双金属协同催化非ROS介导的5-羟甲基糠醛选择氧化

doi:10.1016/S1872-2067(24)60151-8

催化学报 ›› 2024, Vol. 67: 144-156.DOI: 10.1016/S1872-2067(24)60151-8

双金属协同催化非ROS介导的5-羟甲基糠醛选择氧化

张美云^a^,^b, 车鹏华^a, 马红^a(), 刘鑫^a, 张树静^a, 罗杨^a, 徐杰^a()

^a中国科学院大连化学物理研究所, 大连洁净能源国家实验室, 能源催化转化全国重点实验室, 辽宁大连 116023
^b中国科学院大学, 北京 100049

收稿日期:2024-08-02 接受日期:2024-09-20 出版日期:2024-11-30 发布日期:2024-11-30
通讯作者: 马红,徐杰
基金资助:
国家重点研发计划(2022YFA1504902);国家自然科学基金(22272172);国家自然科学基金(22072149);国家自然科学基金(21790331)

Dual-metal synergy unlocking ROS-free catalysis for rapid aerobic oxidation of 5-hydroxymethylfurfural at room temperature

Meiyun Zhang^a^,^b, Penghua Che^a, Hong Ma^a(), Xin Liu^a, Shujing Zhang^a, Yang Luo^a, Jie Xu^a()

^aState Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^bUniversity of Chinese Academy of Sciences, Beijing 100049, China

Received:2024-08-02 Accepted:2024-09-20 Online:2024-11-30 Published:2024-11-30
Contact: Hong Ma, Jie Xu
Supported by:
National Key R&D Program of China(2022YFA1504902);National Natural Science Foundation of China(22272172);National Natural Science Foundation of China(22072149);National Natural Science Foundation of China(21790331)

摘要/Abstract

摘要：

分子氧清洁催化氧化制备有机含氧化学品, 在现代化工和能源化学领域具有重要的研究和应用意义. 在生物质资源化利用中, 5-羟甲基糠醛(HMF)氧化制备可再生聚酯单体2,5-呋喃二甲酸近年备受关注, 有望缓解石油基聚对苯二甲酸乙二醇酯广泛使用所带来的环境问题. 然而, 分子氧活化过程常伴随活性氧物种(ROS)的形成, ROS的复杂性质和难控制性, 会导致产物选择性低、氧化降解以及低碳平衡等问题. 因此, 探索特定活性氧物种的产生与清除机制, 减少ROS的负面影响, 仍然是实现高效高选择性氧化技术的关键挑战.

受到天然酶具有活化分子氧及清除ROS的双重性能启发, 本文报道了一种非ROS介导催化氧化的新方法, 研制出CuCo/N-C双金属纳米催化剂, 通过双金属协同效应在室温下将O₂活化成高活性表面过氧物种, 完全清除了体系中游离的ROS, 从而在温和条件下(25-40 °C)以高产率(89.9%-99.5%)将多种羟基化合物催化氧化为相应的有机羧酸. 使用CuCo/N-C催化剂在25 °C和1 MPa O₂下反应6 h, 生物质平台分子HMF的转化率>99.8%, 2,5-呋喃二甲酸的选择性达到94.5%. 球差校正高角度环形暗场扫描透射电子显微镜等表征表明, Co-N位点和小尺寸Cu₂O位点在氮掺杂碳材料表面高度分散. 自由基捕获-电子顺磁共振波谱和紫外-可见光谱与气相色谱-质谱联用等测试结果表明, CuCo双金属在分子氧室温活化中发挥了协同效应. 在水相体系中, Co-N活性位点通过表面富电子特性原位活化O₂生成H₂O₂, Cu₂O位点在碱性条件下进一步完全清除原位产生的H₂O₂及其分解的OH•自由基, 生成高活性的表面过氧化铜物种, 从而获得了高的选择性和碳平衡. 动力学同位素效应研究结果表明, CuCo/N-C获得了6.7的高KIE值(k_H(PhCH₂OH)/k_D(PhCD₂OH)), 说明C-H键的H脱除为反应的速控步骤, 这可能与表面过氧化铜物种的形成有关.

综上, 本研究提供了一种新的非ROS介导催化氧化策略, 可以有效地促进室温条件下O₂活化产生高活性的表面过氧物种, 清除体系内游离的ROS, 实现了HMF等多种羟基化合物在温和条件下高效高选择性氧化. 该研究提供了生物质资源化利用制备高附加值有机羧酸化学品的新方法, 为设计模拟酶氧化催化剂提供了新思路.

