Abstract
Bio-oil from biomass pyrolysis cannot directly substitute traditional fuel due to compositional deficiencies. Catalytic hydrodeoxygenation (HDO) is the critical and efficient step to upgrade crude bio-oil to high-quality bio-jet fuel by lowering the oxygen content and increasing the heating value. However, the hydrocracking reaction tends to reduce the liquid yield and increase the gas yield, causing carbon loss and producing hydrocarbons with a short carbon-chain. To obtain high-yield bio-jet fuel, the elucidation of the conversion process of biomass catalytic HDO is important in providing guidance for metal catalyst design and optimization of reaction conditions. Considering the complexity of crude bio-oil, this review aimed to investigate the catalytic HDO pathways with model compounds that present typical bio-oil components. First, it provided a comprehensive summary of the impact of physical and electronic structures of both noble and non-noble metals that include monometallic and bimetallic supported catalysts on regulating the conversion pathways and resulting product selectivity. The subsequent first principle calculations further corroborated reaction pathways of model compounds in atom-level on different catalyst surfaces with the experiments above and illustrated the favored C–O/C=O scission orders thermodynamically and kinetically. Then, it discussed hydrogenation effects of different H-donors (such as hydrogen and methane) and catalysts deactivation for economical and industrial consideration. Based on the descriptions above and recent researches, it also elaborated on catalytic HDO of biomass and bio-oil with multi-functional catalysts. Finally, it presented the challenges and future prospective of biomass catalytic HDO.
Abbreviations
- 2,5-DMF:
-
2,5-dimethylfuran
- 4-MP:
-
4-methylphenol
- 5-HMF:
-
5-hydroxymethylfurfural
- 5-MFA:
-
5-methylfurfuryl alcohol
- 5-MFF:
-
5-methylfurfural
- BTEX:
-
Benzene, toluene, ethylbenzene and xylenes
- CHA:
-
Cyclohexane
- CTH:
-
Catalytic transfer hydrogenaration
- DCO:
-
Decarboxylation and/or decarbonylation
- DDO:
-
Direct deoxygenation
- DFT:
-
Density functional theory
- DME:
-
Demethylation
- DMO:
-
Demethoxylation
- FA:
-
Furfuryl alcohol
- FF:
-
Furfrual
- H/C:
-
Hydrogen to carbon ratio
- HAD:
-
Hydroxyalkylation
- HCR:
-
Hydrocracking
- HDO:
-
Hydrodeoxygenation
- HHV:
-
Higher heating value
- HYD:
-
Hydrogenation
- MCH:
-
Methylcyclohexane
- MF:
-
Methylfuran
- MMP:
-
2-methoxy-4-methylphenol
- MTHF:
-
Methyltetrahydrofuran
- Ov :
-
Oxygen vacancy
- THFA:
-
Tetrahydrofurfuryl alcohol
References
International Energy Agency (IEA). Outlook—Key World Energy Statistics 2021—Analysis. 2023–11-13, available at the website of IEA
International Energy Agency (IEA). Overview—World Energy Outlook 2021—Analysis. 2023–11-13, available at the website of IEA
Alabi O, Abubakar A, Werkmeister A, et al. Keeping the lights on or off: Tracking the progress of access to electricity for sustainable development in Nigeria. GeoJournal, 2022, 88(2): 1535–1558
Ganti G, Gidden M J, Smith C J, et al. Uncompensated claims to fair emission space risk putting Paris Agreement goals out of reach. Environmental Research Letters, 2023, 18(2): 024040
Intergovernmental Panel on Climate Change (IPCC). IPCC meets to approve the final component of the Sixth Assessment Report. 2023–11-13, available at the website of IPCC
US Energy Information Administration (EIA). International Energy Outlook 2023. 2023–11-13, available at the website of EIA
Su C W, Pang L D, Qin M, et al. The spillover effects among fossil fuel, renewables and carbon markets: Evidence under the dual dilemma of climate change and energy crises. Energy, 2023, 274: 127304
Ju Y, Liu R, Fu L. Engineering fronts in fields of Energy and Electrical Science and Technologies in the report of Engineering Fronts 2022. Frontiers in Energy, 2023, 17(1): 5–8
Osman A I, Farghali M, Ihara I, et al. Materials, fuels, upgrading, economy, and life cycle assessment of the pyrolysis of algal and lignocellulosic biomass: A review. Environmental Chemistry Letters, 2023, 21(3): 1419–1476
Mujtaba M, Fernandes Fraceto L, Fazeli M, et al. Lignocellulosic biomass from agricultural waste to the circular economy: A review with focus on biofuels, biocomposites and bioplastics. Journal of Cleaner Production, 2023, 402: 136815
Bhoi P R, Ouedraogo A S, Soloiu V, et al. Recent advances on catalysts for improving hydrocarbon compounds in bio-oil of biomass catalytic pyrolysis. Renewable & Sustainable Energy Reviews, 2020, 121: 109676
Popp J, Lakner Z, Harangi-Rákos M, et al. The effect of bioenergy expansion: Food, energy, and environment. Renewable & Sustainable Energy Reviews, 2014, 32: 559–578
Dabros T M H, Stummann M Z, HøJ M, et al. transportation fuels from biomass fast pyrolysis, catalytic hydrodeoxygenation, and catalytic fast hydropyrolysis. Progress in Energy and Combustion Science, 2018, 68: 268–309
Aviation Benefits Beyond Borders. Waypoint 2050. 2023–11-13, available at the website of Aviationbenefits
Andrade M C, Gorgulho Silva C D O, de Souza Moreira L R, et al. Crop residues: Applications of lignocellulosic biomass in the context of a biorefinery. Frontiers in Energy, 2022, 16(2): 224–245
