RuCo合金对糠醛高选择性还原胺化的协同催化机理研究

doi:10.1016/S1872-2067(26)65215-1

催化学报 ›› 2026, Vol. 90: 309-332.DOI: 10.1016/S1872-2067(26)65215-1

• 论文 • 上一篇

RuCo合金对糠醛高选择性还原胺化的协同催化机理研究

吴君^a^,^*(), 白家豪^a, 潘刚^a, 史泰龙^a, 席永杰^b^,^*(), 李福伟^c^,^d^,^*(), 李永^a^,^*()

^a 陕西科技大学材料科学与工程学院, 陕西省无机材料绿色制备与功能化重点实验室, 陕西西安 710021
^b 中国科学院兰州化学物理研究所, 低碳催化与二氧化碳利用国家重点实验室, 甘肃兰州 730000
^c 中国科学院大学化学工程学院, 北京 100049
^d 中国科学院过程工程研究所, 介科学与过程工程国家重点实验室, 北京 100190

收稿日期:2026-02-24 接受日期:2026-04-28 出版日期:2026-11-18 发布日期:2026-09-09
通讯作者: *电子信箱: wjhg168@163.com (吴君),
xiyj@licp.cas.cn (席永杰),
fuweili@ucas.ac.cn (李福伟),
yongli@sust.edu.cn (李永).
基金资助:
国家自然科学基金(21902094);国家自然科学基金(22472177);中国博士后科学基金(2020M683405);陕西省科协青年人才托举计划(20260604);陕西省自然科学基金(2023-JC-QN-0103);陕西省自然科学基金(2026JC-YBMS-0138);介科学与工程全国重点实验室开放基金(MESO-25-D16)

Mechanism insights into the synergistic catalysis of bimetallic RuCo alloys for the highly selective reductive amination of biomass-derived furfural

Jun Wu^a^,^*(), Jiahao Bai^a, Gang Pan^a, Tailong Shi^a, Yongjie Xi^b^,^*(), Fuwei Li^c^,^d^,^*(), Yong Li^a^,^*()

^a Shaanxi Key Laboratory of Green Preparation and Functionalization for Inorganic Materials, School of Materials Science & Engineering, Shaanxi University of Science & Technology, Xi’an 710021, Shaanxi, China
^b State Key Laboratory of Low Carbon Catalysis and Carbon Dioxide Utilization, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China
^c School of Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
^d State Key Laboratory of Mesoscience and Process Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China

Received:2026-02-24 Accepted:2026-04-28 Online:2026-11-18 Published:2026-09-09
Contact: *E-mail:wjhg168@163.com(J. Wu),xiyj@licp.cas.cn(Y. Xi),fuweili@ucas.ac.cn(F. Li),yongli@sust.edu.cn(Y. Li).
Supported by:
National Natural Science Foundation of China(21902094);National Natural Science Foundation of China(22472177);China Postdoctoral Science Foundation(2020M683405);Young Talent Fund of Association for Science and Technology in Shaanxi, China(20260604);Natural Science Foundation of Shaanxi Province(2023-JC-QN-0103);Natural Science Foundation of Shaanxi Province(2026JC-YBMS-0138);Open Fund of State Key Laboratory of Mesoscience and Process Engineering(MESO-25-D16)

摘要/Abstract

摘要：

将可再生生物质高效转化为高附加值含氮化合物, 已成为绿色化学与可持续精细化学品合成的核心课题之一. 其中伯胺作为重要的关键结构单元和合成中间体, 广泛应用于药物、聚合物、农业化学品、染料和表面活性剂的生产, 具有显著的工业价值. 在众多合成路线中, 以分子氢为还原剂, 氨水为氮源的羰基化合物的催化还原胺化反应, 因其操作简便, 原子效率高, 经济效益显著, 被视为生产伯胺最具吸引力且可持续的策略之一. 然而, 由于还原胺化反应网络的复杂性, 在活性氢和氨的作用下, 反应物和中间体的直接还原和胺化之间存在竞争性反应, 高选择性制备伯胺仍是一项巨大的挑战. 因此设计与开发具有双功能活性位点协同催化作用的催化体系有望解决这一问题.

