Polychlorinated diphenyl sulfides: preparation of model compounds, chromatography, mass spectrometry, NMR, and environmental analysis

Polycyclic aromatic sulphur heterocyclic compounds were common pollutants from industrial processes. Some polychlorinated diphenyl sulphides were synthesized by direct chlorination of diphenyl sulphide with sulphuryl chloride and by Friedel-Crafts-type reaction from 1,2-dichlorobenzene and sulphur. The synthesized mixtures were then fractionated by reversed-phase high-performance liquid chromatography, and the structures of the pure compounds were determined by gas chromatography/mass spectrometry and nuclear magnetic resonance. Four stack gases from a waste incinerator and 6 pulp mill effluents from 2 bleaching plants were analysed for these compounds. Trichlorodiphenyl sulphides were detected in 5 pulp mill effluent samples, and tri- and tetrachlorodiphenyl sulphides were detected in 2 stack-gas samples.