3.8 Article

Characterization of polyhalogenated 4-methylphenol dimers (Br/Cl-predioxins) formed during aqueous chlorination of 4-methylphenol solution in the presence of bromide ion

Journal

JOURNAL OF HEALTH SCIENCE
Volume 54, Issue 4, Pages 423-431

Publisher

PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/jhs.54.423

Keywords

polyhalogenated phenoxyphenol; methylated predioxin; water chlorination

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Aqueous 4-methylphenol solution with bromide ion was treated with hypochlorite at 20 degrees 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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