Quantum Chemistry Studies on the Free-radical Growth Mechanism of Polycyclic Arenes from Benzene Precursors

›› 2009, Vol. 17 ›› Issue (3): 394-400.

• CATALYSIS, KINETICS AND REACTORS • Previous Articles Next Articles

Quantum Chemistry Studies on the Free-radical Growth Mechanism of Polycyclic Arenes from Benzene Precursors

ZHANG Riguang¹, WANG Baojun¹, TIAN Yajun², LING Lixia¹

1. Key Laboratory of Coal Science and Technology (Taiyuan University of Technology), Ministry of Education and Shanxi Province, Taiyuan 030024, China;
2. Key Laboratory of Multiphase Reactions, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China

Received:2008-10-13 Revised:2009-04-17 Online:2009-06-28 Published:2009-06-28
Supported by:
Supported by the National Basic Research Program of China (2005CB221203);the National Natural Science Foundation of China (20576087, 20776093, 50534070);the Natural Science Foundation of Shanxi Province (2006011022, 2009021015)

Quantum Chemistry Studies on the Free-radical Growth Mechanism of Polycyclic Arenes from Benzene Precursors

章日光¹, 王宝俊¹, 田亚峻², 凌丽霞¹

1. Key Laboratory of Coal Science and Technology (Taiyuan University of Technology), Ministry of Education and Shanxi Province, Taiyuan 030024, China;
2. Key Laboratory of Multiphase Reactions, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China

通讯作者: WANG Baojun,E-mail:wangbaojun@tyut.edu.cn
基金资助:
Supported by the National Basic Research Program of China (2005CB221203);the National Natural Science Foundation of China (20576087, 20776093, 50534070);the Natural Science Foundation of Shanxi Province (2006011022, 2009021015)

Abstract

Abstract: The free-radical growth mechanisms for the formation of polycyclic arenes (PCAs) were constructed based on the block unit of benzene, and were calculated by the quantum chemistry PM3 method. Two kinds of reaction paths are proposed and discussed. The calculation results show that the formation of PCAs is only controlled by the elimination of H atom from benzene, and the corresponding activation energy is 307.60 kJ·mol^-1. H₂ is only the effluent gas in our proposed reaction mechanism, and the calculation results are in accord with the experimental facts.

Key words: benzene, polycyclic arene, mechanism, quantum chemistry calculation

摘要： The free-radical growth mechanisms for the formation of polycyclic arenes (PCAs) were constructed based on the block unit of benzene, and were calculated by the quantum chemistry PM3 method. Two kinds of reaction paths are proposed and discussed. The calculation results show that the formation of PCAs is only controlled by the elimination of H atom from benzene, and the corresponding activation energy is 307.60 kJ·mol^-1. H₂ is only the effluent gas in our proposed reaction mechanism, and the calculation results are in accord with the experimental facts.

关键词: benzene, polycyclic arene, mechanism, quantum chemistry calculation

ZHANG Riguang, WANG Baojun, TIAN Yajun, LING Lixia. Quantum Chemistry Studies on the Free-radical Growth Mechanism of Polycyclic Arenes from Benzene Precursors[J]. , 2009, 17(3): 394-400.

章日光, 王宝俊, 田亚峻, 凌丽霞. Quantum Chemistry Studies on the Free-radical Growth Mechanism of Polycyclic Arenes from Benzene Precursors[J]. , 2009, 17(3): 394-400.

References

1 Lai, H.J., Lin, M.C.C., Yang, M.H., Li, A.K., “Synthesis of carbon nanotubes using polycyclic aromatic hydrocarbons as carbon sources in an arc discharge”, Mater. Sci. Eng. C, 16, 23-26(2001).
2 Setlur, A.A., Dai, J.Y., lauerhass, J.M., Chang, R.P.H., “Formation of filled carbon nanotubes and nanoparticles using polycyclic aromatic hydrocarbon molecules”, Carbon, 36, 721-723(1998).
3 Dai, Y., Lauerhaas, J.M., Setlur, A.A., Chang, R.P.H., “Synthesis of carbon-encapsulated nanowires using policyclic aromatic hydrocarbon precursors”, Chem. Phys. Lett., 258, 547-553(1996).
4 Wang, H., Frenklach, M., “A detailed kinetic modeling study of aromatics formation in laminar premixed acetylene and ethylene flames”, Combust. Flame, 110, 173-221(1997).
5 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, 121, 122-136(2000).
6 Charles, W., Bauschlicher, Jr., Ricca, A., “Mechanisms for polycyclic aromatic hydrocarbon(PAH) growth”, Chem. Phys. Lett., 326, 283-287(2000).
7 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, 114, 192-213(1998).
8 Tian, Y.J., Hu, Z., Yang, Y., Wang, X.Z., Chen, X., Wu, Q., Ji, W.J., Chen, Y., “In situ TA-MS study of the six-membered-ring-based growth of carbon nanotubes with benzene precursor”, J. Am. Chem. Soc., 126, 1180-1183(2004).
9 Tian, Y.J., Hu, Z., Yang, Y., Chen, X., Ji, W.J., Chen, Y., “Thermal analysis-mass spectroscopy coupling as a powerful technique to study the growth of carbon nanotubes from benzene”, Chem. Phys. Lett., 388, 259-262(2004).
10 Wang, B.J., Wei, X.Y., Xie, K.C., “Study on reaction of N-methyl-2-pyrrolidinone with carbon disulfide using density functional theory”, J. Chem. Ind. Eng.(China), 55, 569-574(2004).(in Chinese)
11 Zheng, C.G., Liu, J., Liu, Z.H., Xu, M.H., Liu, Y.H., “Kinetic mechanism studies on reactions of mercury and oxidizing species in coal combustion”, Fuel, 84, 1215-1220(2005).
12 Zhang, J.L., Wu, C.J., Li, W., Wang, Y.P., Cao, H., “DFT and MM calculation:The performance mechanism of pour point depressants study”, Fuel, 83, 315-326(2004).
13 Rozanska, X., van Santer, R.A., Hutschka, F., “A DFT study of isomerization and transalkylation reactions of aromatics species catalyzed by acidic zeolites”, J. Catal., 202, 141-155(2004).
14 Rozanska, X., Saintigny, X., van Santer, R.A., Hutschka, F., “A DFT study of the cracking reaction of thiophene activated by small zeolitic clusters”, J. Catal., 200, 79-90(2001).
15 Violi, A., Sarofim, A.F., “Quantum mechanical study of molecular weight growth process by combination of aromatic molecules”, Combust. Flame, 126, 1506-1515(2001).
16 Stewart, J.J.P., MOPAC 7.0, Quantum Chemistry Program Exchange, University of Indiana, Bloomington, IN, USA.
17 CS ChemOffice, Cambridge Science Computing Inc., Suite 61, 875 Massachusetts Avenue, Cambridge, MA02139, USA.
18 Dean, J.A., Lange’s Handbook of Chemistry, 2nd edition, Science Press, Beijing(2003).
19 Hu, Z., Yang, Y., Tian, Y.J., Lü, Y.N., Wang, X.Z., Chen, Y., “High-yield production of quasi-aligned carbon nanotubes by catalytic decomposition of benzene”, Nanotechnology, 14, 733-737(2003).

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Quantum Chemistry Studies on the Free-radical Growth Mechanism of Polycyclic Arenes from Benzene Precursors

Quantum Chemistry Studies on the Free-radical Growth Mechanism of Polycyclic Arenes from Benzene Precursors

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