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J.Health Sci., 54(4), 423-431, 2008
Characterization of Polyhalogenated 4-Methylphenol Dimers (Br/Cl-Predioxins) Formed during Aqueous Chlorination of 4-Methylphenol Solution in the Presence of Bromide Ion
Sukeo Onodera,* Toshinari Takahashi,
Shinya Takemoto, and Tsunehiro Oh-i
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamzaki, Noda, Chiba 278-8510, Japan
Aqueous 4-methylphenol solution with bromide ion was treated with hypochlorite at 20°C under various experimental conditions. Changes in the composition of the halogenated products in water were determined by gas chromatographic (GC) and GC-mass spectrometric (GC/MS) analyses of diethyl ether extracts. 4-Methylphenol was shown to produce a variety of halogenated compounds, including polybrominated/chlorinated phenoxyphenols (Br/Cl-predioxins), having one to four halogen atoms, as by-products in the chlorine-treated water. Production of these predioxins is dependent on the number of equivalent of chlorine atoms per mole of compound and on the reaction pH. These results suggest that the chlorine treatment of water contaminated with 4-methylphenol and bromide ion leads to the formation of Br/Cl-predioxins, which are precursor of the highly toxic halogenated dibenzo-p-dioxins.
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