions: reversible isomerization and decomposition. J Phys Chem 1995;99:11452-7.
250. Tsang W, Bedanov V, Zachariah MR. Master equation analysis of thermal activation reactions: energy-transfer constraints on falloff behavior in the decomposition of reactive intermediates with low thresholds. J Phys Chem 1996;100:4011-8.
251. Tsang W, Bedanov V, Zachariah MR. Unimolecular decomposition of large organic radicals with low reaction thresholds: decomposition and reversible isomerization of n-pentyl radicals. Ber Bunsenges Phys Chem 1997;101:491-9.
252. Knyazev VD, Tsang W. Incorporation of non-steady-state unimolecular and chemically activated kinetics into complex kinetic schemes. 1. Isothermal kinetics at constant pressure. J Phys Chem A 1999;103:3944-54.
253. Hausmann M, Hebgen P, Homann K-H, Radicals in flames: analysis via radical scavenging reaction. Twenty-fourth Symposium (International) on Combustion, The Combustion Institute, Pittsburgh, 1992. p. 793-801.
254. Susnow RG, Dean AM, Green WH, Peczak P, Broadbelt LJ. Rate-based construction of kinetic models for complex systems. J Phys Chem A 1997;101:3731-40.
255. Venkatesh PK, Chang AY, Dean AM, Cohen MH, Carr RW. Parameterization of pressure- and temperature-dependent kinetics in multiple well reactions. AIChE J 1997;43: 1331-40.
256. Venkatesh PK, Dean AM, Cohen MH, Carr RW. Chebyshev expansions and sensitivity analysis for approximating the temperature- and pressure- dependence of chemically-activated reactions. Rev Chem Engng 1997;13:1-67.
257. Venkatesh PK. Damped pseudospectral functional forms of the falloff behavior of unimolecular reactions. J Phys Chem A 2000;104:280-7.