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Denatonium, one of the bitterest substances known to man, was recently identified as wastewater borne micropollutant in surface waters. Therefore, photodegradation experiments and electrochemical degradation were performed to identify abiotic and putative biotic transformation products (TPs). Indirect rather than direct photodegradation proved to be important for denatonium removal by solar irradiation and produced seven TPs. Amide hydrolysis, hydroxylation, N-dealkylation, and N-dearylation were revealed as the main mechanisms. Anodic oxidation of denatonium was related to the formation of overall ten products and despite considerable different yields, all TPs from indirect photodegradation were mimicked electrochemically. Among them, lidocaine was the only TP detected after conventional wastewater treatment and in surface waters. The occurrence of lidocaine was however associated with its application as local anesthetic rather than to a degradation of denatonium. The absence of additional products suggests that denatonium degradation is negligible under environmental conditions, supporting the previously described persistent nature of this compound. Advanced water treatment techniques however have the potential to degrade denatonium. About 74% of the initial denatonium load was removed from wastewater during pilot-scale ozonation. The degradation of denatonium was accompanied here with the formation of at least two polar products, which are passing unchanged through a sand filter after ozonation. Both substances have completely unknown (toxicological) properties and this study seems to be the first report about their structures in general, as none of them was found in any of the large compound libraries (e.g. PubChem). Unlabelled Image • Indirect photodegradation and electrochemical oxidation resulted in overall ten TPs. • Five products were identified with a confidence level of 2 or better. • High persistence of denatonium in conventional wastewater treatment and in surface waters observed. • Denatonium removal by ozonation is associated with the formation of polar TPs. [ABSTRACT FROM AUTHOR]

The pharmaceutical torasemide is an important loop diuretic and was 2017 one of the ten most prescribed drugs in Germany. Despite its detection in different compartments of the urban water cycle including drinking water, no studies were so far performed to elucidate its fate in the environment and the occurrence of transformation products (TPs). Therefore, we investigated the phototransformation, microbial degradation, transformation with human liver microsomes and anodic oxidation of torasemide to obtain good coverage of environmentally relevant degradation products. Overall sixteen products were identified, covering the following reaction mechanisms: aromatic and aliphatic hydroxylation, including further oxidation to carboxylic acids and quinone imines, amide cleavage, N-dealkylation, N-dearylation, and sulfonamide hydrolysis to sulfonic acids. Especially the formation of quinone imines could be of concern as they are highly reactive electrophiles. Torasemide itself was observed in all investigated wastewater treatment plant (WWTP) samples and wastewater-impacted surface waters. The maximum detected concentration was about 350 ng L−1. Only three of the sixteen transformation products were generally observed in at least one of the samples and the most frequently detected TPs were the human metabolites hydroxytorasemide (TP 364a) and carboxytorasemide (TP 378a). The complete removal of TP 364a during wastewater treatment was in agreement with the results of microbial degradation experiments. TP 364a was most likely transformed into TP 378a, which was microbially less degraded in lab experiments. Based on estimated concentrations, TP 378a could reach about 1 μg L−1 in the investigated wastewater matrices. Image 1 • Overall sixteen abiotic and biotic products identified for torasemide. • Formation of reactive products proven with trapping experiments using reduced glutathione. • Torasemide and carboxytorasemide detected in all WWTPs and wastewater-impacted surface waters. [ABSTRACT FROM AUTHOR]