title: Nitration processes of acetaminophen in nitrifying activated sludge.
abstract: This work is an attempt to elucidate the quantitative significance of acetaminophen (APAP) nitration in nitrifying activated sludge and to propose a reaction mechanism for this process. The link between nitrification and nitration of APAP was investigated at different scales. Results from field studies showed the occurrence of 3-nitro-APAP and to a lesser extent 3-chloro-5-nitro-APAP at concentration levels in the 50-300 ng/L range in effluents of a full scale wastewater treatment plant (WWTP) operated with nitrogen removal, whereas 3-hydroxy-APAP was eliminated after the nitrification step. Batch experiments with nitrifying activated sludge confirmed APAP transformation by nitration and suggested that nitrifying bacteria may play a role in this transformation process through the release of reactive nitrogen species. In vitro assays provided evidence that nitration through the production of nitrous acid is a very unlikely pathway. In contrast, nitric oxide (*NO) produced by nitrifying bacteria is probably involved in APAP nitration through the formation of peroxynitrite in presence of superoxide anion. The production of 3-nitro-APAP would only account for a few percents of the total transformation rate of APAP in WWTPs. The production of nitrated derivatives is highly relevant because of the potential ecotoxicological risks of these compounds.
authors.affiliation: UMR 5569 'Hydrosciences Montpellier' University of Montpellier I, 15 Avenue Ch. Flahault, BP 14491, 34093 Montpellier cedex 5, France. serge.chiron@univ-provence.fr
authors.forename: Serge
authors.initials: S
authors.lastname: Chiron
authors.forename: Elena
authors.initials: E
authors.lastname: Gomez
authors.forename: Hélène
authors.initials: H
authors.lastname: Fenet
mesh_terms: D000082:Acetaminophen / Q000378:metabolism*; D006735:Horseradish Peroxidase / Q000378:metabolism; D009566:Nitrates / Q000378:metabolism*; D030421:Peroxynitrous Acid / Q000378:metabolism; D012722:Sewage
chemical_list: D009566:Nitrates; D012722:Sewage; D030421:Peroxynitrous Acid; D000082:Acetaminophen; D006735:Horseradish Peroxidase