A quantum mechanical study on the formation of PCDD/Fs from 2-chlorophenol as precursor

Environmental Science and Technology

Volumn 42, Issue 19, 2008, Pages 7301-7308

  Zhang, Qingzhu ^a   Li, Shanqing ^a   Qu, Xiaohui ^a   Shi, Xiangyan ^a   Wang, Wenxing ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CONCENTRATION (PROCESS); MOLECULAR ORBITALS; PHASE INTERFACES; PHENOLS; POLLUTION DETECTION; POTENTIAL ENERGY; POTENTIAL ENERGY SURFACES; QUANTUM CHEMISTRY; QUANTUM THEORY; RATE CONSTANTS;

2-CHLOROPHENOL; CANONICAL VARIATIONAL TRANSITION-STATE THEORY; CHEMICAL PRECURSORS; CHLORINATED PHENOLS; CHLOROPHENOXY; ELEMENTARY STEPS; ENERGY SURFACES; FORMATION PATHWAYS; GAS-PHASE REACTIONS; HOMOGENEOUS GAS; MECHANISM AND KINETICS; MOLECULAR ORBITAL THEORY; PCDD/FS; POLYCHLORINATED DIBENZO-P-DIOXINS AND DIBENZOFURANS; QUANTUM-MECHANICAL STUDY; REACTION TEMPERATURES; SINGLE-POINT ENERGY; SMALL-CURVATURE TUNNELING; WIDE TEMPERATURE RANGE;

RATE CONSTANTS; POLLUTION DETECTION;

2 CHLOROPHENOL; POLYCHLORINATED DIBENZODIOXIN; POLYCHLORINATED DIBENZOFURAN;

CANONICAL ANALYSIS; CHLOROPHENOL; COMBUSTION; CONCENTRATION (COMPOSITION); PCDD; PCDF; QUANTUM MECHANICS;

ARTICLE; CALCULATION; CANONICAL VARIATES ANALYSIS; CHEMICAL REACTION; ENERGY; QUANTUM MECHANICS; TEMPERATURE;

BENZOFURANS; CHLOROPHENOLS; DIMERIZATION; KINETICS; QUANTUM THEORY; TEMPERATURE; TETRACHLORODIBENZODIOXIN;

2-CHLOROPHENOLS; CANONICAL VARIATIONAL TRANSITION-STATE THEORIES; CHEMICAL PRECURSORS; CHLORINATED PHENOLS; CHLOROPHENOXY; ELEMENTARY STEPS; FORMATION PATHWAYS; GAS-PHASE REACTIONS; GASPHASE; MECHANISM AND KINETICS; MOLECULAR ORBITAL THEORY; PCDD/FS; POLYCHLORINATED DIBENZO-P-DIOXINS AND DIBENZOFURANS; QUANTUM-MECHANICAL STUDY; REACTION TEMPERATURE; SINGLE-POINT ENERGY; SMALL-CURVATURE TUNNELING; TEMPERATURE RANGE; THERMAL PROCESS;

EID: 54749152860     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es801599n     Document Type: Article

References (30)

