Skip to main content

Aromatic Amines

  • Chapter

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

Abstract

Aromatic amines represent a category of chemical agents of considerable importance as withnessed by their widespread use as intermediates in the manufacture of drugs, pesticides and plastics, as antioxidants in the preparation of rubber for the manufacture of tires and cables and as curing agents in the preparation of various plastics. In addition, they are widely used as intermediates in the preparation of dyes and pigments extensively employed to color textiles, leathers, rubber, printing inks, paints, lacquers, metal finishes, plastic and paper products, as well as in semi-permament coloring products [1–9].

Keywords

  • Bladder Cancer
  • Aromatic Amine
  • Pigment Yellow
  • Carcinogenic Risk
  • Direct Blue

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.

This is a preview of subscription content, access via your institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Northcott, J.: Aniline and its derivatives, in: Encyclopedia of Chemical Technology (R.E. Kirk and D.F. Othmer (eds)), 3rd ed., Vol. 2, John Wiley & Sons, New York (1978), pp. 309–321

    Google Scholar 

  2. Ferber, K.H.J.: Benzidine and related biphenyldiamines, in: Encyclopedia of Chemical Technology (R.E. Kirk and D.F. Othmer (eds)), 3rd ed., Vol. 3, John Wiley & Sons, New York (1978), pp. 772–778

    Google Scholar 

  3. Dressler, H.: Naphthalene derivatives, in: Encyclopedia of Chemical Technology (R.E. Kirk and D.F. Othmer (eds)), 3rd ed., Vol. 2, John Wiley & Sons, New York (1978), pp. 309–321

    Google Scholar 

  4. IARC: Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man, Vol. 16, Some Aromatic Amines and Related Nitro Compounds — Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals, International Agency for Research on Cancer, Lyon (1978), pp. 51142

    Google Scholar 

  5. IARC: Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man, Vol. 27, Some Aromatic Amines, Anthraquinones and Nitroso Compounds and Inorganic Fluorides Used in Drinking Water and Dental Preparations, International Agency for Research on Cancer, Lyon (1982), pp. 39–188

    Google Scholar 

  6. IARC: Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man, Vol. 29, Some Industrial Chemicals and Dyestuffs. International Agency for Research on Cancer, Lyon (1982), pp. 149–183,239–256,295–300,296–310, 311–320, 321–330

    Google Scholar 

  7. Fishbein, L.: Potential Industrial Carcinogens and Mutagens, Elsevier, Amsterdam (1979), pp. 256–416

    Google Scholar 

  8. Fishbein, L.: Aromatic amines of major industrial importance, use and occurrence, in: Environmental Carcinogens Selected Methods of Analysis, Vol. 4. Some Aromatic Amines and Azo Dyes in the General and Industrial Environment (H. Egan, L. Fishbein, M. Castegnaro, I.K. O’Neill, H. Bartsch (eds)), International Agency for Research on Cancer, Lyon (1981), pp. 51–74

    Google Scholar 

  9. Veys, C.A.: Ann. Occup. Hyg. 15, 11–15 (1972)

    CrossRef  CAS  Google Scholar 

  10. Kriek, E.: Aromatic amines and related compounds as carcinogenic hazards to man, in: Environmental Carcinogenesis (P. Emmelot and E. Kriek (eds.)) Elsevier/North Holland Biomedical Press, Amsterdam (1979), pp. 143–164

    Google Scholar 

  11. Parkes, H.G.: Aromatic amines, in: Chemical Carcinogens (C.E. Searle (ed)) American Chemical Society Monograph No. 173, Washington, DC (1976), pp. 462–480

    Google Scholar 

  12. Lower, G.M., et al.: Environ. Health Persp. 29, 71 (1979)

    CrossRef  CAS  Google Scholar 

  13. Yashida, O., Miyakoga, M.: Etiology of bladder cancer, in: Metabolic Aspects in Analytical and Experimental Epidemiology of Cancer (W. Nakahara, T. Hirayana, K. Wishroka, and A. Sugans (eds.)), University Park Press, Baltimore, MD (1973), pp. 31–39

    Google Scholar 

  14. Case, R.A.M., Hosker, M.E.: Brit. J. Ind. Med 11, 75 (1954)

    CAS  Google Scholar 

  15. Clayson, D.G.: Brit. Med. Bull. 20, 115 (1964)

    CAS  Google Scholar 

  16. Boyland, E.: Brit. Med. Bull. 14, 153 (1958)

    CAS  Google Scholar 

  17. Wilmer, J.L., et al.: Environ. Mutagenesis 3, 627 (1981)

    CrossRef  CAS  Google Scholar 

  18. Anderson, D., Styles, J.A.: Brit. J. Cancer 37, 924 (1978)

    CrossRef  CAS  Google Scholar 

  19. Ashby, J., et al.: Brit. J. Cancer 38, 34 (1978)

    CrossRef  CAS  Google Scholar 

  20. Lazear, E.J., Louie, S.C.: Cancer Lett. 4, 21 (1977)

    CrossRef  Google Scholar 

  21. Garner, R.G., et al.: Cancer Lett. 1, 39 (1975)

    CrossRef  CAS  Google Scholar 

  22. Rao, T.K. et al.: Arch. Toxicol. 49, 185 (1982)

    CrossRef  CAS  Google Scholar 

  23. Miller, E.C., Miller, J.A.: Pharmacol. Res. 18, 805 (1966)

    CAS  Google Scholar 

  24. Miller, J.A.: Cancer Res. 30, 559 (1970)

    CAS  Google Scholar 

  25. Miller, E.C., Miller, J.A.: Biochemical mechanisms of chemical carcinogenesis, in: The Molecular Biology of Cancer (H. Bush (ed.)) Academic Press, New York (1974), pp. 376–402

    Google Scholar 

  26. Miller, E.C.; Miller, J.A.: The metabolism of chemical carcinogens to reactive electrophiles and their possible mechanisms of action in carcinogenesis, in: Chemical Carcinogens (C. E. Searle (ed.)) ACS Monograph 173, Washington, DC (1976), pp. 736–762

