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Formation pathways of brominated products from benzophenone-4 chlorination in the presence of bromide ions

Author:
Xiao, Ming, Wei, Dongbin, Li, Liping, Liu, Qi, Zhao, Huimin, Du, Yuguo
Source:
Journal of Environmental Sciences 2014 v.26 pp. 2387-2396
ISSN:
1001-0742
Subject:
acute toxicity, byproducts, catechol, chlorination, chlorine, disinfection, dose response, esters, ions, pH, phenol
Abstract:
The brominated products, formed in chlorination treatment of benzophenone-4 in the presence of bromide ions, were identified, and the formation pathways were proposed. Under disinfection conditions, benzophenone-4 would undertake electrophilic substitution generating mono- or di-halogenated products, which would be oxidized to esters and further hydrolyzed to phenol derivatives. The generated catechol intermediate would be transformed into furan-like heterocyclic product. The product species were pH-dependent, while benzophenone-4 elimination was chlorine dose-dependent. When the chlorination treatment was performed on ambient water spiked with benzophenone-4 and bromide ions, most of brominated byproducts could be detected, and the acute toxicity significantly increased as well.
Agid:
5471450