2, 4, 4'-Tricholoro-2'-hydroxydiphenyl ether (Irgasan DP300) (I) and its three chlorinated derivatives; 2', 3, 4, 4'-tetracholro-2-hydroxydiphenyl ether (II), 2', 4, 4', 5 -tetrachloro-2-hydroxydiphenyl ether (III) and 2', 3, 4, 4', 5-pentachloro-2-hydroxydiphenyl ether (IV), gave various polychlorinated dibenzo-p-dioxins (PCDDs) by pyrolysis. Some of PCDDs formed were identified by comparison of their
1H-NMR and mass data with those of the standards. The chemical structures of the others were inferred from their
1H-NMR and mass spectra. The results provided that by pyrolysis I gave 2, 8-dichlorodibenzo-p-dioxin (di-CDD) and 2, 7-di-CDD corresponding to the intramolecular dehydrochlorination and the Smiles rearrangement, respectively. However, II, III and IV gave further chlorinated dibenzo-p-dioxins other than PCDDs corresponding to the intramolecular dehydrochlorination, respectively. Especially, III produced 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (2, 3, 7, 8-tetra-CDD) which is the most toxic of PCDDs. This result suggests a new generating pathway of 2, 3, 7, 8-tetra-CDD other than those so far reported.
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