烯烃氢甲酰化的钴基多相催化体系

doi:10.1016/S1872-2067(24)60238-X

催化学报 ›› 2025, Vol. 70: 115-141.DOI: 10.1016/S1872-2067(24)60238-X

烯烃氢甲酰化的钴基多相催化体系

梁超安^a, 曾波^a, 冯保林^b, 史会兵^b, 张凤岐^b, 刘建华^a, 何林^a^,^*(), 丁玉晓^a^,^*(), 夏春谷^a

^a中国科学院兰州化学物理研究所, 低碳催化二氧化碳利用全国重点实验室, 甘肃兰州 730000
^b山东京博石油化工有限公司, 山东滨州 256500

收稿日期:2024-10-22 接受日期:2024-12-29 出版日期:2025-03-18 发布日期:2025-03-20
通讯作者: * 电子信箱: helin@licp.cas.cn (何林),yuxiaoding@licp.cas.cn (丁玉晓).
基金资助:
国家自然科学基金(22202217);国家自然科学基金(22072166);国家自然科学基金(22472182);山东省科技厅支持项目(2023CXGC010607)

Heterogeneous Co-based catalytic systems for alkene hydroformylation

Chao-an Liang^a, Bo Zeng^a, Baolin Feng^b, Huibing Shi^b, Fengqi Zhang^b, Jianhua Liu^a, Lin He^a^,^*(), Yuxiao Ding^a^,^*(), Chungu Xia^a

^aState Key Laboratory of Low Carbon Catalysis and Carbon Dioxide Utilization, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou730000, Gansu, China
^bShandong Chambroad Petrochemicals Co., Ltd, Binzhou256500, Shangdong, China

Received:2024-10-22 Accepted:2024-12-29 Online:2025-03-18 Published:2025-03-20
Contact: * E-mail: helin@licp.cas.cn (L. He),yuxiaoding@licp.cas.cn (Y. Ding).
About author:Lin He (Lanzhou Institute of Chemical Physics, Chinese Academy of Science) received her B.S degree in Chemistry at Lanzhou University in 2005. She earned her PhD at Fudan University under the supervision of Yong Cao in 2013. Then, she joined Matthias Beller’s group at LIKAT as a postdoctoral fellow. Since autumn 2016, she went back to Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences and started her independent research. Her current research is focused on applied catalysis for carbonylation. She has published more than 60 papers in Science, Angew. Chem. Int. Ed. and etc.
Yuxiao Ding (Lanzhou Institute of Chemical Physics, Chinese Academy of Science) received his Ph.D. degree from Institute of Metal Research, Chinese Academy of Sciences in 2015. Afterwards, he joined Max Planck Institute for Chemical Energy Conversion (Germany) as a postdoctoral researcher. Since the end of 2021, he has been working as an independent principal investigator in the State Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences. His research interests mainly focus on carbon surface chemistry, carbon related thermal/electrochemical catalysis/conversion and alkene conversion.
Supported by:
National Natural Science Foundation of China(22202217);National Natural Science Foundation of China(22072166);National Natural Science Foundation of China(22472182);Department of Science &Technology of Shandong Province for their assistance(2023CXGC010607)

摘要/Abstract

摘要：

烯烃氢甲酰化反应是产能规模最大的工业过程之一, 用于满足对醛衍生物及其下游产品的巨大需求. 自20世纪60年代以来, 均相钴配合物是最广泛应用的工业化催化剂. 然而, 多相催化在催化剂与产物分离方面的便捷性、更短的工艺流程以及较低的制造成本方面具有显著优势. 然而, 目前尚未有成功的多相化钴基催化剂应用于工业羰化反应的实例. 为了解决催化剂分离难题并深入阐释反应的催化机制, 本文总结了多相催化体系的最新研究进展, 并详细探讨了其反应性能.

