Apparent Reactivity of Bromine in Bromochloramine Depends on Synthesis Method: Implicating Bromine Chloride and Molecular Bromine as Important Bromine Species
Publication: Journal of Environmental Engineering
Volume 148, Issue 12
Abstract
The chloramination of bromide containing waters results in the formation of bromine containing haloamines: monobromamine (), dibromamine (), and bromochloramine (NHBrCl). Many studies have directly shown that bromamines are more reactive than chloramines in oxidation and substitution reactions with organic water constituents because the bromine atom in oxidants is more labile than the chlorine atom. However, similar studies have not been performed with NHBrCl. It has been assumed that NHBrCl has similar reactivity as bromamines with organic constituents in both oxidation and substitution reactions because NHBrCl, like bromamines, rapidly oxidizes N,N-diethyl-p-phenylenediamine. In this study, we examined the reactivity of NHBrCl with phenol red to determine if NHBrCl reacts as readily as bromamines in an isolated substitution reaction. NHBrCl was synthesized two ways to assess whether NHBrCl or the highly reactive intermediates, bromine chloride (BrCl) and molecular bromine (), were responsible for bromine substitution of phenol red. NHBrCl was found to be much less reactive than bromamines with phenol red and that BrCl and appeared to be the true brominating agents in solutions where NHBrCl is formed. This work highlights the need to reexamine what the true brominating agents are in chloraminated waters containing bromide.
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Data Availability Statement
All data, models, and code generated or used during the study appear in the published article.
Acknowledgments
This work was supported by the National Science Foundation under Grant 1953206.
Disclaimer
The research presented was not performed or funded by EPA and was not subject to EPA’s quality system requirements. The views expressed in this article are those of the author(s) and do not necessarily represent the views or the policies of the US Environmental Protection Agency. Any mention of trade names, manufacturers, or products does not imply an endorsement by the United States Government or the US Environmental Protection Agency. The EPA and its employees do not endorse any commercial products, services, or enterprises.
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Published In
Journal of Environmental Engineering
Volume 148 • Issue 12 • December 2022
Copyright
© 2022 American Society of Civil Engineers.
History
Received: Feb 17, 2022
Accepted: Jul 11, 2022
Published online: Sep 19, 2022
Published in print: Dec 1, 2022
Discussion open until: Feb 19, 2023
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