1,3,5-Trimethoxybenzene (TMB) as a new quencher for preserving redox-labile disinfection byproducts and for quantifying free chlorine and free bromine

Lau, Stephanie S.; Dias, Ryan P.; Martin-Culet, Kayla R.; Race, Nicholas; Schammel, Marella H.; Reber, Keith P.; Roberts, A. Lynn; Sivey, John D.

doi:10.1039/c8ew00062j

Cited by 16 publications

(22 citation statements)

References 39 publications

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“…Chlorine concentrations were determined using 1,3,5-trimethoxybenzene (Section S1). , After 24 h, remaining chlorine was quenched with sodium thiosulfate (final concentration = 1 mM) and samples were extracted for FT-ICR MS analysis. Sodium thiosulfate was used over an organic quencher due to the potential for interference with FT-ICR MS analysis.…”

Section: Methodsmentioning

confidence: 99%

Molecular-Level Insights into the Formation of Traditional and Novel Halogenated Disinfection Byproducts

Milstead

Remucal

2021

ACS EST Water

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Dissolved organic matter (DOM) composition influences the formation of disinfection byproducts (DBPs) during drinking water treatment, yet the role of DOM composition at the molecular level in forming both known and novel DBPs has not been established. We characterized the composition of DOM from drinking water utilities that draw from surface (n = 4) and groundwaters (n = 14), focusing on groundwater because the reactivity of its DOM is poorly understood. We quantified the formation of targeted DBPs, identified novel high molecular weight (HMW) halogenated DBPs, and analyzed DOM transformation after reaction with free available chlorine. Characterization by UV−visible spectroscopy and Fourier transform-ion cyclotron resonance mass spectrometry (FT-ICR MS) reveals a high degree of variability in DOM composition and reactivity with chlorine, particularly among groundwater samples. Despite the variability in DOM composition, novel DBPs with up to three halogens are compositionally similar among all waters and are positively correlated with trihalomethane and, to a lesser extent, haloacetonitrile formation. These relationships demonstrate that some low molecular weight DBPs and novel DBPs detected by FT-ICR MS share similar aromatic precursors, providing evidence that DBPs such as trihalomethanes are a useful proxy for the formation of their HMW counterparts.

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Section: Methodsmentioning

confidence: 99%

Molecular-Level Insights into the Formation of Traditional and Novel Halogenated Disinfection Byproducts

Milstead

Remucal

2021

ACS EST Water

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“…HOCl evolved during heat activation of persulfate in the presence of excess Cl − was monitored by chromatographically measuring chlorinated intermediate(s) generated via the reaction of 1,3,5-trimethoxybenzene as a derivatizing agent with free chlorine species. 22 To avoid misleading results due to the unwanted consumption of 1,3,5-trimethoxybenzene by any remaining radicals with low substrate specificity (e.g., • Cl and SO 4…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Ionic species such as Cl – , Br – , ClO 3 – , BrO 3 – , and SO 4 2– were quantified by an IC (Dionex DX-120) equipped with a Dionex IonPac AS14 and a conductivity detector. HOCl evolved during heat activation of persulfate in the presence of excess Cl – was monitored by chromatographically measuring chlorinated intermediate(s) generated via the reaction of 1,3,5-trimethoxybenzene as a derivatizing agent with free chlorine species . To avoid misleading results due to the unwanted consumption of 1,3,5-trimethoxybenzene by any remaining radicals with low substrate specificity (e.g., • Cl and SO 4 •– ), the measurement was conducted in the presence of 0.5 M MeOH as a radical scavenger.…”

Section: Materials and Methodsmentioning

confidence: 99%

Chloride-Mediated Enhancement in Heat-Induced Activation of Peroxymonosulfate: New Reaction Pathways for Oxidizing Radical Production

Ahn

Choi

Kim

et al. 2021

Environ. Sci. Technol.

