Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts – Electrophilic aromatic substitution and oxidation

Criquet, Justine; Rodrı́guez, Eva M.; Allard, Sébastien; Wellauer, Sven; Salhi, Elisabeth; Joll, Cynthia; Gunten, Urs von

doi:10.1016/j.watres.2015.08.051

Cited by 278 publications

(152 citation statements)

References 47 publications

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“…If the activation barrier for bromination is large enough, anthraquinone derivatives may be kinetically stabilized and resist bromination despite a thermodynamic driving force in favor of bromination. [16] The activation energy for bromine substitution can be altered by attaching different functional groups to the anthraquinone molecule. [15] Furthermore, the barrier to bromination of the oxidized anthraquinone is the most relevant metric for determining irreversible reactivity with bromine, as bromine is likely to reversibly oxidize the reduced form of each anthraquinone derivative rather than substitute an exposed hydrogen on the aromatic ring.…”

Section: Calculation Of Activation Energy For Electrophilic Aromatic mentioning

confidence: 99%

Anthraquinone Derivatives in Aqueous Flow Batteries

Gerhardt

Tong

Gómez‐Bombarelli

et al. 2016

Advanced Energy Materials

225

193

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The authors investigate four anthraquinone derivatives as negative electrolyte candidates for an aqueous quinone-bromide redox flow battery: anthraquinone-2-sulfonic acid (AQS), 1,8-dihydroxyanthraquinone-2,7-disulfonic acid (DHAQDS), alizarin red S (ARS), and 1,4-dihydroxyanthraquinone-2,3-dimethylsulfonic acid (DHAQDMS). The standard reduction potentials are all lower than that of anthraquinone-2,7-disulfonic acid (AQDS), the molecule used in previous quinone-bromide batteries. DHAQDS and ARS undergo irreversible reactions on contact with bromine, which precludes their use against bromine but not necessarily against other electrolytes. DHAQDMS is apparently unreactive with bromine but cannot be reversibly reduced, whereas AQS is stable against bromine and stable upon reduction. The authors demonstrate an AQS-bromide flow cell with higher open circuit potential and peak galvanic power density than the equivalent AQDS-bromide cell. This study demonstrates the use of chemical synthesis to tailor organic molecules for improving flow battery performance.

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Section: Calculation Of Activation Energy For Electrophilic Aromatic mentioning

confidence: 99%

Anthraquinone Derivatives in Aqueous Flow Batteries

Gerhardt

Tong

Gómez‐Bombarelli

et al. 2016

Advanced Energy Materials

225

193

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“…[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. 6,[9][10][11] THM4 and HAA5 (sum of MCAA, DCAA, 51 TCAA, MBAA, and DBAA) are currently regulated for drinking water at 80 µg L -1 and 60 µg L -52 1 by the U.S. Environmental Protection Agency (US EPA), respectively 12 .…”

mentioning

confidence: 99%

“…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] …”

mentioning

confidence: 99%

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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“…Continued exoenzyme activity has been also described as a CO2 source: however, this would not 379 include denitrification enzymes, since none enzymes involved in the denitrification pathway are 380 exoenzymes (Blankinship et al, 2014;Jenkinson and Powlson, 1976a). Chlorination of natural 381 OM may prompt formation of quinones (Criquet et al, 2015), which are intermediates in the OM-382 based abiotic N2O production (Thorn and Mikita, 2000); indeed, regions of the EEMs 383 corresponding to hydroquinones (Cory and McKnight, 2005) appear to be slightly higher in 384 CHCl3 treatments. The benzene derivative produced during nitrosophenol reaction with NO2 − 385 leads to reduced π-electron delocalization (Eq.…”

Section: Artifacts Due To Sterilization Methods For Chemodenitrificatmentioning

confidence: 99%

Effects of sterilization techniques on chemodenitrification and N2O production in tropical peat soil microcosms

Buessecker¹,

Tylor²,

Nye³

et al. 2019

Preprint

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Abstract. Chemodenitrification &#8211; the non-enzymatic process of nitrite reduction &#8211; may be an important sink for fixed nitrogen in tropical peatlands with low oxygen, low pH, high organic matter, and variable ferrous iron concentrations. Assessing abiotic reaction pathways is difficult because sterilization/inhibition agents can alter the availability of reactants by changing iron speciation and organic matter composition. We compared six commonly used soil sterilization techniques &#8211; &#947;-irradiation, chloroform, autoclaving, and chemical inhibitors (mercury, zinc, and azide) &#8211; for their compatibility with chemodenitrification assays for tropical peatland soils (organic-rich low pH soil from the Eastern Amazon). Out of the six techniques, &#947;-irradiation resulted in soil treatments with lowest cell viability and denitrification activity, and least effect on pH, iron speciation, and organic matter composition. Nitrite depletion rates in &#947;-irradiated soils were highly similar to untreated/live soils, whereas other sterilization techniques showed deviations. Chemodenitrification was a dominant process in tropical peatland soils assayed in this study. Abiotic N2O production was low to moderate (3&#8211;16&#8201;% of converted nitrite), and different sterilization techniques lead to significant variations on production rates due to inherent processes or potential artifacts. Our work represents the first methodological basis for testing the abiotic denitrification and N2O production potential in tropical peatland soil.

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Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts – Electrophilic aromatic substitution and oxidation

Cited by 278 publications

References 47 publications

Anthraquinone Derivatives in Aqueous Flow Batteries

Anthraquinone Derivatives in Aqueous Flow Batteries

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

Effects of sterilization techniques on chemodenitrification and N<sub>2</sub>O production in tropical peat soil microcosms

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Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts – Electrophilic aromatic substitution and oxidation

Cited by 278 publications

References 47 publications

Anthraquinone Derivatives in Aqueous Flow Batteries

Anthraquinone Derivatives in Aqueous Flow Batteries

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

Effects of sterilization techniques on chemodenitrification and N&lt;sub&gt;2&lt;/sub&gt;O production in tropical peat soil microcosms

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Effects of sterilization techniques on chemodenitrification and N<sub>2</sub>O production in tropical peat soil microcosms