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Chlorination of benzidine and other aromatic amines in aqueous environments

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Abstract

The fate of aniline,N,N-dimethylaniline and benzidine in chlorinated waters was investigated. Conditions were controlled to approximate the process chlorination of raw water supplies and wastewater secondary effluents.

As the molar ratio, (Cl2)/(amine), was increased, amine depletions increased and leveled off at about (Cl2)/(amine)=1. Depletions in distilled water with ‘free’ chlorine were somewhat higher than those in activated sludge/secondary effluent with combined chlorine. For each amine the number and type of products appeared to be independent of the water matrix and the ratio, (Cl2)/(amine).

For the monophenyl amines ring chlorination was a significant depletion pathway. Extended chlorination of aniline yielded a precipitated product, while theN-substituted amine,N,N-dimethylaniline did not yield a solid product. In contrast to the monophenyl amines, when benzidine (p,p′-diaminobiphenyl) was exposed to chlorinated waters, a solid product resulted immediately. Infra-red analysis of this product indicated a polymeric structure with no ring chlorination. GLC analysis of the chlorination supernatant showed no ring substituted isomers of benzidine.

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Authors and Affiliations

  1. San Jose Creek Water Quality Laboratory, County Sanitation Districts of Los Angeles County, 1965 South Workman Mill Road, 90601, Whittier, California

    R. L. Jenkins, J. E. Haskins, L. G. Carmona & R. B. Baird

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  1. R. L. Jenkins
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  2. J. E. Haskins
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  3. L. G. Carmona
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  4. R. B. Baird
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Jenkins, R.L., Haskins, J.E., Carmona, L.G. et al. Chlorination of benzidine and other aromatic amines in aqueous environments. Arch. Environ. Contam. Toxicol. 7, 301–315 (1978). https://doi.org/10.1007/BF02332058

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  • DOI: https://doi.org/10.1007/BF02332058

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