Advertisement

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

  • Ghulam Ghaus Choudhry
  • Otto Hutzinger
Part of the Residue Reviews book series (RECT, volume 84)

Abstract

Polychlorinated dibenzo-p-dioxins (PCDDs) long have been recognized as by-products from the manufacture of certain chlorinated phenols (Bauer et al. 1961). For example, 2, 4, 5-trichlorophenol is prepared industrially by the hydrolysis of 1, 2, 4, 5-tetrachlorobenzene at elevated temperatures and pressure, a process which can also result in the formation of traces of heterocyclic impurities, including 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) (Crosby et al. 1971). Chlorinated phenols have widespread use as fungicides, bactericides, slimicides, herbicides, etc., and they are also utilized in the production of phenoxy acids such as 2, 4-dichloro-and 2, 4, 5-trichlorophenoxy-acetic acid (2, 4,-D and 2, 4, 5-T, respectively). The annual world production of chlorinated phenols is approximately. 100,000 tons (Nilsson et al. 1974). Likewise, for almost four decades, 2, 4, 5,-T and its derivatives have received wide use as herbicides, especially for control of brush, jungle, and aquatic weeds. For instance, the 1968 U.S. production of these compounds exceeded 60 million lb, and residues have been detected in crops, soil, the atmosphere, rainwater, and surface waters (Crosby and Wong 1973 and references cited therein). In addition to PCDDs, polychlorinated dibenzofurans (PCDFs) have been shown to be present as contaminants in commercial chlorinated phenols and related products (Dobbs and Grant 1979, Buser 1976, Choudhry and Hutzinger 1982 b, Pohland and Yang 1972). Moreover, PCDFs have also been identified as contaminants in a number of industrial products such as polychlorinated biphenyls (PCBs) and hexachlorobenzene (Refs. cited in Choudhry et al. 1977 a).

