Catalytic hydrodeoxygenation of pyrolysis bio-oil to jet fuel: A review

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.

Graphical abstract

Keywords

biomass pyrolysis oil / bio-jet fuel / catalytic hydrodeoxygenation (HDO) / metal catalyst / reaction pathways

References

[1] InternationalEnergy Agency (IEA). Outlook—Key World Energy Statistics 2021—Analysis. 2023–11-13, available at the website of IEA

[2] InternationalEnergy Agency (IEA). Overview—World Energy Outlook 2021—Analysis. 2023–11-13, available at the website of IEA

[3] Alabi O, Abubakar A, Werkmeister A. . Keeping the lights on or off: Tracking the progress of access to electricity for sustainable development in Nigeria. GeoJournal, 2022, 88(2): 1535–1558

[4] Ganti G, Gidden M J, Smith C J. . Uncompensated claims to fair emission space risk putting Paris Agreement goals out of reach. Environmental Research Letters, 2023, 18(2): 024040

[5] IntergovernmentalPanel 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

[6] USEnergy Information Administration (EIA). International Energy Outlook 2023. 2023–11-13, available at the website of EIA

[7] Su C W, Pang L D, Qin M. . 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

[8] 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

[9] Osman A I, Farghali M, Ihara I. . 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

[10] Mujtaba M, Fernandes Fraceto L, Fazeli M. . 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

[11] Bhoi P R, Ouedraogo A S, Soloiu V. . Recent advances on catalysts for improving hydrocarbon compounds in bio-oil of biomass catalytic pyrolysis. Renewable & Sustainable Energy Reviews, 2020, 121: 109676

[12] Popp J, Lakner Z, Harangi-Rákos M. . The effect of bioenergy expansion: Food, energy, and environment. Renewable & Sustainable Energy Reviews, 2014, 32: 559–578

[13] Dabros T M H, Stummann M Z, Høj M. . transportation fuels from biomass fast pyrolysis, catalytic hydrodeoxygenation, and catalytic fast hydropyrolysis. Progress in Energy and Combustion Science, 2018, 68: 268–309

[14] AviationBenefits Beyond Borders. Waypoint 2050. 2023–11-13, available at the website of Aviationbenefits

[15] Andrade M C, Gorgulho Silva C D O, de Souza Moreira L R. . Crop residues: Applications of lignocellulosic biomass in the context of a biorefinery. Frontiers in Energy, 2022, 16(2): 224–245

[16] Xu Y, Liu X, Qi J. . 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

[17] 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

[18] Guo S, Wei X, Che D. . 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

[19] Khalifa O, Xu M, Zhang R. . Steam reforming of toluene as a tar model compound with modified nickel-based catalyst. Frontiers in Energy, 2022, 16(3): 492–501

[20] Li H, Hou C, Zhai Y. . Selective preparation for biofuels and high value chemicals based on biochar catalysts. Frontiers in Energy, 2023, 17(5): 635–653

[21] Yu H, Wu J, Wei W. . Synthesis of magnetic carbonaceous acid derived from waste garlic peel for biodiesel production via esterification. Frontiers in Energy, 2023, 17(1): 176–187

[22] Yan P, Nur Azreena I, Peng H. . Catalytic hydropyrolysis of biomass using natural zeolite-based catalysts. Chemical Engineering Journal, 2023, 476: 146630

[23] Liu X, Chen Z, Lu S. . Heterogeneous photocatalytic conversion of biomass to biofuels: A review. Chemical Engineering Journal, 2023, 476: 146794

[24] Bridgwater A. Fast pyrolysis processes for biomass. Renewable & Sustainable Energy Reviews, 2000, 4(1): 1–73

[25] Wang M, Dewil R, Maniatis K. . Biomass-derived aviation fuels: Challenges and perspective. Progress in Energy and Combustion Science, 2019, 74: 31–49

[26] Yang Y, Xu X, He H. . The catalytic hydrodeoxygenation of bio-oil for upgradation from lignocellulosic biomass. International Journal of Biological Macromolecules, 2023, 242: 124773

[27] Gea S, Hutapea Y A, Piliang A F R. . 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

[28] 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

[29] Figueirêdo M B, Jotic Z, Deuss P J. . Hydrotreatment of pyrolytic lignins to aromatics and phenolics using heterogeneous catalysts. Fuel Processing Technology, 2019, 189: 28–38

