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Volume 3 Anthropogenic Compounds Part K pp 1–29Cite as

Alkylaromatic Chlorohydrocarbons

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

Abstract

Sources, structures, properties, analysis methods, and environmental fate including bioaccumulation and toxicity studies of some groups of alkylaromatic chlorohydrocarbons are reviewed. They are the most abundant chlorohydrocarbons formed in bleaching of pulp with chlorine chemicals. Major substances among them are chlorocymenes and chlorocymenenes (chlorinated methyl isopropyl(ene) benzenes. Other persistent compounds formed are polychlorobibenzyls (stilbene-related compounds), polychloromethylnaphthalenes, polychloroalkylphenanthrenes (especially chlororetenes) and polychlorofluorenes. These compounds occur as persistent contaminants in sediments and bioaccumulate in aquatic biota. Acute and chronic toxicity of only few compounds in these groups has been tested. Isopropyl-PCBs, the main constituents in PCB substitute formulations Chloralkylene-9 and Chloralkylene-12, are more readily degraded in light irradiation and in metabolism than the corresponding non-alkylated PCBs. However, their bioaccumulation in aquatic ecosystem is of concern.

Tetrachlorobenzyltoluenes (TCBTs) as formulation Ugilec 141 are widely used PCB substitutes, especially in mining. There are 96 possible (70 relevant) TCBT isomers. Both Ugilec 141 mixture and nine pure isomers have been studied for their bioaccumulation, metabolism, and effects in aquatic biota and rodents. Based on similarity of toxic effects to PCBs and accumulation in fish and mussels of recipient waters of coal mining areas, TCBTs were not recommended as PCB substitutes.

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  1. Department of Chemistry, University of Jyväskylä, P.O.Box 35, FIN-40351, Jyväskylä, Finland

    Jaakko Paasivirta

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  1. Jaakko Paasivirta
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  1. Universität Bayreuth, Postfach 10 12 51, D-95440, Bayreuth, Germany

    Otto Hutzinger

  2. Department of Chemistry, University of Jyväskylä, P. O. Box 35, FIN-40351, Jyväskylä, Finland

    Jaakko Paasivirta

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Paasivirta, J. (2000). Alkylaromatic Chlorohydrocarbons. In: Hutzinger, O., Paasivirta, J. (eds) Volume 3 Anthropogenic Compounds Part K. The Handbook of Environmental Chemistry, vol 3K. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48915-0_1

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  • DOI: https://doi.org/10.1007/3-540-48915-0_1

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