Keywords

Diphenyl Ether Reductive Dechlorination Photochemical Degradation Photo Degradation Chlorinate Phenol 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Akermark, B.: Photochemical reactions of phenoxy acids and dioxins. In (Ed. C. Ramel) (ed): Chlorinated phenoxy acids and their dioxins. Ecol. Bull. (Stockholm) 27, 75 (1978).Google Scholar
  2. Bauer, H., K. H. Schulz, and U. Spiegelberg: Occupational intoxications in manufacturing chlorophenol compounds. Arch. Gewerbepath. Gewerbehyg. 18, 538 (1961).CrossRefGoogle Scholar
  3. Botre, C., A. Memoli, and F. Alhaique: TCDD solubilization and photodecompo- sition in aqueous solutions. Environ. Sci. Technol. 12, 335 (1978).CrossRefGoogle Scholar
  4. Buser, H. -R.: Analysis of polychlorinated dibenzo-p-dioxins and dibenzofurans in chlorinated phenols by mass fragmentography. J. Chromatogr. 107, 295 (1975).PubMedCrossRefGoogle Scholar
  5. Buser, H-R , Preparation of qualitative standard mixtures of polychlorinated dibenzo-p-dioxins and dibenzofurans by ultra-violet and y-irradiation of the octachloro compounds. J. Chromatogr. 129, 303 (1976).CrossRefGoogle Scholar
  6. Buser, H. R, Formation and identification of tetra-and pentachlorodibenzo-p-dioxins from photolysis of two isomeric hexachlorodibenzo-p-dioxins. Chemosphere 8, 251 (1979).CrossRefGoogle Scholar
  7. Choudhry, G. G., and O. Hutzinger: Mechanistic aspects of the thermal formation of halogenated organic compounds including polychlorinated dibenzo-pdioxins. Part I: Theoretical background and thermochemical decompositions of monomeric aliphatics and aromatics. Toxicol. Environ. Chem. 5, 1 (1982 a).CrossRefGoogle Scholar
  8. Choudhry, G. G., and O. Hutzinger ,Mechanistic aspects of the thermal formation of halogenated organic compounds including polychlorinated dibenzo-p-dioxins. Part II: Thermochemical generation and destruction of dibenzofurans and dibenzop-dioxins. Toxicol. Environ. Chem. 5, 67 (1982 b).CrossRefGoogle Scholar
  9. Choudhry, G. G., and O. Hutzinger , K. Olie, and O. Hutzinger: Mechanisms in the thermal formation of chlorinated compounds including polychlorinated dibenzo-p-dioxins. Presented 10th Internat. Symp. “Advances in Environmental Analytical Chemistry.” Chlorinated dioxins and related compounds: Impact on the environment. Rome (Italy), Oct. 22–24, 1980, pp. 275–301. Oxford and New York: Pergamon Press, (1982 a).Google Scholar
  10. Chlorinated dibenzo-p-dioxins (PCDD’s) from incin-eration processes. Presented ASME/EPA Hazardous Waste Incineration Conf., May 27–29, 1981, Williamsburg, VA. U.S.A. In press (1982 b).Google Scholar
  11. A. A. M. Roof, and O. Hutzinger: Mechanisms in sensitized photochemistry of environmental chemicals. Toxicol. Environ. Chem. 2, 259 (1979).CrossRefGoogle Scholar
  12. G. Sundström, F. W. M. van der Wielen, and O. Hutzinger: Synthesis of chlorinated dibenzofurans by photolysis of chlorinated diphenyl ethers in acetone solution. Chemosphere 6, 327 (1977 a).CrossRefGoogle Scholar
  13. G. Sundström, F. W. M. van der Wielen, and O. Hutzinger , L O Ruzo, and O. Hutzinger: Photochemistry of chlorinated diphenyl ethers. J. Agr. Food Chem. 25, 1371 (1977 b).Google Scholar
  14. Crosby, D. G., and K. W. Moilanen: Photo decomposition of chlorinated biphenyls and dibenzofurans. Bull. Environ. Contam. Toxicol. 6, 372 (1973).CrossRefGoogle Scholar
  15. Crosby, D. G., and K. W. Moilanen, and A. S. Wong: Photodecomposition of 2, 4, 5-trichlorophenoxyacetic acid (2, 4, 5-T) in water. J. Agr. Food Chem. 21, 1052 (1973).CrossRefGoogle Scholar
  16. Crosby, D. G., and K. W. Moilanen, Environmental degradation of 2, 3, 7, 8-tetrachlorodibenzo- p-dioxin (TCDD). Science 195, 1337 (1977).PubMedCrossRefGoogle Scholar