[30] Sun J, Shao S, Hu X. . 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

[31] Wang H, Ruan H, Feng M. . 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

[32] Xue S, Luo Z, Sun H. . 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

[33] Tian X, Wang Y, Zeng Z. . 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

[34] Sun M, Zhang Y, Liu W. . Synergy of metallic Pt and oxygen vacancy sites in Pt–WO_3−x catalysts for efficiently promoting vanillin hydrodeoxygenation to methylcyclohexane. Green Chemistry, 2022, 24(24): 9489–9495

[35] Shivhare A, Hunns J A, Durndell L J. . Metal–acid synergy: Hydrodeoxygenation of anisole over Pt/Al-SBA-15. ChemSusChem, 2020, 13(18): 4775–4775

[36] Teles C A, De Souza P M, Rabelo-Neto R C. . 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

[37] Feng S, Liu X, Su Z. . Low temperature catalytic hydrodeoxygenation of lignin-derived phenols to COLs over the Ru/SBA-15 catalyst. RSC Advances, 2022, 12(15): 9352–9362

[38] Zhang K, Meng Q, Wu H. . Selective hydrodeoxygenation of aromatics to COLs over Ru single atoms supported on CeO₂. Journal of the American Chemical Society, 2022, 144(45): 20834–20846

[39] Cai T, Deng Q, Peng H. . Synthesis of renewable C–C cyclic compounds and high-density biofuels using 5-hydromethylfurfural as a reactant. Green Chemistry, 2020, 22(8): 2468–2473

[40] Yan P, Wang H, Liao Y. . Synthesis of renewable diesel and jet fuels from bio-based furanics via hydroxyalkylation/alkylation (HAA) over S O4 2−/TiO₂ and hydrodeoxygenation (HDO) reactions. Fuel, 2023, 342: 127685

[41] Gao Z, Zhou Z, Wang M. . Highly dispersed Pd anchored on heteropolyacid modified ZrO₂ for high efficient hydrodeoxygenation of lignin-derivatives. Fuel, 2023, 334: 126768

[42] Wang L, Yang Y, Shi Y. . Single-atom catalysts with metal-acid synergistic effect toward hydrodeoxygenation tandem reactions. Chem Catalysis, 2022, 3(1): 100483

[43] 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

[44] Deng Q, Peng H, Yang Z. . A one-pot synthesis of high-density biofuels through bifunctional mesoporous zeolite-encapsulated Pd catalysts. Applied Catalysis B: Environmental, 2023, 337: 122982

[45] Ly H V, Kim J, Hwang H T. . Catalytic hydrodeoxygenation of fast pyrolysis bio-oil from saccharina japonica alga for bio-oil upgrading. Catalysts, 2019, 9(12): 1043

[46] Song Q L, Zhao Y P, Wu F P. . Selective hydrogenolysis of lignin-derived aryl ethers over Co/C@N catalysts. Renewable Energy, 2020, 148: 729–738

[47] Kumar A, Biswas B, Saini K. . Py-GC/MS study of prot lignin with cobalt impregnated titania, ceria and zirconia catalysts. Renewable Energy, 2021, 172: 121–129

[48] Song W, Liu Y, Baráth E. . Synergistic effects of Ni and acid sites for hydrogenation and C–O bond cleavage of substituted phenols. Green Chemistry, 2015, 17(2): 1204–1218

[49] 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

[50] 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

[51] 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

[52] 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

[53] Zhang J, Mao D, Zhang H. . Improving furfural hydrogenation selectivity by enhanced Ni-TiO₂ electronic interaction. Applied Catalysis A, General, 2023, 660: 119206

[54] Xue Y, Sharma A, Huo J. . 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

[55] Yan P, Bryant G, Li M M J. . Shape selectivity of zeolite catalysts for the hydrodeoxygenation of biocrude oil and its model compounds. Microporous and Mesoporous Materials, 2020, 309: 110561

[56] 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

[57] Guan H, Ding W, Liu S. . 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

[58] Ji N, Cheng S, Jia Z. . Fabricating bifunctional Co−Al₂O₃ @USY catalyst via in-situ growth method for mild hydrodeoxygenation of lignin to naphthenes. ChemCatChem, 2022, 14(12): e202200274

[59] 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

[60] Yang Y, Ochoa-Hernández C, De La Peña O’Shea V A. . 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

