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Some polychlorinated diphenyl sulfides were prepared by chlorination of diphenyl sulfide with sulfuryl chloride and by Friedel-Crafts-type reaction from 1,2-dichlorobenzene and sulfur. Individual isomers from the reaction mixtures were isolated by reversed-phase high-performance liquid chromatography. Mass spectra show the degree of chlorination of different compounds, and 'H and I3C NMR spectra verify their structures. Three trichloro isomers were shown to be 2,2',4-, 2,4,4'-, and 2,4',6-trichlorodiphenyl sulfides and two symmetric tetrachloro isomers bis(2,4-dichlorophenyl) and bis(3,4dichlorophenyl) sulfides. Chlorine-induced 13C NMR substituent chemical shifts (SCS) have been calculated and compared with the experimental ones in the case of bis(2,4-dichlorophenyl) sulfide. Four stack gases from a waste incinerator and six pulp mill effluents from two bleaching plants were screened for the polychlorinated diphenyl sulfides. Trichlorodiphenyl sulfides were found from five pulp mill effluent samples and tri-and tetrachlorodiphenyl sulfides from two stack gas samples.