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  4. Formation and reactivity of inorganic and organic chloramines and bromamines during oxidative water treatment
 
research article

Formation and reactivity of inorganic and organic chloramines and bromamines during oxidative water treatment

Heeb, Michele B.  
•
Kristiana, Ma
•
Trogolo, Daniela  
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2017
Water Research

The formation and further reactions of halamines during oxidative water treatment can be relevant for water quality. In this study, we investigated the formation and reactivity of several inorganic and organic halamines (monochloramine, N-chloromethylamine, N-chlorodimethylamine, monobromamine, dibromamine, N-bromomethylamine, N,N-dibromomethylamine, and N-bromodimethylamine) by kinetic experiments, transformation product analysis, and quantum chemical computations. Kinetic model simulations were conducted to evaluate the relevance of halamines for various water treatment scenarios. Halamines were quickly formed from the reaction of chlorine and bromine with ammonia or organic amines. Species-specific second-order rate constants for the reaction of chlorine and bromine with ammonia, methyl- and dimethylamine were in the order of 10(6)-10(8) M(-1)s(-1). The formed halamines were found to be reactive towards phenolic compounds, forming halogenated phenols via electrophilic aromatic substitution (phenol and resorcinol) or quinones via electron transfer (catechol and hydroquinone). At near neutral pH, apparent second-order rate constants for these reactions were in the order of 10(-4)-10(-1) M(-1)s(-1) for chloramines and 10(1)-10(2) M(-1)s(-1) for bromamines. Quantum chemical computations were used to determine previously unknown aqueous pK(a) values, gas phase bond dissociation energies (BDE) and partial atomic charges of the halamines, allowing a better understanding of their reactivities. Kinetic model simulations, based on the results of this study, showed that during zhlorination inorganic and organic chloramines are the main halamines formed. However, their further reactions with organic matter are outcompeted kinetically by chlorine. During ozonation, mainly inorganic bromamines are formed, since ozone quickly oxidizes organic amines. The further reactions of bromamine are typically outcompeted by ozone and thus generally of minor importance. The use of peracetic acid for saline ballast water treatment can result in the formation of substantial amounts of bromamines, which can react with dissolved organic matter and contribute to the formation of brominated products. (C) 2016 Elsevier Ltd. All rights reserved.

  • Details
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Type
research article
DOI
10.1016/j.watres.2016.11.065
Web of Science ID

WOS:000394200800010

Author(s)
Heeb, Michele B.  
Kristiana, Ma
Trogolo, Daniela  
Arey, J. Samuel  
Von Gunten, Urs  
Date Issued

2017

Publisher

Elsevier

Published in
Water Research
Volume

110

Start page

91

End page

101

Subjects

Chloramines

•

Bromamines

•

Oxidative water treatment

•

Partial charge

•

PKa

•

Kinetic modeling

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LTQE  
LMCE  
Available on Infoscience
May 1, 2017
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/136910
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