杂原子掺杂调控ZnO氧空位工程用于电合成尼龙-6前体

doi:10.1016/S1872-2067(26)65062-0

催化学报 ›› 2026, Vol. 87: 243-253.DOI: 10.1016/S1872-2067(26)65062-0

杂原子掺杂调控ZnO氧空位工程用于电合成尼龙-6前体

鹿苏微^a^,¹, 颜红萍^a^,¹, 张宏伟^a^,^b^,¹, 程昱颖^a, 蒋欣欣^a, 彭旭云^a, 黄俊维^a, 李沅锦^a^,^*(), 王昕^c, 梁诗景^a^,^b^,^*(), 江莉龙^a^,^b

^a 福州大学化工学院, 化肥催化剂国家工程研究中心氟氮化工国家重点实验室, 福建福州 350002
^b 清源创新实验室, 福建泉州 362801
^c 香港城市大学化学系, 香港九龙 999077

收稿日期:2025-11-11 接受日期:2026-01-28 出版日期:2026-08-18 发布日期:2026-06-24
通讯作者: ^*电子信箱: yjli@fzu.edu.cn (李沅锦),
lsjliang2012@fzu.edu.cn (梁诗景).
作者简介:¹共同第一作者.
基金资助:
国家自然科学基金(22221005);国家自然科学基金(22378060);国家自然科学基金(22405049);国家自然科学基金(22308056);福建省自然科学基金(2024J02009)

Electrosynthesis of nylon-6 precursor via heteroatom-doping-regulated oxygen vacancies engineering over ZnO

Suwei Lu^a^,¹, Hongping Yan^a^,¹, Hongwei Zhang^a^,^b^,¹, Yuying Cheng^a, Xinxin Jiang^a, Xuyun Peng^a, Junwei Huang^a, Yuanjin Li^a^,^*(), Xin Wang^c, Shijing Liang^a^,^b^,^*(), Lilong Jiang^a^,^b

^a State Key Laboratory of Fluorine & Nitrogen Chemicals, National Engineering Research Center of Chemical Fertilizer Catalyst, College of Chemical Engineering, Fuzhou University, Fuzhou 350002, Fujian, China
^b Qingyuan Innovation Laboratory, Quanzhou 362801, Fujian, China
^c Department of Chemistry, City University of Hong Kong, Kowloon, 999077 Hong Kong SAR, China

Received:2025-11-11 Accepted:2026-01-28 Online:2026-08-18 Published:2026-06-24
About author:¹Contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22221005);National Natural Science Foundation of China(22378060);National Natural Science Foundation of China(22405049);National Natural Science Foundation of China(22308056);Natural Science Foundation of Fujian Province(2024J02009)

摘要/Abstract

摘要：

环己酮肟(CHOX)是一种重要的精细化工中间体, 目前主要通过羟胺法和氨肟法等传统方法合成.然而, 这些方法通常反应条件苛刻,且需要使用贵金属和高腐蚀性硝化剂. 因此, 开发温和、绿色的环己酮肟电合成路线具有重要研究价值. 其中, 在环境条件下使用氮氧化物(NO_x)和环己酮作为原料可持续电合成环己酮肟(ESCO)展现出良好的应用前景. 但是NO_x还原是一个动力学缓慢的多电子转移过程, 形成的NH₂OH关键中间体不稳定, 易转化为热力学稳定的氨. 同时, 析氢反应(HER)和环己酮还原为环己醇等副反应也大大降低了反应效率. 为了克服这些问题, 已经采取了各种措施来实现更加高效的ESCO. 但受限于反应物与中间体吸附能的线性标度关系, 很难平衡ESCO催化活性和FE效率. 因此, 通过合理设计催化剂活性位点, 平衡反应物和中间体的吸附强度, 以实现高效的ESCO过程具有重要意义.