  17. Crosby, D. G., and K. W. Moilanen , K W., Moilanen and A. S. Wong: Environmental generation and degra-Google Scholar
  18. Crosby, D. G., and K. W. Moilanen, A S Wong, J. R. Plimmer, and E. A. Woolson: Photodecomposition of chlorinated dibenzo-p-dioxins. Science 173, 748 (1971).Google Scholar
  19. Desideri, A., A. D. Domenico, R. Vanzati, P. Tancioni, and A. D. Muccio: Photolysis of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) in iso-octane, hexane and cyclohexane. Bull. Chim. Farm. 118, 274 (1979).Google Scholar
  20. Dobbs, A. J., and C. Grant: Photolysis of highly chlorinated dibenzo-p-dioxins by sunlight. Nature 278, 163 (1979).CrossRefGoogle Scholar
  21. Duce, R. A., J. G. Quinn, C. E. Olney, S. R. Piotrowicz, B. J. Ray, and T. L. Wade: Enrichment of heavy metals and organic compounds in the surface micro-layer of Narragansett Bay, Rhode Island. Science 176, 161 (1972).PubMedCrossRefGoogle Scholar
  22. Duke, T. W., J. I. Lowe, and A. J. Wilson, Jr.: Polychlorinated biphenyl (Aroclor 1254) in the water, sediment and biota of Escambia Bay, Florida Bull. Environ, Contam. Toxicol, 5, 171 (1970).CrossRefGoogle Scholar
  23. Firestone, D., J. Ress, N. L. Brown, R. P. Barron, and J. N. Damico: Determination of polychlorodibenzo-p-dioxin and related compounds in commercial chlorophenols. J. Assoc. Official Anal. Chemists 55, 85 (1972).Google Scholar
  24. Gebefilgi, I., R. Baumann, and R. Korte: Photochemischer Abbau von 2, 3, 7, 8-Tetrachlordibenzo-p-dioxin (TCDD) unter simulierten Unweltbedingungen. Naturwissenschaften 64, 486 (1977).CrossRefGoogle Scholar
  25. Harvey, G. R., W. G. Steinhauer, and J. M. Teal: Polychlorobiphenyls in North Atlantic Ocean Water. Science 180, 643 (1973).PubMedCrossRefGoogle Scholar
  26. Hiatt, C. W., W. T. Haskins, and L. Olivier: The action of sunlight on sodium pentachlorophenate. Amer. J. Trop. Med. Hygiene 9, 527 (1960).Google Scholar
  27. Howard, P. H., J. Saxena, and H. Sikka• Determining the fate of chemicals. Environ. Sci. Technol. 12, 398 (1978).CrossRefGoogle Scholar
  28. Hutzinger, O., S. Safe, B. R. Wentzell, and V. Zitko , and V. Zitko: Photochemical degradation of chlorobiphenyls.Environ. Health Perspectives, p. 15 (1972).Google Scholar
  29. Kuwahara, M., N. Kato, and K. Munakata: The photochemical reaction of pentachlorophenol. Part I. The structure of the yellow compound. Agr. Biol. Chem. 30, 232 (1966 a).Google Scholar
  30. Kuwahara, M., N. Kato, and K. Munakata The photochemical reaction of pentachlorophenol. Part II. The chemical structure of minor products. Agr. Biol. Chem. 30, 239 (1966 b).CrossRefGoogle Scholar
  31. Kuwahara, M., N. Kato, and K. Munakata N. Shindo, N. Kato, and K. Munakata: The photochemical reaction of pentachlorophenol. Part III. The chemical structure of a yellow C i g-compound. Agr. Biol. Chem. 33, 892 (1969).CrossRefGoogle Scholar
  32. Lamparski, L. L., R. J. Stehl, and R. L. Johnson; Photolysis of pentachlorophenoltreated wood. Chlorinated dibenzo-p-dioxin formation. Environ. Sci. Technol. 14, 196 (1980).CrossRefGoogle Scholar
  33. Liberti, A., D. Brocco, I. Allergrini, and G. Bertoni: Field photodegradation of TCDD by ultraviolet radiations. In F. Cattabeni, A. Cavallaro, and G. Galli (eds.): Dioxin: Toxicological and chemical aspects, p. 195. New York, London: S. P. Medical & Sci. Books (1978).Google Scholar
  34. Martin, R. L., M. L. Porter, and I. H. Pomerantz: Studies on the formation potential and presence of chlorinated dibenzofurans in chlorobiphenyls. NIEHS Conference, April 2–3–1973. Cited in J. E. Huff, and J. S. Wassom: Chlorinated dibenzodioxins and dibenzofurans. Environ. Health Perspectives, No. 5, p. 283 (1973).Google Scholar