112

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This study is the first to demonstrate the capability of Cl − to markedly accelerate organic oxidation using thermally activated peroxymonosulfate (PMS) under acidic conditions. The treatment efficiency gain allowed heat-activated PMS to surpass heat-activated peroxydisulfate (PDS). During thermal PMS activation at excess Cl − , accelerated oxidation of 4-chlorophenol (susceptible to oxidation by hypochlorous acid (HOCl)) was observed along with significant degradation of benzoic acid and ClO 3 − occurrence, which involved oxidants with low substrate specificity. This indicated that heat facilitated HOCl formation via nucleophilic Cl − addition to PMS and enabled free chlorine conversion into less selective oxidizing radicals. HOCl acted as a key intermediate in the major oxidant transition based on temperaturedependent variation in HOCl concentration profiles, kinetically retarded organic oxidation upon NH 4 + addition, and enabled rapid organic oxidation in heated PMS/HOCl mixtures. Chlorine atom that formed via the one-electron oxidation of Cl − by the sulfate radical served as the primary oxidant and was involved in hydroxyl radical production. This was corroborated by the quenching effects of alcohols and bicarbonates, reactivity toward multiple organics, and electron paramagnetic resonance spectral features. PMS outperformed PDS in degrading benzoic acid during thermal activation operated in reverse osmosis concentrate, which was in conflict with the wellestablished superiority of heat-activated PDS.

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“…Lower reaction rate might hinder proper scavenging in the presence of compounds like amino acids that have high reaction rates with FAC [14]. This is also true for other selective scavengers like trimethoxybenzene (TMB) [49]. Moreover, monochloramine decomposes faster compared with N-chloroglycine [50] and is a stronger oxidant [51] reactive towards moieties such as phenol [52].…”

Section: Methods Development and Validationmentioning

confidence: 99%

Determination of free chlorine based on ion chromatography—application of glycine as a selective scavenger

2020

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Free available chlorine (FAC) is the most widely used chemical for disinfection and in secondary disinfection; a minimum chlorine residual must be present in the distribution system. FAC can also be formed as an impurity in ClO2 production as well as a secondary oxidant in the ClO2 application, which has to be monitored. In this study, a new method is developed based on the reaction of FAC with glycine in which the amine group selectively scavenges FAC and the N-chloroglycine formed can be measured by ion chromatography with conductivity detector (IC-CD). Utilizing IC for N-chloroglycine measurement allows this method to be incorporated into routine monitoring of drinking water anions. For improving the sensitivity, IC was coupled with post-column reaction and UV detection (IC-PCR-UV), which was based on iodide oxidation by N-chloroglycine resulting in triiodide. The method performance was quantified by comparison of the results with the N,N-diethyl-p-phenylenediamine (DPD) method due to the unavailability of an N-chloroglycine standard. The N-chloroglycine method showed limits of quantification (LOQ) of 24 μg L−1 Cl2 and 13 μg L−1 Cl2 for IC-CD and IC-PCR-UV, respectively. These values were lower than those of DPD achieved in this research and in ultrapure water. Measurement of FAC in the drinking water matrix showed comparable robustness and sensitivity with statistically equivalent concentration that translated to recoveries of 102% for IC-CD and 105% for IC-PCR-UV. Repeatability and reproducibility performance were enhanced in the order of DPD, IC-CD, and IC-PCR-UV. Measurement of intrinsic FAC in the ClO2 application revealed that the N-chloroglycine method performed considerably better in such a system where different oxidant species (ClO2, FAC, chlorite, etc.) were present.

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1,3,5-Trimethoxybenzene (TMB) as a new quencher for preserving redox-labile disinfection byproducts and for quantifying free chlorine and free bromine

Abstract: 1,3,5-Trimethoxybenzene can be used to quench residual chlorine and bromine without altering disinfection byproducts that are reactive toward traditional quenchers.

Cited by 16 publications

References 39 publications

Molecular-Level Insights into the Formation of Traditional and Novel Halogenated Disinfection Byproducts

Molecular-Level Insights into the Formation of Traditional and Novel Halogenated Disinfection Byproducts

Chloride-Mediated Enhancement in Heat-Induced Activation of Peroxymonosulfate: New Reaction Pathways for Oxidizing Radical Production

Determination of free chlorine based on ion chromatography—application of glycine as a selective scavenger

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