Activation of Peroxymonosulfate by Benzoquinone: A Novel Nonradical Oxidation Process

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State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin, Heilongjiang 150090, China
Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, Heilongjiang 150040, China
*Phone: 86-451-86283010. Fax: 86-451-86283010. E-mail: [email protected] (J.J.).
*Phone: 86-451-86283010. Fax: 86-451-86283010. E-mail: [email protected] (J.M.).
Cite this: Environ. Sci. Technol. 2015, 49, 21, 12941–12950
Publication Date (Web):October 9, 2015
https://doi.org/10.1021/acs.est.5b03595
Copyright © 2015 American Chemical Society
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Abstract

The reactions between peroxymonosulfate (PMS) and quinones were investigated for the first time in this work, where benzoquinone (BQ) was selected as a model quinone. It was demonstrated that BQ could efficiently activate PMS for the degradation of sulfamethoxazole (SMX; a frequently detected antibiotic in the environments), and the degradation rate increased with solution pH from 7 to 10. Interestingly, quenching studies suggested that neither hydroxyl radical (OH) nor sulfate radical (SO4•–) was produced therein. Instead, the generation of singlet oxygen (1O2) was proved by using two chemical probes (i.e., 2,2,6,6-tetramethyl-4-piperidinol and 9,10-diphenylanthracene) with the appearance of 1O2 indicative products detected by electron paramagnetic resonance spectrometry and liquid chromatography mass spectrometry, respectively. A catalytic mechanism was proposed involving the formation of a dioxirane intermediate between PMS and BQ and the subsequent decomposition of this intermediate into 1O2. Accordingly, a kinetic model was developed, and it well described the experimental observation that the pH-dependent decomposition rate of PMS was first-order with respect to BQ. These findings have important implications for the development of novel nonradical oxidation processes based on PMS, because 1O2 as a moderately reactive electrophile may suffer less interference from background organic matters compared with nonselective OH and SO4•–.

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