本文通过硬模板导向的原位合成策略, 开发了一系列氮掺杂空心碳球负载RuCo合金的双金属纳米催化剂(Ru₂Co₁@NHCS-T, T: 600-800), 并以典型的生物质羰基化合物糠醛还原胺化制备糠胺为探针反应, 系统的评估了双金属催化剂的还原胺化性能和反应机理. 通过RuCo合金效应及金属-载体相互作用, 针对性地调控了双金属RuCo催化剂的电子结构和几何构型, 进而在RuCo合金中构建了由富电子的Ru⁰和缺电子的Co^δ⁺组成的双功能活性位点, 显著提升了RuCo合金的催化活性和选择性. 其中, 优选的Ru₂Co₁@NHCS-600催化剂还原胺化性能尤为显著, 具有优异的稳定性和广泛的底物适用性. 该催化剂在0.1 MPa压力下表现出极高的H₂活化能力, 同时对NH₃, C=O和C=N键表现了出色的吸附和活化能力, 同时对NH₃, C=O和C=N键表现了出色的胺化活性, 获得了98.1%的高糠胺产率和238.65 mol_FUA mol_Sm^-1 h^-1的高反应速率. 动力学评估证实了RuCo双金属催化剂具有较低的表观活化能(28.44 kJ mol^-1), 显著优于单金属Ru@NHCS-600以及绝大多数已报道的催化剂. 利用球差电镜, 原位CO吸附漫反射红外光谱, X-射线光电子能谱和H₂-程序升温脱附等系统性结构表征以及本征动力学测试, 深入研究了催化体系的构效关系. 结果表明, RuCo双金属催化剂表面丰富的金属-N和吡啶-N物种可有效锚定金属纳米颗粒, 并通过电子金属-载体相互作用提高了金属电子密度; 同时Ru和Co之间的d-d轨道耦合效应实现了Co向Ru的电子转移, 从而形成了富电子Ru⁰和缺电子Co^δ⁺双功能活性位点. 值得注意的是, 富电子的Ru⁰活性位点显著增强了对H₂的吸附和解离活化, 而缺电子的Co^δ⁺活性位点则在串联还原胺化过程中协同促进了糠醛, NH₃和席夫碱中间体的吸附和活化. 密度泛函理论计算结果表明, 相比于单金属Ru催化剂, RuCo双金属催化剂对NH₃具有更优的吸附与活化能力, 促进了NH^2*和H^*物种对席夫碱C=N键优先胺化攻击以及紧随其后的加氢断键反应, 并探究了关键席夫碱中间体的氨解反应机理.

综上, 本文提出的双金属RuCo催化剂协同催化策略, 为羰基化合物还原胺化过程中直接还原和胺化的竞争性反应提供了有效的解决途径, 也为生物质可持续转化合成高附加值含氮化合物所需的高性能催化剂的理性设计提供重要指导.

关键词: 协同催化, 双金属催化剂, 还原胺化, 糠醛, 伯胺

Abstract:

The highly selective synthesis of valuable primary amines through the reductive amination of renewable biomass-derived carbonyl compounds under mild conditions remains a significant challenge. Herein, we developed a series of bimetallic nanocatalysts featuring RuCo alloys embedded within N-doped hollow carbon spheres (Ru₂Co₁@NHCS-T, T: 600-800) via the hard template-directed in situ synthesis routes. Through RuCo alloying effects and metal-support interaction, the electronic structure and geometric configuration of bimetallic RuCo catalysts were targetedly modulated and constructed the bifunctional active sites consisted of electron-rich Ru⁰ and electron-deficient Co^δ⁺ within RuCo alloys, achieving the simultaneously improved catalytic activity, primary amine selectivity and stability for biomass-derived furfural reductive amination. The optimized Ru₂Co₁@NHCS-600 catalyst presented a 98.1% furfurylamine yield and a high initial reaction rate of 238.65 mol_FUA mol_Sm^-1 h^-1 under mild conditions of 0.1 MPa hydrogen, markedly outperforming monometallic Ru@NHCS-600 and most previously reported catalysts. The synergistic catalysis of RuCo alloys contributed to the superior catalytic performance of Ru₂Co₁@NHCS-600 for furfural reductive amination based on systematic structure characterizations and intrinsic kinetic evaluations. Notably, the electron-rich Ru⁰ active sites significantly enhanced the adsorption and dissociation activation of H₂, while the electron-deficient Co^δ⁺ sites synergistically promoted the adsorption and activation of furfural, NH₃ and Schiff base intermediate during the tandem reductive amination. Combined with density functional theory calculations, the catalytic advantages of bimetallic RuCo compared with monometallic counterparts and the ammonolysis reaction mechanism for the key Schiff base intermediate were clarified. The proposed synergistic catalysis strategy of bimetallic RuCo catalysts provided important guidance for rational design of high-performance catalysts for sustainable synthesis of valuable nitrogen-containing compounds via biomass conversion.

Key words: Synergistic catalysis, Bimetallic catalyst, Reductive amination, Furfural, Primary amine

吴君, 白家豪, 潘刚, 史泰龙, 席永杰, 李福伟, 李永. RuCo合金对糠醛高选择性还原胺化的协同催化机理研究[J]. 催化学报, 2026, 90: 309-332.

