Recent progress on bimetallic catalysts for the production of fuels and chemicals from biomass and plastics by hydrodeoxygenation

doi:10.1016/S1872-2067(24)60054-9

Chinese Journal of Catalysis ›› 2024, Vol. 62: 1-31.DOI: 10.1016/S1872-2067(24)60054-9

Recent progress on bimetallic catalysts for the production of fuels and chemicals from biomass and plastics by hydrodeoxygenation

Lujie Liu^a, Ben Liu^b, Yoshinao Nakagawa^b^,^*(), Sibao Liu^c, Liang Wang^a, Mizuho Yabushita^b, Keiichi Tomishige^b^,^d^,^*()

^aKey Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China
^bDepartment of Applied Chemistry, School of Engineering, Tohoku University, 6-6-07, Aoba, Aramaki, Aoba-ku, Sendai 980-8579, Japan
^cEngineering Research Center of Polymer Green Recycling of Ministry of Education, Fujian Key Laboratory of Pollution Control & Resource Reuse, College of Environmental and Resources, Fujian Normal University, Fuzhou 350007, Fujian, China
^dAdvanced Institute for Materials Research (WPI-AIMR), Tohoku University, Katahira 2-1-1, Aoba-ku, Sendai, 980-8577, Japan

Received:2024-04-16 Accepted:2024-05-18 Online:2024-07-18 Published:2024-07-10
Contact: *E-mail: yoshinao@erec.che.tohoku.ac.jp (Y. Nakagawa), tomishige@tohoku.ac.jp (K. Tomishige).
About author:Yoshinao Nakagawa (Tohoku University) received his Ph.D. in 2005 from the Graduate School of Engineering, the University of Tokyo. After 4 years of postdoctoral research in the University of Tokyo, he joined the research group of Keiichi Tomishige at University of Tsukuba. He moved to Tohoku University and became an assistant professor in 2010. Since 2013, he has been an associate professor. His current research interests are selective catalytic oxidations and reductions, especially those of biomass-related compounds.
Keiichi Tomishige received his B.S., M.S. and Ph.D. from the Graduate School of Science, Department of Chemistry, the University of Tokyo. During his Ph.D. course in 1994, he moved to the Graduate School of Engineering, The University of Tokyo as a research associate. In 1998, he became a lecturer, and then he moved to Institute of Materials Science, University of Tsukuba as a lecturer in 2001. Since 2004 he has been an associate professor, Graduate School of Pure and Applied Sciences, University of Tsukuba. Since 2010, he has been a professor, School of Engineering, Tohoku University. His research interests are the development of heterogeneous catalysts for production of biomass-derived chemicals and non-reductive CO₂ conversion. He has also a role of Associate Editor of Green Chemistry.
First author contact:
^†Present address: Department of Chemistry, Fudan University, Shanghai 200433, China.
Supported by:
Japan Society for the Promotion of Science(23H05404);Japan Society for the Promotion of Science(23K20034);National Natural Science Foundation of China(22202176);National Natural Science Foundation of China(22208243);National Natural Science Foundation of China(52276209);Postdoctoral Fellowship Program of CPSF(GZB20240650);China Postdoctoral Science Foundation(2021M702802)

Abstract

Abstract:

Valorization of biomass and plastics is an urgent assignment to achieve the goal of carbon neutrality. Hydrodeoxygenation using bimetallic catalysts with distinct active sites is one of the most effective approaches to producing fuels and chemicals via C-O/C-C bonds hydrogenolysis and hydrogenation. Rational design of bimetallic catalysts has been progressed in recent studies owing to the understanding of synergy and strong mutual interaction between metal nanoparticles and metal oxide species. Thus, activity of bimetallic catalysts has been further improved, and the chemoselectivity for suppression of C-C bond dissociation and the regioselectivity among different C-O bonds, which have less been achieved before, are realized in the hydrodeoxygenation reactions. The catalytic performances, catalyst structures, and reaction mechanisms are directly compared and discussed in details based on the C-O bond cleavage using glycerol and 1,2-propanediol hydrogenolysis as model reactions over Ir-, Pt-, and Ru-based bimetallic catalysts. Finally, application of these bimetallic catalysts to conversion of lignocellulose-derived feedstocks, carbonyl compounds, and typical plastic of polycarbonates is introduced.

