Chlorination of Phenols Revisited: Unexpected Formation of α,β-Unsaturated C₄-Dicarbonyl Ring Cleavage Products.

ABSTRACT: Despite decades of research on the fate of phenolic compounds when water is disinfected with hypochlorous acid (HOCl), there is still considerable uncertainty regarding the formation mechanisms and identity of ring cleavage products, especially at higher chlorine doses. This study focuses on the formation of electrophilic ring cleavage products-a class of compounds that poses potential health risks at relatively low concentrations-from the reactions of phenols with chlorine. By monitoring the formation of products of reactions between ring cleavage products and the model nucleophile N-α-acetyl-lysine, we identified the α,β-unsaturated dialdehyde 2-butene-1,4-dial (BDA) and its chlorinated analogue, chloro-2-butene-1,4-dial (Cl-BDA), after the chlorination of phenol, para- and ortho-

SUBMITTER: Prasse C 

PROVIDER: S-EPMC7665061 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature