费托合成与多相氢甲酰化技术耦合制高值化学品的研究进展

doi:10.1016/S1872-2067(25)64701-2

催化学报 ›› 2025, Vol. 73: 16-38.DOI: 10.1016/S1872-2067(25)64701-2

费托合成与多相氢甲酰化技术耦合制高值化学品的研究进展

赵子昂^a^,¹, 姜淼^a^,¹, 李存耀^a, 李怡蕙^a, 朱何俊^a, 林荣和^b(), 袁慎峰^c(), 严丽^a(), 丁云杰^a^,^b^,^d()

^a中国科学院大连化学物理研究所, 洁净能源国家实验室, 辽宁大连 116023
^b浙江师范大学杭州高等研究院, 教育部先进催化材料重点实验室, 浙江杭州 311231
^c浙江大学化学工程与生物工程学院, 浙江杭州 310058
^d中国科学院大连化学物理研究所, 催化基础国家重点实验室, 辽宁大连 116023

收稿日期:2025-02-14 接受日期:2025-03-26 出版日期:2025-06-18 发布日期:2025-06-12
通讯作者: *电子信箱: dyj@dicp.ac.cn (丁云杰),yanli@dicp.ac.cn (严丽),ysf@zju.edu.cn (袁慎峰),catalysis.lin@zjnu.edu.cn (林荣和).
作者简介:¹共同第一作者.
基金资助:
国家重点研发计划(2023YFB4103100);国家重点研发计划(2023YFA1508003);中国科学院前瞻战略科技先导专项(XDA29050300);国家自然科学基金(22002151);中国科学技术协会青年人才托举工程(2023QNRC001);能源催化转化全国重点实验室(2024SKL-B-005);辽宁滨海实验室(LBLG-2024-06);中国科学院青年创新促进会(2021181);辽宁省科学基金(2025JH6/101000016);辽宁省科学基金(2023JH2/101800051);大连市科学基金会(2023RY012)

Integrated Fischer-Tropsch synthesis and heterogeneous hydroformylation technologies toward high-value commodities from syngas

Ziang Zhao^a^,¹, Miao Jiang^a^,¹, Cunyao Li^a, Yihui Li^a, Hejun Zhu^a, Ronghe Lin^b(), Shenfeng Yuan^c(), Li Yan^a(), Yunjie Ding^a^,^b^,^d()

^aDalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^bKey Laboratory of the Ministry of Education for Advanced Catalysis Materials, Hangzhou Institute of Advanced Studies, Zhejiang Normal University, Hangzhou 311231, Zhejiang, China
^cCollege of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310058, Zhejiang, China
^dState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2025-02-14 Accepted:2025-03-26 Online:2025-06-18 Published:2025-06-12
Contact: *E-mail: dyj@dicp.ac.cn (Y. Ding),yanli@dicp.ac.cn (L. Yan),ysf@zju.edu.cn (S. Yuan),catalysis.lin@zjnu.edu.cn (R. Lin).
About author:Ronghe Lin (Hangzhou Institute of Advanced Studies, Zhejiang Normal University) received his B.S. From Taiyuan University of Technology in 2005 and Ph.D. degree in 2010 from Dalian Institute of Chemical Physics (DICP), Chinese Academy of Sciences. He then stayed at DICP until 2015 and was an associate professor since 2013. He did postdoctoral research at ETH Zurich (Switzerland) with Prof. Javier Pérez-Ramírez in 2015-2019. After that he joined Zhejiang Normal University to start independent research centering on studying challenging reactions (selective hydrogenation, CO₂ valorization, etc.) with industrial relevance by coupling advanced catalyst design, kinetic and spectroscopic studies. He has coauthored about 70 peer-reviewed papers.
Shenfeng Yuan (College of Chemical and Biological Engineering, Zhejiang University) received his B.E. degree from Zhejiang University of Technology in 1998 and Ph.D. degree in 2003 from Zhejiang University. He stayed at Zhejiang University since then and was an associate professor since 2005. His research interests involve areas such as synthesis of fine chemicals, extraction, special distillation and development of clean production processes. He has coauthored about 50 peer-reviewed papers.
Li Yan (Dalian Institute of Chemical Physics, Chinese Academy of Sciences) received her B.S. degree from Dalian University of Technology in 2000, and Ph.D. degree from Dalian Institute of Chemical Physics (DICP) in 2006. She stayed at DICP after graduation and become a full professor in 2015. She is now the director of the Research Center for Catalysis in Syngas Conversion and Fine Chemicals (DNL0805) of DICP. Prof. Yan’s research interests are mainly engaged in applied fundamental research on hydroformylation and hydrogenative amination, as well as engineering research of new catalytic processes. She has coauthored about 120 peer-reviewed papers.
Yunjie Ding (Dalian Institute of Chemical Physics, Chinese Academy of Sciences) received his B.S. degree from Hangzhou University in 1985, and Ph.D. degree from Dalian Institute of Chemical Physics (DICP), Chinese Academy of Sciences in 1991. He worked as an associated professor in Zhejiang University from 1991 to 1999, in the period, he carried out postdoctoral research at Texas A&M University (USA) from 1995 to 1998. Then, he moved back to DICP as a full professor and also the group leader of DNL0805. Prof. Ding’s research focuses on heterogeneous catalysis in syngas conversion and fine chemicals, moving from design of advanced catalytic materials, molecular-level understanding of reaction mechanism, to industrialization of novel catalytic technologies. He owns more than 400 authorized patents and more than 13 technologies are commercialized. He is also the co-author of 300 papers in peer-reviewed journals.
¹ Contributed equally to this work.
Supported by:
National Key Research and Development Program of China(2023YFB4103100);National Key Research and Development Program of China(2023YFA1508003);Strategic Priority Research Program of the Chinese Academy of Sciences(XDA29050300);National Natural Science Foundation of China(22002151);Young Elite Scientists Sponsorship Program by CAST(2023QNRC001);State Key Laboratory of Catalysis(2024SKL-B-005);Liaoning Binhai Laboratory(LBLG-2024-06);Youth Innovation Promotion Association CAS(2021181);Science Foundation of Liaoning(2025JH6/101000016);Science Foundation of Liaoning(2023JH2/101800051);Science Foundation of Dalian(2023RY012)