Xu Y, Liu X, Qi J, et al. Compositional and structural study of ash deposits spatially distributed in superheaters of a large biomass-fired CFB boiler. Frontiers in Energy, 2021, 15(2): 449–459
Pan P, Wu Y, Chen H. Performance evaluation of an improved biomass-fired cogeneration system simultaneously using extraction steam, cooling water, and feedwater for heating. Frontiers in Energy, 2022, 16(2): 321–335
Guo S, Wei X, Che D, et al. Experimental study on influence of operating parameters on tar components from corn straw gasification in fluidized bed. Frontiers in Energy, 2021, 15(2): 374–383
Khalifa O, Xu M, Zhang R, et al. Steam reforming of toluene as a tar model compound with modified nickel-based catalyst. Frontiers in Energy, 2022, 16(3): 492–501
Li H, Hou C, Zhai Y, et al. Selective preparation for biofuels and high value chemicals based on biochar catalysts. Frontiers in Energy, 2023, 17(5): 635–653
Yu H, Wu J, Wei W, et al. Synthesis of magnetic carbonaceous acid derived from waste garlic peel for biodiesel production via esterification. Frontiers in Energy, 2023, 17(1): 176–187
Yan P, Nur Azreena I, Peng H, et al. Catalytic hydropyrolysis of biomass using natural zeolite-based catalysts. Chemical Engineering Journal, 2023, 476: 146630
Liu X, Chen Z, Lu S, et al. Heterogeneous photocatalytic conversion of biomass to biofuels: A review. Chemical Engineering Journal, 2023, 476: 146794
Bridgwater A. Fast pyrolysis processes for biomass. Renewable & Sustainable Energy Reviews, 2000, 4(1): 1–73
Wang M, Dewil R, Maniatis K, et al. Biomass-derived aviation fuels: Challenges and perspective. Progress in Energy and Combustion Science, 2019, 74: 31–49
Yang Y, Xu X, He H, et al. The catalytic hydrodeoxygenation of bio-oil for upgradation from lignocellulosic biomass. International Journal of Biological Macromolecules, 2023, 242: 124773
Gea S, Hutapea Y A, Piliang A F R, et al. A comprehensive review of experimental parameters in bio-oil upgrading from pyrolysis of biomass to biofuel through catalytic hydrodeoxygenation. BioEnergy Research, 2023, 16(1): 325–347
Ouedraogo A S, Bhoi P R. Recent progress of metals supported catalysts for hydrodeoxygenation of biomass derived pyrolysis oil. Journal of Cleaner Production, 2020, 253: 119957
Figueirêdo M B, Jotic Z, Deuss P J, et al. Hydrotreatment of pyrolytic lignins to aromatics and phenolics using heterogeneous catalysts. Fuel Processing Technology, 2019, 189: 28–38
Sun J, Shao S, Hu X, et al. Synthesis of oxygen-containing precursors of aviation fuel via carbonylation of the aqueous bio-oil fraction followed by C–C coupling. ACS Sustainable Chemistry & Engineering, 2022, 10(33): 11030–11040
Wang H, Ruan H, Feng M, et al. One-pot process for hydrodeoxygenation of lignin to alkanes using Ru-based bimetallic and bifunctional catalysts supported on zeolite Y. ChemSusChem, 2017, 10(8): 1846–1856
Xue S, Luo Z, Sun H, et al. Product regulation and catalyst deactivation during ex-situ catalytic fast pyrolysis of biomass over nickel-molybdenum bimetallic modified micro-mesoporous zeolites and clays. Bioresource Technology, 2022, 364: 128081
Tian X, Wang Y, Zeng Z, et al. Research progress on the role of common metal catalysts in biomass pyrolysis: A state-of-the-art review. Green Chemistry, 2022, 24(10): 3922–3942
Sun M, Zhang Y, Liu W, et al. Synergy of metallic Pt and oxygen vacancy sites in Pt–WO3−x catalysts for efficiently promoting vanillin hydrodeoxygenation to methylcyclohexane. Green Chemistry, 2022, 24(24): 9489–9495
Shivhare A, Hunns J A, Durndell L J, et al. Metal-acid synergy: Hydrodeoxygenation of anisole over Pt/Al-SBA-15. ChemSusChem, 2020, 13(18): 4775–4775
Teles C A, De Souza P M, Rabelo-Neto R C, et al. Reaction pathways for the HDO of guaiacol over supported Pd catalysts: Effect of support type in the deoxygenation of hydroxyl and methoxy groups. Molecular Catalysis, 2022, 523: 111491
Feng S, Liu X, Su Z, et al. Low temperature catalytic hydrodeoxygenation of lignin-derived phenols to COLs over the Ru/SBA-15 catalyst. RSC Advances, 2022, 12(15): 9352–9362
Zhang K, Meng Q, Wu H, et al. Selective hydrodeoxygenation of aromatics to COLs over Ru single atoms supported on CeO2. Journal of the American Chemical Society, 2022, 144(45): 20834–20846
Cai T, Deng Q, Peng H, et al. Synthesis of renewable C–C cyclic compounds and high-density biofuels using 5-hydromethylfurfural as a reactant. Green Chemistry, 2020, 22(8): 2468–2473
Yan P, Wang H, Liao Y, et al. Synthesis of renewable diesel and jet fuels from bio-based furanics via hydroxyalkylation/alkylation (HAA) over \({{\rm SO}_{4}^{2-}}/{{\rm TiO}_{2}}\) and hydrodeoxygenation (HDO) reactions Fuel, 2023, 342: 127685
Gao Z, Zhou Z, Wang M, et al. Highly dispersed Pd anchored on heteropolyacid modified ZrO2 for high efficient hydrodeoxygenation of lignin-derivatives. Fuel, 2023, 334: 126768
Wang L, Yang Y, Shi Y, et al. Single-atom catalysts with metal-acid synergistic effect toward hydrodeoxygenation tandem reactions. Chem Catalysis, 2022, 3(1): 100483