    Google Scholar 

  27. Irving, E.C.: Species and tissue variations in the metabolic activation of aromatic amines, in: Carcinogens: Identification and Mechanisms of Action (A. C. Grffin and C.R. Shaw (eds.)) Raven Press, New York (1979) 211–227

    Google Scholar 

  28. Irving, C.C.: Metabolic activation of N-hydroxy compounds by conjugation, in: Biological Oxidation of Nitrogen in Organic Molecules (J.W. Bridges, J.W. Gorrod, and D. V. Parke (eds.)) Halsted Press, New York (1971), pp. 75–86

    Google Scholar 

  29. Uehleke, H.: N-Hydroxylation, in: Biological Oxidation of Nitrogen in Organic Molecules (J.W. Bridges, J.W. Gorrod and D.V. Parke (eds.)) Halsted Press, New York (1971), pp. 15–26

    Google Scholar 

  30. Kadlubar, F.F., et al.: Cancer Res. 37, 805 (1977)

    CAS  Google Scholar 

  31. Clayson, D.B.: Brit. J. Cancer 7, 460 (1953)

    CrossRef  CAS  Google Scholar 

  32. Boyland E.: The biochemistry of aromatic hydrocarbons, amines and urethane, in: Physicochemical Mechanisms of Carcinogenesis (E.D. Bergman and B. Pullman (eds.)) Vol. 1, Israel Acad. Sci. and Humanities, Jerusalem (1969), pp. 25–44

    Google Scholar 

  33. Clayson, D.B., Garner, R.C.: Carcinogenic aromatic amines and related compounds, in: Chemical Carcinogens (C.E. Searle (ed.)) American Chemical Society, Washington, DC (1976), pp. 366–461

    Google Scholar 

  34. Roberts, J.J., Warwick, G.P.: Int. J. Cancer 1, 179–196 (1966)

    CrossRef  Google Scholar 

  35. Miller, J.A., Miller, E.C.: Metabolic activation of carcinogenic aromatic amines and amides via N-hydroxylation and N-hydroxyesterification and its relationship to ultimate carcinogens as electrophilic reactants, in: Physico-Chemical Mechanisms of Carcinogenesis (E.D. Bergman and B. Pullman (eds.)) Israel Acad. of Sci. and Humanities (1969), pp. 237–261

    Google Scholar 

  36. Kriek, E., Westra, J.G.: Metabolic activation of aromatic amines and amides and interactions with nucleic acids, in: Chemical Carcinogens and DNA (P.L. Crover (ed.)) CRC Press, Boca Raton, FL (1979), pp. 1–28

    Google Scholar 

  37. Martin, C.N, et al.: Cancer Res. 42, 2678–2686 (1982)

    CAS  Google Scholar 

  38. Jones, T.C.: Preliminary risk assessment. Phase I. Benzidine, its congeners and their derivative dyes and pigments. EPA Publ. No. 560/11–80–019, US Environmental Protection Agency, Washington, DC (1980)

    Google Scholar 

  39. Guerin, M.R., et al.: Environ. Res. 23, 42 (1980)

    CrossRef  CAS  Google Scholar 

  40. Wilson, B.W., et al.: Mutat. Res. 79, 193 (1980)

    CrossRef  CAS  Google Scholar 

  41. Guerin, M.R., et al.: Fuel. 60, 282 (1982)

    CrossRef  Google Scholar 

  42. Buchanan, M.V., et al.: In: Chemical Analysis and Biological Fate: Polynuclear Aromatic Hydrocarbons (M. Cooke and A.J. Dennis (eds.)), Battelle Press, Columbus, OH (1981), pp. 133–144

    Google Scholar 

  43. Haugen, D.A., et al.: Anal. Chem. 54, 32 (1982)

    CrossRef  CAS  Google Scholar 

  44. Tomkins, B.A., Ho, C.H.: Anal. Chem. 54, 91 (1982)

    CrossRef  CAS  Google Scholar 

  45. Pelroy, R. A., Gandolfi, A.: Mutat. Res. 72, 329 (1980)

    CrossRef  CAS  Google Scholar 

  46. Wilson, B.W., et al.: Proc. 29th Conf. Mass Spectrometry and Allied Topics. Abst. No. NPMO85 (1981)

    Google Scholar 

  47. Wilson, B.W., et al.: Proc., 2nd USDOE Environm. Control Symp. 2, 415 (1980)

    Google Scholar 

  48. Hoffmann, D., Wynder, E.L.: in: Chemical Carcinogenesis (C.E. Searle (ed.)) Amer. Chem. Soc., Washington, DC (1976) pp. 366–462

    Google Scholar 

  49. Sugimura, T., et al.: Mutagen-Carcinogens in food with special reference to highly mutagenic pyrolytic production in broiled food, in: Origins of Human Cancer (H.H. Hiatt, J.D. Watson and J.A. Winsten (eds.)) Cold Spring Harbor Laboratory, Cold Spring Harbor, NY (1977), pp. 15611577

    Google Scholar 

  50. Sugimura, T., et al.: Mutagenic heterocyclic amines in cooked food, in: Environmental Carcinogens Selected Methods of Analysis. Vol. 4. Some Aromatic Amines and Azo Dyes in the General and Industrial Environment (H. Egan, L. Fishbein, I.K. O’Neill, M. Castegnaro, H. Bartsch (eds.)) Internat. Agency for Res. Cancer, Lyon (1981), pp. 251–267

    Google Scholar 

  51. Nagao, M. et al.: Cancer Lett. 2, 221 (1977)

    CrossRef  CAS  Google Scholar 

  52. Spingarn, N.E., Weisburger, J.H.: Cancer Lett. 7, 259 (1979)

    CrossRef  CAS  Google Scholar 

  53. Spingarn, N.E. et al.: Cancer Lett. 9, 177 (1980)

    CrossRef  CAS  Google Scholar 

  54. Hoffmann, D., et al.: Nature 221, 254 (1969)

    CrossRef  CAS  Google Scholar 

  55. Masuda, Y., Hoffman, D.: Anal. Chem. 41, 650 (1969)

    CrossRef  CAS  Google Scholar 

  56. IARC: Environmental Carcinogens, Selected Methods of Analysis. Vol.4. Some Aromatic Amines and Azo Dyes in the General and Industrial Environment (H. Egan. L. Fishbein, M. Castegnaro, I.K. O’Neill, H. Bartsch (eds.)), Internat. Agency Res. Cancer, Lyon (1981), pp. 109–247

