New insight into the formation mechanism of PCDD/Fs from 2-chlorophenol precursor

Environmental Science and Technology

Volumn 47, Issue 15, 2013, Pages 8489-8498

  Pan, Wenxiao ^a   Zhang, Dongju ^a   Han, Zhe ^b   Zhan, Jinhua ^a   Liu, Chengbu ^a  

^a SHANDONG UNIVERSITY   (China)

^b QILU UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2-CHLOROPHENOLS; CROSS COUPLING REACTIONS; ENVIRONMENTAL SCIENTISTS; FORMATION MECHANISM; PCDD/F FORMATION; PHENOXY RADICALS; PHENYL RADICALS; POLYCHLORINATED DIBENZO-P-DIOXINS AND DIBENZOFURANS;

ENVIRONMENTAL ENGINEERING; ENVIRONMENTAL PROTECTION;

PHENOLS;

2 CHLOROPHENOL; CARBENOID; HYDROXYL GROUP; POLYCHLORINATED DIBENZODIOXIN; RADICAL;

CHLOROPHENOL; FORMATION MECHANISM; PCDD; PCDF; RADICAL; REACTION KINETICS; THERMODYNAMICS;

ARTICLE; CALCULATION; CHLORINATION; CROSS COUPLING REACTION; DENSITY FUNCTIONAL THEORY; ENERGY; ENTHALPY; GEOMETRY; PRECURSOR; THERMODYNAMICS;

BENZOFURANS; CHLOROPHENOLS; POLYMERS; TETRACHLORODIBENZODIOXIN;

EID: 84881448250     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es400632j     Document Type: Article

References (35)

