Quantum chemical and kinetic study on dioxin formation from the 2,4,6-TCP and 2,4-DCP precursors

Environmental Science and Technology

Volumn 44, Issue 9, 2010, Pages 3395-3403

  Zhang, Qingzhu ^a   Yu, Wanni ^a   Zhang, Ruixue ^a   Zhou, Qin ^a   Gao, Rui ^a   Wang, Wenxing ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BASIS SETS; CANONICAL VARIATIONAL TRANSITIONS; CHLOROPHENOLS; DIBENZOFURANS; DICHLOROPHENOLS; DIOXIN FORMATION; ELEMENTARY STEPS; FORMATION MECHANISM; GASPHASE; GEOMETRICAL PARAMETERS; KINETIC STUDY; MOLECULAR ORBITAL THEORY; MUNICIPAL WASTE INCINERATORS; ORTHO POSITION; PCDD/FS; PCDD/PCDFS; POLYCHLORINATED DIBENZO- P - DIOXINS; PREEXPONENTIAL FACTOR; QUANTUM CHEMICAL; SINGLE-POINT ENERGY; SMALL-CURVATURE TUNNELING; STATIONARY POINTS; TEMPERATURE RANGE; TRICHLOROPHENOL; VIBRATIONAL FREQUENCIES; WASTE COMBUSTION;

ACTIVATION ENERGY; CHLORINE; FLY ASH; MOLECULAR ORBITALS; ORGANIC POLLUTANTS; PHENOLS; REFUSE INCINERATORS; WASTE INCINERATION;

RATE CONSTANTS;

2,4 DICHLOROPHENOL; 2,4,6 TRICHLOROPHENOL; DIBENZOFURAN DERIVATIVE; DIOXIN; POLYCHLORINATED DIBENZODIOXIN;

ACTIVATION ENERGY; CANONICAL ANALYSIS; CHEMICAL ANALYSIS; CHLORINE; COMBUSTION; CURVATURE; FLY ASH; INCINERATION; MUNICIPAL SOLID WASTE; PCDD;

ARTICLE; CANONICAL VARIATES ANALYSIS; CHEMICAL STRUCTURE; GAS ANALYSIS; POLYMERIZATION; QUANTUM CHEMISTRY; TEMPERATURE SENSITIVITY;

CARBON; CHEMISTRY; CHLOROPHENOLS; DIOXINS; ENVIRONMENTAL POLLUTANTS; KINETICS; MODELS, CHEMICAL; PARTICULATE MATTER; QUANTUM THEORY; REFUSE DISPOSAL; SOFTWARE; TEMPERATURE;

EID: 77951803637     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es1004285     Document Type: Article

References (38)

