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Chemistry and Occurrence of Dioxins

  • Alastair Hay
Chapter
Part of the Disaster Research in Practice book series (DRP)

Abstract

The abbreviation “dioxin” has become a common term for anyone referring to the polychlorinated dibenzo-p-dioxins (PCDDs). More often than not “dioxin” has been used as an abbreviation for the dibenzodioxin with four chlorine atoms 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). The terminology for TCDD is quite simple. “Tetrachloro” refers to the four chlorine atoms on the two benzene rings. “Dibenzo” refers to these two benzene molecules, and dioxin describes the two oxygen bridges holding the two benzene rings together (as shown in Figure 1). The designation p, or para, refers to the position of the oxygen atoms in relation to the benzene molecules. The number of PCDD isomers varies depending on how many chlorine atoms are attached to the parent molecule. Four chlorine atoms attached at random on any of the eight positions labeled in Figure 1 confers the greatest degree of flexibility, and hence most isomers occur in the tetrachlorinated group (see Table I).1

Keywords

Chlorine Atom Trace Chemistry Chlorinate Phenol Dioxin Level Dioxin Formation 
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.

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References

  1. 1.
    Rappe, C. Chemical aspects of polychlorinated dibenzodioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs), presented at International Agency for Research on Cancer, January 10–11, 1978.Google Scholar
  2. 2.
    McConnell, E. E., Moore, J. A., Haseman, J. K., and Harris, M. W. The comparative toxicity of chlorinated dibenzo-p-dioxins in mice and guinea pigs, Toxicology and Applied Pharmacology 44, 335–356 (1978).PubMedCrossRefGoogle Scholar
  3. 3.
    Rappe, C. Personal letter, 30 July 1979.Google Scholar
  4. 4.
    Rappe, C., Buser, H. R., and Bosshardt, H. P. Dioxins, dibenzofurans and other polyhalogenated aromatics; production, use, formation and destruction, Annals of the New York Academy of Sciences 320, 1–18 (1979).Google Scholar
  5. 5.
    Milnes, M. H. Formations of 2,3,7,8-tetrachlorodibenzodioxin by thermal decomposition of sodium trichlorophenate, Nature (London) 232, 395–396 (1971).CrossRefGoogle Scholar
  6. 6.
    Sambeth, J. Personal communication to author, reported in Hay. A. Seveso: the crucial questions of reactor safety, Nature (London) 281, 521 (1979).CrossRefGoogle Scholar
  7. 7.
    Sambeth, J. Personal communication to author reported in Hay, A. Seveso: No answers yet, Disasters 2, 163–168 (1978).CrossRefGoogle Scholar
  8. 8.
    Huckins, J. N., Stalling, D. L., and Smith, W. A. Foam-chemical chromatography for analyses of polychlorinated dibenzodioxins in Herbicide Orange, Journal of the Association of Official Analytical Chemists 61, 32–38 (1977).Google Scholar
  9. 9.
    Ahling, B., Lindskog, A., Jansson, B., and Sundstrom, G. Formation of polychlorinated dibenzo-p-dioxins and dibenzofurans during combustion of a 2,4,5-T formulation, Chemosphere 6, 461–466 (1977).CrossRefGoogle Scholar
  10. 10.
    Moore, J. A., McConnell, E. E., Dalgard, D. W., and Harris, M. W. Comparative toxicity of three halogenated dibenzofurans in guinea pigs, mice and Rhesus monkeys, Annals of the New York Academy of Sciences 320, 151–163 (1979).PubMedGoogle Scholar
  11. 11.
    Agriculture and Pollution: The Royal Commission on Environmental Pollution, 7th Report, September 1979 (Chairman, Sir Hans Kornberg).Google Scholar
  12. 12.
    Hay, A. Dioxin source is safe, Nature (London) 274, 526 (1978).CrossRefGoogle Scholar
  13. 13.