本文聚焦于多相催化体系活性金属流失的科学问题, 详细探讨了这一问题在实际催化过程中对催化性能的影响. 在多相催化反应中, 活性金属的流失、聚集或表面活性位点减少等问题常常导致催化剂活性衰减, 进而影响催化反应的效率与稳定性. 本文深入分析了不同载体对活性金属的负载效果, 以及不同载体材料对不同类型烯烃催化活性的影响. 通过对比研究氧化硅、聚合物、碳基材料等载体, 揭示了不同载体对催化活性的不同表现. 具体而言, 载体能够通过调整金属分散度和催化剂表面结构, 显著提升催化剂对特定烯烃的选择性和活性, 而另一些载体则可能由于其本身的特性或其他性质对催化反应产生不利影响. 为了进一步提升钴基催化剂的稳定性, 审慎分析了通过载体改性和添加剂引入来稳定钴物种的策略. 例如, 通过载体的调控、表面官能团的引入以及元素掺杂等手段, 可以有效地抑制钴物种的流失或聚集, 增加催化剂的稳定性. 此外, 研究还探讨了添加助剂对催化剂性能的改善作用, 这些助剂不仅能够稳定金属物种, 还能优化催化反应的选择性和活性. 因此, 载体的设计与改性以及助剂的选择和引入成为解决钴基催化剂流失问题的重要途径, 并为探究多相催化体系至今尚未实现工业化的原因提供了思路. 同时, 本文还对氢甲酰化反应的机理进行了总结, 提出了可能的多相氢甲酰化反应机理. 对于机理的进一步理解将有助于催化剂的设计与优化, 同时也为反应的规模化应用提供了理论依据. 此外, 我们还提出了对多相催化氢甲酰化未来发展方向的洞见, 包括其面临的挑战、潜在的机遇以及应用前景.

综上所述, 多相烯烃氢甲酰化反应的研究是在催化剂的设计与优化以及反应机理的深入认识方面均取得了显著进展. 本综述加深了对多相烯烃氢甲酰化的基础认识, 并为该领域研究提供指导, 以期实现这一技术在工业中的成功应用.

关键词: 钴催化剂, 烯烃加氢甲酰化, 多相催化, 醛衍生物, 钴稳定性

Abstract:

Hydroformylation of olefins is one of the highest-volume industrial reactions to meet the vast demands for aldehydes as well as their derivatives. Homogeneous Co complexes were the original catalysts industrialized since 1960s. Heterogeneous catalysis is considered superior owing to the facile separation of catalysts from products, shorter technical process, and reduced manufacturing costs. Unexpectedly, there has not been a single case of plant using heterogenized Co-based catalyst successfully. To address the separation issue and understand the catalytic mechanism of the reactions, this review summarizes the progress in heterogeneous systems and provides a detailed discussion of their catalytic performance. Strategies for stabilizing Co species through support modification and additive incorporation are carefully considered to elucidate why heterogeneous systems have not yet succeeded on an industrial scale. Furthermore, we provide our insights for the development of heterogeneous catalytic hydroformylation, including the challenges, opportunities, and outlooks. The aim is to deepen the fundamental understanding of heterogeneous alkene hydroformylation, guiding the community's research efforts towards realizing its successful application in the future.

Key words: Cobalt catalysts, Alkene hydroformylation, Heterogeneous catalysis, Aldehyde derivatives, Cobalt stabilization

梁超安, 曾波, 冯保林, 史会兵, 张凤岐, 刘建华, 何林, 丁玉晓, 夏春谷. 烯烃氢甲酰化的钴基多相催化体系[J]. 催化学报, 2025, 70: 115-141.

Chao-an Liang, Bo Zeng, Baolin Feng, Huibing Shi, Fengqi Zhang, Jianhua Liu, Lin He, Yuxiao Ding, Chungu Xia. Heterogeneous Co-based catalytic systems for alkene hydroformylation[J]. Chinese Journal of Catalysis, 2025, 70: 115-141.

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图/表 22

Fig. 1. Reaction pathway of olefin hydroformylation.

Table 1 List of different heterogeneous cobalt-based hydroformylation catalysts.