1. Schecter, A. Dioxin and Health; Plenum Press: New York, 1994.
2. Hung, H.; Blanchard, P.; Poole, G.; Thibert, B.; Chiu, C. H. Measurement of particle-bound polychlorinated dibenzo- p -dioxins and dibenzofurans (PCDD/Fs) in Arctic air at Alert, Nunavat, Canada Atmos. Environ. 2002, 36 (6) 1041-1050
3. Chlorinated dioxins and related compounds; Hutzinger, O.; Frei, R. W.; Merian, E.; Pocchiari, F., Eds.; Pergamon Press: New York, 1982.
4. Ryu, J.; Mulholland, J. A.; Kim, D. H.; Takeuchi, M. Homologue and isomer patterns of polychlorinated dibenzo- p -dioxins and dibenzofurans from phenol precursors: comparison with municipal waste incinerator data Environ. Sci. Technol. 2005, 39 (12) 4398-4406
5. Shaub, W. M.; Tsang, W. Dioxin formation in incinerators Environ. Sci. Technol. 1983, 17 (12) 721-730
6. Altwicker, E. R. Relative rates of formation of polychlorinated dioxins and furans from precursor and de novo reactions Chemosphere 1996, 33 (10) 1897-1904
7. Karasek, F. W.; Dickson, L. C. Model studies of polychlorinated dibenzo- p -dioxin formation during municipal refuse incineration Science 1987, 237 (4816) 754-756
8. 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. 1995, 30 (1) 225-229
9. Babushok, V. I.; Tsang, W. Gas-phase mechanism for dioxin formation Chemosphere 2003, 51 (10) 1023-1029
10. Khachatryan, L.; Burcat, A.; Dellinger, B. An elementary reaction-kinetic model for the gas-phase formation of 1,3,6,8- and 1,3,7,9-tetrachlorinated dibenzo- p -dioxins from 2, 4,6-trichlorophenol Combust. Flame 2003, 132 (3) 406-421
11. 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 (7) 1595-1602
12. Babushok, V.; Tsang, W. 7th International Congress on Combustion By-Products: Origins, Fate, and Health Effects; Research Triangle Park, NC, 2001; p 36.
13. Wegman, R. C. C.; van der Broek, H. H. Chlorophenols in river sediment in the Netherlands Water Res. 1983, 17 (2) 227-230
14. Buisson, R. S. K.; Kirk, P. W. W.; Lester, J. N. Determination of chlorinated phenols in water, wastewater and wastewater sludge by capillary GC-ECD J. Chromatogr. Sci. 1984, 22 (8) 339-342
15. Galceran, M. T.; Jauregui, O. Determination of phenols in sea water by liquid chromatography with electrochemical detection after enrichment by using solid-phase extraction cartridges and disks Anal. Chim. Acta 1995, 304 (1) 75-84
16. Addink, R.; Cnubben, P. A. J. P.; Olie, K. Formation of polychlorinated dibenzo- p -dioxins/dibenzofurnans on fly ash from precursors and carbon model compounds Carbon 1995, 33 (10) 1463-1471
17. Cains, P. W.; Mccausland, L.; Fernandes, A. R.; Dyke, P. Polychlorinated dibenzo- p -dioxins and dibenzofurans formation in incineration: Effects of fly ash and carbon source Environ. Sci. Technol. 1997, 31 (3) 776-785
18. Weber, R.; Hagenmaier, H. PCDD/PCDF formation in fluidized bed incineration Chemosphere 1999, 38 (11) 2643-2654
19. Qu, X. H.; Wang, H.; Zhang, Q. Z.; Shi, X. Y.; Xu, F.; Wang, W. X. Mechanistic and kinetic studies on the homogeneous gas-phase formation of PCDD/Fs from 2,4,5-trichlorophenol Environ. Sci. Technol. 2009, 43 (11) 4068-4075
20. Zhang, Q. Z.; Li, S. Q.; Qu, X. H.; Wang, W. X. A quantum mechanical study on the formation of PCDD/Fs from 2-chlorophenol as precursor Environ. Sci. Technol. 2008, 42 (19) 7301-7308
21. Briois, C.; Ryan, S.; Tabor, D.; Touati, A.; Gullett, B. Formation of polychlorinated dibenzo- p -dioxins and dibenzofurans from a mixture of chlorophenols over fly ash: Influence of water vapor Environ. Sci. Technol. 2007, 41 (3) 850-856
22. Sidhu, S. S.; Maqsud, L.; Dellinger, B.; Mascolo, G. The homogeneous, gas-phase formation of chlorinated and brominated dibenzo- p -dioxin from 2,4,6-trichloro- and 2,4,6-tribromophenols Combust. Flame 1995, 100 (1-2) 11-20
23. Weber, R.; Hagenmaier, H. Mechanism of the formation of polychlorinated dibenzo- p -dioxins and dibenzofurans from chlorophenols in gas phase reactions Chemosphere 1999, 38 (3) 529-549
24. 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 (4) 695-708
25. Khachatryan, L.; Asatryan, R.; Dellinger, B. An elementary reaction kinetic model of the gas-phase formation of polychlorinated dibenzofurans from chlorinated phenols J. Phys. Chem. A 2004, 108 (44) 9567-9572
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. W. M.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Allaham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. GAUSSIAN 03; Pittsburgh, PA, 2003.
27. 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 (33) 6908-6918
28. 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.
29. Baldridge, M. S.; Gordor, R.; Steckler, R.; Truhlar, D. G. Ab initio reaction paths and direct dynamics calculations J. Phys. Chem. 1989, 93 (13) 5107-5119
30. Gonzalez-Lafont, A.; Truong, T. N.; Truhlar, D. G. Interpolated variational transition-state theory: Practical methods for estimating variational transition-state properties and tunneling contributions to chemical reaction rates from electronic structure calculations J. Chem. Phys. 1991, 95 (12) 8875-8894
31. Garrett, B. C.; Truhlar, D. G. Generalized transition state theory. Classical mechanical theory and applications to collinear reactions of hydrogen molecules J. Phys. Chem. 1979, 83 (8) 1052-1079
32. Fernandez-Ramos, A.; Ellingson, B. A.; Garret, B. C.; Truhlar, D. G. Variational Transition State Theory with Multidimensional Tunneling. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Cundari, T. R., Eds.; Wiley-VCH: Hoboken, NJ, 2007.
33. Evans, C. S.; Dellinger, B. Mechanisms of dioxin formation from the high-temperature oxidation of 2-chlorophenol Environ. Sci. Technol. 2005, 39 (1) 122-127
34. 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 (13) 2563-2573
35. Procaccini, C.; Bozzelly, J. W.; Longwell, J. P.; Smith, K. A.; Sarofim, A. F. Presence of chlorine radicals and formation of molecular chlorine in the post-flame region of chlorocarbon combustion Environ. Sci. Technol. 2000, 34 (21) 4565-4570
36. Ritter, E. R.; Bozzelli, J. W. Kinetic study on thermal decomposition of chlorobenzene diluted in hydrogen J. Phys. Chem. 1990, 94 (6) 2493
37. Levy, A. A.; Rains, H. C.; Smiles, S. CCCCLII.-The rearrangement of hydroxy-sulphones. Part I J. Chem. Soc. 1931, 3264-3269
38. Zhang, Q. Z.; Qu, X. H.; Xu, F.; Shi, X. Y.; Wang, W. X. Mechanism and thermal rate constants for the complete series reactions of chlorophenols with H Environ. Sci. Technol. 2009, 43 (11) 4105-4112