Photodegradation of pentachlorophenol and its degradation pathways predicted using density functional theory.

Junya Suegara, Byung-Dae Lee, Maria P Espino, Satoshi Nakai, Masaaki Hosomi

Public Enterprises Agency, Kanagawa Prefectural Government, Japan.

Chemosphere 2005 Oct

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The objectives of the present research were (i) to report the mass balance of chlorine during pentachlorophenol (PCP) photodegradation and (ii) to reveal the photodegradation pathway experimentally with a theoretical proof based on the density functional theory (DFT). The chlorine of PCP was completely mineralized to produce chloride ions after 24h of UV irradiation. As intermediates, 2,3,5,6-tetrachlorophenol, 2,3,4,6-tetrachlorophenol and 2,5-dichlorophenol were identified. At least 80% of the chlorine balance during PCP photodegradation was accounted by PCP, these intermediates, and chloride ions. A DFT calculation showed differences in the C-Cl bond dissociation energy level and the positions of respective PCP molecular and the PCP intermediates. The dechlorination intermediates predicted using the calculated C-Cl bond dissociation energy were consistent with those experimentally confirmed, indicating the feasibility of this theoretical method in predicting the dechlorination pathway.

Citation

Junya Suegara, Byung-Dae Lee, Maria P Espino, Satoshi Nakai, Masaaki Hosomi. Photodegradation of pentachlorophenol and its degradation pathways predicted using density functional theory. Chemosphere. 2005 Oct;61(3):341-6