摘要/Abstract

摘要：

化石能源是现代社会发展的基石. 我国“富煤、贫油、少气”的资源禀赋特征决定了发展新型煤化工不仅是缓解石油资源短缺、保障能源安全的关键路径, 更是推动能源结构转型、落实“双碳”战略目标的必然选择. 开发以合成气(CO/H₂)为原料直接制备液体燃料、醇类及烯烃等高附加值化学品的低碳高效催化技术, 对实现“碳达峰、碳中和”目标具有重要意义. 其中, 费托合成(FTS)与氢甲酰化反应作为合成气转化制液体燃料及含氧化合物的核心工艺, 长期面临催化剂活性与选择性难以协同优化、产物分布调控复杂、均相催化剂分离困难等工业化挑战.

本文系统总结了中国科学院大连化学物理研究所合成气转化与精细化学品催化研究中心(DNL0805)在费托合成和多相氢甲酰化领域二十余年的研究进展. 基于“催化剂设计—反应机理解析—工艺优化—工业示范—产物升级”的全链条创新视角, 重点阐述了以下成果: (1)费托合成产物调控: 针对传统费托合成产物分布宽、产物选择性难以调控的问题, 提出炭载钴基催化剂(Co/AC)的精准设计策略, 通过调节活性中心的精细结构实现费托合成产物选择性定向调变, 首次提出金属钴与碳化钴组成的界面是合成气制高碳α-醇的双活性中心, 完成世界首例万吨级合成气制高碳醇工业试验和15万吨/年炭载钴基浆态床合成气制油工业示范; (2)多相氢甲酰化技术突破: 针对烯烃氢甲酰化反应的技术瓶颈, 提出全新的“均相多相化”催化剂设计理念, 通过有机膦配体结构调控及多孔有机聚合物(POPs)中丰富的高度露裸的P物种与金属离子的多种配位键相对牢固键合的固载化策略, 实现单一烯烃(乙烯、丙烯等)及费托合成副产混合烯烃的高效转化, 并建成全球首套基于固定床工艺的5万吨/年乙烯多相氢甲酰化及其加氢制正丙醇工业装置; (3)产物分离与高值化利用: 开发萃取-精馏耦合技术实现费托产物中烷烃与高碳醇的高效分离, 并进一步通过醇脱水、氧化及烯烃聚合等反应路径, 将高碳醇转化为线性α-烯烃(LAO)、聚α-烯烃(PAO)及短链脂肪酸等高值化学品, 拓展了煤基化学品的产业链. 最后, 从催化剂设计与规模化制备、反应工艺优化及多技术耦合等角度, 探讨合成气催化转化技术的未来发展方向, 为实验室成果向工业应用的跨越提供理论支撑.

本文旨在为高效费托合成与多相氢甲酰化催化体系的构建提供新思路, 同时为推动低碳煤化工技术的高端产业化发展及能源结构的转型提供借鉴.