1. Dickson, L. C.; Lenoir, D.; Hutzinger, O. Quantitative comparison of de novo and precursor formation of polychlorinated dibenzo-p-dioxins under simulated municipal solid waste incinerator postcombustion conditions. Environ. Sci. Technol. 1992, 26, 1822-1828.
2. Addink, R.; Olie, K. Mechanisms of formation and destruction of polychlorinated dibenzo-p-dioxins and dibenzofurans in heterogeneous systems. Environ. Sci. Technol. 1995, 29, 1425-1435.
3. Milligan, M. S.; Altwicker, E. R. Chlorophenol reactions on fly ash. 1. Adsorption/desorption equilibria and conversion to polychlorinated dibenzo-p-dioxins. Environ. Sci. Technol. 1996, 30, 225-229.
4. Karasek, F. W.; Dickson, L. C. Model studies of polychlorinated dibenzo-p-dioxin formation during municipal refuse incineration. Science 1987, 237, 754-756.
5. Shaub, W. M.; Tsang, W. Dioxin formation in incinerators. Environ. Sci. Technol. 1983, 17, 721-730.
6. Altwicker, E. R. Relative rates of formation of polychlorinated dioxins and furans from precursor and de novo reactions. Chemosphere 1996, 33, 1897-1904.
7. Hung, H.; Buekens, A. Comparison of dioxin formation levels in laboratory gas-phase flow reactors with those calculated using the Shaub-Tsang mechanism. Chemosphere 1999, 38, 1595-1602.
8. BabushokV. TsangW. 7th International Congress on Combustion By-Products: Origins, Fate, and Health Effects, Research Triangle Park, North Carolina, 2001; p 36.
9. Evans, C. S.; Dellinger, B. Mechanisms of dioxin formation from the high-temperature pyrolysis of 2-chlorophenol. Environ. Sci. Technol. 2003, 37, 1325-1330.
10. Evans, C. S.; Dellinger, B. Mechanisms of dioxin formation from the high-temperature oxidation of 2-chlorophenol. Environ. Sci. Technol. 2005, 39, 122-127.
11. Sidhu, S.; Edwards, P. Role of phenoxy radicals in PCDD/F formation. Int. J. Chem. Kinet. 2002, 34, 531-541.
12. Altarawneh, M.; Dlugogorski, B. Z.; Kennedy, E. M.; Mackie, J. C. Quantum chemical investigation of formation of polychlorodibenzo-p-dioxins and dibenzofurans from oxidation and pyrolysis of 2-chlorophenol. J. Phys. Chem. A 2007, 111, 2563-2573.
13. Shaub, W. M.; Tsang, W. Dioxin formation in incinerators. Environ. Sci. Technol. 1983, 17, 721-730.
14. Khachatryan, L.; Asatryan, R.; Dellinger, B. Development of expanded and core kinetic models for the gas phase formation of dioxins from chlorinated phenols. Chemosphere 2003, 52, 695-708.
15. Baldridge, M. S.; Gordor, R.; Steckler, R.; Truhlar, D. G. Ab initio reaction paths and direct dynamics calculations. J. Phys. Chem. 1989, 93, 5107-5119.
16. Liu, Y,-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. Molecular modeling of the kinetic isotope effect for the [1,5]-sigmatropic rearrangement of cis-1,3-pentadiene. J. Am. Chem. Soc. 1993, 115, 2408-2415.
17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
18. Zhao, Y.; Truhlar, D. G. Hybrid meta density functional theory methods for therochemistry, thermochemical kinetics, and noncovalent interactions: the MPW1B95 and MPWB1K models and comparative assessments for hydrogen bonding and van der waals interactions. J. Phys. Chem. A 2004, 108, 6908-6918.
19. Fukui, K. The path of chemical reactions - the IRC approach. Acc. Chem. Res. 1981, 14 (12), 363-368.
20. Steckler, R.; Chuang, Y. Y.; Fast, P. L.; Corchade, J. C.; Coitino, E. L.; Hu, W. P.; Lynch, G. C.; Nguyen, K.; Jackells, C. F.; Gu, M. Z.; Rossi, I.; Clayton, S.; Melissas, V.; Garrett, B. C.; Isaacson, A. D.; Truhlar, D. G. POLYRATE Version 9.3; University of Minnesota: Minneapolis., 2002.
21. Louw, R.; Ahonkhai, S. I. Radical/radical va radical/molecule reactions in the formation of PCdd/Fs from (chloro)phenols in incinerators. Chemosphere 2002, 46, 1273-1278.
22. Mackie, J. C.; Doolan, K. R.; Nelson, P. F. Kinetics of the thermal decomposition of methoxybenzene (anisole). J. Phys. Chem. 1989, 93, 664-670.
23. 2. J. Chem. Phys. 2003, 119, 4339-4345.
24. 2Cl. J. Phys. Chem. A 2003, 107, 3069-3075.
25. Baulch, D. L.; Cobos, C. J.; Cox, R. A.; Esser, C.; Frank, P.; Just, Th.; Kerr, J. A.; Pilling, M. J.; Troe, J.; Walker, R. W.; Warnatz, J. Evaluated kinetic data for combustion modelling. J. Phys. Chem. Ref. Data 1992, 21, 411-429.
26. Han, J.; Deming, R. L.; Tao, F. - M. Theoretical study of molecular structures and properties of the complete series of chlorophenols. J. Phys. Chem. A 2004, 108, 7736-7743.
27. He, Y. Z.; Mallard, W. G.; Tsang, W. Kinetics of hydrogen and hydroxyl radical attack on phenol at high temperatures. J. Phys. Chem. 1988, 92, 2196-2201.
28. 2. J. Phys. Chem. A 1998, 102, 7964-7974.
29. 2FO. J. Phys. Chem. A 2004, 108, 5050-5056.
30. Antonio, F.-R.; Emilio, M. - N.; Rios, M. A.; Iesus, R. - O.; Vazquez, S. A.; Estevez, C M. Direct dynamics study of the dissociation and elimination channels in the thermal decomposition of methyl nitrite. J. Am. Chem. Soc. 1998, 120, 7594-7601.