Inhibiting Anodic Passivation and Enhancing Efficiency: the Effect of Ethanol on the Electrooxidation of Phenol to p-Benzoquinone

doi:10.6023/cjoc202512037

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (6): 2450-2457.DOI: 10.6023/cjoc202512037 Previous Articles Next Articles

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抑制阳极钝化与提升效率: 乙醇在苯酚电氧化制对苯醌中的作用机制

黄伟猛, 钮东方^*(), 张新胜^*()

华东理工大学化工学院绿色化工与工业催化全国重点实验室上海 200237

收稿日期:2025-12-25 修回日期:2026-01-29 发布日期:2026-03-27
基金资助:
国家自然科学基金(21972042)

Inhibiting Anodic Passivation and Enhancing Efficiency: the Effect of Ethanol on the Electrooxidation of Phenol to p-Benzoquinone

Weimeng Huang, Dongfang Niu^*(), Xinsheng Zhang^*()

Key Laboratory of Green Chemical Engineering and Industrial Catalysis, School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237

Received:2025-12-25 Revised:2026-01-29 Published:2026-03-27
Contact: * E-mail: dfniu@ecust.edu.cn;xszhang@ecust.edu.cn
Supported by:
National Natural Science Foundation of China(21972042)

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Abstract

To address the critical issues of severe anodic passivation and low selectivity of target products during the electrochemical oxidation of phenol, this study adopted a platinum electrode as the working electrode and introduced ethanol as an additive to investigate the inhibition effect of ethanol on anodic passivation and its promoting effect on the electro- oxidation efficiency of phenol. Results from gas chromatography-mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (FTIR) analyses indicated that the passivation layer is formed by the polymerization of phenol oxidation intermediates. The electrolysis results indicated that ethanol can promote the selective conversion of phenol to p-benzoquinone (p-BQ), thereby enhancing the efficiency of phenol electrooxidation. Combined with the LSV curves of hydroquinone and the contact angle measurements of the platinum electrode, it is inferred that ethanol can accelerate the desorption of p-BQ, thereby slowing down the polymerization of phenol oxidation intermediates, further suppressing the formation of the passivation layer on the electrode surface, and ultimately promoting the selective oxidation of phenol to p-BQ. Under the conditions of 5 mmol/L phenol, 25 F/mol, 25 mA/cm² and 25 ℃, the addition of 0.51 mol/L ethanol to the electrolyte increased the conversion of phenol, as well as the yield and selectivity of p-BQ by 23.5%, 34.1% and 26.2%, respectively. This study demonstrates that ethanol can effectively inhibit anodic passivation and significantly promote the directional conversion of phenol to p-BQ, providing experimental and theoretical support for the process optimization of the electrochemical synthesis of p-BQ and the design of passivation-resistant anodes.

Key words: electrooxidation of phenol, anodic passivation, ethanol additive, Pt electrode

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Weimeng Huang, Dongfang Niu, Xinsheng Zhang. Inhibiting Anodic Passivation and Enhancing Efficiency: the Effect of Ethanol on the Electrooxidation of Phenol to p-Benzoquinone[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2450-2457.

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Fig. & Tab. 8

Figure 1. Effect of ethanol on inhibiting passivation behavior and improving efficiency in phenol electrooxidation

Figure 2. Scanning electron microscopy images of (a) clean and (b) passivated platinum electrode; (c) Nyquist diagram of passivated and clean platinum electrode at open circuit potential; (d) gas chromatography-mass spectrometry spectrum of the passivation species

Figure 3. Fourier transform infrared spectroscopy of the platinum electrode after phenol electrooxidation under conditions (a) without ethanol and (b) with ethanol

Figure 4. Effect of charge passed on (a) conversion of phenol, yield of p-BQ, and (b)selectivity of p-BQ

Figure 5. Effect of concentration of ethanol on (a) conversion of phenol, yield of p-BQ, and (b) selectivity of p-BQ

Scheme 1. Stepwise reaction pathway for the oxidation of phenol to p-BQ

Figure 6. (a) Linear sweep voltammetry curves of hydroquinone with and without ethanol; Contact angle measurements of the platinum electrode surface in electrolyte (b) without and (c) with ethanol

Figure 7. Chronopotentiometric curves of phenol electrooxidation with and without ethanol

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抑制阳极钝化与提升效率: 乙醇在苯酚电氧化制对苯醌中的作用机制

Inhibiting Anodic Passivation and Enhancing Efficiency: the Effect of Ethanol on the Electrooxidation of Phenol to p-Benzoquinone

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