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Carbamazepine (CBZ) is one of the pharmaceuticals most frequently detected in the aqueous environment. This study investigated the transformation products when CBZ is degraded by chlorine under ultraviolet (UV) irradiation (the UV/chlorine process). Detailed pathways for the degradation of CBZ were elucidated using ultra-high performance liquid chromatography (UHPLC)-quadrupole time-of-flight mass spectrometry (QTOF-MS). CBZ is readily degraded by hydroxyl radicals (HO) and chlorine radicals (Cl) in the UV/chlorine process, and 24 transformation products were identified. The products indicate that the 10,11-double bond and aromatic ring in CBZ are the sites most susceptible to attack by HO and Cl. Subsequent reaction produces hydroxylated and chlorinated aromatic ring products. Four specific products were quantified and their evolution was related with the chlorine dose, pH, and natural organic matter concentration. Their yields showed an increase followed by a decreasing trend with prolonged reaction time. CBZ-10,11-epoxide (I), the main quantified transformation product from HO oxidation, was observed with a peak transformation yield of 3-32% depending on the conditions. The more toxic acridine (IV) was formed involving both HO and Cl with peak transformation yields of 0.4-1%. All four quantified products together amounted to a peak transformation yield of 34.5%. The potential toxicity of the transformation products was assayed by evaluating their inhibition of the bioluminescence of the bacterium Vibrio Fischeri. The inhibition increased at first and the decreased at longer reaction times, which was in parallel with the evolution of transformation products., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Cyanogen chloride (CNCl) and trichloramine (NCl3) are important disinfection byproducts in chlorinated swimming pools. However, some unknowns exist regarding the precursors of their formation. In this study, uric acid is shown to be an efficient precursor to formation of CNCl and NCl3. The molar yields of CNCl and NCl3 were observed to be as high as 44% (pH = 6.0, chlorine/precursor molar ratio [Cl/P] = 6.4) and 108% (pH = 7.0, Cl/P = 30), respectively, both being strong functions of Cl/P, pH, and temperature. Analysis of swimming pool water samples, combined with the results of experiments involving chlorination of uric acid, and chlorination of body fluid analog mixtures, indicated that uric acid chlorination may account for a large fraction of CNCl formation in swimming pools. Moreover, given that uric acid introduction to pools is attributable to urination, a voluntary action for most swimmers, these findings indicate important benefits to pool water and air chemistry that could result from improved hygiene habits on the part of swimmers.