Key words: Hydrodeoxygenation, Hydrogenolysis, Bimetallic catalyst, Biomass derivative, Plastic waste

Lujie Liu, Ben Liu, Yoshinao Nakagawa, Sibao Liu, Liang Wang, Mizuho Yabushita, Keiichi Tomishige. Recent progress on bimetallic catalysts for the production of fuels and chemicals from biomass and plastics by hydrodeoxygenation[J]. Chinese Journal of Catalysis, 2024, 62: 1-31.

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Entry	Catalyst	P(H₂)/MPa	Temp./K	Conv./%	Target product [selectivity/%]	Average rate g_{target product} g_NM^‒1 h^‒1	Initial rate g_{target product} g_NM^‒1 h^‒1	Note	Ref.
1	Ir-ReO_x/SiO₂ (4 wt% Ir, Re/Ir = 1) + H₂SO₄	8	393	81	1,3-PrD [46]	5.7	18	highest 1,3-PrD formation rate until 2018	[48]
2	Ir-ReO_x/SiO₂ (4 wt% Ir, Re/Ir = 1) + HZSM-5	8	393	>99.9	propane [98]	1.1	—	total HDO	[49]
3	Ir-ReO_x/SiO₂ (20 wt% Ir, Re/Ir = 0.34)	8	393	69	1,3-PrD [47]	7.4	22	improved activity by high surface concentration of active metals	[33]
4	Ir-ReO_x/TiO₂ (4 wt% Ir, Re/Ir = 0.24)	8	393	69	1,3-PrD [52]	17	52	small surface area support; highest activity among Ir-based catalysts	[50]
5	Ir-FeO_x/TiO₂ (5 wt% Ir, Fe/Ir=0.25)	8	453	>99.9	2-PrOH [30]	0.028	—	first catalyst with high selectivity in 1,2-diols to 2-mono-ols; small surface area support	[36]
5	Ir-FeO_x/TiO₂ (5 wt% Ir, Fe/Ir=0.25)	8	453	29	1,2-PrD [79]	—	0.4		[36]
6	Ir-Fe-Mo/BN (20 wt% Ir, Fe/Ir = 0.13, Mo/Ir = 0.08)	8	453	32	1,2-PrD [75]	—	2.5	highly efficient-trimetallic alloy catalyst for 1,2-diols to 2-mono-ols; small surface area support	[51]
7	Pt/WO_x/AlOOH (1.8 wt% Pt, 8 wt% W)	5	453	100	1,3-PrD [66]	2.3	—	highest 1,3-PrD yield until 2022	[52]
8	Au-Pt/WO₃/Al₂O₃ (0.1 wt% Au, 2 wt% Pt, 7.5 wt% W)	5	453	78	1,3-PrD [55]	1.7	—	activity increase by Au addition (ca. two-fold increase)	[53]
9	Pt/meso-WO_x (2 wt% Pt)	1	413	60	1,3-PrD [36]	0.7	—	single/pseudo-single atom Pt catalyst under low H₂ pressure of 1 MPa	[54]
9	Pt/meso-WO_x (2 wt% Pt)	1	433	16	1,3-PrD [34]	—	3.8		[54]
10	Pt-AlO_x/WO₃(0.4 wt% Pt, 0.2 wt% Al)	3	453	90	1,3-PrD [44]	7.5	—	most effective among WO_x-supported ones	[55]
11	Pt-WO_x/t-ZrO₂ (1.9 wt% Pt, ~7.6 wt% W)	8	413	76	1,3-PrD [65]	5.1	—	most effective among ZrO₂-supported ones	[56]
12	Pt/W-SBA-15 (3 wt% Pt, W/Si=1/640)	4	423	87	1,3-PrD [71]	1.7	—	first report of effective Pt-W catalyst using silica-based support and small W amount	[57]
13	Pt/WO_x/T-Ta₂O₅ (0.68 wt% Pt, 0.51 wt% W)	5	433	87	1,3-PrD [46]	19	—	highest 1,3-PrD formation rate	[58]
14	Pt/Nb₁₄W₃O₄₄ (3 wt% Pt)	8	423	100	1,3-PrD [75]	17	30	highest 1,3-PrD yield & good activity	[59]
15	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt=0.25)	8	413	100	1,3-PrD [57]	2.5	6.5	highest 1,3-PrD yield among catalysts using conventional stable support	[60]
15	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt=0.25)	7	453	100	1-PrOH [65]	3.8	—	overhydrogenolysis of 1-PrOH does not occur	[61]
16	Ru/C (5 wt% Ru) + Amberlyst 15	8	393	79	1,2-PrD [75]	0.13	—	typical system of Ru + acid	[62]
17	Ru-ReO_x/SiO₂ (3.2 wt% Ru, 3.6 wt% Re)	8	433	52	1,2-PrD [45]	20	—	activity increase and suppression of C-C dissociation by Re; similar catalyst used for 1,2-PrD to mixture of PrOHs	[63]
18	Ru-MoO_x/CNTs (2 wt% Ru, 5 wt% Mo)	4	473	47	1,2-PrD [67]	39	—	suppression of C-C dissociation by Mo	[64]
19	Ru-WO_x/C (5 wt% Ru, 2 wt% W)	5	423	73	1,2-PrD [97]	3.2	—	very high suppression of C-C dissociation by W	[65]
20	Rh-ReO_x/SiO₂ (4 wt% Rh, Re/Rh = 0.5)	8	393	100	1-PrOH [76]	11	—	high activity at low temperature; low regioselectivity in diol formation	[42]