Catalyst	Substrate	T (°C)	P (MPa)	t (h)	Conversion (%)	Selectivity (%)		Cobalt leaching (%)	Ref.
Catalyst	Substrate	T (°C)	P (MPa)	t (h)	Conversion (%)	Aldehyde	Alcohol	Cobalt leaching (%)	Ref.
Fibrous Co₃O₄	1-octene	150	5.5	12	92		93	0.23	[47]
Octahedron Co₃O₄	1-octene	170	4	12	88.06	75.26	10.35	0.91	[48]
Co@CoO	1-octene	130	4	8	99	97			[50]
2Fe2Cu-Co₃O₄	1-octene	150	7	4	99.82		50.80		[49]
Co-B	1-octene	120	5	2.5	71.1	98.7			[58]
Co-P-B	1-octene	120	5	2.5	97.2	99.0			[56]
Co-Ni-P-B	1-octene	120	5	4	99.6	96.3			[57]
Ultrafine Co	1-hexene	100	2.5	1	95	38			[54]
Co/SiO₂ (Q-6)	1-hexene	130	5	2	37.1	88.4		1.0	[71]
Co-Pd/SiO₂	1-hexene	130	5	2	89.7	77.9			[134]
Co-Ru/SiO₂ (EG)	1-hexene	130	5	1	93.01	79.66			[72]
CoGa IMC/SiO₂	1-hexene	130	6	5	>99	57.3		1.6	[74]
K-Co/SiO₂	1-Hexene	150	4	6	99.9	74.6	6.4		[75]
CoZrP-2.0 (P/Zr = 2)	1-octene	160	4	6	86.5	91.8		1.7	[84]
CoRh-HT	1-octene	100	5	6	98	96			[77]
Rh-Co-Pi/ZnO	1-decene	100	4	4	>95	>85			[78]
Co-Rh/Fe₃O₄	dicyclopentadiene	140	7	4	100	6.2	90.6		[79]
Co-B/ZrO₂	1-octene	120	5	2.5	86.9	86.4		89.0	[59]
Co-B/SBA-15	1-octene	120	5	2.5	85.6	98.7		20.0	[59]
Co-Ni-B/SBA-15	1-octene	120	5	4	100	91.24			[81]
Co (1%)/β-Mo₂C	propylene	160	4	10	>99	95	5		[112]
Co-PPh₃@POPs	1-hexene	150	3	5	97.6%	45.7%			[121]
SBA-15-RCo	1-octene	100	6.5	8	97.4	91.2			[124]
Co-B/TiO₂	cyclohexene	100	6	1	99.15	65.28	34.72		[89]
Co/phen@TiO₂	n-butyl acrylate	100	4	18	>99	82			[37]
CoFe/NC-800	diisobutylene	130	4	12	92	79.6			[108]
Pd-Co/AC	1-hexene	130	5	2	34.5	47.2			[103]
Co/CNTs	1-octene	130	5	6	25.9	52.4			[107]
Co-B/CNTs	1-octene	120	5	2.5	92.2	96.2		13.0	[59]
Co-Ru/CNTs	1-octene	130	5	6	70.9	65.75			[107]
CoN_x@NC	1-hexene	120	4	7.5	94	80		1.9	[109]
Co/N-C-800	1-hexene	160	4	6	47.2	66.3			[55]
Rh-Co/g-CN	styrene	170	6	7	99.9	7.4	87.8		[110]
Co₃O₄-g-C₃N₄	1-octene	150	7	8	99.9		77.8		[111]
Co/C₆₀₀	1-octene	140	4	18	90	76		0.7	[113]
Co/phen@C	n-butyl acrylate	100	4	18	>99	83			[37]
Co-Ph₃PO/PDMS/SiO₂	mixed octenes	160	5	2.5	24.6	93.7		0.001	[122]
Co/POL-POPh₃	2-octene	150	3	4	94.6	51.1	4.2		[123]

Table 1 List of different heterogeneous cobalt-based hydroformylation catalysts.