    Buser, H. R., and Bosshardt, H. P. Determination of polychlorinated dibenzo-p-dioxins and dibenzofurans in commercial pentachlorophenols by combined gas chromatographymass spectrometry, Journal of the Association Official Analytical Chemists 59, 562–569 (1976).Google Scholar
  14. 14.
    Rappe, D., Marklund, S., Buser, H. R., and Bosshardt, H. P. Formation of polychlorinated dibenzo-p-dioxins (PCDDs) by burning and heating chlorophenates, Chemosphere 7, 269–281 (1978).CrossRefGoogle Scholar
  15. 15.
    Goldstein, J. A., Friesen, M., Linder, R. E., Hickman, P., Hass, J. R., and Bergman, H. Effects of pentachlorophenol on hepatic drug metabolizing enzymes and porphyria related to contamination with chlorinated dibenzo-p-dioxins and dibenzofurans, Biochemical Pharmacology 26, 1549–1557 (1977).PubMedCrossRefGoogle Scholar
  16. 16.
    Vos, J. G., Koeman, J. H., van der Maas, H. L., ten Noever de Brauw, M. C, and de Vos, R. H. Identification and toxicological evaluation of chlorinated dibenzofuran and chlorinated naphthalene in two commercial polychlorinated biphenyls, Food and Cosmetic Toxicology 8, 625–633 (1970).CrossRefGoogle Scholar
  17. 17.
    Vos, J. G., and Koeman, J. H. Comparative toxicologic study with polychlorinated biphenyls in chickens with special reference to porphyria, edema formation, liver necrosis, and tissue residues, Toxicology and Applied Pharmacology 17, 656–668 (1970).PubMedCrossRefGoogle Scholar
  18. 18.
    Niguchi, K. Outline in PCB Poisoning and Pollution, ed. Kentaso Higuchi, Kodansha Ltd., Tokyo, Academic Press, New York (1976), pp. 3–7.Google Scholar
  19. 19.
    Duratsune, M. Epidemiologic Studies on Yusho, in PCB Poisoning and Pollution, ed. Kentaso Higushi, Kodansha Ltd., Tokyo, Academic Press, New York, 1976, pp. 9–23.Google Scholar
  20. 20.
    Tsukamoto, H. The chemical studies on detection of toxic compounds in the rice bran oils used by the patients of Yusho, Fukuoka Acta Med. 60, 496–512 (1969).Google Scholar
  21. 21.
    Kojima, T. Chlorobiphenyls in the sputa and tissues, Fukuoka Acta Med. 62, 25–29 (1971).Google Scholar
  22. 22.
    Kikuchi, M., Mikagi, Y., Hashimoto, M., and Kojima, T. Two autopsy cases of chronic chlorophenyls poisoning, Fukuoka Acta Med. 62, 89–103 (1971).Google Scholar
  23. 23.
    Buser, H. R., Bosshardt, H. P., Rappe, C, and Lindahl, R. Identification of polychlorinated dibenzofuran isomers in flyash and PCB pyrolyses, Chemosphere 7, 419–429 (1978).CrossRefGoogle Scholar
  24. 24.
    Buser, H. R., Bosshardt, H. P., and Rappe, C. Formation of polychlorinated dibenzofurans (PCDFs) from the pyrolysis of PCBs, Chemosphere 7, 109–119 (1978).CrossRefGoogle Scholar
  25. 25.
    Rappe, C., Buser, H. R., Stalling, D. L., Smith, L. M., and Dougherty, R. C. Identification of polychlorinated dibenzofurans in environmental samples, Nature (London), 292, 524–526(1981).CrossRefGoogle Scholar
  26. 26.
    Olie, K., Vermeulen, P. L., and Hutzinger, O. Chlorodibenzo-p-dioxins and chlorodibenzofurans are trace components of flyash and flue gas of some municipal incinerators in the Netherlands, Chemosphere 6, 455–459 (1978).CrossRefGoogle Scholar
  27. 27.
    Buser, H. R., and Bosshardt, H. P. Polychlorieste dibenzo-p-dioxine, dibenzofurane und benzole in der asche dommunaler und industrieller Verbrennungsanlagen, Mitteilungen aus dem Gebiete der Lebensmitteluntersuchung und Hygiene 69, 191–199 (1978).Google Scholar
  28. 28.
    Buser, H. R., Bosshardt, H. P., and Rappe, C. Identification of polychlorinated dibenzo-p-dioxin isomers found in flyash, Chemosphere 7, 165–172 (1978).CrossRefGoogle Scholar
  29. 29.
    “The Trace Chemistries of Fire,” a source of and routes for the entry of chlorinated dioxins into the environment by the Chlorinated Dioxin Task Force, the Michigan Division, Dow Chemical USA (November 1978).Google Scholar
  30. 30.