Cho H J, Kim D, Xu B. Pore size engineering enabled selectivity control in tandem catalytic upgrading of cyclopentanone on zeolite-encapsulated Pt nanoparticles. ACS Catalysis, 2020, 10(15): 8850–8859
Deng Q, Peng H, Yang Z, et al. A one-pot synthesis of high-density biofuels through bifunctional mesoporous zeolite-encapsulated Pd catalysts. Applied Catalysis B: Environmental, 2023, 337: 122982
Ly H V, Kim J, Hwang H T, et al. Catalytic hydrodeoxygenation of fast pyrolysis bio-oil from saccharina japonica alga for bio-oil upgrading. Catalysts, 2019, 9(12): 1043
Song Q L, Zhao Y P, Wu F P, et al. Selective hydrogenolysis of lignin-derived aryl ethers over Co/C@N catalysts. Renewable Energy, 2020, 148: 729–738
Kumar A, Biswas B, Saini K, et al. Py-GC/MS study of prot lignin with cobalt impregnated titania, ceria and zirconia catalysts. Renewable Energy, 2021, 172: 121–129
Song W, Liu Y, Barath E, et al. Synergistic effects of Ni and acid sites for hydrogenation and C–O bond cleavage of substituted phenols. Green Chemistry, 2015, 17(2): 1204–1218
Saidi M, Moradi P. Catalytic hydrotreatment of lignin-derived pyrolysis bio-oils using Cu/γ-Al2O3 catalyst: Reaction network development and kinetic study of anisole upgrading. International Journal of Energy Research, 2021, 45(6): 8267–8284
Sirous-Rezaei P, Park Y K. Catalytic hydropyrolysis of lignin: Suppression of coke formation in mild hydrodeoxygenation of lignin-derived phenolics. Chemical Engineering Journal, 2020, 386: 121348
Lonchay W, Bagnato G, Sanna A. Highly selective hydropyrolysis of lignin waste to benzene, toluene and xylene in presence of zirconia supported iron catalyst. Bioresource Technology, 2022, 361: 127727
Afreen G, Mittal D, Upadhyayula S. Biomass-derived phenolics conversion to C10–C13 range fuel precursors over metal ion-exchanged zeolites: Physicochemical characterization of catalysts and process parameter optimization. Renewable Energy, 2020, 149: 489–507
Zhang J, Mao D, Zhang H, et al. Improving furfural hydrogenation selectivity by enhanced Ni-TiO2 elccoronic interaction. Applied Catalysis A, General, 2023, 660: 119206
Xue Y, Sharma A, Huo J, et al. Low-pressure two-stage catalytic hydropyrolysis of lignin and lignin-derived phenolic monomers using zeolite-based bifunctional catalysts. Journal of Analytical and Applied Pyrolysis, 2020, 146: 104779
Yan P, Bryant G, Li M M J, et al. Shape selectivity of zeolite catalysts for the hydrodeoxygenation of biocrude oil and its model compounds. Microporous and Mesoporous Materials, 2020, 309: 110561
Zheng N, Wang J. Distinctly different performances of two iron-doped charcoals in catalytic hydrocracking of pine wood hydropyrolysis vapor to methane or upgraded bio-oil. Energy & Fuels, 2020, 34(1): 546–556
Guan H, Ding W, Liu S, et al. Catalytic hydrothermal liquefaction of Chinese herb residue for the production of high-quality bio-oil. International Journal of Hydrogen Energy, 2023, 48(30): 11205–11213
Ji N, Cheng S, Jia Z, et al. Fabricating bifunctional Co–Al2O3@USY catalyst via in-sttu growth method for mild hydrodeoxygenation of lignin to naphthenes. ChemCatChem, 2022, 14(12): e202200274
Gamliel D P, Bollas G M, Valla J A. Bifunctional Ni-ZSM-5 catalysts for the pyrolysis and hydropyrolysis of biomass. Energy Technology, 2017, 5(1): 172–182
Yang Y, Ochoa-Hernández C, De La Peña O’Shea V A, et al. Effect of metal-support interaction on the selective hydrodeoxygenation of anisole to aromatics over Ni-based catalysts. Applied Catalysis B: Environmental, 2014, 145: 91–100
Guo H, Zhao J, Chen Y, et al. Mechanistic insights into hydrodeoxygenation of lignin derivatives over Ni single atoms supported on Mo2C. ACS Catalysis, 2024, 14(2): 703–717
Hu Y, Li X, Liu M, et al. Ni-based nanoparticles catalyzed hydrodeoxygenation of ketones, ethers, and phenols to (cyclo) aliphatic compounds. ACS Sustainable Chemistry & Engineering, 2023, 11(42): 15302–15314
Yan P, Tian X, Kennedy E M, et al. The role of Ni sites located in mesopores in the selectivity of anisole hydrodeoxygenation. Catalysis Science & Technology, 2022, 12(7): 2184–2196
Wang W, Zhang H, Zhou F, et al. Al-doped core-shell-structured Ni@mesoporous silica for highly selective hydrodeoxygenation of lignin-derived aldehydes. ACS Applied Materials & Interfaces, 2023, 15(28): 33654–33664
Chen C, Ji X, Xiong Y, et al. Ni/Ce co-doping metal-organic framework catalysts with oxygen vacancy for catalytic transfer hydrodeoxygenation of lignin derivatives vanillin. Chemical Engineering Journal, 2024, 481: 148555
Gong X, Li N, Li Y, et al. The catalytic hydrogenation of furfural to 2-methylfuran over the Mg–Al oxides supported Co–Ni bimetallic catalysts. Molecular Catalysis, 2022, 531: 112651
Strapasson G B, Sousa L S, Báfero G B, et al. Acidity modulation of Pt-supported catalyst enhances C–O bond cleavage over acetone hydrodeoxygenation. Applied Catalysis B: Environmental, 2023, 335: 122863
Zhu L, Li W, Zhang H, et al. Bimetallic ruthenium- and zinc-doped beta zeolite for efficiently depolymerizing Kraft lignin. Fuel, 2023, 349: 128766
Li X. Efficient hydrodeoxygenation of lignocellulose derivative oxygenates to aviation fuel range alkanes using Pd–Ru/hydroxyapatite catalysts. Fuel Processing Technology, 2022, 232: 107263