Entry	Catalyst	P(H₂)/MPa	Temp./K	Conv./%	Target product [selectivity/%]	Average rate g_{target product} g_NM^‒1 h^‒1	Initial rate g_{target product} g_NM^‒1 h^‒1	Note	Ref.
1	Ir-ReO_x/SiO₂ (4 wt% Ir, Re/Ir = 1) + H₂SO₄	8	393	81	1,3-PrD [46]	5.7	18	highest 1,3-PrD formation rate until 2018	[48]
2	Ir-ReO_x/SiO₂ (4 wt% Ir, Re/Ir = 1) + HZSM-5	8	393	>99.9	propane [98]	1.1	—	total HDO	[49]
3	Ir-ReO_x/SiO₂ (20 wt% Ir, Re/Ir = 0.34)	8	393	69	1,3-PrD [47]	7.4	22	improved activity by high surface concentration of active metals	[33]
4	Ir-ReO_x/TiO₂ (4 wt% Ir, Re/Ir = 0.24)	8	393	69	1,3-PrD [52]	17	52	small surface area support; highest activity among Ir-based catalysts	[50]
5	Ir-FeO_x/TiO₂ (5 wt% Ir, Fe/Ir=0.25)	8	453	>99.9	2-PrOH [30]	0.028	—	first catalyst with high selectivity in 1,2-diols to 2-mono-ols; small surface area support	[36]
5	Ir-FeO_x/TiO₂ (5 wt% Ir, Fe/Ir=0.25)	8	453	29	1,2-PrD [79]	—	0.4		[36]
6	Ir-Fe-Mo/BN (20 wt% Ir, Fe/Ir = 0.13, Mo/Ir = 0.08)	8	453	32	1,2-PrD [75]	—	2.5	highly efficient-trimetallic alloy catalyst for 1,2-diols to 2-mono-ols; small surface area support	[51]
7	Pt/WO_x/AlOOH (1.8 wt% Pt, 8 wt% W)	5	453	100	1,3-PrD [66]	2.3	—	highest 1,3-PrD yield until 2022	[52]
8	Au-Pt/WO₃/Al₂O₃ (0.1 wt% Au, 2 wt% Pt, 7.5 wt% W)	5	453	78	1,3-PrD [55]	1.7	—	activity increase by Au addition (ca. two-fold increase)	[53]
9	Pt/meso-WO_x (2 wt% Pt)	1	413	60	1,3-PrD [36]	0.7	—	single/pseudo-single atom Pt catalyst under low H₂ pressure of 1 MPa	[54]
9	Pt/meso-WO_x (2 wt% Pt)	1	433	16	1,3-PrD [34]	—	3.8		[54]
10	Pt-AlO_x/WO₃(0.4 wt% Pt, 0.2 wt% Al)	3	453	90	1,3-PrD [44]	7.5	—	most effective among WO_x-supported ones	[55]
11	Pt-WO_x/t-ZrO₂ (1.9 wt% Pt, ~7.6 wt% W)	8	413	76	1,3-PrD [65]	5.1	—	most effective among ZrO₂-supported ones	[56]
12	Pt/W-SBA-15 (3 wt% Pt, W/Si=1/640)	4	423	87	1,3-PrD [71]	1.7	—	first report of effective Pt-W catalyst using silica-based support and small W amount	[57]
13	Pt/WO_x/T-Ta₂O₅ (0.68 wt% Pt, 0.51 wt% W)	5	433	87	1,3-PrD [46]	19	—	highest 1,3-PrD formation rate	[58]
14	Pt/Nb₁₄W₃O₄₄ (3 wt% Pt)	8	423	100	1,3-PrD [75]	17	30	highest 1,3-PrD yield & good activity	[59]
15	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt=0.25)	8	413	100	1,3-PrD [57]	2.5	6.5	highest 1,3-PrD yield among catalysts using conventional stable support	[60]
15	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt=0.25)	7	453	100	1-PrOH [65]	3.8	—	overhydrogenolysis of 1-PrOH does not occur	[61]
16	Ru/C (5 wt% Ru) + Amberlyst 15	8	393	79	1,2-PrD [75]	0.13	—	typical system of Ru + acid	[62]
17	Ru-ReO_x/SiO₂ (3.2 wt% Ru, 3.6 wt% Re)	8	433	52	1,2-PrD [45]	20	—	activity increase and suppression of C-C dissociation by Re; similar catalyst used for 1,2-PrD to mixture of PrOHs	[63]
18	Ru-MoO_x/CNTs (2 wt% Ru, 5 wt% Mo)	4	473	47	1,2-PrD [67]	39	—	suppression of C-C dissociation by Mo	[64]
19	Ru-WO_x/C (5 wt% Ru, 2 wt% W)	5	423	73	1,2-PrD [97]	3.2	—	very high suppression of C-C dissociation by W	[65]
20	Rh-ReO_x/SiO₂ (4 wt% Rh, Re/Rh = 0.5)	8	393	100	1-PrOH [76]	11	—	high activity at low temperature; low regioselectivity in diol formation	[42]

