Formation of polychlorinated dibenzo-p-dioxins and dibenzofurans from a mixture of chlorophenols over fly ash: Influence of water vapor

Environmental Science and Technology

Volumn 41, Issue 3, 2007, Pages 850-856

  Briois, Christelle ^a   Ryan, Shawn ^a   Tabor, Dennis ^a   Touati, Abderrahmane ^b   Gullett, Brian K ^a  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^b ARCADIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMER DISTRIBUTIONS; WATER VAPOR;

CONCENTRATION (PROCESS); FLY ASH; ISOMERS; PHENOLS; TOXIC MATERIALS;

WASTE INCINERATION;

2 CHLOROPHENOL; 2,4 DICHLOROPHENOL; 2,4,6 TRICHLOROPHENOL; CHLOROPHENOL; POLYCHLORINATED DIBENZODIOXIN; POLYCHLORINATED DIBENZOFURAN; WATER;

CONCENTRATION (PROCESS); FLY ASH; ISOMERS; PHENOLS; TOXIC MATERIALS; WASTE INCINERATION;

CHLOROPHENOL; COMBUSTION; CONCENTRATION (COMPOSITION); EXPERIMENTAL STUDY; FLY ASH; PCDD; PCDF; WATER VAPOR;

ARTICLE; CHEMICAL ANALYSIS; FLUE GAS; FLY ASH; INCINERATION; MUNICIPAL SOLID WASTE; WATER VAPOR;

BENZOFURANS; CARBON; CHLOROPHENOLS; CITIES; ENVIRONMENTAL POLLUTANTS; GASES; INCINERATION; PARTICULATE MATTER; TETRACHLORODIBENZODIOXIN; WASTE PRODUCTS; WATER;

TETRA;

EID: 33846821923     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es0613761     Document Type: Article

References (39)