关键词: 生物质, 双金属协同, 分子氧活化, 5-羟甲基糠醛, 非活性氧物种介导, 选择氧化

Abstract:

Clean catalytic oxidation has a broad prospect in the modern chemical engineering and energy chemistry fields. However, unexpected over-oxidation and disruptive degradation are frequently induced by excessive reactive oxygen species (ROS). Herein, we reported a new ROS-free approach to effectively drive O₂ to be activated into highly reactive surface peroxo species through enzyme-mimicking mechanism. Benefiting from the dual-metal synergy effect between Cu and Co active sites, ROS (H₂O₂ and OH^•) is generated in situ while further scavenged completely into surface peroxo species, which gives rise to very high selectivity and extremely high carbon balance. For example, the CuCo/N-C catalyst affords >99.8% conversion and 94.5% selectivity to 2,5-furanedicarboxylic acid at 25 °C for 6 h in the aerobic oxidation of biomass platform 5-hydroxymethylfurfural. Moreover, it achieved exceptional performance in the oxidation of a variety of hydroxyl compounds to organic acids with high yields (89.9%-99.5%) at a mild temperature (25-40 °C). This exploration introduces an innovative clue for emulating enzyme catalysts, thereby enriching our comprehension and advancement of biologically inspired catalytic oxidations.

Key words: Biomass, Dual metal synergy, Molecular oxygen activation, 5-Hydroxymethylfurfural, Reactive oxygen species free, Selective oxidation

张美云, 车鹏华, 马红, 刘鑫, 张树静, 罗杨, 徐杰. 双金属协同催化非ROS介导的5-羟甲基糠醛选择氧化[J]. 催化学报, 2024, 67: 144-156.

Meiyun Zhang, Penghua Che, Hong Ma, Xin Liu, Shujing Zhang, Yang Luo, Jie Xu. Dual-metal synergy unlocking ROS-free catalysis for rapid aerobic oxidation of 5-hydroxymethylfurfural at room temperature[J]. Chinese Journal of Catalysis, 2024, 67: 144-156.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(24)60151-8

https://www.cjcatal.com/CN/Y2024/V67/I12/144

图/表 10

Scheme 1. Schematic illustration dual-metal synergy of CuCo/N-C, with functions to generate ROS (a) and clearance ROS to form surface peroxo species (b), and realize the rapid oxidation of HMF to FDCA at room temperature (c).

Fig. 1. TEM images (a,b), HRTEM images (c,d), corresponding EDX maps for the overlapped Cu, Co, N, O and C (e-j), and AC HAADF-STEM images (k,l) of CuCo/N-C.

Table 1 The influence of dual-metal synergy in HMF oxidation reaction a.

Entry	Catalyst	Conversion (%)	Yield (%)			Carbon balance (%)
Entry	Catalyst	Conversion (%)	HMFCA	FFCA	FDCA	Carbon balance (%)
1^b	—	14.5	n.d.	n.d.	n.d.	0.0
2^c	—	>99.7	22.7	n.d.	n.d.	22.8
3	Cu/N-C	69.8	27.7	6.3	8.2	60.5
4	Co/N-C	>99.8	33.7	0.2	65.2	99.3
5^d	Cu/N-C+Co/N-C	>99.6	16.7	1.8	73.5	92.4
6	CuCo/N-C	>99.8	n.d.	n.d.	94.3	94.5

Fig. 2. (a) Comparison of non-precious metal catalysts in the oxidation of HMF to FDCA [27⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓⇓-43]. (b) ROS detection at specific conditions. (c) Schematic illustration for O2 activation with CuCo/N-C and deactivation caused by cationic treatment. (d) EPR spectrum for detecting O2•- in toluene with CuCo/N-C. (e) Zeta potential of CuCo/N-C and cationic treated CuCo/N-C. (f) GC spectra for detecting H2O2 via triphenylphosphine oxidation in water in O2. (g) EPR spectrum for detecting OH• in alkaline solution in O2. Reaction conditions: 8 mg catalyst, 2 mL of H2O; 1 MPa O2, 25 °C, 30 min; For detecting O2•-, 2 mL of toluene; for detecting H2O2, 0.2 mmol triphenylphosphine; for detecting OH•, 0.023 mmol metal in catalyst, 0.8 mmol NaOH.