Catalyst (reduction method, reduction temperature/K)	Ir amount /wt%	Re/Ir ratio	D_CO/%	d_TEM/nm	Coverage ^a/%	Valence of Ir		Valence of Re
Catalyst (reduction method, reduction temperature/K)	Ir amount /wt%	Re/Ir ratio	D_CO/%	d_TEM/nm	Coverage ^a/%	XPS	XANES	XPS	XANES
Ir-ReO_x/SiO₂ (G,^b 473)	4	0.83^d	16	2.0	70	0	0	0‒+4	+2.8‒3.1
Ir-ReO_x/SiO₂ (G,^b 473)	20	0.34^d	18	—	47	—	0	—	+2.7
(L,^c 473)	20	0.34^d	18	3.2	54	—	0	—	+1.1
Ir-ReO_x/TiO₂ (G,^b 573)	4	0.30^d	34	1.8	62	0.7	0.5	3.2	+2.7
Ir-ReO_x/TiO₂ (G,^b 573)	4	0.24^e	33	1.9	62	0.7	0.5	3.2	+3.1

Catalyst (reduction method, reduction temperature/K)	Ir amount /wt%	Re/Ir ratio	D_CO/%	d_TEM/nm	Coverage ^a/%	Valence of Ir		Valence of Re
Catalyst (reduction method, reduction temperature/K)	Ir amount /wt%	Re/Ir ratio	D_CO/%	d_TEM/nm	Coverage ^a/%	XPS	XANES	XPS	XANES
Ir-ReO_x/SiO₂ (G,^b 473)	4	0.83^d	16	2.0	70	0	0	0‒+4	+2.8‒3.1
Ir-ReO_x/SiO₂ (G,^b 473)	20	0.34^d	18	—	47	—	0	—	+2.7
(L,^c 473)	20	0.34^d	18	3.2	54	—	0	—	+1.1
Ir-ReO_x/TiO₂ (G,^b 573)	4	0.30^d	34	1.8	62	0.7	0.5	3.2	+2.7
Ir-ReO_x/TiO₂ (G,^b 573)	4	0.24^e	33	1.9	62	0.7	0.5	3.2	+3.1