Jun Wu, Jiahao Bai, Gang Pan, Tailong Shi, Yongjie Xi, Fuwei Li, Yong Li. Mechanism insights into the synergistic catalysis of bimetallic RuCo alloys for the highly selective reductive amination of biomass-derived furfural[J]. Chinese Journal of Catalysis, 2026, 90: 309-332.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(26)65215-1

https://www.cjcatal.com/CN/Y2026/V90/I11/309

图/表 14

Scheme 1. Limitations and corresponding strategies for reported noble and non-noble metal catalysts for furfural reductive amination, along with the synergistic catalysis strategy of bimetallic RuCo catalysts of this work.

Fig. 1. (a) Schematic illustration for the synthesis pathways of Ru2Co1@NHCS-T catalysts. (b) TGA curves of various catalyst precursors. XRD patterns (c) and Raman spectra (d) of various catalysts.

Fig. 2. Morphology and microstructure characterizations: SEM images of PS nanospheres (a), the PDA-RuCo@PS precursor (b) and Ru2Co1@NHCS-600 (c). (d-f) AC-HAADF-STEM images and the particle size distribution histograms of Ru2Co1@NHCS-600. AC-HAADF-STEM images of Ru2Co1@NHCS-600 and the corresponding elemental mappings of C, N, Ru, Co: elemental mappings at 100 nm scale (g), line scan across a RuCo alloy nanoparticle (h), and elemental mappings at 10 nm scale (i).

Fig. 3. N2 adsorption-desorption isotherms (a), the pore size distributions determined by the BJH method (b) and NLDFT/GCMC method (c) based on the adsorption isotherms of various catalysts. (d) H2-TPR profiles of the PDA-Co@PS, PDA-Ru@PS and PDA-Ru2Co1@PS precursors.

Table 1 Reductive amination of furfural with different catalysts.

Entry	Catalyst	Conversion (%)	Selectivity (%)
Entry	Catalyst	Conversion (%)	FUA	FDA	FUI	FAL	Others
1	Blank	62.6	—	—	28.8	—	71.2
2	NHCS-600	74	—	—	23.2	—	76.8
3	Ru₂Co₁@NHCS-600	100	98.1	—	—	1.9	—
4	Ru@NHCS-600	100	53.2	40	—	1.6	5.2
5	Co@NHCS-600	84	—	4.4	28.5	—	67.1
6	Ru@NHCS-600 + Co@NHCS-600	100	69.1	28.5	—	2.4	—
7	Ru₁Co₂@NHCS-600	95	2.6	72.8	24.6	—	—
8	Ru₁Co₁@NHCS-600	100	83	14.6	—	2.4	—
9	Ru₂Cu₁@NHCS-600	90	1.8	74.2	4.6	1.2	18.2
10	Ru₂Ni₁@NHCS-600	100	83.5	6.6	—	1.5	8.4
11	Ru₂Co₁@NHCS-700	100	76.4	21.4	—	2.2	—
12	Ru₂Co₁@NHCS-800	96.4	4.8	86	7.5	0.8	0.9
13	Ru₂Co₁@NC-600	87	—	84.6	—	11.5	3.9
14	Ru₂Co₁@HCS-600	100	31.8	64.4	—	2.3	1.5

Fig. 4. Effects of reaction temperature, ammonia dosage, and catalyst dosage (a), and the different solvents (DIW: deionized water, Meth: methanol, Eth: ethanol, IPA: isopropanol, NPA: n-propanol, Diox: dioxane, Tolu: toluene, n-Hex: n-hexane) (b) on the reductive amination of furfural. (c) The stability tests of Ru2Co1@NHCS-600 catalyst at different reaction times, reaction conditions: furfural (0.5 mmol), catalyst (5 mg), ethanol (5.5 mL), NH3·H2O (1 mL, 25%-28%), H2 (0.1 MPa), 110 °C.

Fig. 5. Time courses for the reductive amination of furfural over Ru2Co1@NHCS-600 (a), Ru@NHCS-600 (b), and Co@NHCS-600 (c) catalysts. (d) GC profiles of the furfural reductive amination process at different reaction times over Ru2Co1@NHCS-600 catalyst. (e) The reaction networks for furfural reductive amination to furfurylamine and the possible byproducts. Reaction conditions: furfural (0.5 mmol), H2 (0.1 MPa), ethanol (5.5 mL), NH3·H2O (1 mL, 25%-28%), Ru2Co1@NHCS-600 (5 mg), 110 °C.