    Google Scholar 

  57. Fishbein, L.: Analysis of carcinogenic and mutagenic aromatic amines, in: Safe Handling of Chemical Carcinogens Mutagens, Teratogens and Highly Toxic Substances. Vol. 1 ( D. B. Walters (ed.)), Ann Arbor Science, Ann Arbor, Michigan (1980), pp. 205–245

    Google Scholar 

  58. Fishbein, L.: Analysis of carcinogenic and mutagenic aromatic amines: An Overview. Toxicol. Environ. Chem. Revs. 3, 145 (1980)

    CrossRef  CAS  Google Scholar 

  59. Parris, G.E.: Residue Revs. 76, 2 (1980)

    Google Scholar 

  60. Society of Dyers Colourists: Colour Index, revised 3rd ed. Additions and Amendments, No. 34, Perkin House, Bradford, UK (1980)

    Google Scholar 

  61. Anon: Chemical Profiles, Schnell Publ. Co., New York, 1 Oct. (1979)

    Google Scholar 

  62. Kouris, C.S., Northcott, J.: Aniline and its derivative, in: Encyclopedia of Chemical Technology (RE. Kirk and D.F. Othmer (eds.)), 2nd. ed., Vol. 2, John Wiley, New York (1963), pp. 411–419

    Google Scholar 

  63. Parke, D.V.: Biochem. J. 77, 493 (1960)

    CAS  Google Scholar 

  64. Williams, R.T.: Detoxification Mechanisms, 2nd ed., Chaptman Hall, Ltd., London (1959, pp. 430–432, 464–465

    Google Scholar 

  65. Boyland, E., et al.: Biochem. J. 65, 417 (1957)

    CAS  Google Scholar 

  66. Boyland, E., et al.: Biochem. J. 86, 263 (1963)

    CAS  Google Scholar 

  67. Kiese, M.: Pharmacol. Rev. 18, 1091 (1966)

    CAS  Google Scholar 

  68. Bray, H.G., et al.: Biochem. J. 47, 483 (1950)

    CAS  Google Scholar 

  69. Grantham, P.H., et al.: Xenobiotica. 2, 551 (1972)

    CrossRef  CAS  Google Scholar 

  70. Kao, J., et al.: Drug Metab. Disp. 6, 549 (1978)

    CAS  Google Scholar 

  71. Piotrowski, J.K.: J. Hyg. Epidemiol. Mecrobiol. Immunol. (Praha) 1, 23 (1957)

    CAS  Google Scholar 

  72. Dutkiewicz, T.: Med. Pracy. 12, 1 (1961)

    CAS  Google Scholar 

  73. Dutkiewicz, T., Piotrowski, J.K.: Pure Appl. Chem. 3, 319 (1961)

    CrossRef  CAS  Google Scholar 

  74. Piotrowski, J.K.: Pral. Lek. 24, 94 (1972)

    CAS  Google Scholar 

  75. Lores, E.M., et al.: J. Chromatog. Sci. 16, 358 (1978)

    CrossRef  CAS  Google Scholar 

  76. Hargesheimer, E.E., et al.: J. Assoc. Off. Anal. Chem. 64, 833 (1981)

    CAS  Google Scholar 

  77. Crosby, D.G., Bowers, J.B.: J. Agr. Food Chem. 16, 839 (1968)

    CrossRef  CAS  Google Scholar 

  78. Bartha, R.: J. Agr. Food Chem. 19, 385 (1971)

    CrossRef  CAS  Google Scholar 

  79. Kaufman, D.D.: J. Agr. Food Chem. 15, 582 (1967)

    CrossRef  CAS  Google Scholar 

  80. Moreale, A., Van Bladel, R.: J. Soil Sci 27, 48 (1976)

    CrossRef  CAS  Google Scholar 

  81. Hsu, T.S., Bartha, R.: Soil Sci. 116, 444 (1973)

    CrossRef  CAS  Google Scholar 

  82. Geisbühler, H., et al.: The substituted ureas, in: Herbicides: Chemistry, Degradation and Mode of Action (P.C. Kearney, D.D. Kaufman (eds.)), 2nd ed., Vol. I, Marcel Dekker, Inc., NY (1975) pp. 209–291

    Google Scholar 

  83. Still, G.G., Herrett, R.A.: Methyl carbamates, carbanilates and acylanilides, ibid., pp. 609–664

    Google Scholar 

  84. Bartha, R., Pramer, D.: Adv. Appl. Microbiol. 13, 317 (1970)

    CrossRef  CAS  Google Scholar 

  85. Kouris, C.S., Northcott, J.: Aniline and its derivatives. in: Encyclopedia of Chemical Technology (R.E. Kirk, D.F. Othmer (eds.)), 2nd ed., Vol. 2, John Wiley, New York (1969), pp. 411–427

    Google Scholar 

  86. Nguyen, Y.V., Phillips, C.R.: Chemosphere 3, 125 (1975)

    CrossRef  Google Scholar 

  87. Gitchell, A., et al.: J. Air Poll. Contr. Assoc. 24, 357 (1974)

    CrossRef  CAS  Google Scholar 

  88. Gitchell, A., et al.: J. Air Poll. Contr. Assoc. 24, 772 (1974)

    CrossRef  CAS  Google Scholar 

  89. Spicer, C.W., et al.: Environ. Sci. Technol. 8, 1028 (1974)

    CrossRef  CAS  Google Scholar 

  90. Patrianakos, C., Hoffmann, D.: J. Anal. Toxicol. 3, 150 (1979)

    CrossRef  CAS  Google Scholar 

  91. Joel, A.R., Grady, C.P., Jr.: J. Water Poll. Cont. Fed. 48, 778 (1977)

    Google Scholar 

  92. Symons, J.M., et al.: Int. J. Air Water Poll. 4, 115 (1962)

    Google Scholar 

  93. Tischler, L.F., Eckenfelder, W.W., Jr.: Linear substrate removal in the activated sludge process. in: Adv. Water Pollution Res., Proc. 4th Intl. Conf. Water Poll. Res. 361 (1969)

