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

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

Chinese Journal of Catalysis ›› 2025, Vol. 73: 16-38.DOI: 10.1016/S1872-2067(25)64701-2

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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)

Abstract

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

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

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