Rate constants of reactions of bromine with phenols in aqueous solution

Gallard, Hervé; Pellizzari, Fabien; Croué, Jean Philippe; Légube, B.

doi:10.1016/s0043-1354(03)00132-5

Cited by 92 publications

(79 citation statements)

References 18 publications

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“…Among various DBPs, the 44 most recognized compounds are trihalomethanes (THMs) and haloacetic acids (HAAs). [2][3][4][5][6][7] In the 45 presence of bromide (Br − ), HOCl can rapidly oxidize naturally occurring Br − to hypobromous 46 acid (HOBr). 8 Upon the reaction between HOCl/HOBr and DOM, four THMs (i.e., THM4, sum 47 of CHCl 3 , CHBrCl 2 , CHBr 2 Cl, and CHBr 3 ) and nine HAAs (i.e., HAA9, sum of monochloro-, 48 dichloro-, trichloro-, monobromo-, dibromo-, bromochloro-, bromodichloro-, dibromochloro-, 49 and tribromo-acetic acids (MCAA, DCAA, TCAA, MBAA, DBAA, BCAA, BDCAA, DBCAA, 50 and TBAA, respectively)) can be formed.…”

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confidence: 99%

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Formation of Bromate and Halogenated Disinfection Byproducts during Chlorination of Bromide-Containing Waters in the Presence of Dissolved Organic Matter and CuO

Liu

Croué

2015

Environ. Sci. Technol.

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Previous studies showed that significant bromate (BrO 3 − ) can be formed via the CuO-catalyzed disproportionation of hypobromous acid (HOBr) pathway. In this study, the influence of CuO on the formation of BrO 3 − and halogenated disinfection byproducts (DBPs) (e.g., trihalomethanes, THMs and haloacetic acids, HAAs) during chlorination of six dissolved organic matter (DOM) isolates was investigated. Only in the presence of slow reacting DOM (from treated Colorado River water, i.e., CRW-BF-HPO), significant BrO 3 − formation is observed, which competes with bromination of DOM (i.e., THM and HAA formation). Reactions between HOBr and 12 model compounds in the presence of CuO indicates that CuO-catalyzed HOBr disproportionation is completely inhibited by fast reacting phenols, while it predominates in the presence of practically unreactive compounds (acetone, butanol, propionic, and butyric acids). In the presence of slow reacting di-and tricarboxylic acids (oxalic, malonic, succinic, and citric acids), BrO 3 − formation varies, depending on its competition with bromoform and dibromoacetic acid formation (i.e., bromination pathway). The latter pathway can be enhanced by CuO due to the activation of HOBr. Therefore, increasing CuO dose (0−0.2 g L −1 ) in a reaction system containing chlorine, bromide, and CRW-BF-HPO enhances the formation of BrO 3 − , total THMs and HAAs. Factors including pH and initial reactant concentrations influence the DBP formation. These novel findings have implications for elevated DBP formation during transportation of chlorinated waters in copper-containing distribution systems.

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“…In the presence of CuO, less oxidant (7. HOBr consumption (≤ 4.6%) was observed and CHBr 3 was the only DBP formed at 2 h (Table 355 1 and thus they are included as fast reacting compounds, [44][45][46][47][48] …”

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Formation of Bromate and Halogenated Disinfection Byproducts during Chlorination of Bromide-Containing Waters in the Presence of Dissolved Organic Matter and CuO

Liu

Croué

2015

Environ. Sci. Technol.

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“…When comparing chemical and electrochemical oxidation of phenol, Comninelis and Nerini (Comninellis and Nerini, 1995) reported that chlorinated by-products formed in the presence of hypochlorite (ClO À ) are rapidly degraded at the anode surface in the case of electrochemical oxidation. On the other hand, in spite of occurring in much lower concentrations than Cl À , Br À is an important scavenger of OH - (Grebel et al, 2010), and HOBr is usually more reactive than active chlorine, especially with phenolic compounds (Gallard et al, 2003). Indeed, Br-based oxidants led to the formation of brominated by-products (i.e.…”

Section: Fig 2 E Proposed Electrochemical Oxidation Pathways Of Metomentioning

confidence: 99%

“…These Br-derivatives were probably formed by HOBr (and/or bromamines) formed either at the anode surface or by indirect oxidation in the bulk (e.g. by HOCl/OCl À ), although the role of Br-based radical reactions cannot be excluded (Deborde and von Gunten, 2008;Gallard et al, 2003). This is especially concerning considering that brominated by-products are suspected to be more toxic, carcinogenic and mutagenic to humans than their chlorinated analogs (Krasner et al, 2006).…”

Section: Fig 2 E Proposed Electrochemical Oxidation Pathways Of Metomentioning

confidence: 99%

Electrochemical degradation of the β-blocker metoprolol by Ti/Ru0.7Ir0.3O2 and Ti/SnO2-Sb electrodes