    Rawls, R. Dow finds support, doubt for dioxin ideas. Chemical and Engineering News, 12 February 1979, pp. 23-27.Google Scholar
  31. 31.
    Rappe, C. Comments on the Dow Report “The Trace Chemistries of Fire,” Letter to Author, 26 March 1979.Google Scholar
  32. 32.
    Rappe, C. Reported in Hay, A., Dispute over Dow Chemical’s theory of dioxin traces, Nature (London) 281, 619–620 (1979).CrossRefGoogle Scholar
  33. 33.
    Bumb, R. R. Personal letter, 7 June 1979.Google Scholar
  34. 34.
    Townsend, D. E. “The Environmental Background: the Fate and Behaviour of Trace Chemicals formed by Combustion,” Dow Chemical Company 1978/1979.Google Scholar
  35. 35.
    Rappe, C. Personal letter, 16 June 1981.Google Scholar
  36. 36.
    Bumb, R. R., Crummett, W. B., Cutie, S. S., Gledhill, J. R., Hummel, R. H., Kagel, R. O., Lamparski, L. L., Luoma, E. V., Miller, D. L., Nestrick, T. J., Shadoff, L. A., Stehl, R. H., and Woods, J. S. Trace chemistries of fire: a source of chlorinated dioxins, Science 210, 385–390 (1980).PubMedCrossRefGoogle Scholar
  37. 37.
    Liberti, A. Formation of organochlorine compounds in incineration processes, presented at workshop on “Impact of Chlorinated Dioxins and Related Compounds on the Environment,” Rome, 22–24 October 1980. Also reported in Hay, A., Chlorinated dioxins and the environment, Nature (London) 289, 351–352 (1981).CrossRefGoogle Scholar
  38. 38.
    Buser, H. R. High resolution gas chromatography of 22 Tetrachlorinated-p-dioxin (TCDD) isomers, presented at workshop on “Impact of Chlorinated Dioxins and Related Compounds on the Environment,” Rome, 22–24 October 1980.Google Scholar
  39. 39.
    Olie, K., Lustenhouwer, J. W. A. and Hutzinger, O. Chlorinated dibenzo-p-dioxins and related compounds in incinerator effluents, presented at workshop on “Impact of Chlorinated Dioxins and Related Compounds on the Environment,” Rome, 22–24 October 1980.Google Scholar
  40. 40.
    Crummett, W. B., Bumb, R. R., Lamparski, L. L., Mahle, N. H., Nestrick, T. J. and Whiting, L. Environmental chlorinated dioxins from combustion—the trace chemistries of fire hypothesis, presented at workshop on “Impact of Chlorinated Dioxins and Related Compounds on the Environment,” Rome, 22–24 October 1980.Google Scholar
  41. 41.
    Stehl, R. H. and Lamparski, L. L. Combustion of several 2,4,5-trichlorophenoxy compounds: formation of 2,3,7,8-tetrachlorodibenzo-p-dioxins, Science 197, 1008–1009 (1977).PubMedCrossRefGoogle Scholar
  42. 42.
    Ahling, B., Lindskog, A., Jansson, B., and Sundstrom, G. Formation of polychlorinated dibenzo-p-dioxins and dibenzo furans during combustion of a 2,4,5-T formulation, Chemosphere 6, 461–466 (1977).CrossRefGoogle Scholar
  43. 43.
    Press statement, Australian National Health and Medical Research Council, 16 June 1978. See also Hay, A., Dioxin source is safe, Nature (London) 274, 526 (1978).CrossRefGoogle Scholar
  44. 44.
    Nilsson, C. A., Andersson, K., Rappe, C, and Westermark, S. O. Chromatographic evidence for the formation of chlorodioxins from chloro-2-phenoxyphenols, Journal of Chromatography 96, 137–147 (1974).CrossRefGoogle Scholar
  45. 45.
    Nilsson, C. A., Norstrom, A., Andersson, K., and Rappe, C. Impurities in commercial products related to pentachlorophenol, in Pentachlorophenol Chemistry, Pharmacology and Environmental Toxicology, ed. K. Ranga Rao, Plenum Press, New York (1978), pp. 313–323.CrossRefGoogle Scholar
  46. 46.
    Buser, H. R., and Rappe, C. Identification of substitution patterns in polychlorinated dibenzo-p-dioxins (PCDDs) by mass spectroscopy, Chemosphere 7, 199–211 (1978).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1982

Authors and Affiliations

  • Alastair Hay
    • 1
  1. 1.Department of Chemical PathologyThe University of LeedsLeedsEngland

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