Chlorination of benzothiazoles and benzotriazoles and transformation products identification by LC-HR-MS/MS

Nika, Maria‐Christina; Bletsou, Anna A.; Koumaki, Elena; Noutsopoulos, Constantinos; Mamais, Daniel; Stasinakis, Athanasios S.; Thomaidis, Nikolaos S.

doi:10.1016/j.jhazmat.2016.03.035

Cited by 37 publications

(22 citation statements)

References 35 publications

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“…Predictions are based on the similarity of the investigated compound (parent drug or TP) to a set of chemicals, used to construct the QSAR model, whose environmental toxicities towards different organisms has been experimentally determined (Melnikow et al, 2016;Nika et al, 2017). In this work, 48-h Daphnia magna LC50 (50% lethal concentration), 96-h fish LC50 and 96-h green algae half-maximum effective concentration (EC50) were estimated.…”

Section: In-silico Ecotoxicity Assessmentmentioning

confidence: 99%

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Free chlorine reactions of angiotensin II receptor antagonists: Kinetics study, transformation products elucidation and in-silico ecotoxicity assessment

Carpinteiro

Castro

Rodrı́guez

et al. 2019

Science of The Total Environment

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Angiotensin II receptor antagonists (ARA II) are widely employed in the treatment of hypertension-related diseases. Because of their partial metabolization and limited biodegradability, these drugs have become ubiquitous pollutants in the aquatic environment, including surface water. This research evaluated the reactivity of the ARA II drugs: irbesartan (IRB), losartan (LOS) telmisartan (TEL) and valsartan (VAL) with free chlorine. Responses of parent compounds and their transformation products (TPs) were followed by liquid chromatography (LC) with quadrupole (Q) time-of-flight (TOF) mass spectrometry. Degradation experiments were carried out using ultrapure and river water samples, adjusted at different pHs and, in some cases, adding a small amount (ng mL level) of bromide salts. Whilst TEL and VAL remained stable in presence of relatively high concentrations of free chlorine (10 mg L), IRB and LOS were removed according to a pseudo-first order kinetics model. Considering an initial chlorine concentration of 10 mg L, their half-lives varied between 6 and 734 min, depending mostly on the water pH. IRB reacted with free chlorine through hydroxylation processes, with and without molecular cleavage and re-arrangements in the imidazolone ring. Its TPs showed a lower in-silico predicted toxicity than the parent drug. In case of LOS, two major competitive degradation routes were identified. They involved replacement of the methanol group attached to the imidazole cycle by chlorine or bromine, and the cleavage of this cycle with removal of the chlorinated carbon and the nitrogen in alpha position. The TPs generated following the first route are predicted to be more toxic than LOS.

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Section: In-silico Ecotoxicity Assessmentmentioning

confidence: 99%

“…Likely, the reaction is initiated with an electrophilic attack to carbon number 5 in this ring, Table 1. Electrophilic halogenation is recognized as one the most common reaction of aromatic pollutants with free chlorine (Nika et al, 2017;Negreira et al, 2012). The ESI(-) MS/MS spectra (Fig.…”

Section: Losartanmentioning

confidence: 99%

Free chlorine reactions of angiotensin II receptor antagonists: Kinetics study, transformation products elucidation and in-silico ecotoxicity assessment

Carpinteiro

Castro

Rodrı́guez

et al. 2019

Science of The Total Environment

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“…Some authors have studied the performance of UVC alone or combined with H2O2 [47,48], ozonation [49], photo-Fenton [50], chlorination [51] and activated peroxomonosulfate [52] to degrade BTH. Some of these works also addressed the treatment of 2-OH-BTH [47,51,52] but, surprisingly, the degradation of theses BTs by EAOPs has not been investigated yet.…”

Section: Introductionmentioning

confidence: 99%

On the positive effect of UVC light during the removal of benzothiazoles by photoelectro-Fenton with UVA light

Brillas

Han

et al. 2019

Applied Catalysis B: Environmental

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Benzothiazole (BTH) and 2-hydroxybenzothiazole (2-OH-BTH) are ubiquitous pollutants in aquatic ecosystems. This article reports their photoelectro-Fenton (PEF) treatment, either alone or mixed, in sulfate medium at pH 3.0 using an IrO2-based/air diffusion cell that generates H2O2 under UVA and/or UVC irradiation. UVC-PEF was more effective than UVA-PEF to remove the target pollutants, which suggests a positive impact of • OH formed via Fenton's reaction and photo-induced homolysis of H2O2 in the former method. In addition, BTH disappeared more quickly than 2-OH BTH. Full-time UVA-/UVC-PEF outperformed UVC-PEF and UVA-PEF to mineralize the mixtures, although requiring a much higher energy consumption. The evolution of generated H2O2 and homogeneous • OH confirmed the positive contribution of UVC photolysis in UVA-PEF. Part-time use of UVC radiation in UVA-PEF yielded a similar total organic carbon removal, with much lower energy consumption. BTH was oxidized to 2-OH-BTH, which was subsequently transformed into other five heteroaromatics.