1. Schecter, A.; Exposure assessment: Measurement of dioxins and related chemicals in human tissues. In Dioxin and Health; Schecter, A., Ed.; Plenum Press: New York, 1994; p 449.
2. Stockholm Convention on Persistent Organic Pollutants; United Nations: Stockholm, 2001; http://chm.pops.int/Convention/ConventionText/tabid/2232/ Default.aspx.
3. Wu, Y. L.; Lin, L. F.; Hsieh, L. T.; Wang, L. C.; Chang-Chien, G. P. Atmospheric dry deposition of polychlorinated dibenzo-p-dioxins and dibenzofurans in the vicinity of municipal solid waste incinerators J. Hazard. Mater. 2009, 162 (1) 521-529
4. Evans, C. S.; Dellinger, B. Mechanisms of dioxin formation from the high-temperature pyrolysis of 2-chlorophenol Environ. Sci. Technol. 2003, 37 (24) 1325-1330
5. 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
6. Babushok, V. I.; Tsang, W. Gas-phase mechanism for dioxin formation Chemosphere 2003, 51 (10) 1023-1029
7. Briois, C.; Visez, N.; Baillet, C.; Sawerysyn, J. P. Experimental study on the thermal oxidation of 2-chlorophenol in air over the temperature range 450-900 C Chemosphere 2006, 62 (11) 1806-1816
8. Suárez, E.; Suárez, D.; Menéndez, M. I.; López, R.; Sordo, T. L. Formation of trichlorinated dibenzo-p-dioxins from 2,4-dichlorophenol and 2,4,5-trichlorophenolate: A theoretical study ChemPhysChem 2006, 7 (11) 2331-2338
9. Okamoto, Y.; Tomonari, M. Formation pathways from 2,4,5-trichlorophenol (TCP) to polychlorinated dibenzo-p-dioxins (PCDDs): An ab initio study J. Phys. Chem. A 1999, 103 (38) 7686-7691
10. 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
11. Zhang, Q. Z.; Yu, W. N.; Zhang, R. X.; Zhou, Q.; Gao, R.; Wang, W. X. Quantum chemical and kinetic study on dioxin formation from the 2,4,6-TCP and 2,4-DCP precursors Environ. Sci. Technol. 2010, 44 (9) 3395-3403
12. 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) 4028-4075
13. Xu, F.; Yu, W. N.; Zhou, Q.; Gao, R.; Sun, X. Y.; Zhang, Q. Z.; Wang, W. X. Mechanism and direct kinetic study of the polychlorinated dibenzo- p -dioxin and dibenzofuran formations from the radical/radical cross-condensation of 2,4-dichlorophenoxy with 2-chlorophenoxy and 2,4,6-trichlorophenoxy Environ. Sci. Technol. 2011, 45 (2) 643-650
14. Olie, K.; Addink, R.; Schoonenboom, M. Metals as catalysts during the formation and decomposition of chlorinated dioxins and furans in incineration processes J. Air Waste Manage. Assoc. 1998, 48 (2) 101-105
15. Ismo, H.; Kari, T.; Juhani, R. Formation of aromatic chlorinated compounds catalyzed by copper and iron Chemosphere 1997, 34 (12) 2649-2662
16. Konduri, R.; Altwicker, E. Analysis of time scales pertinent to dioxin/furan formation on fly ash surfaces in municipal solid waste incinerators Chemosphere 1994, 28 (1) 23-45
17. 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- 2,4,6-tribromophenols Combust. Flame 1995, 100, 11-20
18. 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
19. Shaub, W. M.; Tsang, W. Dioxin formation in incinerators Environ. Sci. Technol. 1983, 17 (12) 721-730
20. 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
21. Tuppurainen, K.; Halonen, I.; Ruokojärvi, P.; Tarhanen, J.; Ruuskanen, J. Formation of PCDDs and PCDFs in municipal waste incineration and its inhibition mechanisms: A review Chemosphere 1998, 36 (7) 1493-1511
22. Zhang, Q. Z.; Li, S. Q.; Qu, X. H.; Shi, X. Y.; 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
23. Kaiser, R. I.; Parker, D. S. N.; Zhang, F. PAH formation under single collision conditions: Reaction of phenyl radical and 1,3-butadiene to form 1,4-dihydronaphthalene J. Phys. Chem. A 2012, 116 (17) 4248-4258
24. Shukla, B.; Susa, A.; Miyoshi, A.; Koshi, M. Role of phenyl radicals in the growth of polycyclic aromatic hydrocarbons J. Phys. Chem. A 2008, 112 (11) 2362-2369
25. Bonnichon, F.; Richard, C.; Grabner, G. Formation of an α-ketocarbene by photolysis of aqueous 2-bromophenol ChemComm 2001, 1, 73-74
26. Lomnicki, S.; Truong, H.; Dellinger, B. Mechanisms of product formation from the pyrolytic thermal degradation of catechol Chemosphere 2008, 73 (4) 629-633
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; 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.; Martin, R. L.; Morokuma, K.; V. Zakrzewski, G.; Voth, G.;, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, CT, 2010.
28. Zhao, Y.; Lynch, B. J.; Truhlar, D. G. Development and assessment of a new hybrid density functional model for thermochemical kinetics J. Phys. Chem. A 2004, 108 (14) 2715-2719
29. Nicolaides, A.; Smith, D. M.; Jensen, F.; Radom, L. Phenyl radical, cation, and anion. The triplet-singlet gap and higher excited states of the phenyl cation J. Am. Chem. Soc. 1997, 119 (34) 8083-8088
30. McFerrin, C. A.; Hall, R. W.; Dellinger, B. Ab initio study of the formation and degradation reactions of chlorinated phenols J. Mol. Struct. (THEOCHEM) 2009, 902, 5-14
31. Burcat, A.; Rusci, B. Third Millennium Ideal Gas and Condensed Phase Thermochemical Database for Combustion With Updates from Active Thermochemical Tables; ANL-05/20; Argonne National Laboratory: Argonne, IL, 2001; http://www.chem.leeds.ac.uk/combustion/combustion.html.
32. p (T), of 1,4-dioxin, 2,3-benzodioxin, furan, 2,3-benzofuran, and twelve monochloro and dichloro dibenzo-p-dioxins and dibenzofurans J. Phys. Chem. 2003, 32 (4) 1713-1735
33. Monks, P. S. Gas-phase radical chemistry in the troposphere Chem. Soc. Rev. 2005, 34 (5) 376-395
34. Han, Z.; Zhang, D. J.; Sun, Y. M.; Liu, C. B. Reexamination of the reaction of 4-chlorophenol with hydroxyl radical Chem. Phys. Lett. 2009, 474, 62-66
35. Sidhu, S.; Edwards, P. Role of phenoxy radicals in PCDD/F formation Int. J. Chem. Kinet. 2002, 34 (9) 531-541