Catalyst	Ir amount /wt%	Re/Ir ratio	Shells	CN	R/nm
Ir-ReO_x/SiO₂^a	4	0.83	Re-O	1.4	0.202
Ir-ReO_x/SiO₂^a	4	0.83	Re-Ir (or -Re)	6.2	0.268
Ir-ReO_x/SiO₂^b	20	0.34	Re-O	0.8	0.214
Ir-ReO_x/SiO₂^b	20	0.34	Re-Ir (or -Re)	8.6	0.268
Ir-ReO_x/TiO₂^c	4	0.24	Re-O	0.6	0.211
Ir-ReO_x/TiO₂^c	4	0.24	Re-Ir (or -Re)	8.8	0.264

Recent progress on bimetallic catalysts for the production of fuels and chemicals from biomass and plastics by hydrodeoxygenation

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Catalyst	Re/Ir ratio	Condition	Reaction order
4 wt%-Ir Ir-ReO_x/SiO₂	0.83	20 wt%-67 wt% glycerol aq., 8 MPa H₂, 393 K	~0.0 (glycerol)
4 wt%-Ir Ir-ReO_x/SiO₂	0.83	67 wt% glycerol aq., 2-8 MPa H₂, 393 K	~1.0 (H₂)
20 wt%-Ir Ir-ReO_x/SiO₂	0.34	20 wt%-67 wt% glycerol aq., 8 MPa H₂, 393 K	0.03 (glycerol)
20 wt%-Ir Ir-ReO_x/SiO₂	0.34	67 wt% glycerol aq., 2-8 MPa H₂, 393 K	1.1 (H₂)
4 wt%-Ir Ir-ReO_x/TiO₂	0.24	40 wt%-80 wt% glycerol aq., 8 MPa H₂, 393 K	0.2 (glycerol)
4 wt%-Ir Ir-ReO_x/TiO₂	0.24	67 wt% glycerol aq., 2-8 MPa H₂, 393 K	0.9 (H₂)

Catalyst	Substrate	t/h	Conv./%	C-based main products (selectivity/%)
Ir_c-r-FeO_x/TiO₂^a	1,2-PrD	24	14.5	2-PrOH (56.0), 1-PrOH (24.6)
	1,2-PrD	72 ^b	97.1	2-PrOH (54.2), 1-PrOH (22.8)
	Glycerol	24	29.2	1,2-PrD (79.4), 2-PrOH (1.5), 1-PrOH (8.6)
		42 ^b	93.7	1,2-PrD (66.7), 2-PrOH (4.7), 1-PrOH (13.1)
		144	>99.9	2-PrOH (30.4), 1-PrOH (32.1)
Ir-FeO_x/BN	1,2-PrD	24	11.5	2-PrOH (62.6), 1-PrOH (17.0)
Ir-FeO_x/BN	Glycerol	24	28.5	1,2-PrD (83.9), 2-PrOH (1.0), 1-PrOH (8.6)

Catalyst	Fe/Ir ratio	Particle size/nm		Valence of Ir (XANES)	Valence of Fe (XANES) Fe³⁺/Fe²⁺/Fe⁰	Shells	CN	R/nm
Catalyst	Fe/Ir ratio	d_XRD	d_TEM	Valence of Ir (XANES)	Valence of Fe (XANES) Fe³⁺/Fe²⁺/Fe⁰	Shells	CN	R/nm
Ir_c-r-FeO_x/TiO₂	0.25	3.4	3.4	0.7	9/26/65	Fe-O	1.4	0.197
	0.25	3.4	3.4	0.7	9/26/65	Fe-Ir	4.8	0.263
	1	3.6	3.4	1.9	21/54/25	Fe-O	2.3	0.199
						Fe-Ir	2.5	0.268
						Fe-(O)-Fe	1.4	0.287
Ir-FeO_x/BN	0.25	2.4	1.7	0.6	1/23/76	Fe-O	0.4	0.201
Ir-FeO_x/BN	0.25	2.4	1.7	0.6	1/23/76	Fe-Ir	5.1	0.262