Xia Q, Chen Z, Shao Y, et al. Direct hydrodeoxygenation of raw woody biomass into liquid alkanes. Nature Communications, 2016, 7(1): 11162
Zhao M, Hu J, Wu S, et al. Hydrodeoxygenation of lignin-derived phenolics over facile prepared bimetallic RuCoNx/NC. Fuel, 2022, 308: 121979
Resende K A, Teles C A, Jacobs G, et al. Hydrodeoxygenation of phenol over zirconia supported Pd bimetallic catalysts. The effect of second metal on catalyst performance. Applied Catalysis B: Environmental, 2018, 232: 213–231
Zhao Y P, Wu F P, Song Q L, et al. Hydrodeoxygenation of lignin model compounds to alkanes over Pd-Ni/HZSM-5 catalysts. Journal of the Energy Institute, 2020, 93(3): 899–910
Shu R, Li R, Liu Y, et al. Enhanced adsorption properties of bimetallic RuCo catalyst for the hydrodeoxygenation of phenolic compounds and raw lignin-oil. Chemical Engineering Science, 2020, 227: 115920
Liu T, Tian Z, Zhang W, et al. Selective hydrodeoxygenation of lignin-derived phenols to alkyl COLs over highly dispersed RuFe bimetallic catalysts. Fuel, 2023, 339: 126916
Sunil More G, Rajendra Kanchan D, Banerjee A, et al. Selective catalytic hydrodeoxygenation of vanillin to 2-methoxy-4-methyl phenol and 4-methyl cyclohexanol over Pd/CuFe2O4 and PdNi/CuFe2O4 catalysts. Chemical Engineering Journal, 2023, 462: 142110
Li R, Qiu J, Chen H, et al. Hydrodeoxygenation of phenolic compounds and raw lignin-oil over bimetallic RuNi catalyst: An experimental and modeling study focusing on adsorption properties. Fuel, 2020, 281: 118758
Zhang J, Sun K, Li D, et al. Pd-Ni bimetallic nanoparticles supported on active carbon as an efficient catalyst for hydrodeoxygenation of aldehydes. Applied Catalysis A, General, 2019, 569: 190–195
Liu X. In-sttu studies on the synergistic effect of Pd–Mo bimetallic catalyst for anisole hydrodeoxygenation. Molecular Catalysis, 2022, 230: 112591
Ding W, Li H, Zong R, et al. Controlled hydrodeoxygenation of biobased ketones and aldehydes over an alloyed Pd–Zr catalyst under mild conditions. ACS Sustainable Chemistry & Engineering, 2021, 9(9): 3498–3508
Salakhum S, Yutthalekha T, Shetsiri S, et al. Bifunctional and bimetallic Pt–Ru/HZSM-5 nanoparticles for the mild hydrodeoxygenation of lignin-derived 4-propylphenol. ACS Applied Nano Materials, 2019, 2(2): 1053–1062
Mortensen P M, Gardini D, Damsgaard C D, et al. Deactivation of Ni-MoS2 by bio-oil impurities during hydrodeoxygenation of phenol and octanol. Applied Catalysis A, General, 2016, 523: 159–170
Chandler D S, Seufitelli G V S, Resende F L P. Catalytic route for the production of alkanes from hydropyrolysis of biomass. Energy & Fuels, 2020, 34(10): 12573–12585
Li T, Su J, Wang H, et al. Catalytic hydropyrolysis of lignin using NiMo-doped catalysts: Catalyst evaluation and mechanism analysis. Applied Energy, 2022, 316: 119115
Stummann M Z, HøJ M, Davidsen B, et al. Effect of the catalyst in fluid bed catalytic hydropyrolysis. Catalysis Today, 2020, 355: 96–109
Su J, Li T, Luo G, et al. Co-hydropyrolysis of pine and HDPE over bimetallic catalysts: Efficient BTEX production and process mechanism analysis. Fuel Processing Technology, 2023, 249: 107845
He C, Ruan T, Ouyang X, et al. Selective hydrodeoxygenation of monophenolics from lignin bio-oil for preparing cyclohexanol and its derivatives over Ni-Co/Al2O3-MgO catalyst. Industrial Crops and Products, 2023, 202: 117045
Miao F, Luo Z, Zhou Q, et al. Study on the reaction mechanism of C8+ aliphatic hydrocarbons obtained directly from biomass by hydropyrolysis vapor upgrading. Chemical Engineering Journal, 2023, 464: 142639
Khromova S A, Smirnov A A, Bulavchenko O A, et al. Anisole hydrodeoxygenation over Ni–Cu bimetallic catalysts: The effect of Ni/Cu ratio on selectivity. Applied Catalysis A, General, 2014, 470: 261–270
Liu M, Zhang J, Zheng L, et al. Significant promotion of surface oxygen vacancies on bimetallic CoNi nanocatalysts for hydrodeoxygenation of biomass-derived vanillin to produce methylCOL. ACS Sustainable Chemistry & Engineering, 2020, 8(15): 6075–6089
Blanco E, Carrales-Alvarado D, Belen Dongil A, et al. Effect of the support functionalization of mono- and bimetallic Ni/Co supported on graphene in hydrodeoxygenation of guaiacol. Industrial & Engineering Chemistry Research, 2021, 60(51): 18870–18879
Zhang Y, Wang W, Fan G, et al. Defect-decorated NiFe bimetallic nanocatalysts for the enhanced hydrodeoxygenation of guaiacol. ChemCatChem, 2022, 14(19): e202200585
Zhang Y, Fan G, Yang L, et al. Cooperative effects between Ni–Mo alloy sites and defective structures over hierarchical Ni–Mo bimetallic catalysts enable the enhanced hydrodeoxygenation activity. ACS Sustainable Chemistry & Engineering, 2021, 9(34): 11604–11615
Han Q, Rehman M U, Wang J, et al. The synergistic effect between Ni sites and Ni–Fe alloy sites on hydrodeoxygenation of lignin-derived phenols. Applied Catalysis B: Environmental, 2019, 253: 348–358
Lei X, Du X, Xin H, et al. Chemical-switching strategy for the production of green biofuel on NiCo/MCM-41 catalysts by tuning atmosphere. Fuel, 2022, 315: 123118
Jaswal A, Singh P P, Kar A K, et al. Production of 2-methyl furan, a promising 2nd generation biofuel, by the vapor phase hydrodeoxygenation of biomass-derived furfural over TiO2 supported Cu Ni bimetallic catalysts. Fuel Processing Technology, 2023, 245: 107726
