Behavior of the antimicrobial triclosan (5-chloro-2-(2,4-dichlorophenoxy)phenol) was investigated under laboratory chlorination conditions and in a wastewater treatment plant discharging 380 million liters daily to the Delaware River, USA. Reactions of triclosan with chlorine were investigated using concentrations and exposure time typical of municipal wastewater treatment plants, i.e., 1 h contact time and average 1–2 mg/L residual chlorine. In reagent water, triclosan reacted quickly, transforming into mono- and dichlorinated species and further into dichlorophenol and trichlorophenol. However, triclosan remained stable for up to 2 h in wastewater samples chlorinated under these conditions. To confirm observed behavior under field conditions, a liquid chromatography tandem mass spectrometry-based analytical method capable of monitoring triclosan and its transformation products in wastewater was developed. Qualitative and quantitative wastewater characterization before and after chlorination are presented. Triclosan was present at the same concentration (P > 0.05) in pre-chlorination and post-chlorination aqueous wastewater samples (mean 368 ng/L). This finding is consistent with the non-detection of specific triclosan transformation products above sample reporting limits (30.0–100 ng/L), but contrasts markedly with detection of chlorination transformation products reported in reagent water. These data suggest the importance of influent matrix components in chlorination reactions of triclosan in contaminated wastewater under treatment plant conditions.

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