关键词: 工业化, 费托合成, 多相催化, 烯烃氢甲酰化, 工艺开发

Abstract:

Fischer-Tropsch synthesis (FTS) and hydroformylation are pivotal chemical processes for converting syngas and olefins into valuable hydrocarbons and chemicals. Recent advancements in catalyst design, reaction mechanisms, and process optimization have significantly improved the efficiency, selectivity, and sustainability of these processes. This Account introduces the relevant research activities in the Research Center for Catalysis in Syngas Conversion and Fine Chemicals (DNL0805) of Dalian Institute of Chemical Physics (DICP), Chinese Academy of Sciences. The reactions of interests include FTS, heterogeneous hydroformylation of olefins, alcohol dehydration and oxidation, and α-olefin polymerization, with the emphasis on developing innovative catalysts and processes to address the challenges of traditional processes. Exemplified by the discovery of robust Co-Co₂C/AC for FTS and Rh₁/POPs-PPh₃ for heterogeneous hydroformylation of olefins, it demonstrates how lab-scale fundamental understandings on the active sites of catalysts leads to pilot-plant scale-up and finally commercial technologies. Perspectives on the challenges and directions for future developments in these exciting fields are provided.

Key words: Commercialization, Fischer-Tropsch synthesis, Heterogeneous catalysis, Olefin hydroformylation, Processes development

赵子昂, 姜淼, 李存耀, 李怡蕙, 朱何俊, 林荣和, 袁慎峰, 严丽, 丁云杰. 费托合成与多相氢甲酰化技术耦合制高值化学品的研究进展[J]. 催化学报, 2025, 73: 16-38.

Ziang Zhao, Miao Jiang, Cunyao Li, Yihui Li, Hejun Zhu, Ronghe Lin, Shenfeng Yuan, Li Yan, Yunjie Ding. Integrated Fischer-Tropsch synthesis and heterogeneous hydroformylation technologies toward high-value commodities from syngas[J]. Chinese Journal of Catalysis, 2025, 73: 16-38.

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图/表 25

Fig. 1. Scope of this account.

Fig. 2. The 150 kt a-1 slurry phase reactor using the Co/AC catalyst for clean liquid fuels production in Yulin, Shaanxi, China.

Fig. 3. The 200 kt a-1 fix-bed reactor using the Co/SiO2 catalyst for high-quality wax production in Wuhai, Inner Mongolia, China.

Fig. 4. (a) Scheme of high alcohol synthesis over bi-functional catalysts from syngas. (b) The interface between metallic Co and Co2C phase and the formation mechanism of alcohol through CO dissociative adsorption and non-dissociative adsorption. Copyrights: (a) Adopted with permission from Ref. [25]. Copyright 2013, Elsevier. (b) Reprinted with permission from Ref. [16]. Copyright 2015, American Chemical Society.

Fig. 5. Schematic illustrations of the fine structure of Co2C@Co and Co@Co2C active sites (a) and the FTS mechanism on Co-Co2C catalyst (b). Copyrights: Adopted with permission from Ref. [17]. Copyright 2018, American Chemical Society.

Fig. 6. The reaction network of FTS reaction.

Fig. 7. (a) The synthesis route of Rh/POPs-PPh3 catalysts. (b) Stability of Rh/POPs-PPh3 catalysts in ethylene hydroformylation. (c) Sulfur poisoning and self-recovery of Rh/POPs-PPh3 catalysts. Copyrights: (a) Reprinted with permission from Ref. [18]. Copyright 2015, Elsevier. Reprinted with permission from Ref. [42]. Copyright 2023, John Wiley and Sons.

Fig. 8. 50 kt/a commercial facility of ethylene hydroformylation based on heterogeneous mononuclear Rh complex catalyst to produce propanal/n-propanol.

Fig. 9. (a) The synthesis method of Rh/POPs-1bp&10P catalysts. (b) Catalytic performance of Rh/POPs-bp&P catalysts in propylene hydroformylation. (c) Stability of Rh/POPs-1bp&10P catalysts in propylene hydroformylation. (d) The synthesis route of Rh/POPs-bp&P(OPh)3 catalysts. (e) In situ FTIR observed after syngas adsorption processes over Rh/POPs-bp&P(OPh)3 catalysts. (f) A plausible pathway after syngas adsorption on Rh/POPs-bp&P(OPh)3 catalysts. Reprinted with permission from Ref. [20]. Copyright 2016, Royal Society of Chemistry. Reprinted with permission from Ref. [43]. Copyright 2018, Elsevier.

