Riboflavin Photosensitized Oxidation of 2,4-Dichlorophenol: Assessment of Possible Chlorinated Dioxin Formation

Science  22 Oct 1971:
Vol. 174, Issue 4007, pp. 407-408
DOI: 10.1126/science.174.4007.407


Dimeric products are formed by riboflavin-sensitized photooxidation of 2,4-dichlorophenol. The products of this reaction were examined to determine whether chlorinated dibenzo-p-dioxins could be formed from chlorophenols in water by the action of light of wavelengths greater than 280 nanometers. Dimers are formed by union of phenoxy radicals through carbon-carbon or carbon-oxygen bonds. 4,6-Dichloro-2-(2,4-dichlorophenoxy) phenol was obtained in greater quantity than other dimers. Products were characterized by combined gas chromatography and mass spectrometry. Chlorinated dibenzo-p-dioxins which could result from ring closure of a 2-phenoxyphenol derivative were not detected in the products of photolysis. The failure to detect chlorinated dibenzo-p-dioxins may result from the rapid photolytic breakdown of the lower chlorinated dibenzop-dioxins. Under environmental conditions, dioxins are unlikely products of the lower chlorinated phenols or phenoxyalkanoic acids.