Gas chromatographic-mass spectrometric analysis of chlorinated phenoxyphenols in the technical chlorophenol formulation ky-5′☆

Abstract The content of polychlorinated phenoxyphenol (PCPP) impurities in the technical chlorophenol formulation Ky-5 (wood preservative) was studied. The phenolic fraction was shown to contain predioxins and isopredioxins, the structures of the components being verified by gas chromatography mass spectrometry of non-derivatized, methylated and acetylated fractions. 2,6-Dichloro-4-(2,4,6-trichlorophenoxy)phenol and 2,6-dichloro-4-(2,3,4,6-tetrachlorophenoxy)phenol were identified by the comparison of their retention times and the mass spectra of their methyl and acetyl derivatives with those of authentic specimens. The amounts of the above components in Ky-5 were ca. 0.8 and 0.2%, respectively. The estimated total amount of PCPPs may be as high as 4-5%. For the formation of various PCPP components three probable routes are postulated, viz., ortho-, meta- or para- elimination of HC1 from two chlorophenol molecules during the production of Ky-5.