Lu K L, Yin F, Wei X Y, et al. Promotional effect of metallic Co and Fe on Ni-based catalysts for p-cresol deoxygenation. Fuel, 2022, 321: 124033
Zhou M H, Xue Y Q, Ge F. MOF-derived NiM@C catalysts (M = Co, Mo, La) for in-siiu hydrogenation/hydrodeoxygenation of lignin-derived phenols to cycloalkanes/COL. Fuel, 2022, 329: 125446
Zhou X, Rauchfuss T B. Production of hybrid diesel fuel precursors from carbohydrates and petrochemicals using formic acid as a reactive solvent. ChemSusChem, 2013, 6(2): 383–388
Li L, Nie X, Chen Y, et al. Computational insights into the hydrodeoxygenation of phenolic compounds over Pt–Fe catalysts. Journal of Physical Chemistry, 2021, 125, 26: 14239–14252
Liu X, An W, Wang Y, et al. Hydrodeoxygenation of guaiacol over bimetallic Fe-alloyed (Ni, Pt) surfaces: Reaction mechanism, transition-state scaling relations and descriptor for predicting C–O bond scission reactivity. Catalysis Science & Technology, 2018, 8(8): 2146–2158
Konadu D, Kwawu C R, Tia R, et al. Mechanism of guaiacol hydrodeoxygenation on Cu(111): Insights from density functional theory studies. Catalysts, 2021, 11(4): 523
Fraga G, Yin Y, Konarova M, et al. Hydrocarbon hydrogen carriers for catalytic transfer hydrogenation of guaiacol. International Journal of Hydrogen Energy, 2020, 45(51): 27381–27391
Gao M, Tan H, Zhu P, et al. Why phenol is selectively hydrogenated to cyclohexanol on Ru(0001): An experimental and theoretical study. Applied Surface Science, 2021, 558: 149880
Zhou J, An W, Wang Z, et al. Hydrodeoxygenation of phenol over Ni-based bimetallic single-atom surface alloys: Mechanism, kinetics and descriptor. Catalysis Science & Technology, 2019, 9(16): 4314–4326
Nie X, Zhang Z, Wang H, et al. Effect of surface structure and Pd doping of Fe catalysts on the selective hydrodeoxygenation of phenol. Catalysis Today, 2021, 371: 189–203
Wu B, Li L, Wang H, et al. Role of MoOx/Ni(111) interfacial sites in direct deoxygenation of phenol toward benzene. Catalysis Science & Technology, 2023, 13(7): 2201–2211
Tan H, Rong S, Zhao R, et al. Targeted conversion of model phenolics in pyrolysis bio-oils to arenes via hydrodeoxygenation over MoOx/BaO@SBA-15 catalyst. Chemical Engineering Journal, 2022, 438: 135577
Itthibenchapong V, Chakthranont P, Sattayanon C, et al. Understanding the promoter effect of bifunctional (Pt, Ni, Cu)-MoO3−x/TiO2 catalysts for the hydrodeoxygenation of p-cresol: A combined DFT and experimental study. Applied Surface Science, 2021, 547: 149170
Khan T S, Singh D, Samal P P, et al. Mechanistic investigations on the catalytic transfer hydrogenation of lignin-derived monomers over Ru catalysts: Theoretical and kinetic studies. ACS Sustainable Chemistry & Engineering, 2021, 9(42): 14040–14050
Yan P, Tian X, Kennedy E M, et al. Influence of promoters (Fe, Mo, W) on the structural and catalytic properties of Ni/BEA for guaiacol hydrodeoxygenation. ACS Sustainable Chemistry & Engineering, 2021, 9(46): 15673–15682
Liu R, An W, Stepped M. Stepped M@Pt(211) (M = Co, Fe, Mo) single-atom alloys promote the deoxygenation of lignin-derived phenolics: Mechanism, kinetics, and descriptors. Catalysis Science & Technology, 2021, 11(21): 7047–7059
Tan Q, Wang G, Long A, et al. Mechanistic analysis of the role of metal oxophilicity in the hydrodeoxygenation of anisole. Journal of Catalysis, 2017, 347: 102–115
Chia M, Pagán-Torres Y J, Hibbitts D, et al. Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium–rhenium catalysts. Journal of the American Chemical Society, 2011, 133(32): 12675–12689
Tan Q, Wang G, Nie L, et al. Different product distributions and mechanistic aspects of the hydrodeoxygenation of m-cresol over platinum and ruthenium catalysts. ACS Catalysis, 2015, 5(11): 6271–6283
Deepa A K, Dhepe P L. Function of metals and supports on the hydrodeoxygenation of phenolic compounds. ChemPlusChem, 2014, 79(11): 1573–1583
Runnebaum R C, Nimmanwudipong T, Block D E, et al. Catalytic conversion of compounds representative of lignin-derived bio-oils: A reaction network for guaiacol, anisole, 4-methylanisole, and cyclohexanone conversion catalysed by Pt/γ-Al2O3. Catalysis Science & Technology, 2012, 2(1): 113–118
Furimsky E. Catalytic hydrodeoxygenation. Applied Catalysis A, General, 2000, 199(2): 147–190
Kanchan D R, Banerjee A. Linear scaling relationships for furan hydrodeoxygenation over transition metal and bimetallic surfaces. ChemSusChem, 2023, 16(18): e202300491
Fang W, Liu S, Steffensen A K. On the role of Cu+ and CuNi alloy phases in mesoporous CuNi catalyst for furfural hydrogenation. ACS Catalysis, 2023, 13(13): 8437–8444
Chen L, Shi Y, Chen C, et al. Precise control over local atomic structures in Ni–Mo bimetallic alloys for the hydrodeoxygenation reaction: A combination between density functional theory and microkinetic modeling. Journal of Physical Chemistry C, 2022, 126(9): 4319–4328
Zhang Z, Zhang Z, Zhang X, et al. Single pot selective conversion of furfural into 2-methylfuran over a Co-CoOx/AC bifunctional catalyst. Applied Surface Science, 2023, 612: 155871
