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Aspects of formation and degradation of polychlorinated dibenzo-p-dioxins and dibenzofurans

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Chinese Science Bulletin

Abstract

The research progress on the mechanisms of formation and degradation of polychlorinated dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) is reviewed. The primary sources of PCDD/Fs are chemical, thermal, photochemical and enzymatic reactions. Most of the thermal sources result in emissions into air. The studies on the photodegradation and biodegradation offer promise for destruction of PCDD/Fs in environment.

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References

  1. ES&T Editors, Dioxin risk,Environ. Sci. Technol., 1995, 29: 4A.

  2. Bao, Z. C., Wang, K. O., Kang, J. X.et al., Analysis of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofuans in pentachlorophenol and sodium pentachlorophenate,Environ. Chem. (in Chinese), 1995, 14: 317.

    Article  CAS  Google Scholar 

  3. Bao, Z. C., Wang, K. O., Kang, J. X.et al., Analysis of 2, 3, 7, 8-substituted PCDDs and PCDFs in thermolysis waste of HCH,Environ. Chem. (in Chinese), 1994, 13: 309.

    Google Scholar 

  4. Ding, X. L., Bao, Z. C., Zhang, Z.et al., Analysis of PCDDs and PCDFs in Chinese polychlorinated biphenyls,Environ. Chem. (in Chinese), 1990, 9(6): 39.

    CAS  Google Scholar 

  5. Li, L. J., Jiang, K., Determination of toxic equivalents of PCDD/Fs in two Chinese commercial PCBs by13 C isotope dilution method,Acta Scientiae Circumtantiae (in Chinese), 1995, 15: 433.

    CAS  Google Scholar 

  6. Zheng, M. H., Bao, Z. C., Wang, K. O.et al., Levels of PCDDs and PCDFs in the bleached pulp from Chinese pulp and paper industry,Bull. Environ. Contam. Toxicol., 1997, 59: 90.

    Article  PubMed  CAS  Google Scholar 

  7. Jiang, K., Li, L. J., Chen, Y. D.et al., Determination of PCDD/Fs from Chinese schistosomiasis areas and discussion of its significance for eco-environment,Chinese Sci. Bull., 1995, 40: 846.

    Google Scholar 

  8. Zheng, M. H., Bao, Z. C., Wang, K. O.et al., Polychlorinated dibenzo-p-dioxins and dibenzofurans in lake sediments from Chinese schistosomiasis areas,Bull. Environ. Contam. & Toxicol., 1997, 59: 653.

    Article  CAS  Google Scholar 

  9. Wu, W. Z., Shramm, K. W., Henklmann, B.et al., PCDD/Fs, PCBs, HCHs and HCB in sediments and soils of Ya-Er Lake area in China: Results on residual levels and correlation to the organic carbon and the particle size,Chemosphere, 1997, 34: 191.

    Article  CAS  Google Scholar 

  10. Nestrick, T. J., Lamparski, L. L., Isomer-specific determination of chlorinated dioxins for assessment of formation and potential environmental emission for wood combustion,Anal. Chem., 1982, 54: 2292.

    Article  CAS  Google Scholar 

  11. Sheffield, A., Sources and releases of PCDD’s and PCDF’s to the Canadian environment,Chemosphere, 1985, 14: 811.

    Article  Google Scholar 

  12. Thomas, V.M., Spiro, T. G., The U.S, dioxin inventory: Are there missing sources?Environ. Sci. Technol., 1996, 301 82A.

    Google Scholar 

  13. Gribble, G. W., The natural production of chlorinated compounds,Environ. Sci. Technol., 1994, 28: 310A.

    Article  CAS  Google Scholar 

  14. Svenson, A., Kjeller, L-O., Rappe, C., Enzyme-mediated formation of 2, 3, 7, 8-tetrachlorinated dibenzodioxins and dibenzofurans,Environ. Sci. Technol., 1989, 23: 900.

    Article  CAS  Google Scholar 

  15. Rappe, C., Dioxin patterns and source identification,Fresenius J. Anal. Chem., 1994, 348: 63.

    Article  CAS  Google Scholar 

  16. Silk, P. J., Lonergan, G. C., Arsenault, T. L.et al., Evidence of natural organochlorine formation in peat bogs,Chemosphere, 1997, 35: 2865.

    Article  CAS  Google Scholar 

  17. Lamparski, L. L., Stehl, R. H., Photolysis of pentachlorophenol-treated wood: Chlorinated dibenzo-dioxin formation,Environ. Sci. Technol., 1980, 14: 196.

