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

Heeb, Michèle B.; Kristiana, Ina; Trogolo, Daniela; Arey, J. Samuel; Gunten, Urs von

doi:10.1016/j.watres.2016.11.065

Cited by 123 publications

(84 citation statements)

References 60 publications

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“…It can be concluded that MBA reacts with phenol by bromination rather than by derivatization into indophenol, as is the case for MCA. This is consistent with the kinetics results recently provided by Heeb et al [4], who studied the reactivity of inorganic and organic N-chloramines and N-bromamines with phenolic compounds (in aqueous solutions at pH 7), as surrogates for dissolved organic matter (DOM); the reaction rate of MBA (2.1 × 10 2 M −1 s −1 ) with phenol was about two orders of magnitude lower than with HOBr (6.5 × 10 4 M −1 s −1 ), but about four orders of magnitude higher than that of MCA (1.6 × 10 −2 M −1 s −1 ).…”

Section: Gc-ms Characterization Of the Products Of The Reaction Betwesupporting

confidence: 94%

“…These results seem to be in close agreement with current knowledge of chlorine chemistry in seawater, according to which two competitive reactions occur in presence of ammonia: (a) bromide oxidation and (b) monochloramination. The reported rate constants are (1.55−6.84) × 10 3 and (1.9−5.7) × 10 6 M −1 s −1 , respectively [3][4][5][37][38][39].…”

Section: Investigation Of the Berthelot Reaction In Chlorinated Seawatermentioning

confidence: 99%

“…On the other hand, it is well documented that the fate of TRO in the aquatic environment, its effect on aquatic life, and its potential to generate organohalogen by-products (OXBPs) strongly depend on the chemical nature of the oxidant species that compose it. Studies have ranked chlorine-produced oxidants in ascending order of stability as: NHBr 2 < NH 2 Br < HOBr/BrO − < HOCl/ClO − < NH 2 Cl [4,15,16]. Isaac and Morris [17] found that some organic N-chloramines were more stable than inorganic chloramines, while Antelo et al [18] reported that organic N-bromamines were less stable than their chlorinated analogues.…”

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confidence: 99%

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Is It Possible to Measure Monobromamine Using Colorimetric Methods Based on the Berthelot Reaction, Like for Monochloramine?

2020

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Analytical methods based on the Berthelot reaction were recently adapted for determining monochloramine (MCA: NH2Cl) in freshwater. The specificity of the Berthelot reaction with regard to MCA is related to the need for two exchangeable hydrogen atoms to form indophenol blue. MCA can thus be distinguished from organic N-chloramines, which have only one exchangeable hydrogen atom. Monobromamine (MBA: NH2Br) may be formed during chlorination of seawater containing ammonium ions. Quantifying MBA is quite challenging and no method has been reported for its specific determination in seawater. As MBA also has two exchangeable hydrogen atoms, its reactivity might be analogous to that of MCA, but this hypothesis has never been investigated. The aim of this study was to examine the applicability of the so-called “indophenol method” for the determination of the MBA in freshwater and seawater samples. The reaction between MBA and Berthelot reagents was studied in both ultrapure water and artificial seawater. The reaction products were characterized by using gas chromatography coupled to mass spectrometry (GC–MS), Fourier transform-ion cyclotron resonance mass spectrometry (FT–ICR MS), and UV–vis spectroscopy. Results showed that colorimetric methods based on the Berthelot reaction were not suitable for measuring MBA in freshwater or seawater, since NH2Br reacts with alkaline phenol derivative via electrophilic substitution to form ortho- and para-brominated phenols instead of forming indophenol.

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Section: Gc-ms Characterization Of the Products Of The Reaction Betwesupporting

confidence: 94%

Section: Investigation Of the Berthelot Reaction In Chlorinated Seawatermentioning

confidence: 99%

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confidence: 99%

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Is It Possible to Measure Monobromamine Using Colorimetric Methods Based on the Berthelot Reaction, Like for Monochloramine?

