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Experimental and theoretical insights into the involvement of radicals in triclosan phototransformation.
MedLine Citation:
PMID:  23282071     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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: 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 d(8)-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.
Authors:
Sarah Kliegman; Soren N Eustis; William A Arnold; Kristopher McNeill
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-1-2
Journal Detail:
Title:  Environmental science & technology     Volume:  -     ISSN:  1520-5851     ISO Abbreviation:  Environ. Sci. Technol.     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-1-3     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0213155     Medline TA:  Environ Sci Technol     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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