Catalyst	Substrate	T (°C)	P (MPa)	t (h)	Conversion (%)	Selectivity (%)		Cobalt leaching (%)	Ref.
Catalyst	Substrate	T (°C)	P (MPa)	t (h)	Conversion (%)	Aldehyde	Alcohol	Cobalt leaching (%)	Ref.
Fibrous Co₃O₄	1-octene	150	5.5	12	92		93	0.23	[47]
Octahedron Co₃O₄	1-octene	170	4	12	88.06	75.26	10.35	0.91	[48]
Co@CoO	1-octene	130	4	8	99	97			[50]
2Fe2Cu-Co₃O₄	1-octene	150	7	4	99.82		50.80		[49]
Co-B	1-octene	120	5	2.5	71.1	98.7			[58]
Co-P-B	1-octene	120	5	2.5	97.2	99.0			[56]
Co-Ni-P-B	1-octene	120	5	4	99.6	96.3			[57]
Ultrafine Co	1-hexene	100	2.5	1	95	38			[54]
Co/SiO₂ (Q-6)	1-hexene	130	5	2	37.1	88.4		1.0	[71]
Co-Pd/SiO₂	1-hexene	130	5	2	89.7	77.9			[134]
Co-Ru/SiO₂ (EG)	1-hexene	130	5	1	93.01	79.66			[72]
CoGa IMC/SiO₂	1-hexene	130	6	5	>99	57.3		1.6	[74]
K-Co/SiO₂	1-Hexene	150	4	6	99.9	74.6	6.4		[75]
CoZrP-2.0 (P/Zr = 2)	1-octene	160	4	6	86.5	91.8		1.7	[84]
CoRh-HT	1-octene	100	5	6	98	96			[77]
Rh-Co-Pi/ZnO	1-decene	100	4	4	>95	>85			[78]
Co-Rh/Fe₃O₄	dicyclopentadiene	140	7	4	100	6.2	90.6		[79]
Co-B/ZrO₂	1-octene	120	5	2.5	86.9	86.4		89.0	[59]
Co-B/SBA-15	1-octene	120	5	2.5	85.6	98.7		20.0	[59]
Co-Ni-B/SBA-15	1-octene	120	5	4	100	91.24			[81]
Co (1%)/β-Mo₂C	propylene	160	4	10	>99	95	5		[112]
Co-PPh₃@POPs	1-hexene	150	3	5	97.6%	45.7%			[121]
SBA-15-RCo	1-octene	100	6.5	8	97.4	91.2			[124]
Co-B/TiO₂	cyclohexene	100	6	1	99.15	65.28	34.72		[89]
Co/phen@TiO₂	n-butyl acrylate	100	4	18	>99	82			[37]
CoFe/NC-800	diisobutylene	130	4	12	92	79.6			[108]
Pd-Co/AC	1-hexene	130	5	2	34.5	47.2			[103]
Co/CNTs	1-octene	130	5	6	25.9	52.4			[107]
Co-B/CNTs	1-octene	120	5	2.5	92.2	96.2		13.0	[59]
Co-Ru/CNTs	1-octene	130	5	6	70.9	65.75			[107]
CoN_x@NC	1-hexene	120	4	7.5	94	80		1.9	[109]
Co/N-C-800	1-hexene	160	4	6	47.2	66.3			[55]
Rh-Co/g-CN	styrene	170	6	7	99.9	7.4	87.8		[110]
Co₃O₄-g-C₃N₄	1-octene	150	7	8	99.9		77.8		[111]
Co/C₆₀₀	1-octene	140	4	18	90	76		0.7	[113]
Co/phen@C	n-butyl acrylate	100	4	18	>99	83			[37]
Co-Ph₃PO/PDMS/SiO₂	mixed octenes	160	5	2.5	24.6	93.7		0.001	[122]
Co/POL-POPh₃	2-octene	150	3	4	94.6	51.1	4.2		[123]

Fig. 2. (a) SEM images of fibrous Co3O4 nanocatalyst. (b) Recycle study of nano-Co3O4 catalyst. Reprinted with permission from Ref. [47], Copyright 2017, Elsevier, Amsterdam. (c) Catalytic performance of 1-heptene hydroformylation reaction. (d) Catalytic reaction diagram of Co3O4 1-hexene with different morphologies Reprinted with permission from Ref. [48], Copyright 2020, Elsevier, Amsterdam.

