Journal of Environmental Science International (한국환경과학회지)

The Korean Environmental Sciences Society (한국환경과학회)
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The Role of (Chloro-) Phenols in the Formation of Polychlorinated Dibenzofurans in Municipal Waste Incinerators

  • Ryu, Jae-Yong (Environmental Research Team, Daegu-Gyeongbuk Development institute) ;
  • Jang, Seong-Ho (Department of Environmental System Engineering, Pusan National University)
  • Published : 2007.01.31
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Abstract

Comparing predicted PCDF isomer patterns with those obtained from a municipal waste incinerator assessed the role of two-phenol condensation pathways in the formation of PCDFs. Complete PCDF homologue and isomer distributions were obtained from a Fluidized Bed Incinerator (FBI). Two-phenol condensation model, dependent only on the distributions of phenols, was developed to predict the PCDF congeners produced from phenol precursors. R-squared values from linear correlations are presented for the dichlorinated through hexa-chlorinated isomer distributions between measured and predicted. They range from 0.00: to 0.1 far the di-chlorinated through hexa-chlorinated isomer sets. Agreement between predicted and measured PCDF isomer distributions was very poor for all homologues. Two-phenol condensation pathways are not likely to be the pre-dominant pathways in the formation of PCDF in a FBI. However, dibenzofuran (DF) is likely to be produced from a condensation of two phenols. This work demonstrates the use of PCDF homologue and isomer patterns for testing PCDF formation mechanism from two-phenol condensation pathways in municipal waste incinerators.