    Article  CAS  Google Scholar 

  18. Vollmuth, S., Zajc, A., Niessner, R., Formation of polychlorinated dihenzo-p-dioxins and polychlorinated dibenzofurans during the photolysis of pentachlorophenol-containing water,Environ. Sci. Technol., 1994, 28: 1145.

    Article  CAS  Google Scholar 

  19. Kjeller, L-O., Rappe, C., Time trends in levels, patterns and prufiles for polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls in a sediment core from the Baltic Proper,Environ. Sci. Technol., 1995, 29: 346.

    Article  CAS  Google Scholar 

  20. Kjeller, L-O., Jones, K. C., Johnston, A. E.et al., Evidence for a decline in atmospheric emission of PCDD/Fs in the U. K,Environ. Sci. Technol., 1996, 30: 1398.

    Article  CAS  Google Scholar 

  21. Hutzinger, O., Gerg, M. V. D., Olie, K.et al., Dioxins and furans in the environment: evaluating toxicological risk from different sources by multicriteria analysis, inDioxins in the Environment (eds. Kamrin, M. A., Rodgers, P. W.), NY and London: Hemisphere Publishing Co., 1985, 9.

    Google Scholar 

  22. Zheng, M. H., Bao, Z. C., Wang, K. O.et al., Fomation of polychlorinated dibenzo-p-dioxins and dibenzofurans by heating hexachlorocyclohexane in the presence of FeCl3,Environ. Chem. (in Chinese), 1995, 14: 179.

    CAS  Google Scholar 

  23. Zheng, M. H., Bao, Z. C., Xu, X. B.et al., Formation of PCDD/Fs from the pyrolysis of HCH in the presence of iron oxide,Chemosphere, 1996, 32: 595.

    Article  Google Scholar 

  24. EHP Editors, Agent orange down under,Environ. Health Perspectiues, 1995, 103: 222.

    Google Scholar 

  25. Zheng, M. H., Bao, Z. C., Xu, X. B.et al., Discussion on the formation of polychlorinated debenzo-p-dioxin and dibenzofurans in the bleaching of pulp,China Pulp & Paper, 1996, 15(3): 48.

    CAS  Google Scholar 

  26. Hanson, D.,C&EN, 1994, 30: 13.

    Google Scholar 

  27. Harnly, M., Stephens, R., Mclaughlin, C.et al., Polychlorinated dibenw-p-dioxin and dibenzofuran contamination metal recovery facilities, open bum sites, and a railroad car incineration facility,Environ. Sci. Technol., 1995, 29: 677.

    Article  CAS  Google Scholar 

  28. Olie, K., Vermeulen, P., Hutzinger, O., Chlorodibenzo-p-dioxins and chlororodibenzofurans are trace components of fly ash and flue gas of some of municipal incinerators in Netherland,Chemospkre, 1977, 6: 455.

    Article  CAS  Google Scholar 

  29. EPA,Environmental News, Dallas: USEPA, Sept. 13, 1994.

    Google Scholar 

  30. Luijk, R., Formation of polyhalogenated dibenzo-p-dioxins and dibenzofurans during thermal degradation proceeses,Universiteit van Amsterdam, 1993.

  31. Born, J. G. P., Louw, R., Mulder, P., Fly ash mediated (oxy)chlorination of phenol and its role in PCDD/F formation,Chemosphere, 1993, 26: 2087.

    Article  CAS  Google Scholar 

  32. Milligan, M. S., Altwicker, E. R., Chlorophenol reaction on fly wh. 1. Adsorption/desorption equilibria and conversion to polychlorinated dibenzo-p-dioxins,Environ. Sci. Technol., 1996, 30: 225.

    Article  CAS  Google Scholar 

  33. Cains, P. W., Mccausland, L. J., Fernandes, A. R.et al., Polychlorinated dibenzo-p-dioxins and dibenzofurans formation in incineration: Effects of fly ash and carbon source,Environ. Sci. Technol., 1997, 31: 776.

    Article  CAS  Google Scholar 

  34. Sommeling, P. M., Mulder, P., Louw, R., Formation of PCDFs during chlorination and oxidation of chlorobenzene in chlorine/oxygen mixture arnund 340 °C.,Chemosphere, 1994, 29: 2015.

    Article  CAS  Google Scholar 

  35. Dickson, L. C., Lenoir, D., Hutzinger, O., Quantitative comparison ofde novo and precursor formation of polychlorinated dibezo-p-dioxins under simulated municipal solid waste incineration postcombustion conditions,Environ. Sci. Technol., 1992, 26: 1822.

