N-dealkylation of amines during water disinfection - Revealing a new direction in the formation of disinfection by-products.

Autor: Mazur DM; Department of Materials Science, MSU-BIT University, Shenzhen, 517182, China., Surmillo AS; Lomonosov Moscow State University, Chemistry Department, Leninskie Gory 1/3, Moscow, 119991, Russia., Sypalov SA; Lomonosov Northern (Arctic) Federal University, Core Facility Center 'Arktika', Nab. Severnoy Dviny 17, Arkhangelsk, 163002, Russia., Varsegov IS; Lomonosov Northern (Arctic) Federal University, Core Facility Center 'Arktika', Nab. Severnoy Dviny 17, Arkhangelsk, 163002, Russia., Ul'yanovskii NV; Lomonosov Northern (Arctic) Federal University, Core Facility Center 'Arktika', Nab. Severnoy Dviny 17, Arkhangelsk, 163002, Russia., Kosyakov DS; Lomonosov Northern (Arctic) Federal University, Core Facility Center 'Arktika', Nab. Severnoy Dviny 17, Arkhangelsk, 163002, Russia., Lebedev AT; Department of Materials Science, MSU-BIT University, Shenzhen, 517182, China; Lomonosov Northern (Arctic) Federal University, Core Facility Center 'Arktika', Nab. Severnoy Dviny 17, Arkhangelsk, 163002, Russia. Electronic address: mocehops@yandex.ru.
Jazyk: angličtina
Zdroj: Chemosphere [Chemosphere] 2024 Feb; Vol. 350, pp. 141117. Date of Electronic Publication: 2024 Jan 04.
DOI: 10.1016/j.chemosphere.2024.141117
Abstrakt: Among numerous disinfection by-products (DBP) forming during aqueous chlorination nitrogen containing species are of special concern due to their toxicological properties. Nevertheless, corresponding reaction products of these natural and anthropogenic compounds are not sufficiently studied so far. An interesting reaction involves dealkylation of the substituted amine moiety. Here we present the results of the comparative study of one-electron oxidation and aqueous chlorination of several aliphatic and aromatic amines. The reaction products were reliably identified with gas chromatography - high resolution mass spectrometry (GC-HRMS), high pressure liquid chromatography - electrospray ionization high resolution mass spectrometry HPLC-ESI/HRMS), and electrochemistry - electrospray ionization high resolution mass spectrometry (EC-ESI/HRMS). Certain similarities dealing with the formation of the corresponding aldehydes and substitution of alkyl groups at the nitrogen atom for hydrogen were shown for the studied processes. The mechanism of the substituted amines' aqueous chlorination involving one-electron oxidation is proposed and confirmed by the array of the observed reaction products. Alternative reactions taking place in conditions of aqueous chlorination, i.e. aromatic electrophilic substitution, may successfully compete with dealkylation and produce major products.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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