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Polycyclic Aromatic and Heteroaromatic Hydrocarbons

  • Chapter
Anthropogenic Compounds

Part of the book series: The Handbook of Environmental Chemistry ((HEC3,volume 3 / 3A))

Abstract

Only a limited number of polycyclic aromatic hydrocarbons (PAH) and structurally related hetero-aromatic systems such as anthracene, pyrene or carbazole are industrially produced in pure form. They normally serve as a starting material for the synthesis of dyestuffs, herbicides and pesticides or pharmaceuticals. None of these commercially available pure PAH and hetero-aromatic systems show acute toxic or carcinogenic effects. Coal tar, which is a by-product in the manufacture of metallurgical coke, is the main source for the industrial production of these chemicals. The quantity of coal tar which is co-produced in the coal carbonization process amounts presently to about 16 M tonnes p.a.; three-quarters of this raw material is processed in the existing 127 coal tar refineries throughout the world [1]. The exposure of the environment with these chemicals occuring in the up-grading of coal tar can, however, be neglected in comparison with the exposure with PAH and hetero-aromatic systems from other sources.

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References

  1. Collin, G., Mildenberg, R.: Chem. and Ind. 1978, 567

    Google Scholar 

  2. Grimmer, G.: in: Luftqualitätskriterien für ausgewählte polycyclische aromatische Kohlenwasserstoffe, ed. Umweltbundesamt (FRG ), 1979