Hamid A H, Ali L, Shittu T, et al. Transformation of levoglucosan into liquid fuel via catalytic upgrading over Ni-CeO2 catalysts. Molecular Catalysis, 2023, 547: 113382
Asada D, Ikeda T, Muraoka K, et al. Density functional theory study of deoxydehydration reaction by TiO2-supported monomeric and dimeric molybdenum oxide catalysts. Journal of Physical Chemistry C, 2022, 126(48): 20375–20387
Banerjee A, Mushrif S H. Reaction pathways for the deoxygenation of biomass-pyrolysis-derived bio-oil on Ru: A DFT study using furfural as a model compound. ChemCatChem, 2017, 9(14): 2828–2838
Wang X B, Xie Z Z, Guo L, et al. Mechanism of dibenzofuran hydrodeoxygenation on the surface of Pt(111): A DFT study. Catalysis Today, 2021, 364: 220–228
Chen H, Liu J, Li W, et al. Mechanism insights into the decarbonylation of furfural to furan over Ni/MgO: A molecular simulation study. Energy & Fuels, 2023, 37(14): 10594–10602
Zhang J, Jia Z, Yu S, et al. Regulating the Cu0–Cu+ ratio to enhance metal-support interaction for selective hydrogenation of furfural under mild conditions. Chemical Engineering Journal, 2023, 468: 143755
Pino N, Sitthisa S, Tan Q, et al. Structure, activity, and selectivity of bimetallic Pd–Fe/SiO2 and Pd–Fe/γ-Al2O3 catalysts for the conversion of furfural. Journal of Catalysis, 2017, 350: 30–40
Lin W, Chen Y, Zhang Y, et al. Surface synergetic effects of Ni-ReOx for promoting the mild hydrogenation of furfural to tetrahydrofurfuryl alcohol. ACS Catalysis, 2023, 13(17): 11256–11267
Luo J, Cheng Y, Niu H, et al. Efficient Cu/FeOx catalyst with developed structure for catalytic transfer hydrogenation of furfural. Journal of Catalysis, 2022, 413: 575–587
Zhao H, Liao X, Cui H, et al. Efficient Cu–Co bimetallic catalysts for the selective hydrogenation of furfural to furfuryl alcohol. Fuel, 2023, 351: 128887
Yuan E, Wang C, Wu C, et al. Constructing a Pd–Co interface to tailor a d-band center for highly efficient hydroconversion of furfural over cobalt oxide-supported Pd catalysts. ACS Applied Materials & Interfaces, 2023, 15(37): 43845–43858
Šivec R, Huš M, Likozar B, et al. Furfural hydrogenation over Cu, Ni, Pd, Pt, Re, Rh and Ru catalysts: Ab initio modelling of adsorption, desorption and reaction micro-kinetics. Chemical Engineering Journal, 2022, 436: 135070
Xue J, Wang Y, Meng Y, et al. Theoretical investigation of decarbonylation mechanism of furfural on Pd(111) and M/Pd(111) (M = Ru, Ni, Ir) surfaces. Molecular Catalysis, 2020, 493: 111054
Liu W, Yang Y, Chen L, et al. Atomically-ordered active sites in NiMo intermetallic compound toward low-pressure hydrodeoxygenation of furfural. Applied Catalysis B: Environmental, 2021, 282: 119569
Shi Y. Exploring the reaction mechanisms of furfural hydrodeoxygenation on a CuNiCu(111) bimetallic catalyst surface from computation. ACS Omega, 2020, 5(29): 18040–18049
Gunawan R, Cahyadi H S, Insyani R, et al. Density functional theory investigation of the conversion of 5-(hydroxymethyl)furfural into 2,5-dimethylfuran over the Pd(111), Cu(111), and Cu3Pd(111) surfaces. Journal of Physical Chemistry C, 2021, 125(19): 10295–10317
Hsiao Y W, Zong X, Zhou J, et al. Selective hydrodeoxygenation of 5-hydroxymethylfurfural (HMF) to 2,5-dimethylfuran (DMF) over carbon supported copper catalysts using isopropyl alcohol as a hydrogen donor. Applied Catalysis B: Environmental, 2022, 317: 121790
Zhang Y, Zhan S, Liu K, et al. Heterogeneous hydrogenation with hydrogen spillover enabled by nitrogen vacancies on boron nitride-supported Pd nanoparticles. Angewandte Chemie International Edition 62, 2023, 62(9): e202217191
Kim H, Yang S, Lim Y H, et al. Enhancement in the metal efficiency of Ru/TiO2 catalyst for guaiacol hydrogenation via hydrogen spillover in the liquid phase. Journal of Catalysis, 2022, 410: 93–102
Redina E A, Vikanova K V, Kapustin G I, et al. Selective room-temperature hydrogenation of carbonyl compounds under atmospheric pressure over platinum nanoparticles supported on ceria-zirconia mixed oxide. European Journal of Organic Chemistry, 2019, 2019(26): 4159–4170
Kasabe M M, Kotkar V R, Dongare M K, et al. Phenol hydrogenation to COL catalysed by palladium supported on CuO/CeO2. Chemistry, an Asian Journal, 2023, 18(11): e202300119
Yung M M, Foo G S, Sievers C. Role of Pt during hydrodeoxygenation of biomass pyrolysis vapors over Pt/HBEA. Catalysis Today, 2018, 302: 151–160
Rong S, Tan H, Pang Z, et al. Synergetic effect between Pd clusters and oxygen vacancies in hierarchical Nb2O5 for lignin-derived phenol hydrodeoxygenation into benzene. Renewable Energy, 2022, 187: 271–281
Rios-Escobedo R, Ortiz-Santos E, Colín-Luna J A, et al. Anisole hydrodeoxygenation: A comparative study of Ni/TiO2-ZrO2 and commercial TiO2 supported Ni and NiRu catalysts. Topics in Catalysis, 2022, 65(13–16): 1448–1461
Zanuttini M S, Gross M, Marchetti G, et al. Furfural hydrodeoxygenation on iron and platinum catalysts. Applied Catalysis A, General, 2019, 587: 117217
Guo L, Tian Y, He X, et al. Hydrodeoxygenation of phenolics over uniformly dispersed Pt–Ni alloys supported by self-pillared ZSM-5 nanosheets. Fuel, 2022, 322: 124082