    Article  CAS  Google Scholar 

  36. Froese, K. I,. Hutzinger, O., Mechanisms of formation of polychlorinated benzenes and phenols hy heterogeneous reactions of C2 aliphatics,Environ. Sci. Technol., 1997, 31: 542.

    Article  CAS  Google Scholar 

  37. Stieglitz, L., Zwick, G., Beck, J.et al., On thede novo synthesis of PCDD/PCDF on fly ash of municipal waste incinerators.Chemosphere, 1989, 18: 1219.

    Article  Google Scholar 

  38. Luijk, R., Akkennan, D. M., Slot, P.et al., Mechanism of formation of polychlorinated dibenzo-p-dioxins and dibenzofurans in the catalyzed combustion of carbon,Environ. Sci., Technol., 1994, 28: 312.

    Article  CAS  Google Scholar 

  39. Froese, K. L., Hutzinger, O., Polychlorinated benzene, phenol, dibenzo-p-dioxin, and dibenzofuran in heterogeneous combustion reactions of acetylene,Environ. Sci. Technol., 1996, 30: 998.

    Article  CAS  Google Scholar 

  40. Stromberg, B., Carbon dioxide—A precursor for dioxins?Chemosphere, 1991, 23: 1515.

    Article  Google Scholar 

  41. Milligan, M. S., Altwicker, E. R., The relationship betweende novo synthesis of polychlorinated dibenzo-p-dioxins and dibenzofurans and low-temperature carbon gasification in fly ash,Environ. Sci. Technol., 1993, 27: 1595.

    Article  CAS  Google Scholar 

  42. Milligan, M. S., Altwicker, E. R., Mechanistic aspects of thede novo synthesis of polychlorinated dibenzo-p--dioxins and furans in fly ash from experiments using isotopically labeled reagents,Environ. Sci. Technol., 1995, 29: 1353.

    Article  CAS  Google Scholar 

  43. Crosby, D. G., Woolson, A. S., Photodecomposition of chlorinated dibenzo-p-dioxins,Science, 1971, 173: 748.

    Article  PubMed  CAS  Google Scholar 

  44. Buser, H. R., Preparation of qualitative standard mixtures of polychlorinated dibenzo-p-dioxins and dibenzofurans by ultraviolet and γ-inrradiation of the octachloro, compounds,J. Chromatogr., 1976, 129: 303.

    Article  PubMed  CAS  Google Scholar 

  45. Hung, H.-S., Ingram, L. L., Effect of solvents on the photodegradation rates of octachlorodibenzo-p-dioxin,Bull. Environ. Toxicol., 1990, 44: 380.

    Article  CAS  Google Scholar 

  46. Zheng, M. H., Bao, Z. C., Xu, X. B.et al., Mechanism of photodegradation of polychlorinated dibenzo-p-dioxins in carbon tetrachloride,Chemosphere, 1996, 32: 603.

    Article  Google Scholar 

  47. Bao, Z. C., Zheng, M. H., Wang, K. O., Ultraviolet photolysis of polychlorinated dibenzo-p-dioxins in chloroform,Environ. Chem. (in Chinese), 1995, 14: 190.

    CAS  Google Scholar 

  48. Friesen, K. J., Mulr, D. C. G., Webeter, G. R. B., Evidence of Sensitized photolysis of polychlorinated dibenzo-p-dioxins in nature water under sunlight conditions,Environ. Sci. Technol., 1990, 24: 1739.

    Article  CAS  Google Scholar 

  49. Dung, M. H., O’Keef, P. W., Comparative rates of photolyeis of polychlorinated dibenzofurans in organic solvents and in aqueous solutions,Envriron. Sci. Technol., 1994, 28: 549.

    Article  CAS  Google Scholar 

  50. Friesen, K. J., Foga, M. M., Loewen, M. D., Aquatic photodegradation of polychlorinated dibenzofurans: Rates and photopduct analysis,Environ. Sci. Technol., 1996, 30: 2504.

    Article  CAS  Google Scholar 

  51. Miller, G. C., Hebert, V. R., Photolysis of octachlorodibenzo-p-dioxin on soil: prcduction of 2, 3, 7, 8-TCDD,Chemosphere, 1989, 18: 1265.