    Google Scholar 

  3. Suess, M.J.: Sci. Total Environ. 6, 239 (1976)

    Article  CAS  Google Scholar 

  4. Gräf, W.: Med. Klinik, 15, 561 (1965)

    Google Scholar 

  5. Borneff, J., Selenka, F., Kunte, H., Maximos, A.: Environ. Res. 2, 22 (1968)

    Article  CAS  Google Scholar 

  6. Blumer, M.: Sci. American 1976, März, p. 34

    Google Scholar 

  7. Arcos I.C., Argus, M.F.: Chemical Induction of Cancer, vol. IIA. Academic Press, New York — London 1974

    Google Scholar 

  8. Badger, G.M.: Proc. Roy. Soc. 1956, 87

    Google Scholar 

  9. Lang, K.F., Buffleb, H., Zander, M.: Erdöl/Kohle 16, 944 (1963)

    CAS  Google Scholar 

  10. Zander, M.: Intern. J. Environ. Anal. Chem. 4, 109 (1975)

    Article  CAS  Google Scholar 

  11. Burrows, I.E., Lindsey, A.J.: Chem. Ind. 1961 1395

    Google Scholar 

  12. Stelzner, R., Kuh, A.: Lit. Reg. Org. Chem. 3, 21 (1921)

    Google Scholar 

  13. Patterson, A.M.: J. Amer. Chem. Soc. 47, 543 (1925)

    Article  CAS  Google Scholar 

  14. IUPAC-Rules 1957

    Google Scholar 

  15. The Ring Index. Amer. Chem. Soc., Washington 1960

    Google Scholar 

  16. Lunnon, W.F.: in: Graph Theory and Computing. Academic Press, New York — London 1972 p. 87

    Google Scholar 

  17. Clar, E.: Polycyclic Hydrocarbons. Academic Press New York-London 1964

    Google Scholar 

  18. Coulson, C.A., Rushbrooke, G.S.: Proc. Cambridge Phil. Soc. 36, 193 (1940)

    CAS  Google Scholar 

  19. Clar, E., Zander, M.: J. Chem. Soc. (London) 1958, 1861

    Google Scholar 

  20. Clar, E.: The Aromatic Sextet. John Wiley and Sons, New York 1972

    Google Scholar 

  21. Polansky, O.E., Derflinger, G.: Int. J. Quantum Chem. 1, 379 (1967)

    Article  CAS  Google Scholar 

  22. Fratev, R., Polansky, O.E., Zander, M.: Z. Naturforsch. 30, 1704 (1975)

    Google Scholar 

  23. Zander, M.: Angew. Chem. 72, 513 (1960)

    Article  CAS  Google Scholar 

  24. Brown, R.D.: Quart. Revs. 6, 63 (1952)

    Article  CAS  Google Scholar 

  25. Streitwieser, A.: Molecular Orbital Theory for Organic Chemists. John Wiley and Sons, New York 1961

    Google Scholar 

  26. Dewar, M.S.J., Dougherty, R.C.: The PMO Theory of Organic Chemistry. Plenum Press, New York 1975

    Book  Google Scholar 

  27. Zander, M.: Z. Naturforsch. 33a, 1395 (1978)

    Google Scholar 

  28. Zander, M.: Z. Naturforsch. 34a, 521 (1979)

    Google Scholar 

  29. Moradpour, A., Nicoud, J.F., Balavoine, G., Kagan, H., Tsouraris, G.: J. Amer. Chem. Soc. 93, 2353 (1971)

    Article  Google Scholar 

  30. Laarhoven, W.H., Cuppen, Th.J.M.: Tetrahedron Lett. 1971, 163

    Google Scholar 

  31. Zander, M., Franke, W.H.: Chem. Ber. 107, 727 (1974)

    Article  CAS  Google Scholar 

  32. Hausigk, D.: Chem. Ber. 101, 473 (1968)

    Article  CAS  Google Scholar 

  33. Zander, M.: in: Houben-Weyl (Meth. d. org. Chem.), G. Thieme Verlag, Stuttgart, in press

    Google Scholar 

  34. Borwitzky, H., Schomburg, G.: J. Chromatogr. 170, 99 (1979)

    Article  CAS  Google Scholar 

  35. Lao, R.C., Oja, H., Thomas, R.S., Monkman, J.L.: Symp. Rec. Adv. Analyt. Chem. Pollutants, Halifax, N.S., Aug. 23–25, 1972

    Google Scholar 

  36. Grimmer, G., Böhnke, H., Glaser, A.: Erdöl/Kohle 30, 411 (1977)

    CAS  Google Scholar 

  37. Janini, G.M., Muschik, G.M., Schroer, I.A., Zielinski, W.L.: Analyt. Chem. 48, 1879 (1976)

    Article  CAS  Google Scholar 

  38. Sauerland, H.D., Zander, M.: Erdöl/Kohle 19, 502 (1966)

    CAS  Google Scholar 

  39. Snowdon, L.R.: Analytic. Chem. 50, 379 (1978)

    Article  CAS  Google Scholar 

  40. Thoms, R., Zander, M.: Erdöl/Kohle 30, 403 (1977)

    CAS  Google Scholar 

  41. Thoms, R., Zander, M.: Fresenius Z. Analyt. Chem. 282, 443 (1976)

    Article  CAS  Google Scholar 

  42. Blümer, G.-P., Zander, M.: DGMK-Compendium (Suppl. to Erdöl/Kohle) 1978/79, p. 1472

    Google Scholar 

  43. Soedigdo, S., Angus, W.W., Flesher, J.W.: Analyt. Biochem. 67, 684 (1975)

    Article  Google Scholar 

  44. Dark, W.A.: Internat. Laboratory 1975, 44

    Google Scholar 

  45. Blümer, G.-P., Zander, M.: Fresenius Z. Analyt. Chem. 288, 277 (1977)

    Article  Google Scholar 

  46. Blümer, G.-P., Zander, M.: ibid., 296, 409 (1979)

    Google Scholar 

  47. Borneff, J., Kunte, H.: Arch. Hyg. 153, 220 (1969)

    CAS  Google Scholar 

  48. Bartle, K.D., Collin, G., Stadelhofer, J.W., Zander, M.: J. Chem. Techn. Biotechn. 29, 531 (1979)

    Article  CAS  Google Scholar 

  49. Zander, M.: Phosphorimetry — The Application of Phosphorescence to the Analysis of Organic Compounds. Academic Press, New York 1968