  35. >Martin, R. L., M. L. Porter, and I. H. Pomerantz , National Academy of Sciences, Washington, D.C.: The effects of herbicides in South Vietnam. Report by Committee on Effects of Herbicides in Vietnam, Div. Sci. Assembly of Life Sciences. Nat. Res. Council (1974).Google Scholar
  36. Nestrick, T. J., L. L. Lamparski, and D. I. Townsend: Identification of tetrachlorodibenzo-p-dioxin isomers at 1 ng level by photolytic degradation and pattern recognition techniques. Anal. Chem. 52, 1865 (1980).CrossRefGoogle Scholar
  37. Nilsson, C. -A., and L. Renberg: Further studies on impurities in chlorophenols. J. Chromatogr. 89, 325 (1974).CrossRefGoogle Scholar
  38. K. Anderson, C. Rappe, and S. -O. Westermark: Chromatographic evidence for the formation of chlorodioxins from chloro-2-phenoxyphenols. J. Chromatogr. 96, 137 (1974).CrossRefGoogle Scholar
  39. Norris, L. A.: The movement, persistence, and fate of the phenoxy herbicides and TCDD in the forest. Residue Reviews 80, 65 (1981).Google Scholar
  40. Norström, A., K., Anderson, and C. Rappe: Studies on the formation of chlorodibenzofurans by irradiation or pyrolysis of chlorinated diphenyl ethers. Chemosphere 6, 241 (1977).CrossRefGoogle Scholar
  41. >Norström, A., K., Anderson, and C. Rappe, Formation of chlorodibenzofurans by irradiation of chlorinated diphenyl ethers. Chemosphere 5, 21 (1976).CrossRefGoogle Scholar
  42. Ogata, Y., K. Takagi, and I. Ishino: Photochemical rearrangement of diaryl ethers. Tetrahedron 26, 2703 (1970).CrossRefGoogle Scholar
  43. Plimmer, J. R., and U. I. Klingebiel: Riboflavin photosensitized oxidation of 2, 4-dichlorophenol: Assessment of possible chlorinated dioxin formation. Science 174, 407 (1971).Google Scholar
  44. Plimmer, J. R., and U. I. Klingebiel, D. G. Crosby, and A. S. Wong: Photochemistry of dibenzo-p-dioxins. Adv. Chem. Series 120, 44 (1973).Google Scholar
  45. Pohland, A. E., and G. C. Yang: Preparation and characterization of chlorinated dibenzo-p-dioxins. J. Agr. Food Chem. 20, 1093 (1972).CrossRefGoogle Scholar
  46. Schmidt, T. T., R. W. Risebrough, and R. Gress: Input of polychlorinated biphenyls into California coastel waters from urban sewage outfalls. Bull. Environ. Contam. Toxicol. 6, 235 (1971).PubMedCrossRefGoogle Scholar
  47. Stehl, R. H., R. R. Papenfuss, R. A. Bredeweg, and R. W. Roberts: The stability of pentachlorophenol and chlorinated dioxins to sunlight, heat, and cornbustion. Adv. Chem. Ser. 120, 119 (1973).CrossRefGoogle Scholar
  48. Veith, G. D., and G. F. Lee: Review of chlorinated biphenyl contamination in natural waters. Water Research 4, 265 (1970).CrossRefGoogle Scholar
  49. Villanueve, E. C., V. W. Burse, and R. W. Jennings: Chlorodibenzo-p-dioxin contamination of two commercially available pentachlorophenols. J. Agr. Food Chem. 21, 739 (1973).CrossRefGoogle Scholar
  50. Wipf, H. K., E. Homberger, N. Neuner, and F. Schenker: Field trials on photo-degradation of TCDD on vegetation after spraying with vegetable oil. In F. Cattabeni, A. Cavallaro, and G. Galli (eds.): Dioxin; Toxicological and chemical aspects, p. 201. New York, London: S. P. Medical & Sci. Books (1978).Google Scholar
  51. Wong, A. S., and D. G. Crosby: Decontamination of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) by photochemical action. In F. Cattabeni, A. Cavallaro, and G. Galli (eds.): Dioxin: Toxicological and chemical aspects p. 185. New York, London: SP Medical & Sci. Books, (1978).Google Scholar
  52. Wong, A. S., and D. G. Crosby , Manuscript received March 1, 1982; accepted March 19, 1982.Google Scholar

Copyright information

© Springer-Verlag New York Inc. 1982

Authors and Affiliations

  • Ghulam Ghaus Choudhry
    • 1
  • Otto Hutzinger
    • 1
  1. 1.Laboratory of Environmental and Toxicological ChemistryUniversity of AmsterdamAmsterdamThe Netherlands

Personalised recommendations