Aqueous ozonation of furans: Kinetics and transformation mechanisms leading to the formation of α,β-unsaturated dicarbonyl compounds

Zoumpouli, Garyfalia A.; Zhang, Zhuoyue; Wenk, Jannis; Prasse, Carsten

doi:10.1016/j.watres.2021.117487

Cited by 18 publications

(8 citation statements)

References 49 publications

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“…It was also previously identified by Peter et al (as a m/z 333.2212 adduct) within the "toxicant signature" of coho salmon mortality events and by Klockner et al (as a HRMS feature with the C 16 H 22 N 2 O 2 formula) as a stable tire marker. 36,39 The α,β-unsaturated dicarbonyl diamide structure proposed for TP 274 is similar to TPs observed in aqueous ozonation of phenols and furans, 55,58,59 some of which are reactive with lysine and cysteine groups and capable of protein damage. 58,60 4-ADPA, 4s DPA, and 4-NDPA.…”

Section: ■ Introductionmentioning

confidence: 60%

“…36,39 The α,β-unsaturated dicarbonyl diamide structure proposed for TP 274 is similar to TPs observed in aqueous ozonation of phenols and furans, 55,58,59 some of which are reactive with lysine and cysteine groups and capable of protein damage. 58,60 4-ADPA, 4s DPA, and 4-NDPA. 4-Nitrosodiphenylamine (4s DPA; C 12 H 10 N 2 O) was the seventh most abundant TP based on ESI+ peak area and was standard-confirmed (Table S6).…”

Section: ■ Introductionmentioning

confidence: 60%

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Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Zhao

Tian

et al. 2023

Environ. Sci. Technol.

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6PPD, a tire rubber antioxidant, poses substantial ecological risks because it can form a highly toxic quinone transformation product (TP), 6PPD-quinone (6PPDQ), during exposure to gas-phase ozone. Important data gaps exist regarding the structures, reaction mechanisms, and environmental occurrence of TPs from 6PPD ozonation. To address these data gaps, gas-phase ozonation of 6PPD was conducted over 24–168 h and ozonation TPs were characterized using high-resolution mass spectrometry. The probable structures were proposed for 23 TPs with 5 subsequently standard-verified. Consistent with prior findings, 6PPDQ (C18H22N2O2) was one of the major TPs in 6PPD ozonation (∼1 to 19% yield). Notably, 6PPDQ was not observed during ozonation of 6QDI (N-(1,3-dimethylbutyl)-N′-phenyl-p-quinonediimine), indicating that 6PPDQ formation does not proceed through 6QDI or associated 6QDI TPs. Other major 6PPD TPs included multiple C18H22N2O and C18H22N2O2 isomers, with presumptive N-oxide, N,N′-dioxide, and orthoquinone structures. Standard-verified TPs were quantified in roadway-impacted environmental samples, with total concentrations of 130 ± 3.2 μg/g in methanol extracts of tire tread wear particles (TWPs), 34 ± 4 μg/g-TWP in aqueous TWP leachates, 2700 ± 1500 ng/L in roadway runoff, and 1900 ± 1200 ng/L in roadway-impacted creeks. These data demonstrate that 6PPD TPs are likely an important and ubiquitous class of contaminants in roadway-impacted environments.

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Section: ■ Introductionmentioning

confidence: 60%

Section: ■ Introductionmentioning

confidence: 60%

Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Zhao

Tian

et al. 2023

Environ. Sci. Technol.

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“…62 However, highly toxic α,β-unsaturated dicarbonyls are a significant byproduct of these reactions. 62…”

Section: Discussion: Implications For Drinking Water Treatmentmentioning

confidence: 99%

“…Chevrier et al 61 observed a reduced bladder cancer risk from ozone disinfected drinking water in comparison with chlorinated water, while furans were recently reported to be highly reactive towards ozone. 62 However, highly toxic α,β-unsaturated dicarbonyls are a significant byproduct of these reactions. 62…”

Section: Treatmentmentioning

confidence: 99%

The formation of furan-like disinfection byproducts from phenolic precursors

Diana

Farré

Sanchís

et al. 2023

Environ. Sci.: Water Res. Technol.

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“…It is reported that FFA has a high reactivity toward O 3 with k app of 1.2 × 10 7 M −1 s −1 . 53 Though the rate constant of FFA with O( 3 P) was unknown, it was expected to be higher than that of O 3 considering the reactive nature of O( 3 P). Furthermore, the weak ESR signal by using DMPO as a spin-trapping reagent 54 (Figure S4d increased with the increase of PI doses within the investigated range.…”

mentioning

confidence: 99%

Ozone- and Hydroxyl Radical-Induced Degradation of Micropollutants in a Novel UVA-LED-Activated Periodate Advanced Oxidation Process

Yang

Zeng

et al. 2023

Environ. Sci. Technol.

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In this study, novel light emitting diode (LED)-activated periodate (PI) advanced oxidation process (AOP) at an irradiation wavelength in the ultraviolet A range (UVA, UVA-LED/PI AOP) was developed and investigated using naproxen (NPX) as a model micropollutant. The UVA-LED/PI AOP remarkably enhanced the degradation of NPX and seven other selected micropollutants with the observed pseudo-first-order rate constants ranging from 0.069 ± 0.001 to 4.50 ± 0.145 min–1 at pH 7.0, demonstrating a broad-spectrum micropollutant degradation ability. Lines of evidence from experimental analysis and kinetic modeling confirmed that hydroxyl radical (•OH) and ozone (O3) were the dominant species generated in UVA-LED/PI AOP, and they contributed evenly to NPX degradation. Increasing the pH and irradiation wavelength negatively affected NPX degradation, and this could be well explained by the decreased quantum yield (ΦPI) of PI. The degradation kinetics of NPX by the UVA-LED/PI AOP in the presence of water matrices (i.e., chloride, bicarbonate, and humic acid) and in real waters were examined, and the underlying mechanisms were illustrated. A total of nine transformation products were identified from NPX oxidation by the UVA-LED/PI AOP, mainly via hydroxylation, dealkylation, and oxidation pathways. The UVA-LED/PI AOP proposed might be a promising technology for the treatment of micropollutants in aqueous solutions. The pivotal role of ΦPI during light photolysis of PI may guide the future design of light-assisted PI AOPs.

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Aqueous ozonation of furans: Kinetics and transformation mechanisms leading to the formation of α,β-unsaturated dicarbonyl compounds

Cited by 18 publications

References 49 publications

Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

The formation of furan-like disinfection byproducts from phenolic precursors

Ozone- and Hydroxyl Radical-Induced Degradation of Micropollutants in a Novel UVA-LED-Activated Periodate Advanced Oxidation Process

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