W/Pt ratio	Shells	CN	R/nm	Conv.^a /%	Selectivity to 1,3-PrD^a/%
0.063	W-Pt (or -W)	5.5	0.269	<2	—
	W-O	1.7	0.193
	W=O	1.4	0.173
0.13	W-Pt (or -W)	3.6	0.268	9	56
	W-O	1.3	0.193
	W=O	1.5	0.173
0.25	W-Pt (or -W)	2.8	0.264	56	65
	W-O	1.6	0.195
	W=O	1.3	0.175
0.5	W-Pt (or -W) W-O W=O	2.7	0.263	8	56
		2.3	0.198
		1.4	0.179
1	W-Pt (or -W)	2.4	0.264	<2	—
	W-O	2.6	0.198
	W=O	1.4	0.178

Gas/solvent (reaction system)	α-C		β-C
Gas/solvent (reaction system)	-CH₂-	-CHD-	-CH₂-	-CHD-
D₂/H₂O (A)	100%	n.d.	100%	n.d.
H₂/D₂O (B)	0%	100%	19%	81%

Re/Ru ratio	Shells	CN	R/nm	Average valence of Re (XANES)	ReO_x species
0.5	Re-Ru	2.6	0.267	+1.0	ReO_x clusters (major), Re metal particles (minor)
	Re-Re	2.1	0.273
	Re-O	1.7	0.204
1	Re-Ru	1.7	0.265	+1.8	ReO_x clusters (minor), Re metal particles (major)
	Re-Re	8.0	0.273
	Re-O	1.4	0.199

Substrate	Catalyst	Temp./K	P(H₂) /MPa	Conv. /%	Selectivity (main product)/%	Average rate mmol_{target product} g_catal.^‒1 h^‒1	Ref.
Erythritol	Ir-ReO_x/SiO₂ (4 wt% Ir, Re/Ir=1)	373	8	47	25 (1,4-BuD)	0.26	[113]
	Ir-ReO_x/SiO₂ (4 wt% Ir, Re/Ir=1)	373	8	97	35 (1-BuOH)	0.19
	Ir-ReO_x/TiO₂(4 wt% Ir, Re/Ir=0.25)	373	8	36	33 (1,4-BuD)	0.81
	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt=0.25)	413	8	99	54 (1,4-BuD)	0.22	[61]
	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt=0.25)	453	7	100	57 (1-BuOH)	0.39	[61]
	Pt/W/Ti-SBA-15 (4 wt% Pt, W/Pt=0.25)	463	5	94	35 (1,4-BuD)	0.27	[119]
	Ir_c-r-FeO_x/TiO₂(5 wt% Ir, Fe/Ir=0.25)	453	8	100	30 (2,3-BuD)	0.03	[36]
	Ir-FeO_x/BN (5 wt% Ir, Fe/Ir=0.25)	453	8	100	32 (2,3-BuD)	0.03	[37]
	Ir-Fe-Mo/BN (20 wt% Ir, Fe/Ir=0.13, Mo/Ir=0.08)	453	8	>99	36 (2,3-BuD)	1.0	[51]
	Ru-ReO_x/TiO₂ (P25, 2 wt% Ru, Re/Ru=1)	473	2.5	100	55.0 (diols mixture)	1.3	[69]
	Rh-ReO_x/ZrO₂ (4 wt% Rh, Re/Rh=0.5)	473	12	80	29 (diols mixture)	1.5	[116,117]
	Ru-MoO_x/Mo₂C (2 wt% Ru, Mo/Ru=1)	513	4	100	38 (BuOHs mixture)	0.12	[118]
1,4-AHERY	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt=0.25)	413	8	100	54 (1,3-BuD)	0.16	[60]
1,4-AHERY	Rh-MoO_x/SiO₂ (4 wt% Rh, Mo/Rh=0.13)	393	8	100	51 (2-BuOH)	1.0	[120]

Substrate	Catalyst	Temp. /K	P(H₂) /MPa	Additive /solvent	Conv. /%	Yield (main product) /%-C	Ref.
Xylitol	Ir-ReO_x/SiO₂(4 wt% Ir, Re/Ir = 1)	413	8	HZSM-5/n-dodecane+ water	100	18 (1-PeOH), 19 (2-/3-PeOHs)	[49]
	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt = 0.25)	453	7	None/water	100	30 (1-PeOH), 9 (2-PeOH), 20 (3-PeOH)	[61]
	Ru-MoO_x/Mo₂C (2 wt% Ru, Mo/Ru = 1)	513	4	None/water	100	28 (1-PeOH), 7 (2-PeOH), 1 (3-PeOH)	[118]
	Ru/MnO_x/C	473	6	None/water	80	22 (glycols), 10 (glycerol)	[121]
Xylan	Ir-ReO_x/SiO₂ (4 wt% Ir, Re/Ir = 2)	413	6	H₂SO₄/n-dodecane+ water	97	<1 (1-PeOH), 14 (2-PeOH), 18 (3-PeOH)	[122]

