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Understanding of the Oxidation Behavior of Benzyl Alcohol by Peroxymonosulfate via Carbon Nanotubes Activation

  • Jiaquan Li
    Jiaquan Li
    WA School of Mines: Minerals, Energy and Chemical Engineering, Curtin University, WA 6102, Australia
    More by Jiaquan Li
  • Mengting Li
    Mengting Li
    Guangdong Key Laboratory of Environmental Catalysis and Health Risk Control, School of Environmental Science and Engineering, Institute of Environmental Health and Pollution Control, Guangdong University of Technology, Guangzhou 51006, China
    More by Mengting Li
  • Hongqi Sun
    Hongqi Sun
    School of Engineering, Edith Cowan University, Joondalup, WA 6027, Australia
    More by Hongqi Sun
  • Zhimin Ao*
    Zhimin Ao
    Guangdong Key Laboratory of Environmental Catalysis and Health Risk Control, School of Environmental Science and Engineering, Institute of Environmental Health and Pollution Control, Guangdong University of Technology, Guangzhou 51006, China
    *E-mail: [email protected] (Z.A.).
    More by Zhimin Ao
  • Shaobin Wang*
    Shaobin Wang
    School of Chemical Engineering, The University of Adelaide, Adelaide, SA 5005, Australia
    *E-mail: [email protected] (S.W.).
    More by Shaobin Wang
  • , and 
  • Shaomin Liu*
    Shaomin Liu
    WA School of Mines: Minerals, Energy and Chemical Engineering, Curtin University, WA 6102, Australia
    Beijing Advanced Innovation Centre for Soft Matter Science and Engineering, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, China
    *E-mail: [email protected] (S.L.).
    More by Shaomin Liu
Cite this: ACS Catal. 2020, 10, 6, 3516–3525
Publication Date (Web):February 11, 2020
https://doi.org/10.1021/acscatal.9b05273
Copyright © 2020 American Chemical Society
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Abstract

Selective oxidation of benzyl alcohol (BzOH) into benzaldehyde (BzH) is very important in synthetic chemistry. Peroxymonosulfate (PMS) is a cheap, stable, and soluble solid oxidant, holding promise for organic oxidation reactions. Herein, we report the catalytic PMS activation via carbon nanotubes (CNTs) for the selective oxidation of BzOH under mild conditions without other additives. A remarkable promotion of BzH yield with a selectivity over 80% was achieved on modified CNTs, i.e., O-CNTs via the radical oxidation process, and the oxygen functionalities for catalysis were comprehensively investigated by experimental study and theoretical exploration. To understand the different surface oxygen species on CNTs for the activation of PMS, density functional theory (DFT) calculations were performed to investigate the adsorption behavior of PMS on various CNTs. The electrophilic oxygen was identified as the electron captor to activate PMS by O–O bond cleavage to form SO5•– and SO4•– radicals. The nucleophilic carbonyl groups can also induce a redox cycle to generate OH and SO4•– radicals, but phenolic hydroxyl groups impede the radical process with antioxidative functionality. The carbocatalysis-assisted PMS activation may provide a cheap process for the selective oxidation of alcohols into aldehydes or ketones. The insight achieved from this fundamental study may be further applied to other organic syntheses via selective oxidation.

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  • Experimental material, characterizations, and catalytic results; TEM images; reaction rate constants of different quenching agents and radicals; EPR spectra of OCNT-800 and OCNT-800-KI; and selective deactivation pathways (PDF)

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