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Aquatic degradation of triclosan and formation of toxic chlorophenols in presence of low concentrations of free chlorine

Aquatic degradation of triclosan and formation of toxic chlorophenols in presence of low concentrations of free chlorine,10.1007/s00216-005-0116-4,Ana

Aquatic degradation of triclosan and formation of toxic chlorophenols in presence of low concentrations of free chlorine   (Citations: 18)
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The degradation of 2-(2,4-dichlorophenoxy)-5-chlorophenol (triclosan) in chlorinated water samples was investigated. Sensitive determination of the parent compound and its transformation products was achieved by gas chromatography with mass spectrometry detection after sample concentration, using a solid-phase extraction sorbent and silylation of the target compounds. Experiments were accomplished using ultrapure water spiked with chlorine and triclosan concentrations in the low mg/l and ng/ml ranges respectively. Chlorination of the phenolic ring and cleavage of the ether bond were identified as the main triclosan degradation pathways. Both processes led to the production of two tetra- and a penta-chlorinated hydroxylated diphenyl ether, as well as 2,4-dichlorophenol. The formation of 2,3,4-trichlorophenol was not detected in any experiment; however, significant amounts of 2,4,6-trichlorophenol were noticed. All of these five compounds were also identified when triclosan was added to tap-water samples with free chlorine concentrations below 1 mg/l. Minor amounts of three di-hydroxylated phenols, containing from one to three atoms of chlorine in their structures, were also identified as unstable triclosan chlorination by-products. The analysis of several raw wastewater samples showed the co-existence of important concentrations of triclosan and its most stable by-products (2,4-dichlorophenol and 2,4,6-trichlorophenol), reinforcing the potential occurrence of the described transformations when products containing triclosan are mixed with chlorinated tap water.
Journal: Analytical and Bioanalytical Chemistry - ANAL BIOANAL CHEM , vol. 383, no. 7, pp. 1119-1126, 2005
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    • ...Triclosan exposure is also linked with bio antibiotic effects, a possible development of microbial resistance (Larkin, 1999) and the formation of toxic chlorophenols in the presence of low concentrations of free chlorine (Canosa et al., 2005)...
    • ...of this compound by solar light is probable (Canosa et al., 2005)...
    • ...These observations are consistent with previous reports and could be explained by triclosan being able to take part in the polymerisation reaction more readily at relatively high concentration and lower pH value (Canosa et al., 2005; Latch et al., 2003)...

    Zhongliang Chenet al. Photolytic degradation of triclosan in the presence of surfactants

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