Fig. 6. The plots of the natural logarithm of furfurylamine concentration with respect to reaction time under 100-130 °C over Ru2Co1@NHCS-600 (a) and Ru@NHCS-600 (b) catalysts. (c) The corresponding Arrhenius plots for the reaction rate constants. Note: The results for each reaction were obtained from three repeated experiments. (d) The IRR and TOF over various catalysts. (e) Comparisons of conditions and performances with the previously reported catalysts [8,9,13,23,42,49,51]. Reaction conditions: furfural (0.5 mmol), H2 (0.1 MPa), ethanol (5.5 mL), NH3·H2O (1 mL, 25%-28%), catalyst (5 mg).

Table 2 Reductive amination of various aldehydes and ketones catalyzed by the Ru2Co1@NHCS-600 catalyst.

Entry	Tem. (°C)	Time (h)	H₂ (MPa)	Con. (%)	Yield (%)
1	110	1.5	0.1	100	98.3
2	110	1.5	0.1	100	96.2
3	110	4	0.1	100	96.9
4	90	2	0.1	96.6	91.8
5	90	2	0.1	100	87.2
6	110	4	0.3	100	95.1
7	110	4	0.5	100	94.8
8	110	6	0.5	100	85.7
9	110	6	0.3	100	90.7
10	110	5	0.1	98.9	91.4
11	130	8	1	94.4	92.1
12	130	12	0.5	98.5	90.2
13^b	130	18	0.5	93.9	81.7

Fig. 7. The XPS spectra of survey scan (a), relative contents of C, N, O, Ru and Co elements (b), and the high-resolution C 1s and Ru 3d (c), N 1s (d), Ru 3p (e), and Co 2p (f) for various monometallic and bimetallic catalysts.

Fig. 8. In-situ CO-DRIFTS spectra of the Ru2Co1@NHCS-600 (a), Ru@NHCS-600 (b), Co@NHCS-600 (c), and the corresponding DRIFTS spectra (d) after outgassed CO by Ar. (e) H2-TPD profiles of various monometallic and bimetallic catalysts. (f) FTIR spectra of various catalysts after adsorption of Schiff base.

Fig. 9. Structure-performance relationship of the various Ru2Co1@NHCS catalysts: The correlations between the IRR and the specific surface area (BET) (a), and the average particle size (b) of RuCo alloys determined by TEM images, and the content of surface metal-N species determined by XPS (c). The correlations between H2 desorption and the binding energy of Ru0 3p3/2 peak and the content of surface Ru0 species (d), and the correlations between IRR and H2 desorption (e), and the content of surface Coδ+ species (f).

Fig. 10. Spin-resolved DOS for the Ru(0001) (a), Co(0001) (b), and RuCo(0001) (c) models. The positive and negative values represent the upper and lower spin states, respectively, the energy scale is referenced to the Fermi level (EF = 0). Adsorption energies and stable adsorption configurations for the Schiff base, NH3 and H2 on Ru(0001) (d), Co(0001) (e) and RuCo(0001) (f) surfaces. Color code: C, gray; N, dark blue; H, cyan; O, red; Co, pale red; Ru, pale blue.

Fig. 11. (a) Schematic molecular models of the Schiff base ammonolysis reaction mechanism on RuCo(0001). A0: side view of metal sites on the RuCo(0001) surface; A1: adsorption of the Schiff base; A2, adsorption of NH3; TS1, NH3 dissociation into NH2* and H*; A3, co-adsorbed NH2* and H*; TS2, configurational rearrangements of adsorbed NH2* and Schiff base leading to nucleophilic attack of NH2* on the C=N bond; A4, NH2* bonds to the C atom of C=N group; TS3, approach of H* to the N atom of C=N bond; A5, bonding of H* to the N atom; TS4, further weakening of the formed C-N bond in the Schiff base intermediate; A6, stable adsorption of the Schiff‑base‑derived amination intermediate; A7, adsorption of two H* resulting from dissociation of H2 molecules; TS5, approach of an H* to the C atom of C=N bond; A8, bonding of H* to the C atom; TS6, approach of the second H* to the N atom; A9, bonding of the second H* to the N atom, yielding two molecules of furfurylamine. Color code: C, gray; N, dark blue; H, cyan; O, red; Co, pale red; Ru, pale blue. (*) denotes active species. (b) Isosurface plots of the charge-density difference for a Schiff base adsorbed on RuCo(0001): top view (upper) and side view (lower), the amount of electron transfer is given by Bader charge analysis. (c) Schematic illustration of the synergistic catalysis mechanism for the reductive amination of furfural to furfurylamine over the bimetallic RuCo catalyst.

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RuCo合金对糠醛高选择性还原胺化的协同催化机理研究

Mechanism insights into the synergistic catalysis of bimetallic RuCo alloys for the highly selective reductive amination of biomass-derived furfural

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