Experimental and theoretical insights into the involvement of radicals in triclosan phototransformation

Sarah Kliegman, Soren N. Eustis, William A. Arnold, Kristopher McNeill

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

The phototransformation of triclosan has been a matter of longstanding interest due to both its prevalence in the environment and the discovery of 2,8-dichlorodibenzodioxin as a photoproduct. In this study, photolysis of triclosan resulted in several primary photoproducts including the following: 2,8-dichlorodibenzodioxin (4%), 4,5′-dichloro-[1,1′-biphenyl]-2, 2′-diol (10%), 5-chloro-2-(4-chlorophenoxy)phenol (0.5%), and 2,4-dichlorophenol (7%). Trapping studies using d8-isopropanol showed deuterium incorporation in 5-chloro-2-(4-chlorophenoxy)phenol, providing strong evidence for the involvement of organic radicals in this reaction. Density functional calculations of the excited states of triclosan support the involvement of a radical intermediate in the mechanisms responsible for the dioxin, biphenyl, and phenoxyphenol photoproducts. The pathways for C-Cl bond cleavage and cyclization reactions are discussed.

Original languageEnglish (US)
Pages (from-to)6756-6763
Number of pages8
JournalEnvironmental Science and Technology
Volume47
Issue number13
DOIs
StatePublished - Jul 2 2013

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