Fig. 3. (a) DESs used for the synthesis of Co catalysts. (b) Schematic representation of the hydroformylation reaction catalysed by Co@CoO core-shell nanoparticle. (c) In situ FTIR spectra of CO adsorption on Co@CoO-PEG, the spectra were recorded after CO adsorption for 3 (a), 8 (b), 14 (c), 19 (d), 24 (e), 30 (f) min and Ar purging for 7 min (g) [50]. (d) H2-TPR profiles of monometal doped (left) and bimetal co-doped Co3O4 (right). Reprinted with permission from Ref. [49], Copyright 2023, Elsevier, Amsterdam.

Fig. 4. (a) XRD patterns of fresh and thermal-treated Co-B samples. (a) Fresh Co-B; (b) Co-B-N2-300; (c) Co-B-N2-500, (d) Co-B-H2-300, e metal Co [58]. (b) TEM images of cobalt nanoparticles of the catalyst with diameter distribution. Pressure-time plots and curve for mercury poisoning tests of hydroformylation of 1-hexene catalyzed by the cobalt nanoparticle catalyst (c) and RhCl(PPh3)3 (d) [54].

Fig. 5. (a) Schematic representation of the elution of active metal in the presence of a protective agent for active metals. (b) In situ FTIR transmission spectroscopy recorded desorption in the vacuum condition for 15 min over “a” SiO2 and the “b” Co/SiO2 catalyst at 100 °C. Reprinted with permission from Ref. [38], Copyright 2018, American Chemical Society, Washington, DC. (c) In situ FTIR transmission spectroscopy recorded over “A” Co/SiO2 and “B” CoGa IMC/SiO2 catalysts by introducing 5 MPa syngas as the reaction gas after the adsorption of 1-hexene in vacuum at 423 K. From the bottom to top in each panel: 0, 0.5, 1, 2, 3, 4, 7, 10, 20, 25, and 30 min. (d) The amount of cobalt leaching of Co/SiO2 and CoGa IMC/SiO2 catalysts under different reaction pressures. Reprinted with permission from Ref. [74], Copyright 2022, Elsevier, Amsterdam.

Fig. 6. (a) Electronic and chemical properties of catalysts. electron localization function contour maps. (b) Charge difference maps. (c) Catalytic performance of catalysts in the alkene hydroformylation. (d) In situ reaction cycling test. Reprinted with permission from Ref. [76], Copyright 2024, American Chemical Society, Washington, DC.

Fig. 7. (a) Schematic representation of the Rh-Co-Pi/ZnO catalysed hydroformylation reaction. Reprinted with permission from Ref. [78], Copyright 2021, American Chemical Society, Washington, DC. (b) Schematic diagram of ZrP-catalyzed olefin hydroformylation reaction. (Reprinted with permission from Ref. [84], Copyright 2022, Elsevier, Amsterdam.

Fig. 8. (a) Schematic representation of hydroformylation over Co-Co2C/AC catalysts. Reprinted with permission from Ref. [100], Copyright 2014, American Chemical Society, Washington, DC. (b) Mechanistic catalysts for the hydroformylation reaction of 1-hexene on silica zeolite-1/Pd-Co/AC with synthesis gas [103].

Fig. 9. (a) Schematic illustration of the preparation processes of CoFe/NC catalysts. Reprinted with permission from Ref. [108], Copyright 2022, American Chemical Society, Washington, DC. (b) Co contents of samples, measured by ICP-AES [55]. (c) Schematic preparation of CoNx@NC catalysts. (d) Reaction profiles for experiments performed with CoNx@NC as catalyst (red line) and after hot filtration (grey dotted line) [109].

Fig. 10. (a) Illustrations of the formation process of the Rh Co/g-CN catalyst. (b) Plausible mechanism for tandem hydroformylation-hydrogenation of styrene catalyzed by Rh Co/g-CN [110]. (c) In situ DRIFTS spectra on 5 %Co3O4-g-C3N4 [111]. (d) Schematic representation of metal-support interactions of Co1/β-Mo2C catalysts in optimising charge density and stabilising active sites [112].

