Activating peroxymonosulfate by halogenated and methylated quinones: performance and mechanism

Hong, Zhigang; Qiao, Liping; He, Jing; Li, Na; Zhang, Dongmei; Yu, Kai; You, Hong; Jiang, Jie

doi:10.1039/c9ra04789a

Cited by 21 publications

(9 citation statements)

References 37 publications

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“…Generally, the formation of 1 O 2 from the activation of SO 5 2− by TCBQ might be kinetically feasible, which might provide some theoretical support for the removal of sulfamethoxazole by PMS in the presence of 2,6dichloro-1,4-benzoquinone and tetrafluoro-1,4-benzoquinon with 1 O 2 as the primary oxidizing specie. 35 These results are supported by Figures S19 and S20.…”

Section: Peroxomonosulfatesupporting

confidence: 69%

Mechanical Insights into Activation of Peroxides by Quinones: Formation of Oxygen-Centered Radicals or Singlet Oxygen

Song

Yang

et al. 2022

Environ. Sci. Technol.

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In this work, the mechanism of the activation of peroxides by quinones has been investigated through quantum chemical calculations. Hydrogen peroxide (H 2 O 2 ), peroxomonosulfate (PMS), peracetic acid (PAA), and CH 3 OOH were chosen as the model peroxides and p-benzoquinone (p-BQ) and tetrachloro-1,4-benzoquinone (TCBQ) as the model quinones. The nucleophilic attack of peroxides can occur on the carbonyl and olefinic carbons of quinones. For p-BQ, the nucleophilic attack of HO 2 − , CH 3 OO − , PMS, and PAA might prefer to occur on the carbonyl carbons, which have more positive atomic charges. Then, further transformation could not be induced from the addition of HO 2 − and CH 3 OO − to p-BQ. Comparatively, singlet oxygen ( 1 O 2 ) could be generated in the cases of PMS and PAA. For TCBQ, the chlorine atoms cause the olefinic carbons to carry more positive atomic charges, and then, HO 2 − preferred to add to the olefinic carbons, which might induce the formation of the hydroxyl radical ( • OH). The activation of PMS by TCBQ was similar to that by p-BQ, with the kinetical feasibility of 1 O 2 formation. These findings may provide some theoretical insights into the reaction of peroxides with quinones, especially into the interconnection between the substitutes and the formation of oxygen-centered radicals (e.g., • OH) and 1 O 2 .

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Section: Peroxomonosulfatesupporting

confidence: 69%

Mechanical Insights into Activation of Peroxides by Quinones: Formation of Oxygen-Centered Radicals or Singlet Oxygen

Song

Yang

et al. 2022

Environ. Sci. Technol.

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“…The formation of a dioxirane intermediate has been observed and proposed to play a key role in PMS oxidation processes. 18,25,26 Therefore, quinone-like and phenol-like structures have been proposed to have positive effects on the removal of organic contaminants through PMS activation. Quinone-like and phenol-like functional groups are important constituents in dissolved organic matter (DOM), which is ubiquitous in aquatic environments.…”

Section: ■ Introductionmentioning

confidence: 99%

Photosensitized Transformation of Peroxymonosulfate in Dissolved Organic Matter Solutions under Simulated Solar Irradiation

Nie

Zou

Yan

et al. 2022

Environ. Sci. Technol.

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Sulfate radical (SO 4•− )-mediated advanced oxidation processes via peroxymonosulfate (PMS) activation have been extensively investigated. However, the phototransformation of PMS in sunlit dissolved organic matter (DOM) solution has not been previously examined. For the first time, the photosensitized transformation of PMS in DOM-enriched solutions under simulated solar irradiation was observed. The generation of reactive species, including 1 O 2 , SO 4•− , and • OH, was confirmed by electron paramagnetic resonance and quantified by chemical probes. SO 4•− was the primary reactive species generated via the reaction of excited triplet DOM ( 3 DOM*) with PMS. 3 DOM* acted as a reactive reductant and was quickly oxidized by PMS, with an estimated reaction rate constant of (4.09 ± 0.21) × 10 8 M −1 s −1 . Compared to 3 DOM*, one-electron-reducing DOM (DOM •− ) was a minor contributor to the photosensitized transformation of PMS, and the contribution of DOM •− relied on the phenolic constituents. In addition, a series of different types of DOM, including terrestrial DOM, autochthonous DOM, and effluent organic matter and its fractions, were employed to examine the photosensitized transformation kinetics of PMS. Overall, the photosensitized transformation of PMS by irradiated DOM could be a useful and economical approach to generate SO 4•− under environmentally relevant conditions.

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“…The concentration of Na 2 S 2 O 8 and monoaromatics were 5 mM and 100 μg/L, respectively, and the total volume was 40 mL. Samples were withdrawn and quenched with Na 2 S 2 O 3 periodically before analysis (Huber et al, 2005 ; Zhou et al, 2015 ; Zhang et al, 2019 ). A preliminary study demonstrated that Na 2 S 2 O 3 did not react with typical organics (1,2-dichloroethane, bromobenzene, and 1,2,4-trichlorobenzene) and had no interference with the analysis of the organics.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, new activating methods which utilize naturally occurring materials such as metal ores and organics have attracted much attention (Lin et al, 2019 ; Wu et al, 2019 ; Zhang et al, 2020 ). Quinones and organic matters containing quinone-like groups are ubiquitous in natural environment (Siqueira et al, 1991 ; Cory and McKnight, 2005 ), and they have been found to be effective as the accelerator or activator in advanced oxidation process (Zhou et al, 2015 ; Zhang et al, 2019 ). For instance, quinones increased the oxidation rate of contaminants in Fenton-like system, which was ascribed to their role as an electron shuttle (Duesterberg and Waite, 2007 ).…”

Section: Introductionmentioning

confidence: 99%

Efficiency and Quantitative Structure-Activity Relationship of Monoaromatics Oxidation by Quinone-Activated Persulfate

et al. 2021

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Quinones and quinone-containing organics have potential of activating persulfate to produce sulfate radical. In this work, the optimal condition for quinone activation of persulfate was investigated. It was found representative monoaromatics were degraded fastest in alkaline environment (pH 10.0), but excessive alkalinity restrained the reaction instead. The mechanisms to explain this phenomenon were speculated. The effect of initial quinone concentration on persulfate oxidation was also investigated at pH 10.0. In addition, a quantitative structure-activity relationship model was established with 15 kinds of monoaromatics, which revealed the most negative atomic net charges on carbon atom played an important role on degradation rates. Chemicals with a smaller qC- were easier oxidized in quinone-activate system. This finding helps further exploration of effective activator in alkaline environment.

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Activating peroxymonosulfate by halogenated and methylated quinones: performance and mechanism

Abstract: This work describes the efficiency and mechanism of peroxymonosulfate (PMS) activation by benzoquinone with different functional groups for sulfamethoxazole degradation.

Cited by 21 publications

References 37 publications

Mechanical Insights into Activation of Peroxides by Quinones: Formation of Oxygen-Centered Radicals or Singlet Oxygen

Mechanical Insights into Activation of Peroxides by Quinones: Formation of Oxygen-Centered Radicals or Singlet Oxygen

Photosensitized Transformation of Peroxymonosulfate in Dissolved Organic Matter Solutions under Simulated Solar Irradiation

Efficiency and Quantitative Structure-Activity Relationship of Monoaromatics Oxidation by Quinone-Activated Persulfate

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