Mechanism of p-Substituted Phenol Oxidation at a Ti4O7 Reactive Electrochemical Membrane

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Department of Chemical Engineering, University of Illinois at Chicago, 810 South Clinton Avenue, Chicago, Illinois 60607, United States
Department of Civil and Environmental Engineering and Villanova Center for the Advancement of Sustainable Engineering, Villanova University, Villanova, Pennsylvania 19085, United States
*Phone: 312-996-0288; fax: 312-996-0808; e-mail: [email protected]
Cite this: Environ. Sci. Technol. 2014, 48, 10, 5857–5867
Publication Date (Web):April 28, 2014
https://doi.org/10.1021/es5010472
Copyright © 2014 American Chemical Society
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Abstract

This research investigated the removal mechanisms of p-nitrophenol, p-methoxyphenol, and p-benzoquinone at a porous Ti4O7 reactive electrochemical membrane (REM) under anodic polarization. Cross-flow filtration experiments and density functional theory (DFT) calculations indicated that p-benzoquinone removal was primarily due to reaction with electrochemically formed OH, while the dominant removal mechanism of p-nitrophenol and p-methoxyphenol was a function of the anodic potential. At low anodic potentials (1.7–1.8 V/SHE), p-nitrophenol and p-methoxyphenol were removed primarily by an electrochemical adsorption/polymerization mechanism on the REM. Increasing anodic potentials (1.9–3.2 V/SHE) resulted in the electroassisted adsorption mechanism contributing far less to p-methoxyphenol removal compared to p-nitrophenol. DFT calculations indicated that an increase in anodic potential resulted in a shift in p-methoxyphenol removal from a 1e direct electron transfer (DET) reaction that resulted in radical formation and significant adsorption/polymerization, to a 2e DET reaction that formed nonadsorbing products (i.e., p-benzoquinone). However, the anodic potentials were too low for the 2e DET reaction to be thermodynamically favorable for p-nitrophenol. The decreased COD adsorption for p-nitrophenol at higher anodic potentials was attributed to reaction of soluble/adsorbed organics with OH. These results provide the first mechanistic explanation for p-substituted phenolic compound removal during advanced electrochemical oxidation processes.

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Experimental setup, REM filtration experimental results, and Fukui Function values. This material is available free of charge via the Internet at http://pubs.acs.org.

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