    Google Scholar 

  94. Neurath, G.B., et al.: Food Cosm. Toxicol. 15, 275 (1977)

    CrossRef  CAS  Google Scholar 

  95. Meijers, A.P., VanderLeer, R.W.: Water Res. 10, 597 (1976)

    CrossRef  CAS  Google Scholar 

  96. Greve, D.A., Wegman, R.C.C.: Schriftenr. Ver. Wasser. Buden. Lufthyg. (Berlin) 46, 59 (1975)

    CAS  Google Scholar 

  97. Wegman, R.C.C., Dekorte, G.A.L.: Int. J. Environ. Anal. Chem. 9, 1 (1981)

    Google Scholar 

  98. Herzel, F., Schmidt, G.: Gesund. Ing. 98, 221 (1977)

    CAS  Google Scholar 

  99. Hushon, J., et al.: An Assessment of Potentially Carcinogenic, Energy-Related Contaminants in Water. Prepared for US Dept. of Energy and National Cancer Inst., Mitre Corp., McLean, VA (1980), p. 71, 72, 102

    Google Scholar 

  100. Shackelford, W.M., Keith, L.H.: Frequency of Organic Compounds Identified in Water. EPA Report 600/4–76–062, Environmental Research Laboratory, Athens, GA (1976), pp. 9, 58, 59, 78

    Google Scholar 

  101. Games, L.M., Hites, R.A.: Anal. Chem. 49, 1433 (1977)

    CrossRef  CAS  Google Scholar 

  102. Hamaker, J.W.: Decomposition: Quantitatives aspects. in: Organic Chemicals in the Soil Environment (C.A.I. Goring, J.W. Hamaker), Marcel Dekker, New York (1972), 253

    Google Scholar 

  103. Zoeteman, B.C.J., et al.: Chemosphere 9, 231 (1980)

    CrossRef  CAS  Google Scholar 

  104. Zepp, R.G., et al.: Environ. Sci. Tech. 9, 1144 (1975)

    CrossRef  CAS  Google Scholar 

  105. Struif, B., et al.: Vom Wasser 45, 53 (1975)

    CAS  Google Scholar 

  106. Kaussmaul, H.: Behavior of persistent organic compounds in bank-filtrated Rhine water. in: Aquatic Pollutants (O. Hutzinger, H. VanLelyveld, B.C.J. Zoeteman (eds.)), Pergamon Press, Oxford (1978), p. 265

    Google Scholar 

  107. Parris, G.E.: Environ. Sci. Technol. 14, 1099 (1980)

    CrossRef  CAS  Google Scholar 

  108. Hauser, C.S., Krivonak, A.E.: J. Agr. Food Chem. 26, 1164 (1978)

    CrossRef  Google Scholar 

  109. Furukawa, T., Brindley, D.D.: Clays, Clay Minerals 21, 279 (1973)

    CrossRef  CAS  Google Scholar 

  110. Pillai, P., et al.: Chemosphere 11, 299 (1982)

    CrossRef  CAS  Google Scholar 

  111. Helling, C.S., Krivonak, A.E.: J. Agr. Food Chem. 26, 1164 (1978)

    CrossRef  CAS  Google Scholar 

  112. Süss, A., et al.: Z. Pflanzenernaehr. Bodenkd. 141, 57 (1978)

    CrossRef  Google Scholar 

  113. Hsu, T.S., Bartha, R.: Soil Sci. 118, 213 (1974)

    CrossRef  CAS  Google Scholar 

  114. Bordelleau, L.M., et al.: J. Agr. Food Chem. 20, 573 (1972)

    CrossRef  Google Scholar 

  115. Cerniglia, C.E., et al.: Arch. Microbiol. 130, 272 (1981)

    CrossRef  CAS  Google Scholar 

  116. Alexander, M.: Science 211, 132 (1981)

    CrossRef  CAS  Google Scholar 

  117. Ferris, J.P. et al.: Arch. Biochem. Biophys. 156, 97 (1973)

    CrossRef  CAS  Google Scholar 

  118. Smith, R.V., Rosazza, J.P.: Arch. Biochem. Biophys. 161, 551 (1974)

    CrossRef  CAS  Google Scholar 

  119. Daly, J.W., et al.: Experentia 28, 1129 (1972)

    CrossRef  CAS  Google Scholar 

  120. Booth, J., Boyland, E.: Biochem. J. 91, 362 (1964)

    CAS  Google Scholar 

  121. Bordeleau, L.M., Bartha, R.: Can. J. Microbiol. 18, 1873 (1972)

    CrossRef  CAS  Google Scholar 

  122. Kaufman, D.D., et al.: J. Agr. Food Chem. 21, 127 (1973)

    CrossRef  CAS  Google Scholar 

  123. Kearney, P.C., Plimmer, J.R.: J. Agr. Food Chem. 20, 584 (1972)

    CrossRef  CAS  Google Scholar 

  124. Burge, W.D.: Soil Biol. Biochem. 4, 379 (1972)

    CrossRef  CAS  Google Scholar 

  125. Lu, A.Y.H., et al.: Arch. Biochem. Biophys. 153, 294 (1972)

    CrossRef  CAS  Google Scholar 

  126. Archakov, A. I., et al.: Biochem. Pharm. 23, 1053 (1974)

    CrossRef  CAS  Google Scholar 

  127. Schenkman, J.B., et al.: Biochem. Pharm. 23, 1148 (1974)

    CrossRef  CAS  Google Scholar 

  128. Smith, R.V., Rosazza, J. P.: Arch. Biochem. Biophys. 161, 551 (1974)

    CrossRef  CAS  Google Scholar 

  129. Bachofer, R., et al.: FEBS Letters 50, 288 (1975)

    CrossRef  CAS  Google Scholar 

  130. Jerina, D.M., et al.: Biochemistry 9, 147 (1970)

    CrossRef  CAS  Google Scholar 

  131. Patel, T.R., Gibson, D. T.: J. Bacteriol. 119, 879 (1974)

    CAS  Google Scholar 

  132. Calamari, D., et al.: Chemosphere 9, 753 (1980)

    CrossRef  CAS  Google Scholar 

  133. Jolley, R.L.: Chlorination effects on organic constituents in effluents from domestic sanitary sewage treatment plants. Oak Ridge National Laboratory Publ. No. ORNL-TM-4290, Oak Ridge National Laboratory, Oak Ridge, TN (1973)