Fig. 10. (a) The synthesis route of Rh/y-3v-POPs-PPh3 series catalysts. (b) 13C 2D R-SLF spectra and F1 dimension slices of 13C peak at 132 ppm spectra over Rh/y-3v-POPs-PPh3 series catalysts. (c) The synthesis route of Rh/m-3v-POPs-PPh3 catalyst. (d) Catalytic performance of 1-octene hydroformylation over Rh/m-3v-POPs-PPh3 catalyst. Reprinted with permission from Ref. [45]. Copyright 2021, Royal Society of Chemistry. Reprinted with permission from Ref. [46]. Copyright 2022, American Chemical Society.

Fig. 11. (a) The structure diagram of Rh/POPs-PPO&PPh3 series catalysts. (b) In situ DRIFTs with CO on Rh/POPs-PPO&PPh3 series catalysts. (c) Path I for linear aldehyde and path II for branched aldehyde formation. (d) DFT calculations for Rh/POPs-PPO&PPh3 series catalysts. Reprinted with permission from Ref. [47]. Copyright 2023, Elsevier.

Fig. 12. The mass fraction of each stage under different extraction ways. Reproduced with permission from Ref. [49].

Table 1 Main distillation fractions of FTS products.

Fraction	Main components
Fraction	Alcohol	Paraffin
Fraction I	C₁-C₃	C₅-C₇
Fraction II	C₄, C₅	C₈, C₉
Fraction III	C₆, C₇	C₁₀, C₁₁
Fraction IV	C₈, C₉	C₁₂, C₁₃
Fraction V	C₁₀, C₁₁	C₁₄, C₁₅
Fraction VI	C₁₂₊	C₁₆₊

Table 2 Systems whose LLE data have been measured.

System	T/K	Model	Ref.
Ethanol + butanol + octane + water	298.15	NRTL	[50]
Ethanol + butanol + nonane + water
Ethanol + butanol + octane + Nonane + water
Ethanol + butanol + octane + water + tetradecane	298.15	NRTL	[51]
Ethanol + butanol + nonane + water + tetradecane
Ethanol + butanol + octane + nonane + water + tetradecane
Ethanol + hexanol + decane + water	298.15	UNIQUAC	[52]
Ethanol + hexanol + undecane + water
Ethanol + heptanol + decane + water
Ethanol + heptanol + undecane + water
Ethanol + hexanol + heptanol + decane + undecane + water
Ethanol + octanol + dodecane + water	293.15 298.15 303.15	NRTL	[53]
Ethanol + octanol + Tridecane + water
Ethanol + nonanol + Dodecane + water
Ethanol + nonanol + Tridecane + water
Ethanol + octanol + nonanol + dodecane + tridecane + water
Ethanol + decanol + tetradecane + water	293.15 298.15 303.15	UNIQUAC	[54]
Ethanol + decanol + pentadecane + water
Ethanol + undecanol + tetradecane + water
Ethanol + undecanol + pentadecane + water
Ethanol + decanol + undecanol + tetradecane + pentadecane + water
Ethanol + decanol + undecanol + tetradecane + pentadecane + water + octadecane	303.15 308.15 313.15	UNIQUAC	[54]

Fig. 13. Comparison of experimental and predicted LLE mass fraction for different systems. (a) Ethanol + Butanol + Octane + Nonane + Water. Reproduced with permission from Ref. [50]. (b) Ethanol + Butanol + Octane + Nonane + Water + Tetradecane. Reproduced with permission from Ref. [51]. (c) Ethanol + Hexanol + Heptanol + Decane + Undecane + Water. Reproduced with permission from Ref. [52]. (d) Ethanol + Octanol + Nonanol + Dodecane + Tridecane + Water. Reproduced with permission from Ref. [53]. (e) Ethanol + Decanol + Undecanol + Tetradecane + Pentadecane + Water. Reproduced with permission from Ref. [54]. (f) Ethanol + Decanol + Undecanol + Tetradecane + Pentadecane + Water + Octadecane. Reproduced with permission from Ref. [54].

Fig. 14. Process flow chart for the separation of Fraction V. Reproduced with permission from Refs. [54].

Table 3 Optimized Operating Parameters for the separation of Fraction V. Reproduced with permission from Ref. [54].

Operation		Columns			Solvent ratio		NSTAGE
Extraction		T101			4		3
		T102			0.4		2
		T103			0.3		1
Operation	Columns		NSTAGE	FEED STAGE		Reflux ratio		Pressure (atm)
Distillation	T104		11	5		1.5		0.25
	T105		30	18		4.5		1
	T106		35	20		3.5		0.03
	T107		14	2		2		0.2
	T108		20	10		1.5		0.03

Table 4 Separation experimental results of Fractions II-V.