    Google Scholar 

  50. Particulate Polycyclic Organic Matter, National Academy of Sciences, Washington, D.C. 1972

    Google Scholar 

  51. Went, F.W.: Proc. Nat. Acad. Sci. USA 46, 212 (1960)

    Article  CAS  Google Scholar 

  52. Hidy, G.M.: Proc. 3rd Univers. Rochester Conf., Environm. Toxicol., June, 1970

    Google Scholar 

  53. Junge, C.E.: J. Atmos. Sci. 26, 603 (1969)

    Article  Google Scholar 

  54. Kotrappa, P.: Proc. 3rd Univers. Rochester Conf. Environm. Toxicol. June, 1970

    Google Scholar 

  55. Corn, M., Montgomery, T.L., Esmen, N.A.: Environ. Sci. Techn. 5, 155 (1971)

    Article  CAS  Google Scholar 

  56. Krstulovic, A.M., Rosie, D.M., Brown, P.R.: Internat. Laboratory 1977, 11

    Google Scholar 

  57. Fuks, N.A.: The Mechanics of Aerosols. Macmillan, New York 1964

    Google Scholar 

  58. Hidy, G.M., Brock, J.R.: The Dynamics of Aerocolloidal Systems. Pergamon Press, New York 1970

    Google Scholar 

  59. Chamberlain, A.C.: Atmos. Environ. 4, 57 (1970)

    Article  CAS  Google Scholar 

  60. Neuberger, H., Hosier, C.L., Kocmond: in: Tromp, S.W. and Weihe, W.H. (Eds.) Biometeorology, Vol. 2. Pergamon Press, Oxford 1967, p. 693

    Google Scholar 

  61. Rosinski, J., Nagamoto, C.T.: Kolloid-Z. 204, 78 (1966)

    Google Scholar 

  62. Andelmann, J.B., Suess, J.N.: Bull. World Health Org. 43, 479 (1970)

    Google Scholar 

  63. Neff, J.M., Cox, B.A., Dixit, D., Anderson, J.W.: Marine Biol. 38, 279 (1976)

    Article  CAS  Google Scholar 

  64. Blümer, G.-P., Gundermann, K.-D., Zander, M.: Chem. Ber. 110, 2005 (1977)

    Google Scholar 

  65. Fukui, K., Yonezawa, T., Shingu, H.: J. Chem. Phys. 20, 722 (1952)

    Article  CAS  Google Scholar 

  66. Southern, P.F., Waters, W.A.: J. Chem. Soc. (London) 1960, 4340

    Google Scholar 

  67. Kortüm, G., Braun, W.: Liebigs Ann. Chem. 632, 104 (1960)

    Article  Google Scholar 

  68. Inscoe, M.N.: Analytic. Chem. 36, 2505 (1964)

    Article  Google Scholar 

  69. Polansky, O.E.: Z. Naturforsch. 29a, 529 (1974)

    Google Scholar 

  70. Gräf, W., Nothoff, G.: Arch. Hyg. 147, 135 (1965)

    Google Scholar 

  71. Reichert, J.K.: Arch. Hyg. 152, 277 (1968)

    CAS  Google Scholar 

  72. Boyland, E.: Biochem. Soc. Symp. 5, 40 (1950)

    CAS  Google Scholar 

  73. Jerina, D.M., Daly, J.W., Witkop, B., Zaltzman-Nirenberg, B., Udenfriend, S.: J. Amer. Chem. Soc. 90, 6525 (1968)

    Article  CAS  Google Scholar 

  74. Daly, J.W., Jerina, D.M., Witkop, B.: Experientia 28, 1129 (1972)

    Article  CAS  Google Scholar 

  75. Pullmann, A., Pullmann, B.: Adv. Cancer Res. 3, 117 (1955)

    Article  Google Scholar 

  76. Oesch, F.: Xenobiotica 3, 305 (1973)

    Article  CAS  Google Scholar 

  77. Buening, M.K.: Proc. Nat. Acad. Sci. USA 75, 5358 (1978)

    Article  CAS  Google Scholar 

  78. Jerina, D.M. et al.: in: de Serres, F.J. (Ed.) In Vitro Metabolic Activation in Mutagenesis Testing. Elsevier, Amsterdam 1976

    Google Scholar 

  79. Wood, A.W. et al.: Proc. Nat. Acad. Sci. USA 74, 3176 (1977)

    Article  CAS  Google Scholar 

  80. Wislocki, P.G. et al.: Cancer Res. 38, 693 (1978)

    CAS  Google Scholar 

  81. Slaga, T.J. et al.: Cancer Res. 38, 1699 (1978)

    CAS  Google Scholar 

  82. Boyland, E., Sims, P.: Biochem. J. 84, 583 (1962)

    CAS  Google Scholar 

  83. Berenbom, M., Young, L.: Biochem. J. 49, 165 (1951)

    CAS  Google Scholar 

  84. Sims, P.: Biochem. J. 73, 389 (1959)

    CAS  Google Scholar 

  85. Freundenthal, R.I., Hundley, S.G., Cattaneo, S.M.: in: Jones, P.W. and Freundenthal, R.I. (Eds.) Carcinogenesis, Vol. 3. Raven Press, New York 1978