Fig. 11. (a) Illustrations of the formation process of cobalt-based materials. (b) 1-octene hydroformylation with pyrolyzed and steam pyrolyzed catalysts. (c) Cobalt leaching determined by ICP-OES. (d) image of the final solutions at 120 °C. Conditions: 1-octene (2 mmol), catalyst (25 mg), toluene (5 mL), CO/H2 (40 bar), 18 h, (e) Recycling of Co@C600 catalyst in the 1-octene hydroformylation [113].

Fig. 12. (a) Synthesis routes of Co-PPh3@POPs catalysts [121]. (b) Construction of POL-POPh3 polymer and Co/POL-POPh3 catalyst, (c) Recycling tests of the Co/POL-POPh3 catalyst [123]. (d) Schematic representation of cobalt carbonyl grafting on SBA-15 surface through organosilane ligand. Reprinted with permission from Ref. [124], Copyright 2016, Elsevier, Amsterdam.

Fig. 13. Structures and molecular formulas of the MOFs used in hydroformylation. (a) MixUMCM-1-NH2; (b) MOF-74(Zn). Here, bdc represents 1,4-benzenedicarboxylate; abdc represents 2-amino-1, 4-benzenedicarboxylate, btb represents 4,4′,4′′-benzene-1,3, 5-triyl-trisbenzoate and dobdc represents 2,5-dioxido-1, 4-benzenedicarboxylate. Hydrogen and nitrogen atoms are omitted for clarity [133].

Fig. 14. The diagram illustrates the catalytic cycle mechanism of a biphasic reaction.

Fig. 15. (a) Structure of trisodium salt of tris (m-sulfophenyl) phosphine (TPPTS). (b) Trisodium salt of trisulfonated tris (biphenyl) phosphine (BiphTS). (c) Structure of CTAB surfactant. (d) Structure of Marlipal O13/18 surfactant.

Fig. 16. (a) Process scheme (1-Reaction, 2-Cobalt recovery in the ionic liquid, 3-Separation). (b) Recycling experiments with or without pyridine [148]. (c) Structure of the pre-catalyst Co2(CO)6[P(3-FC6H4)3]2 and HCo(CO)3[P(3-FC6H4)3] [150].

Fig. 17. (a) Homogeneous catalytic mechanism of hydroformylation. (b,c) Proposed reaction pathways for hydroformylation of 1-heptene on Co3O4 octahedron. Reprinted with permission from Ref. [48], Copyright 2020, Elsevier, Amsterdam. (d) Mechanism of hydroformylation catalyzed by different metals doped with Co3O4. Reprinted with permission from Ref. [49], Copyright 2023, Elsevier, Amsterdam.

Fig. 18. (a) Proposed hydroformylation mechanism involving ZrP-supporting single-atom Co(II) catalyst. Reproduced with permission from Ref. [84]. Copyright 2022 Elsevier, Inc. (b) The reaction pathway of 2-octene hydroformylation to linear aldehydes on Co/POL-POPh3 [123].

Fig. 19. Possible heterogeneous catalytic mechanism of hydroformylation.

Fig. 20. (a) Elution and protection strategies for active metal cobalt during hydroformylation. (b) Stabilization of the active metal on the support by means of a protective agent. (c) Stabilization of the active metal on the carrier by introduction of a heteroatomic nitrogen species. (d) Introduction of active metals on non-precious metal stabilized supports.

Fig. 21. (a) Common biphasic reaction. (b) Addition of surfactant to increase reaction contact area. (c) Formation of stable ligand-modified cobalt catalysts. (d) Introduction of amphiphilic materials to enhance interfacial mass transfer ('S' stands for substrate, 'P' for product, 'L' for ligand).

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烯烃氢甲酰化的钴基多相催化体系

Heterogeneous Co-based catalytic systems for alkene hydroformylation

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