Fraction	Purity of products/%
Fraction	Alcohol	Paraffin
Fraction II	99.63	99.71
Fraction III	99.59	99.55
Fraction IV	99.53	99.58
Fraction V [54]	99.40	99.51

Fig. 15. Experimental and calculated values of interfacial tension for different high alcohol-hydrocarbon-ethanol-water systems. Reproduced with permission from Ref. [55].

Fig. 16. (a) Stability performance of 0.4% Na/ reveals that the purity of both sources of decanol is above 98%, but the types of γ-Al2O3 in n-decanol dehydration at T = 602 K, LHSV = 0.25 h-1. (b) Catalytic performance of 0.4% Na/γ-Al2O3 for C8-C12 α-alcohol dehydration: S1, α-olefin, S2, iso-olefin. (c) Correlations between α-decene yield and the acid-base amounts of catalysts. Copyrights: Reprinted with permission from Ref. [66]. Copyright 2020, American Chemical Society.

Fig. 17. (a) Comparison on the performance of 0.4% Na/γ-Al2O3 in dehydration of different-decanol at 585-588 K and LHSV = 0.4 h-1. (b) Long-term stability performance of 1 L pellet catalyst (1-2 mm diameter) in a pilot plant test, using FTS-derived n-decanol as feed. (c) Ten-kilogram scale FTS-derived α-decene from the pilot test.

Fig. 18. Ambience (a) and high-pressure setup (b) for PAO synthesis. (c,d) Conversion and KV100 of the crude polymerization products under different conditions: 1-decene 150 g, t = 2 h, (c) nZr/n1-decene = 4 × 10-5, nAl/nZr = 100, T = 408 K, P = 1 atm; (d) nZr/n1-decene = 6 × 10-5, nAl/nZr = 70, t = 2 h, PH2 = 2 MPa, catalyst diluted in 3 times toluene.

Fig. 19. Comparison on KV100 (a), KV 40 (b), and viscosity index (c) of PAO4, 6, 8, 20, 40 from different companies.

Fig. 20. (a,b) The n-heptanol conversion (X) and product selectivity (S) on different catalysts. The reaction kinetics (c) and cycling perofrmance (d) of PtBi/NC0.01. (e) Performance of PtBi/NC0.01 in the oxidation of C5-C9 linear n-alcohols, benzyl alcohol, and cyclopentanol. (f) Comparison of TOF between PtBiNC0.01 and the previously reported catalysts. Reaction conditions: toluene 12 cm3, (a-d) n-heptanol 3.5 mmol, (a,b) Wcat. = 50 mg, T = 383 K, P = 0.1 MPa, t = 15 min; (c,d) Wcat. = 100 mg, T = 393 K, P = 0.2 MPa, d, t = 5 h; (e) substrates 2.4 mmol, P = 0.2 MPa, Wcat. = 50 and 100 mg for n-pentanol and the other alcohols, respectively. Copyrights: Reprinted with permission from Ref. [73]. Copyright 2023, American Chemical Society.

Abbreviations

Abbreviation	Full name
ASF	Anderson-Schulz-Flory
CGT	Concentration gradient theory
DFT	Density functional theory
DICP	Dalian Institute of Chemical Physics
DRIFTs	Diffuse reflectance infrared Fourier transform spectroscopy
EXAFS	Extended X-ray absorption fine structure
fcc	Faced centered cubic
FTIR	Fourier transform infrared spectroscopy
FTS	Fischer-Tropsch synthesis
GHSV	Gas hourly space velocity
HAADF-STEM	High-angle annular dark-field scanning transmission election microscope
HAS	High alcohol synthesis
HRTEM	High-resolution transmission electron spectroscopy
hcp	Hexagonal close-packed
LAO	Linear α-olefins
LHSV	Liquid hourly space velocity
LLE	Liquid-liquid equilibrium
PAO	Poly-α-olefins
POPs-PPh₃	Porous organic polymers
r_c	Reaction rate
Rh₁/POPs-PPh₃	Porous organic polymer-stabilized mononuclear Rh complex
TOF	Turnover frequency
XANES	X-ray absorption near edge structure
XPS	X-ray photoelectron spectroscopy
XRD	X-ray diffraction

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费托合成与多相氢甲酰化技术耦合制高值化学品的研究进展

Integrated Fischer-Tropsch synthesis and heterogeneous hydroformylation technologies toward high-value commodities from syngas

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