2020

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“…The maximum apparent second‐order rate constant for oxidation of the neutral amines with chlorine should be at a pH of ~8.5 (Heeb et al ). Therefore, for the experiments at pH 8 and 9 (the tests at pH 8 typically had a pH level of 8.2–8.3, and the tests at pH 9 typically had a pH level of 9.0–9.2), prechlorination efficiency was close to the optimum.…”

Section: Resultsmentioning

confidence: 99%

“…Certain water quality parameters, such as pH, temperature, and time, can exert important effects on precursor abatement and nitrosamine formation and will vary with source water and season. Maximum precursor abatement by free chlorine is anticipated at pH ~8.5–9 for the maximum co‐occurrence of the active oxidant (HOCl, pK a = 7.5) and the neutral amine precursors (pK a ~10–11) (Heeb et al , Lee & von Gunten ). Free chlorine contact time and temperature are also important (McCurry et al , Charrois & Hrudey ).…”

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confidence: 99%

Impact of Combined Chlorination and Chloramination Conditions onN‐Nitrosodimethylamine Formation

Krasner¹,

Lee²,

Mitch³

et al. 2018

Journal AWWA

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SwitzerlandBench-scale chloramination under uniform formation conditions was used to examine N-nitrosodimethylamine (NDMA) formation in settled and (bio)filtered drinking water and treated wastewater. In this study, water temperature, pH, postchloramination time, and chlorineto-nitrogen (Cl 2 /N) weight ratio were varied to investigate NDMA formation in various water types. Wastewater and certain polymers were investigated as sources of NDMA precursors. Nitrified biofilters were found to be another precursor source. NDMA formation in nitrified biofilter effluent and polymer-impacted water was the highest at Cl 2 /N of 3-5; NDMA formation was the highest at Cl 2 /N of 5-7 in wastewater-impacted waters. Other tests at Cl 2 /N of 4.75 evaluated the impact of pH and temperature, with a 3 min prechlorination, which can result in some precursor abatement. At pH 7, NDMA formation increased with increasing temperature, whereas at pH 8 and 9, low temperature sometimes yielded higher NDMA formation because of lower precursor abatement during prechlorination and, thus, higher NDMA formation during postchloramination.

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Modeling chloramine stability and disinfection byproduct formation in groundwater high in bromide

Shimabuku,

Henrie,

Schultise

et al. 2024

AWWA Water Science

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Bromide can promote monochloramine decomposition and disinfection byproduct (DBP) formation. Monochloramine and total chlorine stability as well as total trihalomethane and haloacetic acid formation were examined in groundwater with high bromide levels (300–1700 μg/L) following chlorine or KMnO₄ preoxidation. An N,N‐Diethyl‐p‐phenylenediamine (DPD)‐based total chlorine method detected chloramines and brominated amines (e.g., NH2Br, NHBrCl). An indophenol‐based monochloramine method showed minimal interference from brominated amines. Differences between these methods' measurements likely indicated brominated amine concentrations. Substantial total chlorine demands (up to ~3.5 mg/L in 4 days) following chlorine preoxidation were observed due to the presence of brominated amines. Total chlorine measurements were more stable and DBP formation was limited following KMnO₄ preoxidation because ammonia was dosed before chlorine, which inhibited brominated amine formation. A kinetic model developed elsewhere for dissolved organic matter (DOM)‐free water generally tracked with experimental results but some deviations occurred possibly because DOM consumed bromochloramine or its reaction intermediates.

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

Cited by 123 publications

References 60 publications

Is It Possible to Measure Monobromamine Using Colorimetric Methods Based on the Berthelot Reaction, Like for Monochloramine?

Is It Possible to Measure Monobromamine Using Colorimetric Methods Based on the Berthelot Reaction, Like for Monochloramine?

Impact of Combined Chlorination and Chloramination Conditions onN‐Nitrosodimethylamine Formation

Modeling chloramine stability and disinfection byproduct formation in groundwater high in bromide

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