    Google Scholar 

  86. Flesher, J.W., Sydnor, K.L.: Int. J. Cancer 11, 433 (1973)

    Article  CAS  Google Scholar 

  87. Sloane, N.H.: Biochim. Biophys. Acta 107, 599 (1965)

    Article  CAS  Google Scholar 

  88. Sloane, N.H., Davis, T.K.: Arch. Biochem. Biophys. 163, 46 (1974)

    Article  CAS  Google Scholar 

  89. Sloane, N.H., Uzgiris, V.I., Seeley, D.: in: Jones, P.W. and Freundenthal, R.I. (Eds.) Carcinogenesis, Vol. 3. Raven Press, New York 1978

    Google Scholar 

  90. Sims, P.: Biochem. J. 98, 215 (1966)

    CAS  Google Scholar 

  91. Habig, W.H., Pabst, M.J., Jacoby, W.B.: J. Biol. Chem. 249, 7130 (1974)

    CAS  Google Scholar 

  92. Gelboin, H.V. et al.: in: Screening tests in chemical carcinogenesis, IARC Sci. Publ. No. 12, Lyon 1976

    Google Scholar 

  93. Boyland, E., Williams, K.: Biochem. J. 94, 190 (1965)

    CAS  Google Scholar 

  94. Pabst, M.J., Habig, W.H., Jacoby, W.B.: Biochem. Biophys. Res. Commun. 52, 1123 (1973)

    Article  CAS  Google Scholar 

  95. Booth, J., Sims, P.: Biochem. Pharmacol. 23, 2547 (1974)

    Article  CAS  Google Scholar 

  96. Raha, C.R., Gallagher, C.H., Shubik, P.: Proc. Soc. Exp. Biol. Med. 143, 531 (1973)

    Article  CAS  Google Scholar 

  97. Sims, P., Grover, P.L.: Adv. Canc. Res. 20, 165 (1974)

    Article  CAS  Google Scholar 

  98. Gibson, D.T.: Science 161, 1093 (1968)

    Article  CAS  Google Scholar 

  99. Groenewegen, I.D., Stolp, H.: Erdöl, Kohle 28, 206 (1975)

    CAS  Google Scholar 

  100. Shabad, L.M.: Z. Krebsforsch. 70, 204 (1968)

    Article  CAS  Google Scholar 

  101. Stanford Res. Internat., part II, Environm. Protection Agency, Washington 1978

    Google Scholar 

  102. Donn, B.: Astrophys. J. 152, 129 (1968)

    Article  Google Scholar 

  103. Ames, B.N.: in: Hollaender, A. (Ed.) Chemical mutagenesis, principles and methods for their detection. Plenum Press, New York 1971

    Google Scholar 

  104. Ames, B.N., Durston, E.W., Yamasaki, E., Lee, F.D.: Proc. Nat. Acad. Sci. 70, 2281 (1973)

    Article  CAS  Google Scholar 

  105. Ames, B.N., McCann, J., Yamasaki, E.: Mutation Res. 31, 347 (1975)

    Article  CAS  Google Scholar 

  106. Ames, B.N., McCann, J.: IARC Sci. Publ. 12, 493 (1976)

    CAS  Google Scholar 

  107. Berwald, Y., Sachs, L.: J. Nat. Cancer Inst. 35, 641 (1965)

    CAS  Google Scholar 

  108. Smith, W.E., Cooper, N.S., Wynder, E.L.: Proc. Amer. Assoc. Cancer Res. 1, 45 (1954)

    Google Scholar 

  109. Kracht, J., Klein, U.E., Baghirzade, M.: Verhandl. Dtsch. Ges. Pathologie, 45. Tagung, Münster 1961

    Google Scholar 

  110. Purchase, I.F.H. et al.: Nature 264, 624 (1976)

    Article  CAS  Google Scholar 

  111. IARC Monographs, Vol. 3, Lyon 1973

    Google Scholar 

  112. Bingham, E., Falk, H.L.: Arch. Environm. Health 19, 779 (1969)

    Article  CAS  Google Scholar 

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Zander, M. (1980). Polycyclic Aromatic and Heteroaromatic Hydrocarbons. In: Anthropogenic Compounds. The Handbook of Environmental Chemistry, vol 3 / 3A. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-38522-6_3

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  • DOI: https://doi.org/10.1007/978-3-540-38522-6_3

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