    Google Scholar 

  134. Jenkins, R.L., et al.: Arch. Environ. Contam. Toxicol. 7, 301 (1978)

    CrossRef  CAS  Google Scholar 

  135. Noller, C.R.: Chemistry of Organic Compounds, W.W. Saunders Co., Philadelphia (1958), pp. 475–490; 695–697

    Google Scholar 

  136. Geisbühler, H., et al.: Weed Res. 3, 277 (1963)

    CrossRef  Google Scholar 

  137. Dalton, R.L., et al.: Weeds 14, 31 (1966)

    CrossRef  CAS  Google Scholar 

  138. Kaufman, D.D., Kearney, P.G.: Appl. Microbiol. 13, 443 (1965)

    CAS  Google Scholar 

  139. Bartha, R., et al.: Appl. Microbiol. 15, 67 (1967)

    CAS  Google Scholar 

  140. Bartha, R., Pramer, D.: Science 156, 1617 (1967)

    CrossRef  CAS  Google Scholar 

  141. Chisaka, H., Kearney, P.C.: J. Agr. Food Chem. 18, 854 (1970)

    CrossRef  CAS  Google Scholar 

  142. Bartha, R.: Weed Sci. 17, 471 (1969)

    CAS  Google Scholar 

  143. Walker, N. Harris, D.: J. Appl. Bact. 32, 457 (1969)

    CrossRef  CAS  Google Scholar 

  144. Ebing, W.: Ber. Landw. 51, 742 (1974)

    Google Scholar 

  145. Engelhardt, G., et al.: Chemosphere 2/3, 85 (1977)

    Google Scholar 

  146. Plimmer, J.R., et al.: J. Agr. Food Chem. 18, 859 (1970)

    CrossRef  CAS  Google Scholar 

  147. Briggs, G.G., Walker, N.: Soil Biol. Biochem. 5, 695 (1973)

    CrossRef  CAS  Google Scholar 

  148. Tweedy, B.G., et al.: Science 168, 482 (1970)

    CrossRef  CAS  Google Scholar 

  149. Wallnöfer, P.R., et al.: Pest. Biochem. Physiol. 7, 481 (1977)

    CrossRef  Google Scholar 

  150. Bollag, J.M., Russel, S.: Microbiol. EC. 3, 65 (1976)

    CrossRef  CAS  Google Scholar 

  151. Ross, J.A., Tweedy, B. G.: Bull. Environ. Contam. 10, 234 (1973)

    CrossRef  CAS  Google Scholar 

  152. Hegeman, G.D.: J. Bacteriol. 91, 1140 (1966)

    CAS  Google Scholar 

  153. Burge, W.D.: Soil Sci. Soc. Am. Proc. 37, 392 (1973)

    CAS  Google Scholar 

  154. Corke, C.T., et al.: J. Agr. Food Chem. 27, 644 (1979)

    CrossRef  CAS  Google Scholar 

  155. Fletcher, C.L., Kaufman, D.D.: J. Agr. Food Chem. 27, 1127 (1979)

    CrossRef  CAS  Google Scholar 

  156. Jones, T.C.: TSCA Chemical Assessment Series. Preliminary Risk Assessment Phase 1. Benzidine, Its Congeners, and Their Derivative Dyes and Pigments. EPA–560/11–80–019, Office of Pesticides and Toxic Substances, Washington, DC (1980), p. 10

    Google Scholar 

  157. US Environmental Protection Agency. Chemicals in Commerce Information System (CICIS), Office of Pesticides and Toxic Substances, Chemical Information Division, Washington, DC (1981)

    Google Scholar 

  158. Boeniger, M.: The Carcinogenicity and Metabolism of Azo Dyes, Especially Those Derived from Benzidine, DHHS/NIOSH Publication No. 80–110, Robert A. Taft Laboratories, Cincinnati, Ohio (1980), p. 3

    Google Scholar 

  159. The Society of Dyers and Colourists: Colour Index, 3rd ed., Vol. 4, Lund Humphries, Bradford, UK (1971), p. 4742

    Google Scholar 

  160. The Society of Dyers and Colourists: Colour Index, 3rd ed., Vol. 6, Lund Humphries, Bradford, UK (1975), p. 6405

    Google Scholar 

  161. JRB Associates, Inc.: Survey of the Manufacture, Import and Uses for Benzidine, Related Substances and Related Dyes and Pigments. Prepared for the US Environmental Protection Agency. McLean, VA (1979)

    Google Scholar 

  162. National Toxicology Program: Second Annual Report on Carcinogens. NTP Report 81–43, US Dept. of Health and Human Services, Washington, DC, December (1981), pp. 53–55, 253–255

    Google Scholar 

  163. Collier, H.B.: Clin. Biochem. 7, 3 (1974)

    CrossRef  CAS  Google Scholar 

  164. Auerbach Associates, Inc.: Benzidine Derived Dyes and/or Pigments. Rept. No. PB-284854. Prepared for US Consumer Products Safety Commission. Philadelphia, PA (1978), p. 28

    Google Scholar 

  165. IARC: IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol.1, Lyon (1972), pp. 80–86

    Google Scholar 

  166. IARC: IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, Supplement 1, Chemicals and Industrial Processes Associated with Cancer in Humans, IARC Monographs Volumes 1–20, Lyon (1979), p. 25

    Google Scholar 

  167. International Labour Office: Cancer of the Bladder among Workers in Aniline Factories (Studies and Reports) Series F, No. 1, Geneva (1921)

