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. 2019 Aug 30;9(47):27224-27230.
doi: 10.1039/c9ra04789a. eCollection 2019 Aug 29.

Activating peroxymonosulfate by halogenated and methylated quinones: performance and mechanism

Hong Zhang  1   2 , Lina Qiao  2 , Jing He  1   2 , Na Li  1   2 , Dongmei Zhang  1   2 , Kai Yu  1   2 , Hong You  1   2 , Jie Jiang  1   2
Affiliations

Activating peroxymonosulfate by halogenated and methylated quinones: performance and mechanism

Hong Zhang et al. RSC Adv. .

Abstract

Activation of peroxymonosulfate (PMS) by halogenated and methylated quinones for destroying sulfamethoxazole (SMX) was investigated, where 2,6-dimethyl-1,4-benzoquinone (DMBQ), 2,6-dichloro-1,4-benzoquinone (DCBQ), and tetrafluoro-1,4-benzoquinone (TFBQ) were chosen as model quinones. The PMS could be activated by halogenated and methylated quinones efficiently for SMX degradation, and the process showed high pH and quinones dependency. Different from PMS activated by ultraviolet (UV), singlet oxygen (1O2) instead of hydroxyl radical (˙OH) and sulfate radical (SO4˙-) was the primary oxidizing species in the activation process. The formation of 1O2 was confirmed by various quenching studies combined with chemical probes (9,10-diphenylanthracene (DPA)). By sampling in situ and monitoring in real time, droplet spray ionization mass spectrometry (DSI-MS) was applied to capture and identify the intermediates generated in the activation process. A possible mechanism for PMS activation was proposed accordingly. It was found that a series of reactions between PMS and halogenated/methylated quinones formed a dioxirane intermediate, and the subsequent decomposition of this intermediate produced the 1O2. These findings would help to better understand the interactions between PMS and quinones, and provide a novel activator for PMS activation toward environmental contaminants.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Fig. 1
Fig. 1. Effect of pH on SMX degradation. (a) pH 7; (b) pH 8; (c) pH 9; (d) pH 10. Experimental conditions: [PMS]0 = 0.50 mM, [SMX]0 = 10 μM, [BQ]0 = 20 μM, 20 mM borate buffer, and T = 25 °C.
Fig. 2
Fig. 2. Effect of quinones concentrations on SMX degradation. (a) DMBQ; (b) DCBQ; (c) TFBQ. Experimental conditions: [PMS]0 = 0.50 mM, [SMX]0 = 10 μM, 20 mM borate buffer, pH = 10, and T = 25 °C.
Fig. 3
Fig. 3. Effect of scavengers on SMX degradation in PMS activated by DMBQ, DCBQ and TFBQ. Experimental conditions: [PMS]0 = 0.50 mM, [Quinone]0 = 20 μM, [SMX]0 = 10 μM, 20 mM borate buffer, pH = 10, and T = 25 °C.
Fig. 4
Fig. 4. (a) MS/MS spectra of DPAO2 generated in PMS/different quinones/DPA; (b) effect of PMS concentrations on the generation of DAPO2.
Fig. 5
Fig. 5. In situ and real-time characterization of intermediates in PMS/different quinones using DSI-MS. (a) PMS/DMBQ, (b) PMS/DCBQ, and (c) PMS/TFBQ. Mass spectra displayed the reaction time of 40 s for each case.
Fig. 6
Fig. 6. Possible mechanism of PMS activated by halogenated and methylated quinones.
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