1. Zimmermann, R.; Heger, H. J.; Blumenstock, M.; Dorfner, R.; Schramm, K.-W.; Boesl, U.; Kettrup, A. On-line measurements of chlorobenzene in waste incineration flue gas as a surrogate for the emission of polychlorinated dibenzo-p-dioxins/furans (I-TEQ) using mobile resonance laser ionization time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 1999, 13, 307-314.
2. Blumenstock, M.; Zimmermann, R.; Schramm, K. W.; Kaune, A.; Nikolai, U.; Lenoir, R.; Kettrup, A. Estimation of the dioxin emission (PCDD/F I-TEQ) from the concentration of low chlorinated aromatic compounds in the flue and stack gas of a hazardous waste incinerator. J. Anal. Appl Pyrolysis 1999, 49, 179-190.
3. Blumenstock, M.; Zimmermann, R.; Schramm, K.-W.; Kettrup, A. Influence of combustion conditions on the PCDD/F-, PCB-, PCBz- and PAH- concentrations in the post-combustion chamber of a waste incineration pilot plant. Chemosphere 2000, 40, 987-993.
4. Gullett, B. K.; Wikström, E. Mono- to tri-chlorinated dibenzo-dioxin (CDD) and dibenzofuran (CDF) congeners/homologues as indicators of CDD and CDF emissions from municipal waste and waste/coal combustion. Chemosphere 2000, 40, 1015-1019.
5. Kaune, A.; Lenoir, D.; Nikolai, U; Kettrup, A. Estimating concentrations of polychlorinated dibenzo-p-dioxins and dibenzofurans in the stack gas of a hazardous waste incinerator from concentrations of chlorinated benzenes and biphenyls. Chemosphere 1994, 29, 2083-2096.
6. Tuppurainen, K. A.; Ruokojärvi, P.; Asikainen, A. H.; Aatamila, M.; Ruuskanen, J. Homologue and isomer patterns of polychlorinated dibenzo-p-dioxins and dibenzofurans from phenol precursors: comparison with Municipal Waste Incinerator data. Environ. Sci. Technol. 2000, 34, 4958-4962.
7. Heger, H. J.; Zimmermann, R.; Blumenstock, M.; Kettrup, A. On-line measurements at incineration plants: PAHs and a PCDD/F surrogate compound at stationary combustion conditions and during transient emission puffs. Chemosphere 2001, 42, 691-696.
8. Oh, J.-E.; Touati, A.; Gullett, B. K.; Mulholland, J. A. PCDD/F TEQ indicators and their mechanistic implications. Environ. Sci. Technol. 2004, 38, 4694-4700.
9. Dickson, L. C.; Lenoir, D.; Hutzinger, O. Quantitative comparison of de novo and precursors formation of polychlorinated dibenzo-p-dioxins under simulated municipal solid waste incinerator post combustion conditions. Environ. Sci. Technol. 1992, 26, 1822-1828.
10. Altwicker, E. R.; Milligan, M. S. Formation of dioxins: competing rates between chemically similar precursors and de novo reactions. Chemosphere 1993, 27, 301-307.
11. Jay, K.; Stieglitz, L. Identification and quantification of volatile organic components in emissions of waste incineration plants. Chemosphere 1995, 30, 1249-1260.
12. Taylor, P. H.; Dellinger, B.; Lee, C. C. Development of a thermal stability based ranking of hazardous organic compound incinerability. Environ. Sci. Technol. 1990, 24, 316-328.
13. Born, J. G. P.; Mulder, P.; Louw, R. Fly ash mediated reactions of phenol and monochlorophenols: oxychlorination, deep oxidation, and condensation. Environ. Sci. Technol. 1993, 27, 1849-1863.
14. Luijk, R.; Akkerman, D. M.; Slot, P.; Olie, K.; Kapteijn, F. Mechanism of formation of polychlorinated dibenzo-p-dioxins and dibenzofurans in the catalyzed combustion of carbon. Environ. Sci. Technol. 1994, 28, 312-321.
15. 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, 11-20.
16. Mulholland, J. A.; Ryu, J.-Y. Formation of polychlorinated dibenzo-p-dioxins by CuCl2 catalyzed condensation of 2,6 chlorinated phenols. Combust. Sci. Technol. 2001, 169, 107-126.
17. 2 from chlorinated phenols with one ortho- chlorine. Proc. Combust. Inst. 2002, 29, 2455-2461.
18. Ryu, J.-Y.; Mulholland, J. A. Metal-mediated chlorinated dibenzo-p-dioxin (CDD) and dibenzofuran (CDF) formation from phenols. Chemosphere 2005, 58, 977-988.
19. 13C-labeled carbon. Environ. Sci. Technol. 2001, 35, 3892-3898.
20. Cieplik, M. K.; De Jong, V.; Bozovic, J.; Liljelind, P.; Marklund, S.; Louw R. Formation of dioxins from combustion micropollutants over MSWI fly ash. Environ. Sci. Technol. 2006, 40, 1263-1269.
21. Stieglitz, L.; Zwick, G.; Beck, J.; Bautz, H.; Roth, W. The role of particulate carbon in the de-novo synthesis of polychlorinated dibenzodioxins and furans in fly ash. Chemosphere 1990, 20, 1953-1958.
22. Jay, K.; Stieglitz, L. On the mechanism of formation of polychlorinated aromatic compounds with copper (II) chloride. Chemosphere 1991, 22, 987-996.
23. Wikstrom, E.; Ryan, S.; Touati, A.; Gullett, B. K. Key parameters for de novo formation of polychlorinated dioxins and dibenzofurans. Environ. Sci. Technol. 2003, 37, 1962-1970.
24. Tuppurainen, K.; Aatamila, M.; Ruokojarvi, P.; Halonen, I.; Ruuskanen, J. Effect of liquid inhibitors on PCDD/F formation. Prediction of particle-phase PCDD/F concentrations using PLS modeling with gas-phase chlorophenol concentrations as independent variables. Chemosphere 1999, 38, 2205-2217.
25. Lomnicki, S.; Dellinger, B. Formation of PCDD/F from the pyrolysis of 2-chlorophenol on the surface of dispersed copper oxide particles. Proc. Combust. Inst. 2002, 29, 2463-2468.
26. Evans, S. C.; Dellinger, B. Mechanism of dioxin formation from the high-temperature pyrolysis of 2-chlorophenol. Environ. Sci. Technol. 2003, 37, 1325-1330.
27. Evans, S. C.; Dellinger, B. Mechanisms of dioxin formation from the high-temperature oxidation of 2-chlorophenol. Environ. Sci. Technol. 2005, 39, 122-127.
28. 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, 1806-1816.
29. Ghorishi, S. B.; Altwicker, E. R. Rapid formation of polychlorinated dioxin/furans during the heterogeneous combustion of 1,2-dichlorobenzene and 2,4-dichlorophenol. Chemosphere 1996, 32, 133-144.
30. U.S. EPA. Test Method 0023a. In SW-856 (NTIS PB88- - 23922.3); Office of Solid Waste and Emergency Response: Washington, DC, 1996.
31. Ryan, S. P.; Tabor, D.; Gullett, B. K.; Oudejans, L.; Touati, A. Determination of the vapor pressure of select polychlorinated dibenzo-p-dioxinsanddibenzofuransat 75-275°C. Chem. Eng. Sci. 2005, 60, 787-796.
32. 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.
33. Weber, R.; Hagenmaier, H. On the mechanism of the formation of polychlorinated dibenzofurans from chlorophenols. Organohalogen Compd. 1997, 31, 480-485.
34. Wiater-Protas, I.; Louw, R. Gas-phase chemistry of chlorinated phenols - formation of dibenzofurans and dibenzodioxins in slow combustion. Eur. J. Org. Chem. 2001, 20, 3945-3952.
35. Lomnicki, S.; Dellinger, B. A detailed mechanism of the surface-mediated formation of PCDD/F from the oxidation of 2-chlorophenol on a CuO/silica surface. J. Phys. Chem. A 2003, 107, 4387-4395.
36. Truce, W. E;, Kreider, E. M.; Brand, W. W. The Smiles and related rearrangements of aromatic systems. Org. React. 1970, 18, 99.
37. Muller, E. A.; Rull, L. F.; Vega, L. F.; Gubbins, K. E. Adsorption of water on activated carbons: a molecular simulation study. J. Phys. Chem. 1996, 100, 1189-1196.
38. Addink, R.; Olie, K. Mechanisms of formation and destruction of polychlorinated dibenzo-p-dioxins and dibenzofurans in heterogeneous systems. Environ. Sci. Technol. 1995, 29, 1425-1432.
39. Milligan, M. S.; Altwicker, E. R. Chlorophenol reactions on fly ash. 2. Equilibrium surface coverage and global kinetics. Environ. Sci. Technol. 1996, 30, 230-236.