    Google Scholar 

  168. Ames, B.N., et al.: Proc. Natl. Acad. Sci. USA. 70, 2281 (1973)

    CrossRef  CAS  Google Scholar 

  169. Bos, R.P., et al.: Toxicology 16, 113 (1980)

    CrossRef  CAS  Google Scholar 

  170. Fahmy, M.J., Fahmy, O.G.: Mutat. Res. 56, 31 (1977)

    CrossRef  CAS  Google Scholar 

  171. Painter, R.B.: J. Environ. Pathol. Toxicol. 2, 65 (1978)

    CAS  Google Scholar 

  172. Amlacher, E., Ziebarth, D.: Arch. Geschwulstforsch. 49, 490 (1979)

    CAS  Google Scholar 

  173. Martin, C.N., et al.: Cancer Res. 38, 2621 (1978)

    CAS  Google Scholar 

  174. Williams, G.M.: Cancer Lett. 4, 69 (1978)

    CrossRef  CAS  Google Scholar 

  175. Pienta, R.J.: Transformation of Syrian hamster embryo cells by diverse chemicals and correlation with their reported carcinogenic and mutagenic activities. in: Chemical Mutagens (F.J. deSerres and A. Hollaender (eds.)) Vol. 6, Plenum, New York (1980), pp. 175–202

    CrossRef  Google Scholar 

  176. Bassendowska-Karska, E.: Pol. Tyg. Lek. 35, 53 (1980)

    CAS  Google Scholar 

  177. Meigs, J.W., et al.: Arch. Ind. Hyg. 4, 533 (1951)

    CAS  Google Scholar 

  178. Sciarini, L.J., Meigs, J.W.: Arch. Environ. Hlth. 2, 423 (1961)

    CrossRef  CAS  Google Scholar 

  179. Kellner, H.M., et al.: Arch Toxicol. 31, 61 (1973)

    CrossRef  CAS  Google Scholar 

  180. Bradshaw, L., Clayson, D.B.: Nature 176, 974 (1955)

    CrossRef  CAS  Google Scholar 

  181. Clayson, D.B., et al.: Acta Uni. Int. Cancrum. 15, 581 (1959)

    Google Scholar 

  182. Shriner, C.R., et al.: Rev. Environmental Effects on the Environmental Effects of Pollutants: II Benzidine (EPA–600–1–78–024 ORNL/EIS–86) US Environmental Protection Agency, Health Effects Research Laboratory and Oak Ridge Laboratory, Oak Ridge, TN (1978), pp. 41 – 65

    Google Scholar 

  183. Haley, T.J.: Clin. Toxicol. 8, 13 (1975)

    CrossRef  CAS  Google Scholar 

  184. Zavon, M.R., et al.: Arch. Environ. Hlth. 27, 1 (1973)

    Google Scholar 

  185. Radding, S.B., et al.: Rev. Environmental Fate of Selected Chemicals. EPA 566/5–75–001, US Environdmental Protection Agency, Office of Toxic Substances, Washington, DC (1975)

    Google Scholar 

  186. US Environmental Protection Agency: Status Assessment of Toxic Chemicals No. 5, Benzidine, Industrial Pollution Control Division, Cincinnati, OH, Sept. 6 (1977)

    Google Scholar 

  187. Mitre Corporation: Scoring of Organic Air Pollutants, Chemistry, Production and Toxicity of Selected Organic Chemicals, McClean, VA (1976)

    Google Scholar 

  188. Takemura, N., et al.: Int. J. Pollut. 9, 665 (1965)

    CAS  Google Scholar 

  189. Furukawa, T., Brindley, G.M.: Clayminer 21, 279 (1973)

    CAS  Google Scholar 

  190. McBride, M.B.: Clays, Clay Material 27, 224 (1979)

    CrossRef  CAS  Google Scholar 

  191. Zierath, D. L., et al.: Soil Sci. 129, 277 (1980)

    CrossRef  CAS  Google Scholar 

  192. Malaney, G.W., et al.: J. Water Poll. Control Fed. 39, 2020 (1967)

    CAS  Google Scholar 

  193. Tabak, H.H., Barth, E.F.: J. Water Poll. Control Fed. 50, 552 (1979)

    Google Scholar 

  194. Caulfield, M.J., et al.: Cancer Res. 39, 2155 (1979)

    CAS  Google Scholar 

  195. Cotruvo, J.A., et al.: Ann. NY Acad. Sci. 298, 124 (1977)

    CrossRef  CAS  Google Scholar 

  196. Simmon, V.F., et al.: Ozone methods and ozone chemistry of selected organics in water. 2. Mutagenic assays. in: Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Ozone Press International, Cleveland, OH (1978), pp. 126–133

    Google Scholar 

  197. Lu, P.Y., et al.: Arch. Environ. Contam. Toxicol. 6, 129 (1977)

    CrossRef  CAS  Google Scholar 

  198. Thomas, A.W., et al.: J. Am. Ind. Hyg. Assoc. 39, A-18 to A-24 (1978)

    Google Scholar 

  199. NIOSH: Spec. Occupational Hazard Rev. Benzidine-based Dyes, DHEW (NIOSH) Publication No. 80–109, Washington, DC (1980)

    Google Scholar 

  200. NIOSH: Techn. Rep.: Carcinogenicity and Metabolism of Azo Dyes, Especially those Derived from Benzidine. National Institute for Occupational Safety and Health, Cincinnati, OH, July (1980)

    Google Scholar 

  201. Anon: Chem. Reg. Reptr. 4, 63 (1980)

    Google Scholar 

  202. DHEW/NIOSH/NCI, Joint Intelligence Bull. No. 24, Direct Black 38, Direct Blue 6, and Direct Brown 95, Benzidine derived dyes. NIOSH Publ. No. 78–148, Dept. of Health, Education and Welfare, Washington, DC (1978)

    Google Scholar 

  203. Anon: Occup. Health Safety Lett 10, 6 (1980)

    Google Scholar 

  204. US Environmental Protection Agency: Benzidine: Proposed Toxic Pollutant Effluent Standards, 40 CFR Part 129. Federal Register. 41 [127] June 30 (1973)

    Google Scholar 

  205. The Society of Dyers and Colourists: Colour Index, 3rd ed., Vol. 2, Lund Humphries, Bradford, UK (1971), pp. 2223–2382, 2439

    Google Scholar 

  206. Nat. Cancer Inst. 13-Week Subchronic Toxicity Studies of Direct Blue 6, Direct Black 38 and Direct Brown 95 Dyes, NCI-66 TR-108, DHEW Publ. No. (NIH) 78–1358 Bethesda, MD (1978)