Substrate	Catalyst	Temp. /K	P(H₂) /MPa	Additive /solvent	Yield (main product)/%-C	Ref.
Sorbitol	Ir-ReO_x/SiO₂(4 wt% Ir, Re/Ir = 1)	413	8	None/n-dodecane+water	36 (3-HxOH), 8 (2-HxOH), <1(1-HxOH)	[49]
	Pt-WO_x/SiO₂ (4 wt% Pt, W/Pt = 0.25)	453	8	None/water	36 (3-HxOH), 12 (2-HxOH), 12 (1-HxOH)	[61]
	Ru-MoO_x/CMK-3 (2 wt% Ru, Mo/Ru = 1)	523	4	None/water	7 (HxOHs), 17 (1,6-HxD)	[129]
	Ru-WO_x/CNT (4 wt% Ru, W/Ru = 0.25)	478	5	Ca(OH)₂/water	35 (1,2-PrD), 26 (EG)	[130]
Cellulose	Ir-ReO_x/SiO₂(4 wt% Ir, Re/Ir = 2)	413	8	H₂SO₄/n-decane+water	40 (3-HxOH), 18 (2-HxOH), 2 (1-HxOH)	[125]
	Ru-WO_x/Biochar (5 wt% Ru, W/Ru = 4.4)	493	3	None/water	69 (EG)	[126]
	Ru-WO_x/HZSM-5 (5 wt% Ru, W/Ru = 2.8)	508	3	None/water	77 (Ethanol)	[127]
	Pt/WO_x (2 wt% Pt)	518	6	None/water	30 (Ethanol)	[128]
	MoO_x/Pt/WO_x (2 wt% Pt, Mo/Pt = 0.1)	518	6	None/water	43 (Ethanol)	[128]

Catalyst	Substrate	Temp./K	P(H₂)/MPa	Additive/solvent	Yield (main product)/%-C	Ref.
Ir-ReO_x/SiO₂(4 wt% Ir, Re/Ir = 1)	xylitol	413	8	HZSM-5/n-dodecane+water	96 (n-pentane)	[49]
Ir-ReO_x/SiO₂(4 wt% Ir, Re/Ir = 2)	xylan	463	6	H₂SO₄+HZSM-5/n-dodecane+water	70 (n-pentane)	[125]
Ir-ReO_x/SiO₂(4 wt% Ir, Re/Ir = 1)	sorbitol	413	8	HZSM-5/n-dodecane+water	95 (n-hexane)	[49]
Ir-ReO_x/SiO₂(4 wt% Ir, Re/Ir = 2)	cellulose	453	6	H₂SO₄/n-decane+water	84 (n-hexane)	[125]
Ir-WO_x/SiO₂(4 wt% Ir, W/Ir = 0.06)	cellulose	483	8	HZSM-5/n-dodecane+water	85 (C6 alkanes)	[147]

Catalyst	M'/M	Yield /% (based on C6 ring)
Catalyst	M'/M	C15 cycloalkane	C7,C8,C9 cycloalkanes	C7,C8,C9 oxygenates (1O)	Aromatics	S-C15 oxygenates (1O)	US-C15 oxygenates (1O)	C15 oxygenates (2O)
Ru-ReO_x/SiO₂	0.5	93	5	1	1	0	0	0
Pt-ReO_x/SiO₂	0.5	0	0	0	<1	<1	<1	<1
Pd-ReO_x/SiO₂	0.5	<1	0	<1	1	<1	<1	<1
Ir-ReO_x/SiO₂	0.5	<1	0	<1	<1	<1	<1	<1
Rh-ReO_x/SiO₂	0.5	32	2	1	<1	3	1	<1
Ru-MoO_x/SiO₂	0.5	2	1	2	<1	5	1	1
Ru-WO_x/SiO₂	0.5	6	2	2	<1	6	<1	1
Ru/SiO₂	0	<1	1	3	1	1	1	1
Ru-ReO_x/SiO₂	0.05	31	4	2	<1	45	0	4
Ru-ReO_x/SiO₂	0.13	73	5	1	<1	18	0	<1
Ru-ReO_x/SiO₂	0.25	90	5	1	<1	1	0	<1
Ru-ReO_x/SiO₂	1	46	3	2	<1	44	0	<1
ReO_x/SiO₂	—	<1	<1	<1	<1	<1	<1	<1
Ru/SiO₂+ReO_x/SiO₂	—	1	<1	1	<1	1	2	1