Fig. 3. (a) The detect process of ROS with the addition of CuCo/N-C under specific conditions. (b) MS spectrum of triphenylphosphine oxide formed by the oxidation of triphenylphosphine in water. (c) UV-Vis spectrums of KI solution in water with addition of CuCo/N-C and CuCo/N-C treated with the cationic reagent. (d) EPR spectrum of alkaline solution over CuCo/N-C. (e) the EPR spectra of the treated CuCo/N-C in different pH solution. (f) High-resolution Cu 2p XPS spectra. (g) High-resolution O 1s XPS spectra of the fresh CuCo/N-C, CuCo/N-C treated without HMF and CuCo/N-C treated with HMF. Reaction conditions: for (b), 0.023 mmol metal in catalyst, 0.2 mmol triphenylphosphine, 2 mL of H2O, 1 MPa O2, 25 °C, 30 min, for (d), 0.023 mmol metal in CuCo/N-C, 0.8 mmol NaOH, 2 mL of H2O, 25 °C, 1 MPa O2, 30 min.

Fig. 4. The intensity of DMPO-OH• adducts in the EPR spectra of the H2O2 + NaOH system with addition of different catalysts (a); the time curve of the intensity of DMPO-OH• adducts in the EPR spectra of the H2O2 + NaOH system with and without addition of CuCo/N-C (b); EPR spectrum of the DMPO-OH• adducts in the H2O2 + NaOH system (c) and in the H2O2 + NaOH system with addition of CuCo/N-C (d). Reaction conditions: in H2O2 + NaOH system, 0.8 mmol NaOH, 1.6 mL of H2O, 400 μL of 30 wt% H2O2; in isopropanol (IPA) experiment, 0.2 mmol HMF, 0.023 mmol metal in catalyst, 0.8 mmol NaOH, 2 mL of H2O, 1 MPa O2, 25 °C, 3 h.

Fig. 5. Raman spectra of Cu2O-Treated and Cu2O (a), CP-HMF and CP (b), CuO-HMF and CuO (c). (d) FTIR of Cu2O, Cu2O-Treated and CP. (e) XRD of Cu2O-Treated and Cu2O-O2. (f) CP-HMF and CuO-HMF. Scheme of transformation and cycle in Cu2O and CP (g), CuO and Cu (h). (CP represents copper peroxide nanodots synthesized according to the literature [44]).

Fig. 6. The yield in the reaction of HMF oxidation over CuCo/N-C with H2O2 adding in one time, and H2O2 adding in the speed of 0.0028 mL/min and O2 bubbling (a,b); The HPLC traces for HMF oxidation over CuCo/N-C with O2 bubbling (c); relevance of NaOH usage and catalytic performance of the CuCo/N-C (d); recycling experiments of CuCo/N-C (e). Reaction conditions: for (a), (b) and (c), 0.5 mmol HMF, 20 mg catalyst, 2 mmol NaOH, H2O, 20 mL/min O2 or 2 mL of 30 % H2O2, 25 °C; for (d), 0.2 mmol HMF, 0.023 mmol metal, 2 mL of H2O, 1 MPa O2, 25 °C, 3 h; for (e), 0.2 mmol HMF, 0.023 mmol metal in catalyst, 0.8 mmol NaOH, 2 mL of H2O, 1 MPa O2, 25 °C, 6 h.

Fig. 7. The reaction time profile of PhCH2OH oxidation over CuCo/N-C (a); The reaction time profile of PhCD2OH oxidation over CuCo/N-C (b); Linear fitting of ln(C0/Ct) against the reaction time of PhCH2OH (c); and PhCD2OH (d) over CuCo/N-C. Reaction conditions: 0.5 mmol benzyl alcohol, 0.023 mmol metal in catalyst, 2.0 mmol NaOH, 5 mL of H2O, 20 mL/min O2, 25 °C.

Table 2 Catalytic oxidation of various hydroxyl compounds to corresponding acids over the CuCo/N-C catalyst.

Entry	Temperature (°C)	Time (h)	Yield (%)
1	25	5	95.4
2	25	8	91.6
3	25	5	99.5
4	25	8	96.9
5	25	24	89.9
6	25	5	93.9
7	25	5	90.4
8	25	10	92.3
9	40	10	96.7
10	40	15	91.3

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双金属协同催化非ROS介导的5-羟甲基糠醛选择氧化

Dual-metal synergy unlocking ROS-free catalysis for rapid aerobic oxidation of 5-hydroxymethylfurfural at room temperature

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