    Google Scholar 

  207. Walker, R.: Food Cosmet. Toxicol. 8, 659 (1970)

    CrossRef  CAS  Google Scholar 

  208. Lazear, E.J., et al.: Toxicol. Lett. 4, 519 (1979)

    CrossRef  CAS  Google Scholar 

  209. Nony, C.R., et al.: J. Anal. Toxicol. 4, 132 (1980)

    CrossRef  CAS  Google Scholar 

  210. Tanaka, K.T.: Japan J. Ind. Hlth. 22, 194 (1980)

    CAS  Google Scholar 

  211. Yoshida, O., Miyakawa, M.: Metabolic aspects in analytical and experimental epidemiology of cancer, in: Etiology of Bladder Cancer (W. Nakahara (ed.)), University Park Press, Baltimore, MD, (1973)

    Google Scholar 

  212. Hitz, H.R., et al.: J. Soc. Dyers Col. 94, 71 (1978)

    CrossRef  CAS  Google Scholar 

  213. Cerniglia, C.E., et al.: Biochem. Biophys. Res. Communs, (1982), in press

    Google Scholar 

  214. Gardiner, D.K., Borne, B.J.: J. Soc. Dyers Col. 94, 339 (1978)

    CrossRef  CAS  Google Scholar 

  215. Gerarde, H.W., Gerarde, D.F.: J. Occup. Med. 16, 322 (1974)

    CAS  Google Scholar 

  216. IARC: Monogr. Evaluation of the Carcinogenic Risk of Chemicals to Man, Vol.4, Internat. Agency for Res. Cancer, Lyon, (1974) pp. 49–55, 65–71, 97–111

    Google Scholar 

  217. Stanford Res. Inst.: A Study of Industrial Data on Candidate Chemicals for Testing. Prepared for US Environmental Protection Agency, EPA–560/5–77–06, Menlo Park, CA, Aug. (1977)

    Google Scholar 

  218. Bell, D.R.: Final Environmental Impact Statement: Proposed Regulation (administration action) Handling of Certain Carcinogens, US Occupational Safety and Health Administration, Washington, DC (1973), pp. 13–16

    Google Scholar 

  219. Garner, R.C., et al.: Cancer Lett. 1, 39 (1975)

    CrossRef  CAS  Google Scholar 

  220. Hsu, R.S., Sikka, H.C.: Toxicol. Appl. Pharmacol. 64, 306 (1982)

    CrossRef  CAS  Google Scholar 

  221. US Environmental Protection Agency: Ambient Water Quality Criteria for Dichlorobenzidine (EPA 440/5–80–040, PB 81–11717), Office of Water Regulations and Standards, Criteria and Standards Division, Washington, DC (1980), pp. C–1–C–4

    Google Scholar 

  222. Appleton, H.T., Sikka, H.C.: Environ. Sci. Technol. 14, 50 (1980)

    CrossRef  CAS  Google Scholar 

  223. Sikka, H.C., et al.: Fate of 3,3’–dichlorobenzidine in aquatic environments, EPA 600/3–78–003, US Environmental Protection Agency, Washington, DC

    Google Scholar 

  224. Appleton, H., et al.: Fate of 3,3’-dichlorobenzidine in the aquatic environment, in: Aquatic Pollutants: Transformation and Biological Effects (O. Hutzinger, L.H. Van Lelyveld and B.C.J. Zoetman (eds.))

    Google Scholar 

  225. Banerjee, S., et al.: Environ. Sci, Technol. 12, 1425 (1978)

    CrossRef  CAS  Google Scholar 

  226. Johnson, W.M., Parnes, W.D.: Ann. NY Acad. Sci. 329, 277 (1979)

    CrossRef  Google Scholar 

  227. USDA: Quantities of Pesticides used by Farmers in 1966 Agricultural Rep. No. 179. US Dep. Agriculture, Washington, DC, April (1970)

    Google Scholar 

  228. Masuda, Y., Hoffmann, D.: Anal. Chem. 41, 650 (1969)

    CrossRef  CAS  Google Scholar 

  229. Hoffmann, D., et al.: Nature 221, 254 (1969)

    CrossRef  CAS  Google Scholar 

  230. Patrianakos, C., Hoffmann, D.: J. Anal. Toxicol. 3, 150 (1979)

    CrossRef  CAS  Google Scholar 

  231. IARC: Monogr. Evaluation of the Carcinogenic Risk of Chemicals to Man, Vol. 16, Internat. Agency for Research on Cancer, Lyon (1978), pp. 325–336

    Google Scholar 

  232. Kehe, H.J., Kouris, C.S.: Diarylamines. in: Encyclopedia of Chemical Technology (R.E. Kirk and D.F. Othmer (eds.)), 2nd ed., Vol. 7, Wiley Sons, New York (1965), pp. 40–49

    Google Scholar 

  233. Society of Dyers and Colourists: Colour Index, 3rd ed., Vol.4, Yorkshire, UK (1971), pp. 4223, 4453, 4454, 4808

    Google Scholar 

  234. Society of Dyers and Colourists: Colouor Index, revised 3rd ed., Vol. 5, Yorkshire, UK (1975), pp. 5033, 5034, 5084

    Google Scholar 

  235. Veys, C.A.: A Study of the Incidence of Bladder Tumours in Rubber Workers (Thesis for Doctorate of Medicine). Faculty of Medicine, University of Liverpool, Liverpool, UK (1973)

    Google Scholar 

  236. NIOSH: Current Intelligence Bulletin; Metabolic Precursors of a Known Humn Carcinogen, beta-Naphthylamine, US Dept. of Health, Education and Welfare, Rockville, MD (1976), pp. 1–3

