Chlorinated naphthalene formation from the oxidation of dichlorophenols

Chemosphere

Volumn 67, Issue 9, 2007, Pages

  Kim, Do Hyong ^a   Mulholland, James A ^a   Ryu, Jae Yong ^b  

^a Georgia Institute of Technology   (United States)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Dibenzo p dioxin; Dibenzofuran; Dichlorophenol; Polychlorinated naphthalene

Indexed keywords

COMBUSTION; OXIDATION; PHENOLS; SUBSTITUTION REACTIONS;

DIBENZO-P-DIOXIN; DIBENZOFURAN; DICHLOROPHENOL; POLYCHLORINATED NAPHTHALENE;

NAPHTHALENE;

CARBON MONOXIDE; DIBENZOFURAN; DIHYDROFULVALENE; NAPHTHALENE; POLYCHLORINATED DIBENZOFURAN; POLYCHLORINATED NAPHTHALENE; TETRACHLORONAPHTHALENE; UNCLASSIFIED DRUG; WATER;

COMBUSTION; NAPHTHALENE; OXIDATION; PHENOLS; SUBSTITUTION REACTIONS;

CHLORINATED HYDROCARBON; CHLOROPHENOL; COMBUSTION; DIOXIN; OXIDATION; PCDF;

ARTICLE; CHEMICAL REACTION; CHLORINATION; COMBUSTION; ELIMINATION REACTION; OXIDATION;

TETRA;

EID: 33847659098     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2006.05.095     Document Type: Article

References (27)

1. Abad E., Caixach J., and Rivera J. Dioxin like compounds from municipal waste incinerator emissions: assessment of the presence of polychlorinated naphthalenes. Chemosphere 38 (1999) 109-120
2. Akki U., and Mulholland J.A. Gas-phase formation of dioxin and other aromatic products from 2,6-dichlorophenol pyrolysis. Organohalogen Compd. 31 (1997) 475-479
3. Born J.G.P., Louw R., and Mulder P. Formation of dibenzodioxins and dibenzofurans in homogeneous gas-phase reactions of phenols. Chemosphere 19 (1989) 401-406
4. Castaldi M.J., Marinov N.M., Melius C.F., Huang J., Senken S.M., Pitz W.J., and Westbrook C.K. Experimental and modeling investigation of aromatic and polycyclic aromatic hydrocarbon formation in a premixed ethylene flame. Proc. Combust. Inst. 26 (1996) 693-702
5. Cieplik M.K., Epema O.J., and Louw R. Thermal hydrogenolysis of dibenzo-p-dioxin and dibenzofuran. Eur. J. Org. Chem. 2002 (2002) 2792-2799
6. Eiceman G.A., Clement R.E., and Karasek F.W. Analysis of fly ash from municipal incinerators for trace organic compounds. Anal. Chem. 51 (1979) 2343-2350
7. Evan C.S., and Dellinger B. Mechanisms of dioxin formation from the high-temperature oxidation of 2-chlorophenol. Environ. Sci. Technol. 39 (2005) 122-127
8. Frenkalch M., and Warnatz J. Detailed modeling of PAH profiles in a sooting low-pressure acetylene flame. Combust. Sci. Technol. 51 (1987) 265-283
9. Frenklach M., Clary D.W., Cardiner W.C., and Stein S.E. Detailed kinetic modeling of soot formation in shock-tube pyrolysis of acetylene. Proc. Combust. Inst. 20 (1984) 887-901
10. Iino F., Imagawa T., Takeuchi M., and Sadakata M. De novo synthesis mechanism of polychlorinated dibenzofurans from polycyclic aromatic hydrocarbons and the characteristic isomer of polychlorinated naphthalenes. Environ. Sci. Technol. 33 (1999) 1038
11. Imagawa T., and Lee C.W. Correlation of polychlorinated napthalenes with polychlorinated dibenzofurans formed from waste incineration. Chemosphere 44 (2001) 1511-1520
12. Imagawa T., and Takeuchi M. Relation between isomer compositions of polychlorinated naphthalens and congener compositions of PCDDs/PCDFs from incinerators. Organohalogen Compd. 23 (1995) 487-490
13. Järnberg U., Asplund C., and Jakobsson E. Gas chromatographic retention of polychlorinated naphthalenes on non-polar, polarizable, polar and semectic capillary columns. J. Chromatogr. 683A (1994) 385-396
14. Kim D.H., Mulholland J.A., and Ryu J.-Y. Formation of polychlorinated naphthalenes from chlorophenols. Proc. Combust. Inst. 30 (2004) 1249-1257
15. Manion J., and Louw R. Rates, products, and mechanisms in the gas-phase hydrogenolysis of phenol between 922 and 1175 K. J. Phys. Chem. 93 (1989) 3563-3574
16. Marinov N.M., Castaldi M.J., Melius C.F., and Tsang W. Aromatic and polycyclic aromatic hydrocarbon formation in a premixed propane flame. Combust. Sci. Technol. 128 (1997) 295-342
17. McEnally C.S., and Pfefferle L.D. The use of carbon-13-labeled fuel dopants for identifying naphthalene formation pathways in non-premixed flames. Proc. Combust. Inst. 28 (2000) 2569-2576
18. 5 cyclopentadienyl moiety. Proc. Combust. Inst. 26 (1996) 685-692
19. Nakahata D.-T., and Mulholland J.A. Effects of dichlorophenol substitution pattern on furan and dioxin formation. Proc. Combust. Inst. 28 (2000) 2701-2707
20. Olie K., Vermeulen P.L., and Hutzinger O. Chlorodibenzo-p-dioxins and chlorodibenzofurans are trace components of fly ash and flue gas of some incinerators in the Netherlands. Chemosphere 6 (1977) 455-459
21. Sakai S., Hiraoka M., Takeda N., and Shiozaki K. Behavior of coplanar PCBs and PCNs in oxidative conditions of municipal waste incineration. Chemosphere 32 (1996) 79-88
22. Schneider M., Stieglitz L., Will R., and Zwick G. Formation of polychlorinated naphthalenes on fly ash. Chemosphere 37 (1998) 2055-2070
23. Sidhu S.S., Maquad L., Dellinger B., and 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 100 (1995) 11-20
24. Spielmann R., and Cramers C.A. Cyclopentadienic compounds as intermediates in the thermal degradation of phenols. Kinetics of thermal decomposition of cyclopentadiene. Chromatographia 5 (1972) 295-300
25. Weber R., and Hagenmaier H. Mechanism of the formation of polychlorinated dibenzo-p-dioxins and dibenzofurans from chlorophenols in gas-phase reactions. Chemosphere 38 (1999) 529-549
26. Weber R., Iino F., Imagawa T., Takeuchi M., Sakurai T., and Sadakata M. Formation of PCDF, PCDD, PCB, and PCN in de novo synthesis from PAH: Mechanistic aspects and correlation to fluidized bed incinerators. Chemosphere 44 (2001) 1429-1438
27. Yang Y., Mulholland J.A., and Akki U. Formation of furans by gas-phase reactions of chlorophenols. Proc. Combust. Inst. 27 (1998) 1761-1768