Wu X, Liu C, Wang H, et al. Origin of strong metal-support interactions between Pt and anatase TiO2 facets for hydrodeoxygenation of m-cresol on Pt/TiO2 catalysts. Journal of Catalysis, 2023, 418: 203–215
Li T, Miao K, Zhao Z, et al. Understanding cellulose pyrolysis under hydrogen atmosphere. Energy Conversion and Management, 2022, 254: 115195
Wang H, Li T, Su J, et al. Noncatalytic hydropyrolysis of lignin in a high pressure micro-pyrolyzer. Fuel Processing Technology, 2022, 233: 107289
Geng Y, Li H. Hydrogen spillover-enhanced heterogeneously catalyzed hydrodeoxygenation for biomass upgrading, ChemSusChem, 2022, 15(8): e202102495
Alayoglu S, An K, Melaet G, et al. Pt-mediated reversible reduction and expansion of CeO2 in Pt nanoparticle/mesoporous CeO2 catalyst: In situ X-ray spectroscopy and diffraction studies under redox (H2 and O2) atmospheres. Journal of Physical Chemistry C, 2013, 117(50): 26608–26616
Ahmed F, Alam M K, Muira R, et al. Adsorption and dissociation of molecular hydrogen on Pt/CeO2 catalyst in the hydrogen spillover process: A quantum chemical molecular dynamics study. Applied Surface Science, 2010, 256(24): 7643–7652
Messou D, Bernardin V, Meunier F, et al. Origin of the synergistic effect between TiO2 crystalline phases in the Ni/TiO2-catalyzed CO2 methanation reaction. Journal of Catalysis, 2021, 398: 14–28
Zhang S, Xia Z, Zhang M, et al. Boosting selective hydrogenation through hydrogen spillover on supported-metal catalysts at room temperature. Applied Catalysis B: Environmental, 2021, 297: 120418
Shin H, Choi M, Kim H. A mechanistic model for hydrogen activation, spillover, and its chemical reaction in a zeolite-encapsulated Pt catalyst. Physical Chemistry Chemical Physics, 2016, 18(10): 7035–7041
Newman C, Zhou X, Goundie B, et al. Effects of support identity and metal dispersion in supported ruthenium hydrodeoxygenation catalysts. Applied Catalysis A, General, 2014, 477: 64–74
Moogi S, Jae J, Kannapu H P R, et al. Enhancement of aromatics from catalytic pyrolysis of yellow poplar: Role of hydrogen and methane decomposition. Bioresource Technology, 2020, 315: 123835
Moogi S, Pyo S, Farooq A, et al. Biomass enhancement of bioaromatics production from food waste through catalytic pyrolysis over Zn and Mo-loaded HZSM-5 under an environment of decomposed methane. Chemical Engineering Journal, 2022, 446: 137215
Austin D, Wang A, He P, et al. Catalytic valorization of biomass derived glycerol under methane: Effect of catalyst synthesis method. Fuel, 2018, 216: 218–226
Peng H, Wang A, He P, et al. Solvent-free catalytic conversion of xylose with methane to aromatics over Zn–Cr modified zeolite catalyst. Fuel, 2019, 253: 988–996
Cheng Y T, Huber G W. Production of targeted aromatics by using Diels–Alder classes of reactions with furans and olefins over ZSM-5. Green Chemistry, 2012, 14(11): 3114
He P, Shan W, Xiao Y, et al. Performance of Zn/ZSM-5 for in situ catalytic upgrading of pyrolysis bio-oil by methane. Topics in Catalysis, 2016, 59(1): 86–93
Wang A, Austin D, Qian H, et al. Catalytic valorization of furfural under methane environment. ACS Sustainable Chemistry & Engineering, 2018, 6(7): 8891–8903
Tshikesho R S, Kumar A, Huhnke R L, et al. Catalytic co-pyrolysis of red cedar with methane to produce upgraded bio-oil. Bioresource Technology, 2019, 285: 121299
Wang A, Austin D, Song H. Investigations of thermochemical upgrading of biomass and its model compounds: Opportunities for methane utilization. Fuel, 2019, 246: 443–453
Tang P, Zhu Q, Wu Z, et al. Methane activation: The past and future. Energy & Environmental Science, 2014, 7(8): 2580–2591
Doan H A, Wang X, Snurr R Q. Computational screening of supported metal oxide nanoclusters for methane activation: Insights into homolytic versus heterolytic C–H bond dissociation. Journal of Physical Chemistry Letters, 2023, 14(21): 5018–5024
Xu Y, Liu S, Guo X, et al. Methane activation without using oxidants over Mo/HZSM-5 zeolite catalysts. Catalysis Letters, 1995, 30(1–4): 135–149
Xu J, Zheng A, Wang X, et al. Room temperature activation of methane over Zn modified H-ZSM-5 zeolites: Insight from solid-state NMR and theoretical calculations. Chemical Science, 2012, 3(10): 2932
Luzgin M V, Rogov V A, Arzumanov S S, et al. Understanding methane aromatization on a Zn-modified high-silica zeolite. Angewandte Chemie International Edition, 2008, 47(24): 4559–4562
Gabrienko A A, Arzumanov S S, Luzgin M V, et al. Methane activation on Zn2+-exchanged ZSM-5 zeolites. The effect of molecular oxygen addition. Journal of Physical Chemistry C, 2015, 119(44): 24910–24918
Wang A, Song H. Maximizing the production of aromatic hydrocarbons from lignin conversion by coupling methane activation. Bioresource Technology, 2018, 268: 505–513
He P, Wang A, Meng S, et al. Impact of Al sites on the methane co-aromatization with alkanes over Zn/HZSM-5. Catalysis Today, 2019, 323: 94–104
Wang A, Austin D, Karmakar A, et al. Methane upgrading of acetic acid as a model compound for a biomass-derived liquid over a modified zeolite catalyst. ACS Catalysis, 2017, 7(5): 3681–3692
Du L, Luo Z, Wang K, et al. Catalytic co-conversion of poplar pyrolysis vapor and methanol for aromatics production via ex-situ configuration. Journal of Analytical and Applied Pyrolysis, 2022, 165: 105571