本文提出了一种杂原子掺杂调控ZnO中氧空位的策略用于实现高效的ESCO. 其中ZnO催化剂在电催化硝酸盐还原中被证明能有效削弱NH₂OH的吸附, 从而抑制其过度氢化为NH₃. 而氧空位(Vo)位点可以作为电子捕获中心, 捕获NO₃^-并促进电子转移增强电催化性能. 但是ZnO中富含电子的Vo位点很容易被*H占据, 从而降低NO₃^-还原效率. 为此, 本研究选用离子半径与Zn相近的Cu作为掺杂剂, 通过调控Cu含量制备了一系列富空位铜掺杂ZnO电催化剂(Cu-ZnO_1‒_x)用于ESCO. 在ZnO结构中适量引入Cu可以显著提高Vo的浓度, 形成富电子环境来调节Vo位点的局域电子态, 从而促进Vo的稳定化. 由于Cu掺杂剂和Vo的协同作用, 优化后的Cu-ZnO_1‒_x催化剂在-0.8 V vs. RHE下实现了1238.8 μmol h^-1 mg_cat.^-1的环己酮肟产率, FE为68.2%, 性能优于多数已报道催化剂. 此外, 由于Cu掺杂对Vo位点的稳定作用, Cu-ZnO_1‒_x催化剂可以保持至少24 h的长期活性. 密度泛函理论(DFT)计算表明, Cu掺杂可以有效降低ZnO中Vo位点的形成能, 促进其稳定存在. 同时, 掺杂Cu和Vo的协同作用减弱了H*吸附, 平衡了NO₃^-与NH₂OH的吸附行为, 从而有利于ESCO, 并抑制HER和NH₃生成等副反应. 结合多种原位表征和DFT计算, 阐明了ESCO反应机理: *NO₃ → *NO₃H → *NO₂ → *NO₂H → *NO → *HNO → *NHOH → *NH₂OH, 随后NH₂OH和环己酮通过C-N偶联自发形成CHOX. Cu掺杂调节ZnO_1‒_x中的Vo可以有效地降低决速步的反应势垒.

综上, 本研究证明了杂原子掺杂调节氧空位工程策略的有效性, 该策略可平衡催化剂上反应物和中间体的吸附强度, 从而实现环己酮肟的高效电合成. 因此, 这项工作为ESCO高效电催化剂的设计与合成提供了新的思路.

关键词: 环己酮肟, 氧空位, 铜掺杂, C-N偶联反应, 电催化

Abstract:

Electrocatalysis is a green alternative to directly synthesize cyclohexanone oxime (CHOX, Nylon-6 precursor) via electrocatalytic reduction of nitrogen oxides to NH₂OH and spontaneous C-N coupling with cyclohexanone, but suffering from a low-yield or poor Faradaic efficiency (FE) because of the scaling relationship. Herein, a strategy of heteroatom-doping-regulated oxygen vacancies (Vo) engineering was proposed to design a robust Cu-ZnO_1‒_x catalyst for efficient electrosynthesis of cyclohexanone oxime (ESCO). The complete characterizations and theoretical studies revealed that the doped-Cu can reduce Vo sites formation energy and regulate their local electronic state. The synergistic effect between doped Cu and Vo led to the break of the scaling relationship, presenting the enhancement of NO₃^- adsorption/dissociation, the weakness of H* adsorption, and the balance of the NH₂OH adsorption for further C-N coupling reaction. Therefore, the hydrogen evolution reaction and NH₂OH reduction to NH₃ side reactions can be suppressed. The optimized Cu-ZnO_1‒_x delivered an outstanding activity with a 1238.8 μmol h^‒1 mg_cat.^‒1 yield and 68.2% FE. Lastly, the reaction mechanism was established following *NO₃ → *NO₃H → *NO₂ → *NO₂H → *NO → *HNO → *NHOH → *NH₂OH and spontaneous C-N coupling with cyclohexanone to form CHOX. The outstanding ESCO performance on Cu-ZnO_1‒_x catalyst demonstrates the effectiveness of this heteroatom-doping-regulated Vo engineering strategy.

Key words: Cyclohexanone oxime, Oxygen vacancy, Cu-doping, C-N coupling reaction, Electrocatalytic

鹿苏微, 颜红萍, 张宏伟, 程昱颖, 蒋欣欣, 彭旭云, 黄俊维, 李沅锦, 王昕, 梁诗景, 江莉龙. 杂原子掺杂调控ZnO氧空位工程用于电合成尼龙-6前体[J]. 催化学报, 2026, 87: 243-253.