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“…Chlorination is the most common disinfection method used in WWTPs due to its high effectiveness, increased availability in the market and its low cost [22].…”

Section: Chlorinationmentioning

confidence: 99%

“…Chlorine dose in WWTPs usually varies from 5 to 20 mg L -1 depending on chlorine demand, wastewater characteristics and discharge requirement of a particular WWTP [24]. Although, the main purpose of chlorination is to eliminate pathogens, investigations have shown that chlorine reacts with micropollutants and natural organic matter in water and forms halogenated by-products which are toxic and can cause long-term health effects [22,25].…”

Section: Chlorinationmentioning

confidence: 99%

Identification of transformation products of emerging contaminants during tertiary treatment processes and their disposal in the environment by mass spectrometric techniques

Nika¹,

Νίκα²

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Η διαθέσιμη βιβλιογραφία έχει καταδείξει την ατελή απομάκρυνση των αναδυόμενων ρύπων κατά τη βιολογική επεξεργασία που λαμβάνει χώρα στα Κέντρα Επεξεργασίας Λυμάτων (ΚΕΛ). Παρόλο που ο πρωταρχικός ρόλος της τριτοβάθμιας επεξεργασίας είναι η εξάλειψη των μικρορύπων, το παρεχόμενο οξειδωτικό μέσο αντιδρά με τους αναδυόμενους ρύπους, καταλήγοντας στο σχηματισμό άγνωστων προϊόντων μετασχηματισμού. Ο κύριος στόχος της παρούσας διπλωματικής εργασίας ήταν η διερεύνηση της απομάκρυνσης αναδυόμενων ρύπων καθώς και η ταυτοποίηση των προϊόντων μετασχηματισμού τους, τα οποία παράγονται κατά τις μεθόδους απολύμανσης που εφαρμόζονται σαν τριτοβάθμια επεξεργασία στα ΚΕΛ. Αρχικά παρουσιάζεται μια εισαγωγή για τους αναδυόμενους ρύπους και τον πιθανό μετασχηματισμό τους κατά τη διάρκεια των διεργασιών που εφαρμόζονται στα ΚΕΛ, και ιδιαιτέρως κατά τη διάρκεια της χλωρίωσης και οζόνωσης. Στη συνέχεια παρουσιάζονται συγκεκριμένες πορείες εργασίας και τεχνικές σχετικές με την ταυτοποίηση αναδυόμενων ρύπων και των προϊόντων μετασχηματισμού τους, οι οποίες βασίζονται σε αναλύσεις φασματομετρίας μάζας υψηλής διακριτικής ικανότητας. Το πειραματικό μέρος της παρούσας διπλωματικής εργασίας αποτελείται από τα ακόλουθα τρία μέρη: (α) Χλωρίωση βενζοτριαζολών και βενζοθειαζολών και ταυτοποίηση των προϊόντων μετασχηματισμού τους με υγροχρωματογραφία συζευγμένη με φασματομετρία μάζας υψηλής διακριτικής ικανότητας (Κεφάλαιο 3), (β) Οζόνωση ρανιτιδίνης: επίδραση των πειραματικών συνθηκών και ταυτοποίηση προϊόντων μετασχηματισμού (Κεφάλαιο 4) και (γ) Απομάκρυνση και μετασχηματισμός της σιταλοπράμης και τεσσάρων προϊόντων βιομετατροπής της κατά τη διάρκεια πειραμάτων οζόνωσης (Κεφάλαιο 5).Είναι πεποίθησή μας πως οι μελέτες αυτές θα συνεισφέρουν στην περαιτέρω ανάπτυξη της περιβαλλοντικής ανάλυσης, διεγείροντας το ενδιαφέρον των κανονιστικών αρχών, σχετικά με την ενσωμάτωση επιβλαβών προϊόντων μετασχηματισμού, τα οποία παράγονται κατά την τριτοβάθμια επεξεργασία των ΚΕΛ, σε ελέγχους ρουτίνας.

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Chlorination of benzothiazoles and benzotriazoles and transformation products identification by LC-HR-MS/MS

Cited by 37 publications

References 35 publications

Free chlorine reactions of angiotensin II receptor antagonists: Kinetics study, transformation products elucidation and in-silico ecotoxicity assessment

Free chlorine reactions of angiotensin II receptor antagonists: Kinetics study, transformation products elucidation and in-silico ecotoxicity assessment

On the positive effect of UVC light during the removal of benzothiazoles by photoelectro-Fenton with UVA light

Identification of transformation products of emerging contaminants during tertiary treatment processes and their disposal in the environment by mass spectrometric techniques

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