    Article  Google Scholar 

  52. Zhang, Z. J., Bao, Z. C., Zheng, M. H.et al., The UV photodegradation of polychlorinated dibenzo-p-dioxins on the surface of soil,Environ. Chem. (in Chinese), 1996, 15: 541.

    CAS  Google Scholar 

  53. Dougherty, E. J., Mcpeters, A. L., Overcash, M. R., Kinetics of photodegradation of 2, 3, 7, 8-tetrachlorodibenzo-pdioxin: theoretical maximum rate of mil decontamination,Chemosphere, 1991, 23: 589.

    Article  CAS  Google Scholar 

  54. Mcpeters, A. L., Overcash, M. R., Demonstration of photodegradation by sunlight of 2, 3, 7, 8-tetrachlrodibenzo-p-dioxin in 6 cm mil columns,Environ. Sci. Tcchnol., 1993, 27: 1221.

    Article  CAS  Google Scholar 

  55. Hosoya, K., Kimata, K., Fukunishi, K.et al., Photodecompoeition of 1, 2, 3, 4-TCDD and 2, 3, 7, 8-tetrachlorodibenzop-dioxin (TCDD) in water-alcohol media on a soil support,Chemphere, 1995, 31: 3687.

    CAS  Google Scholar 

  56. Yan, Q., Kappila, S., Sivils, L. D.et al., Effect of sensitizers and inhibeiton, on phototransformation of polychlorinated dibenzo-p-dioxins (PCDDs),Chemosphere, 1995, 31: 3627.

    Article  CAS  Google Scholar 

  57. Schuler, F., Schmid, P., Schlatter, Ch., Photodegradation of polychlorrinated dibenzo-p-dioxins and dibenzofurans in cuticular waxes of Laurel cherry,Chemosphere, 1998, 36: 21.

    Article  CAS  Google Scholar 

  58. Zhang, Z. J., Bao, Z. C., Wang, K. O.et al., The photolysis of chlorinated dibenzo-p-dioxin with titanium dioxide as catalyst,Environ. Chem. (in Chinese), 1996, 15: 47.

    Google Scholar 

  59. Vollmuth, S., Niessner, R., Degradation of PCDD, PCDF, PAH, PCB and chlorinated phenols during the destruction-treatment of landfill sewagewater in laboratory model reactor (UV, ozone, and UV/ozone),Chemosphere, 1995, 30: 2317.

    Article  CAS  Google Scholar 

  60. Smmer, S., Karmps, R., Kleinermanns, K., Photooxidation of exhaust pollutants: V Photooxidation and photoreduction of polychlorinated dibenzo-p-dioxins and dibenzofurans,Chemosphere, 1996, 33: 2221.

    Article  Google Scholar 

  61. Orazio, C. E., Kapilla, S., Puri, P. K., Persistence of chlorinated dioxins and furans in the soil environment,Chemosphere, 1992, 25: 1467.

    Article  Google Scholar 

  62. Du, X. Y., Zhu, N. Q., Xia, X. J.et al., A perliminary approach to biodegradation of polychlorinated dibenzo-p-dioxins (PCDDs),Environ. Chem. (in Chinese), 1995, 14: 187.

    Article  CAS  Google Scholar 

  63. Adriaens, P., Gribic’-Galic, D., Reductive dechlorination of PCDD/F by anaerobic cultures and sediments,Chemosphere, 1994; 29: 2253.

    Article  CAS  Google Scholar 

  64. Disse, C., Weber, H., Hamann, R.,et al., Comparison of PCDD and PCDF concentrations after aerobic and anaerobic digestion of sewage sludge,Chemosphere, 1995, 31: 3617.

    Article  PubMed  CAS  Google Scholar 

  65. Hilarides, R. J., Gray, K. A., Guzzetta, J.et al., Feasibility system design and economic evaluation of radiolytic degradation of 2, 3, 7, 8-tetrachlomdibenzo-p-dioxin on soil,Water Enuiron. Res., 1996, 66: 178.

    Article  Google Scholar 

  66. Oku, A., Tomari, K., Kamada, T.et al., Destruction of PCDDs and PCDFs: A convenient method using alkalimetal hydroxide in 1, 3-dimethyl-2-imidazolidinone (DMI),Chemosphere, 1995, 31: 3873.

    Article  CAS  Google Scholar 

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Zheng, M., Liu, P., Bao, Z. et al. Aspects of formation and degradation of polychlorinated dibenzo-p-dioxins and dibenzofurans. Chin.Sci.Bull. 44, 1249–1257 (1999). https://doi.org/10.1007/BF02885839

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