    Google Scholar 

  237. Scott, T.S., Williams, M.H.C.: Brit. J. Ind. Med. 14, 150 (1957)

    CAS  Google Scholar 

  238. Innes, J.R.M., et al.: J. Natl. Cancer Inst. 42, 1101 (1969)

    CAS  Google Scholar 

  239. Kummer, R., Tordoir, W.F., Tidjschr. Geneeskd. 53, 415 (1975)

    Google Scholar 

  240. Batten, P.L., Hathway, D.E.: Brit. J. Cancer 35, 342 (1977)

    CrossRef  CAS  Google Scholar 

  241. Stasenkova, K.P.: Toksikol. Novykh. Prom. Khim. Veshchestv. 10, 90 (1968)

    Google Scholar 

  242. Ku, Y., Alvarez, G.: Chemosphere 11, 41 (1982)

    CrossRef  CAS  Google Scholar 

  243. Pitter, P.: Water Res. 10, 231 (1976)

    CrossRef  CAS  Google Scholar 

  244. Baird, R., et al.: J. Water Pollut. Control Fed. 49, 1609 (1977)

    CAS  Google Scholar 

  245. Stula, E.F., et al.: J. Environ. Pathol. Toxicol. 1, 31 (1977)

    CAS  Google Scholar 

  246. Gianatasio, P.A.: Rubber Age, July (1969) pp. 51–59

    Google Scholar 

  247. Wagoner, J.K.: Ann. NY Acad. Sci. 329, 328 (1979)

    CrossRef  Google Scholar 

  248. Russfield, A.B., et al.: Toxicol. Appl. Pharmacol. 31, 47 (1975)

    CrossRef  CAS  Google Scholar 

  249. Stula, E.F., et al.: Toxicol. Appl. Pharmacol. 31, 159 (1975)

    CrossRef  CAS  Google Scholar 

  250. McCann, J.,-et al.: Proc. Natl. Acad. Sci. 72, 5135 (1975)

    CrossRef  Google Scholar 

  251. McQueen, C.A., et al.: Toxicol. Appl. Pharmacol. 58, 231 (1981)

    CrossRef  CAS  Google Scholar 

  252. Rappaport, S.M., Morales, R.: Anal. Chem. 51, 19 (1979)

    CrossRef  CAS  Google Scholar 

  253. Comprehensive Cancer Center of Metropolitan Detroit: How widespread the hazard of industrial carcinogens: The Adrian Experience, in: Environmental Cancer Alert (C.M. King (ed.)) Vol. 3, Michigan Cancer Foundation, Detroit (1979), pp. 1–2

    Google Scholar 

  254. Zimmermann, L.: Justification for inclusion of 4,4’-methylenebis(2-chloroaniline) in the National Toxicology Program. Personal Communication, April 27 (1981)

    Google Scholar 

  255. Jenkins, F.P., et al.: Food Cosmet. Toxicol. 10, 671 (1972)

    CrossRef  CAS  Google Scholar 

  256. Case, R.A.M., et al.: Brit J. Ind. Med. 11, 75 (1974)

    Google Scholar 

  257. Goldwater, L.J., et al.: Arch. Environ. Hlth. 11, 814 (1965)

    CrossRef  CAS  Google Scholar 

  258. Mancuso, T.F., El-Attar, A.A.: J. Occup. Med., 9, 277 (1967)

    CAS  Google Scholar 

  259. Hueper, W.C., et al.: J. Ind. Hyg. 20, 46 (1938)

    CAS  Google Scholar 

  260. Bonser, G.M., et al.: Brit. J. Cancer 10, 353 (1956)

    Google Scholar 

  261. Bonser, G.M.: J. Pathol. Bacteriol. 55, 1 (1943)

    Google Scholar 

  262. Conzelman, G.M., Jr., Moultox, J.E.: J. Natl. Cancer Inst. 42, 825 (1969)

    Google Scholar 

  263. Purchase, I.F.H., et al.: Brit. J. Cancer 44, 892 (1981)

    CrossRef  CAS  Google Scholar 

  264. Saffiotti, U., et al.: Induction of bladder cancer in hamsters fed aromatic amines, in: Bladder Cancer: A Symposium, Aesculapius, Birmingham, Alabama (1967), p. 129

    Google Scholar 

  265. Sellakamur, A.R., et al.: Proc. Am. Assoc. Cancer Res. 10, 78 (1969)

    Google Scholar 

  266. Conzelman, G.M., Jr., Moultox, J.E.: J. Nati. Cancer Inst. 49, 193 (1972)

    CAS  Google Scholar 

  267. Hadidian, Z., et al.: J. Natl. Cancer Inst. 41, 985 (1968)

    CAS  Google Scholar 

  268. Bonser, G.M., et al.: Brit. J. Cancer 6, 412 (1952)

    CrossRef  CAS  Google Scholar 

  269. Hicks, R.M., et al.: Experimental induction of bladder tumours by a two-stage system. in: Carcinogenesis, Vol. 2, Mechanisms of Tumour Promotion and Carcinogenesis (Slaga, T.J. (ed.)), Raven Press, New York (1978), p. 475–489, Swak, D., Bantwell, R.K.

    Google Scholar 

  270. Gehrmann, G.H., et al.: Occupational carcinoma of the bladder. In: Proc. IX Internat. Congr. Ind. Med., Wright, Bristol (1949), p. 427

    Google Scholar 

  271. Radomski, J.L., et al.: Cancer Res. 40, 3537 (1980)

    CAS  Google Scholar 

  272. Radomski, J.L., et al.: Cancer Res. 31, 1461 (1971)

    CAS  Google Scholar 

  273. Deichmann, W.B., Radomski, J.L., J. Natl. Cancer Inst. 43, 263 (1969)

    CAS  Google Scholar 

  274. Kadlubar, F. F., et al.: Cancer Res. 38, 3628 (1978)

    CAS  Google Scholar 

  275. deSerres, F.J., Ashby, E.J. (eds.): Short-term tests for carcinogens. Rep. Internat. Collaborative Program, Elsevier/North Holland, Amsterdam (1981), p. 130

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and Permissions

Copyright information

© 1984 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Fishbein, L. (1984). Aromatic Amines. In: Anthropogenic Compounds. The Handbook of Environmental Chemistry, vol 3 / 3C. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-38819-7_1

Download citation

  • DOI: https://doi.org/10.1007/978-3-540-38819-7_1

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-15233-1

  • Online ISBN: 978-3-540-38819-7

  • eBook Packages: Springer Book Archive