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Oxidative removal of quinclorac by permanganate through a rate-limiting [3 + 2] cycloaddition reaction

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Abstract

Quinclorac, a widely used herbicide in agriculture, has been recognized as an emerging environmental pollutant owing to its long persistence and potential risk to humans. However, no related information is available on the degradation of quinclorac by employing oxidants. Herein, the reactivity of quinclorac with permanganate was systematically investigated in water by combining experimental and computational approaches. The reaction followed overall second-order kinetics pointing to a bimolecular rate-limiting step. The second-order rate constant was found to be 3.47 × 10−3 M−1 s−1 at 25 °C, which was independent of pH over the range from 5 to 9 and was dependent on temperature over the range from 19 to 35 °C. The initial product was identified by UPLC-Q-TOF-MS to be mono-hydroxylated quinclorac, which was more susceptible to further oxidation. The result could be supported by the complete simulation of the reaction process in DFT calculations, indicating the [3 + 2] cycloaddition oxidation of the benzene ring in the rate-limiting step. The plausible mechanism was then proposed, accompanied by the analysis of the HOMO indicating the hydroxylation position and of the ESP suggesting a more electron-rich moiety. Considering the high effectiveness and low toxicity, permanganate oxidation was considered to be a very promising technique for removing quinclorac from aquatic environments.

Graphical abstract: Oxidative removal of quinclorac by permanganate through a rate-limiting [3 + 2] cycloaddition reaction

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Publication details

The article was received on 21 Jan 2018, accepted on 09 Mar 2018 and first published on 13 Mar 2018


Article type: Paper
DOI: 10.1039/C8EM00024G
Citation: Environ. Sci.: Processes Impacts, 2018, Advance Article
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    Oxidative removal of quinclorac by permanganate through a rate-limiting [3 + 2] cycloaddition reaction

    D. Song, H. Cheng, X. Jiang, H. Sun, F. Kong, R. Liang, Z. Qiang, H. Liu and J. Qu, Environ. Sci.: Processes Impacts, 2018, Advance Article , DOI: 10.1039/C8EM00024G

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