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References

  1. Altwicker, E. R. and M.S. Milligan, 1993, Formation of dioxins: Competing rates between chemically similar precursors and de novo reactions, Chemosphere 27, 301 https://doi.org/10.1016/0045-6535(93)90306-P
  2. Luijk, R., D. Akkerman, P. Slot, K. Olie and F. Kepteijn, 1994, Mechanism of formation of polychlorinated dibenzo-p-dioxins and dibenzofurans in the catalyzed combustion of carbon, Environ. Sci. Technol., 28, 312 https://doi.org/10.1021/es00051a019
  3. Altwicker, E. R., 1996, Relative rates of formation of polychlorinated dioxins and furans from precursors and de novo reactions, Chemosphere, 33, 1897 https://doi.org/10.1016/0045-6535(96)00312-8
  4. Ballschmitter, K., W. Zoller and H. Buchert, 1985, Class, Th. Correlation between substitution pattern and reaction pathway in the formation of polychlorodibenzofurans, Fres. Z. Anal. Chem., 322, 587 https://doi.org/10.1007/BF00464594
  5. Dickson, L. C., D. Lenoir and O. Hutzinger, 1989, Surface-catalyzed formation of chlorinated dibenzodioxins and dibenzofurans during ncineration, Chemosphere, 19, 277 https://doi.org/10.1016/0045-6535(89)90324-X
  6. Stieglitz, L. and H. Vogg, 1987, On formation conditions of PCDD/PCDF in fly ash from municipal waste incinerators, Chemosphere, 16, 1917 https://doi.org/10.1016/0045-6535(87)90188-3
  7. Huang, H. and A. Buekens, 1995, On the mechanisms of dioxin formation in combustion processes, Chemosphere, 31, 4099 https://doi.org/10.1016/0045-6535(95)80011-9
  8. Born, J. G. P., R. Louw and P. Mulder, 1989, Formation of dibenzodioxins and dibenzofurans in homogeneous gas-phase reactions of phenols, Chemosphere, 19, 401 https://doi.org/10.1016/0045-6535(89)90342-1
  9. Born, J. G. P., P. Mulder and R. Louw, 1993, Fly ash mediated reactions of phenol and monochlorophenols: oxychlorination, deep oxidation, and condensation, Environ. Sci. Technol., 27, 1849 https://doi.org/10.1021/es00046a013
  10. Hell, K., L. Stieglitz, G. Zwick and R. Will, 1997, Mechanistic aspects of the De-novo-synthesis of PCDD/PCDF on model fly ash, Organohalogen Compd., 31, 492
  11. Stieglitz, L., G. Zwick, J. Beck, H. Bautz and W. Roth, 1989, Carbonaceous particles in fly ash - a source for the de-novo-synthesis of organochlorocompounds, Chemosphere, 19, 283 https://doi.org/10.1016/0045-6535(89)90325-1
  12. Mulholland, J. A. and J. Y. Ryu, 2001, Formation of polychlorinated dibenzo-p-dioxins by $CuCl_2$catalyzed condensation of 2,6 chlorinated phenols, Combust. Sci. Technol., 169, 107 https://doi.org/10.1080/00102200108907842
  13. Wikstrom, E. and S. Marklund, 2000, Secondary formation of chlorinated dibenzo-p-dioxins, dibenzofurans, biphenyls, benzenes and phenols during MSW combustion, Environ. Sci. Technol., 34, 604 https://doi.org/10.1021/es9906498
  14. Schramm, K. W., A. Wehrmeier, D. Lenoir, B. Henkelmann, K. Hahn, R. Zimmermann and A. Kettrup, 1996, Deduction of a typical pattern for the isomers of tetra- to heptachloro-dibenzo p-dioxins and -furans formed in combustion processes. Organohalogen Compd, 27, 196
  15. Wehrmeier, A., D. Lenoir, K. W. Schramm, R. Zimmermann, K. Hahn, B. Henkelmann and A. Kettrup, 1998, Patterns of isomers of chlorinated dibenzo-p-dioxins as tool for elucidation of thermal formation mechanism, Chemosphere, 36, 2775 https://doi.org/10.1016/S0045-6535(97)10236-3
  16. lino, F., T. Imagawa and B. Gullett, 2000, Dechlorination- controlled polychlorinated dibenzofuran isomer patterns from municipal waste incinerators, Environ. Sci. Technol., 34, 3143 https://doi.org/10.1021/es9913131
  17. lino, F., K. Tsuchiya, T. Imagawa and B. Gullett, 2001, An isomer prediction model based on dechlorination kinetics for polychlorinated naphthalenes, polychlorinated dibenzo-p-dioxins, and polychlorinated biphenyls from municipal waste incinerators, Environ. Sci. Technol., 35, 3175 https://doi.org/10.1021/es001857z
  18. Ryu, J. Y., J. A. Mulholland, J. E. Oh, D. T. Nakahata and D. H. Kim, 2004, Prediction of polychlorinated dibenzofuran congener distribution from gas-phase phenol condensation pathways, Chemosphere, 55, 1447 https://doi.org/10.1016/j.chemosphere.2004.01.002
  19. Tuppurainen, K., I. Halonen, P. Rukojarvi, J. Tarhanen and J. Ruuskanen, 1998, Formation of PCDDs and PCDFs in municipal waste incineration and its inhibition mechanisms: A review, Chemosphere, 36, 1493 https://doi.org/10.1016/S0045-6535(97)10048-0
  20. Lomnicki, S. and B. A. Dellinger, A 2003, Detailed mechanism of the surface-mediated formation of PCDD/F from oxidation of 2-chlorophenol on a CuO/Silica surface, J. Phys. Chem., 107, 4387 https://doi.org/10.1021/jp026045z
  21. Ryu, J. Y., J. A. Mulholland, M. Takeuchi, D. H. Kim and T. Hatanaka, 2006, CuCl2-catalyzed PCDD/F formation and congener patterns from phenols, Chemosphere, 61, 1312
  22. Weber, R. and H. Hagenmaier, 1999, PCDD/PCDF formation in fluidized bed incineration, Chemosphere, 38, 2643 https://doi.org/10.1016/S0045-6535(98)00472-X
  23. Zimmermann, R., M. Blumenstock, H. J. Heger, K. W. Schramm and A. Kettrup, 2001, Emission of non chlorinated and chlorinated aromatics in the flue gas of incineration plants during and after transient disturbances of combustion conditions: delayed emission effects, Environ. Sci. Technol., 35, 1019 https://doi.org/10.1021/es000143l
  24. Tuppurainen, K., A. Marjaleena, P. Ruokojarvi, I. Halonen and 1. Ruuskanen, 1999, 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, 38, 2205 https://doi.org/10.1016/S0045-6535(98)00439-1
  25. Tuppurainen, K., P. Ruokojarvi and A. Asikainen, 2000, Marjaleena Aatamila, Ruuskanen, J. Chlorophenols as precursors of PCDDlFs in incineration processes: correlations, PLS modeling, and reaction mechanisms, Environ. Sci. Technol., 34, 4958 https://doi.org/10.1021/es991429x
  26. Wikstrom, E., S. Ryan, A. Touati and B. K. Gullett, 2004, In situ formed soot deposit as a carbon source for polychlorinated dibenzo-p- dioxins and dibenzofurans, Environ. Sci. Technol., 38, 2097 https://doi.org/10.1021/es034564p
  27. lino, F. and D.Ph., 1999, Dissertation, Formation mechanisms of dioxins from municipal waste incinerators, University of Tokyo, Japan
  28. Hatanaka, T., A. Kitajima and M. Takeuchi, 2004, Role of copper chloride in the formation of polychlorinated dibenzo-p-dioxins and dibenzofurans during incineration. Chemosphere, 57, 73 https://doi.org/10.1016/j.chemosphere.2004.04.058
  29. Ryu, J. Y., J. A. Mulholland, J. E. Dunn, F. lino and B. K. Gullett, 2004, Potential Role of chlorination pathways in PCDD/F formation in a municipal waste incinerator, Environ. Sci. Technol., 38, 5112 https://doi.org/10.1021/es0497227
  30. Tuppurainen, K., A. Asikainen, P. Ruokojarvi and J. Ruuskanen, 2003, Perspectives on the formation of polychlorinated dibenzo-p-dioxins and dibenzofurans during municipal solid waste (MSW) incineration and other combustion processes, Acc. Chem. Res., 36, 652 https://doi.org/10.1021/ar020104+
  31. Weber, R., F. lino, T. Imagawa, M. Takeuchi, T. Sakurai and M. Sadakata, 2001, Formation of PCDF, PCDD, PCB, and PCN in de novo synthesis from PAH: Mechanistic aspects and correlation to fluidized bed incinerators, Chemosphere, 44, 1429 https://doi.org/10.1016/S0045-6535(00)00508-7
  32. Hell, K., L. Stieglitz, E. R. Altwicker, R. Addink and R. Will, 2001, Reactions of 2,4,6-trichlorophenol model fly ash: Oxidation to CO and $O_2$, condensation to PCDD/F and conversion into related compounds, Chemosphere, 42, 697 https://doi.org/10.1016/S0045-6535(00)00244-7