Suwei Lu, Hongping Yan, Hongwei Zhang, Yuying Cheng, Xinxin Jiang, Xuyun Peng, Junwei Huang, Yuanjin Li, Xin Wang, Shijing Liang, Lilong Jiang. Electrosynthesis of nylon-6 precursor via heteroatom-doping-regulated oxygen vacancies engineering over ZnO[J]. Chinese Journal of Catalysis, 2026, 87: 243-253.

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图/表 6

Scheme 1. Synthesis routes for CHOX.

Fig. 1. Morphology and structural characterizations of catalysts. XRD patterns (a) and Raman spectra (b) of ZnO, ZnO1?x and Cu-ZnO1?x. HRTEM (c) and HAADF-STEM and corresponding mapping image (d) of Cu-ZnO1?x. (e) EPR spectra for ZnO, ZnO1?x and Cu-ZnO1?x. (f) Schematic diagram of Cu2+ introducing and replacing Zni to achieve Cu-ZnO1?x. O 1s XPS spectra (g) and Zn 2p XPS spectra (h) for ZnO, ZnO1?x and Cu-ZnO1?x. (i) Cu 2p XPS spectra for Cu-ZnO1?x.

Fig. 2. Electrochemical performance. (a) LSV curves of ZnO, ZnO1?x, and Cu-ZnO1?x in 1 mol L?1 KOH solution containing 0.2 mol L?1 NO3- and 0.1 mol L?1 cyclohexanone. Yield (b) and FE (c) of CHOX over ZnO, ZnO1?x, and Cu-ZnO1?x at different potentials. (d) Distribution of electrocatalytic products over ZnO, ZnO1?x, and Cu-ZnO1?x at -0.8 V vs. RHE. (e) Time-dependent FEs over Cu-ZnO1?x for ESCO. (f) Comparison of the reported catalytic performance.

Fig. 3. Theoretical investigations of various ZnO models. Local structures and Vo formation energy (ΔE) of Pristine ZnO (a), ZnO1?x (b), and Cu-ZnO1?x (c). All structural diagrams are top views. Color scheme: Gray for Zn, orange for Cu, and red for O. (d?f) ZnO, ZnO1?x, Cu-ZnO1?x surface models and atomic charges derived from Bader charge analysis. (g) Free energy diagram of hydrogen production in these models.

Fig. 4. Adsorption of NO3? on various catalyst models. Adsorption free energies (a) and charge density difference (b) of NO3? adsorbed on ZnO, ZnO1?x, Cu-ZnO and Cu-ZnO1?x. (c) Adsorption free energies of NH2OH on ZnO, ZnO1?x, Cu-ZnO and Cu-ZnO1?x. The color code is the same as in Fig. 1, yellow and blue contours denote the accrual and expenditure of electrons, respectively.

Fig. 5. Investigations of mechanism. (a) In-situ DEMS measurements for ESCO with Cu-ZnO1?x at -0.8 V vs. RHE over five continuous cycles. The mass signals increased rapidly upon the reduced potential and gradually decreased after the potential was removed. In-situ Raman spectra (b) and in-situ FTIR spectra (c) for ESCO with Cu-ZnO1?x in 1 mol L?1 KOH solution containing 0.2 mol L?1 NO3? and 0.1 mol L?1 cyclohexanone. (d) Operando EPR spectra of ZnO, ZnO1?x and Cu-ZnO1?x in 1 mol L?1 KOH solution containing 0.2 mol L?1 NO3? and 0.1 mol L?1 cyclohexanone. (each line was collected after 10 min electrolysis at -0.8 V vs. RHE). (e) The ESCO pathway, validated through in-situ characterization results. (f) Reaction-free energy profiles of ESCO over ZnO, ZnO1?x and Cu-ZnO1?x surfaces.

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杂原子掺杂调控ZnO氧空位工程用于电合成尼龙-6前体

Electrosynthesis of nylon-6 precursor via heteroatom-doping-regulated oxygen vacancies engineering over ZnO

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