Catalyst	M'/M	Yield /% (based on C6 ring)
Catalyst	M'/M	C15 cycloalkane	C7,C8,C9 cycloalkanes	C7,C8,C9 oxygenates (1O)	Aromatics	S-C15 oxygenates (1O)	US-C15 oxygenates (1O)	C15 oxygenates (2O)
Ru-ReO_x/SiO₂	0.5	93	5	1	1	0	0	0
Pt-ReO_x/SiO₂	0.5	0	0	0	<1	<1	<1	<1
Pd-ReO_x/SiO₂	0.5	<1	0	<1	1	<1	<1	<1
Ir-ReO_x/SiO₂	0.5	<1	0	<1	<1	<1	<1	<1
Rh-ReO_x/SiO₂	0.5	32	2	1	<1	3	1	<1
Ru-MoO_x/SiO₂	0.5	2	1	2	<1	5	1	1
Ru-WO_x/SiO₂	0.5	6	2	2	<1	6	<1	1
Ru/SiO₂	0	<1	1	3	1	1	1	1
Ru-ReO_x/SiO₂	0.05	31	4	2	<1	45	0	4
Ru-ReO_x/SiO₂	0.13	73	5	1	<1	18	0	<1
Ru-ReO_x/SiO₂	0.25	90	5	1	<1	1	0	<1
Ru-ReO_x/SiO₂	1	46	3	2	<1	44	0	<1
ReO_x/SiO₂	—	<1	<1	<1	<1	<1	<1	<1
Ru/SiO₂+ReO_x/SiO₂	—	1	<1	1	<1	1	2	1

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Catalyst	Re/M ratio	Conv. /%	Selectivity /%-C
Catalyst	Re/M ratio	Conv. /%	n-C18 alkane	n-C17 alkane	n-C16 alkane	Stearyl alcohol
ReO_x/SiO₂	—	6	6	1	0	93
Ir-ReO_x/SiO₂	3	100	94	6	<1	0
Ru-ReO_x/SiO₂	3	100	52	41	4	0
Pd-ReO_x/SiO₂	3	15	2	3	0	95
Pt-ReO_x/SiO₂	3	11	12	4	<1	84
Rh-ReO_x/SiO₂	3	48	7	22	<1	70
Ir-ReO_x/SiO₂	0.5	25	28	8	<1	64
Ir-ReO_x/SiO₂	1	32	27	7	<1	66
Ir-ReO_x/SiO₂	2	70	43	5	<1	52
Ir-ReO_x/SiO₂	2.5	99	47	5	<1	47
Rh-ReO_x/SiO₂	0.5	5	5	47	0	48

Substrate	Catalyst	Reaction conditions	Conv. /%	Amine yield /%	Ref.
Hexanamide	Ru-WO_x/MgAl₂O₄ (4 wt% Ru, W/Ru = 8)	473 K, 5 MPa H₂, 0.5 MPa NH₃, 16 h, cyclopentyl methyl ether (CPME) solvent	>99	83	[210]
CyCONH₂	Ru-WO_x/MgAl₂O₄ (4 wt% Ru, W/Ru = 8)		>99	80	[210]
CyCONH₂	Ru-WO_x/SiO₂(2 wt% Ru, 1 wt% W)	433 K, 5 MPa H₂, 12 h, 1,2-dimethoxyethane (DME) solvent	94	78	[102]
	Ru-MoO_x/SiO₂(2 wt% Ru, 0.2 wt% Mo)	433 K, 5 MPa H₂, 12 h, DME solvent	90	73	[214]
	Rh-MoO_x/SiO₂ (4 wt% Rh, Mo/Rh = 1) +CeO₂	413 K, 8 MPa H₂, 4 h, DME solvent	>95	63	[209]