Li S, Liu B, Truong J, et al. One-pot hydrodeoxygenation (HDO) of lignin monomers to C9 hydrocarbons co-catalysed by Ru/C and Nb2O5. Green Chemistry, 2020, 22(21): 7406–7416
Lu Q, Yang X, Zhu X. Analysis on chemical and physical properties of bio-oil pyrolyzed from rice husk. Journal of Analytical and Applied Pyrolysis, 2008, 82(2): 191–198
Pidtasang B, Sukkasi S, Pattiya A. Effect of in-situ addition of alcohol on yields and properties of bio-oil derived from fast pyrolysis of eucalyptus bark. Journal of Analytical and Applied Pyrolysis, 2016, 120: 82–93
Kim Y M, Jae J, Kim B S, et al. Catalytic co-pyrolysis of torrefied yellow poplar and high-density polyethylene using microporous HZSM-5 and mesoporous Al-MCM-41 catalysts. Energy Conversion and Management, 2017, 149: 966–973
Ahmed M H M, Batalha N, Mahmudul H M D, et al. A review on advanced catalytic co-pyrolysis of biomass and hydrogen-rich feedstock: Insights into synergistic effect, catalyst development and reaction mechanism. Bioresource Technology, 2020, 310: 123457
Wu P, Zhao D, Lu G, et al. Supported Pd–Au bimetallic nanoparticles as an efficient catalyst for the hydrodeoxygenation of vanillin with formic acid at room temperature. Green Chemistry, 2022, 24(3): 1096–1102
Alemán-Vázquez L O, Cano-Domínguez J L, García-Gutiérrez J L. Effect of tetralin, decalin and naphthalene as hydrogen donors in the upgrading of heavy oils. Procedia Engineering, 2012, 42: 532–539
Shafaghat H, Lee I G, Jae J, et al. Pd/C catalyzed transfer hydrogenation of pyrolysis oil using 2-propanol as hydrogen source. Chemical Engineering Journal, 2019, 377: 119986
Boscagli C, Raffelt K, Grunwaldt J D. Reactivity of platform molecules in pyrolysis oil and in water during hydrotreatment over nickel and ruthenium catalysts. Biomass and Bioenergy, 2017, 106: 63–73
Boscagli C, Yang C, Welle A, et al. Effect of pyrolysis oil components on the activity and selectivity of nickel-based catalysts during hydrotreatment. Applied Catalysis A, General, 2017, 544: 161–172
Ambursa M M, Juan J C, Yahaya Y, et al. A review on catalytic hydrodeoxygenation of lignin to transportation fuels by using nickel-based catalysts. Renewable & Sustainable Energy Reviews, 2021, 138: 110667
Lan X, Hensen E J M, Weber T. Hydrodeoxygenation of guaiacol over Ni2P/SiO2-reaction mechanism and catalyst deactivation. Applied Catalysis A, General, 2018, 550: 57–66
Khanh Tran Q, Vu Ly H, Anh Vo T, et al. Highly selective hydrodeoxygenation of wood pallet sawdust pyrolysis oil to methyl phenol derivatives using cobalt and iron on activated carbon supported catalysts. Energy Conversion and Management: X, 2022, 14: () 100184
Tian Y, Guo L, Qiao C, et al. Dynamics-driven tailoring of sub-nanometric Pt–Ni bimetals confined in hierarchical zeolite for catalytic hydrodeoxygenation. Applied Catalysis B: Environmental, 2023, 336: 122945
Chen S, Yan P, Yu X, et al. Conversion of lignin to high yields of aromatics over Ru–ZnO/SBA-15 bifunctional catalysts. Renewable Energy, 2023, 215: 118919
Hita I, Cordero-Lanzac T, Kekäläinen T, et al. In-depth analysis of raw bio-oil and its hydrodeoxygenated products for a comprehensive catalyst performance evaluation. ACS Sustainable Chemistry & Engineering, 2020, 8(50): 18433–18445
Cordero-Lanzac T, Palos R, Hita I, et al. Revealing the pathways of catalyst deactivation by coke during the hydrodeoxygenation of raw bio-oil. Applied Catalysis B: Environmental, 2018, 239: 513–524
Wu T, Dang Q, Wu Y, et al. Catalytic hydropyrolysis of biomass over NiMo bimetallic carbon-based catalysts. Journal of Environmental Chemical Engineering, 2023, 11(3): 110024
Wang J, Jiang J, Li D, et al. Integrated hydropyrolysis and vapor-phase hydrodeoxygenation process with Pd/Al2O3 for production of advanced oxygen-containing biofuels from cellulosic wastes. Fuel Processing Technology, 2024, 254: 107948
Liu Y, Chen L, Chen Y, et al. Pilot study on production of aviation fuel from catalytic conversion of corn stover. Bioresource Technology, 2023, 372: 128653
Ma D, Lu S, Liu X, et al. Depolymerization and hydrodeoxygenation of lignin to aromatic hydrocarbons with a Ru catalyst on a variety of Nb-based supports. Chinese Journal of Catalysis, 2019, 40(4): 609–617
Li R, Zhao Z, Zhang B, et al. Catalytic hydroprocessing of white pine pyrolysis bio-oil over cobalt-molybdenum carbide in a continuous packed-bed reactor. BioEnergy Research, 2021, 14(2): 588–597
Onwudili J A, Scaldaferri C A. Catalytic upgrading of intermediate pyrolysis bio-oil to hydrocarbon-rich liquid biofuel via a novel two-stage solvent-assisted process. Fuel, 2023, 352: 129015
Acknowledgements
This work was supported by the National Natural Science Foundation of China (Grant No. 52236011).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Competing Interests The authors declare that they have no competing interests.
Rights and permissions
About this article
Cite this article
Luo, Z., Zhu, W., Miao, F. et al. Catalytic hydrodeoxygenation of pyrolysis bio-oil to jet fuel: A review. Front. Energy (2024). https://doi.org/10.1007/s11708-024-0943-7
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11708-024-0943-7