2011

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BioassaysHalogenated by-product Micropollutant a b s t r a c t Electrochemical oxidation has been proposed for the elimination of pesticides, pharmaceuticals and other organic micropollutants from complex waste streams. However, the detrimental effect of halide ion mediators and the generation of halogenated by-products in this process have largely been neglected thus far. In this study, we investigated the electrochemical oxidation pathways of the b-blocker metoprolol in reverse osmosis concentrate (ROC) from a water reclamation plant using titanium anodes coated with Ti/SnO 2 -Sb exhibited higher oxidizing power for the same applied specific electrical charge, the generation of large fractions of chloro-, chloro-bromo-and bromo derivatives was observed for both electrode coatings. However, degradation rates of metoprolol and its degradation products were generally higher for the Ti/SnO 2 -Sb anode. Chemical analyses of metoprolol and its by-products were complemented with bioanalytical tools in order to investigate their toxicity relative to the parent compound. Results of the bioluminescence inhibition test with Vibrio fischeri and the combined algae test with Pseudokirchneriella subcapitata indicated a substantial increase in non-specific toxicity of the reaction mixture due to the formed halogenated by-products, while the specific toxicity (inhibition of photosynthesis) remained unchanged. ª 2011 Elsevier Ltd. All rights reserved. IntroductionThe unique ability of electrochemical processes to oxidize and/ or reduce organic compounds at controlled electrode potentials and using only electrons as reagents represents a great advantage over existing advanced oxidation processes (AOPs). Due to the generation of a variety of reactive oxygen species (ROS) at the anode (e.g. OH -, H 2 O 2 , O 2 , O 3 ), electrochemical oxidation is considered to be versatile and capable of oxidizing persistent organic micropollutants, nitrogen species and microorganisms (Comninellis et al., 2010). In recent years, there has been an increasing interest in applying electrochemical oxidation for the treatment of refractory waste streams such as landfill leachate and reverse osmosis concentrate (ROC) from water treatment processes (Anglada et al., 2009;Van Hege et al., 2004;Dialynas et al., 2008;Perez et al., 2010). Due to the high concentrations of organic contaminants, disposal of these streams represents a major problem as they require an on-site treatment. A v a i l a b l e a t w w w . s c i e n c e d i r e c t . c o m j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / w a t r e s w a t e r r e s e a r c h 4 5 ( 2 0 1 1 ) 3 2 0 5 e3 2 1 40043-1354/$ e see front matter ª

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“…The reaction rate of bromine with phenol-like organic compounds was estimated to be about 10 3 -fold higher than with chlorine. 36,37 The potential formation of brominated byproducts from organic compounds including organic UV filters in chlorinated seawater pools is a matter of concern for health risk considerations. Several studies have shown that brominated byproducts are considerably more toxic than their chlorinated analogues.…”

Section: Introductionmentioning

confidence: 99%

Degradation of Organic UV filters in Chlorinated Seawater Swimming Pools: Transformation Pathways and Bromoform Formation

Manasfi

Coulomb

Ravier

et al. 2017

Environ. Sci. Technol.

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Organic ultraviolet (UV) filters are used in sunscreens and other personal-care products to protect against harmful effects of exposure to UV solar radiation. Little is known about the fate of UV filters in seawater swimming pools disinfected with chlorine. The present study investigated the occurrence and fate of five commonly used organic UV filters, namely dioxybenzone, oxybenzone, avobenzone, 2-ethylhexyl-4-methoxycinnamate, and octocrylene, in chlorinated seawater swimming pools. Pool samples were collected to monitor the variation of UV filter concentrations during pool opening hours. Furthermore, laboratory-controlled chlorination experiments were conducted in seawater spiked with UV filters to investigate the reactivity of UV filters. Extracts of chlorination reaction samples were analyzed using high-resolution mass spectrometry and electron-capture detection to identify the potentially formed byproducts. In the collected pool samples, all the UV filters except dioxybenzone were detected. Chlorination reactions showed that only octocrylene was stable in chlorinated seawater. The four reactive UV filters generated brominated transformation products and disinfection byproducts. This formation of brominated products resulted from reactions between the reactive UV filters and bromine, which is formed rapidly when chlorine is added to seawater. Based on the identified byproducts, the transformation pathways of the reactive UV filters were proposed for the first time.Bromoform was generated by all the reactive UV filters at different yields. Bromal hydrate was also detected as one of the byproducts generated by oxybenzone and dioxybenzone.

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Rate constants of reactions of bromine with phenols in aqueous solution

Cited by 92 publications

References 18 publications

Formation of Bromate and Halogenated Disinfection Byproducts during Chlorination of Bromide-Containing Waters in the Presence of Dissolved Organic Matter and CuO

Formation of Bromate and Halogenated Disinfection Byproducts during Chlorination of Bromide-Containing Waters in the Presence of Dissolved Organic Matter and CuO

Electrochemical degradation of the β-blocker metoprolol by Ti/Ru0.7Ir0.3O2 and Ti/SnO2-Sb electrodes

Degradation of Organic UV filters in Chlorinated Seawater Swimming Pools: Transformation Pathways and Bromoform Formation

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