[61] Guo H, Zhao J, Chen Y. . Mechanistic insights into hydrodeoxygenation of lignin derivatives over Ni single atoms supported on Mo₂C. ACS Catalysis, 2024, 14(2): 703–717

[62] Hu Y, Li X, Liu M. . Ni-based nanoparticles catalyzed hydrodeoxygenation of ketones, ethers, and phenols to (cyclo) aliphatic compounds. ACS Sustainable Chemistry & Engineering, 2023, 11(42): 15302–15314

[63] Yan P, Tian X, Kennedy E M. . The role of Ni sites located in mesopores in the selectivity of anisole hydrodeoxygenation. Catalysis Science & Technology, 2022, 12(7): 2184–2196

[64] Wang W, Zhang H, Zhou F. . 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

[65] Chen C, Ji X, Xiong Y. . 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

[66] Gong X, Li N, Li Y. . The catalytic hydrogenation of furfural to 2-methylfuran over the Mg–Al oxides supported Co–Ni bimetallic catalysts. Molecular Catalysis, 2022, 531: 112651

[67] Strapasson G B, Sousa L S, Báfero G B. . Acidity modulation of Pt-supported catalyst enhances C–O bond cleavage over acetone hydrodeoxygenation. Applied Catalysis B: Environmental, 2023, 335: 122863

[68] Zhu L, Li W, Zhang H. . Bimetallic ruthenium- and zinc-doped beta zeolite for efficiently depolymerizing Kraft lignin. Fuel, 2023, 349: 128766

[69] Li X. Efficient hydrodeoxygenation of lignocellulose derivative oxygenates to aviation fuel range alkanes using Pd–Ru/hydroxyapatite catalysts. Fuel Processing Technology, 2022, 232: 107263

[70] Xia Q, Chen Z, Shao Y. . Direct hydrodeoxygenation of raw woody biomass into liquid alkanes. Nature Communications, 2016, 7(1): 11162

[71] Zhao M, Hu J, Wu S. . Hydrodeoxygenation of lignin-derived phenolics over facile prepared bimetallic RuCoN_x/NC. Fuel, 2022, 308: 121979

[72] Resende K A, Teles C A, Jacobs G. . 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

[73] Zhao Y P, Wu F P, Song Q L. . Hydrodeoxygenation of lignin model compounds to alkanes over Pd-Ni/HZSM-5 catalysts. Journal of the Energy Institute, 2020, 93(3): 899–910

[74] Shu R, Li R, Liu Y. . Enhanced adsorption properties of bimetallic RuCo catalyst for the hydrodeoxygenation of phenolic compounds and raw lignin-oil. Chemical Engineering Science, 2020, 227: 115920

[75] Liu T, Tian Z, Zhang W. . Selective hydrodeoxygenation of lignin-derived phenols to alkyl COLs over highly dispersed RuFe bimetallic catalysts. Fuel, 2023, 339: 126916

[76] Sunil More G, Rajendra Kanchan D, Banerjee A. . 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

[77] Li R, Qiu J, Chen H. . 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

[78] Zhang J, Sun K, Li D. . Pd-Ni bimetallic nanoparticles supported on active carbon as an efficient catalyst for hydrodeoxygenation of aldehydes. Applied Catalysis A, General, 2019, 569: 190–195

[79] Liu X. In-situ studies on the synergistic effect of Pd–Mo bimetallic catalyst for anisole hydrodeoxygenation. Molecular Catalysis, 2022, 230: 112591

[80] Ding W, Li H, Zong R. . 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

[81] Salakhum S, Yutthalekha T, Shetsiri S. . 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

[82] Mortensen P M, Gardini D, Damsgaard C D. . Deactivation of Ni-MoS₂ by bio-oil impurities during hydrodeoxygenation of phenol and octanol. Applied Catalysis A, General, 2016, 523: 159–170

[83] 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

[84] Li T, Su J, Wang H. . Catalytic hydropyrolysis of lignin using NiMo-doped catalysts: Catalyst evaluation and mechanism analysis. Applied Energy, 2022, 316: 119115

[85] Stummann M Z, Høj M, Davidsen B. . Effect of the catalyst in fluid bed catalytic hydropyrolysis. Catalysis Today, 2020, 355: 96–109

[86] Su J, Li T, Luo G. . Co-hydropyrolysis of pine and HDPE over bimetallic catalysts: Efficient BTEX production and process mechanism analysis. Fuel Processing Technology, 2023, 249: 107845

[87] He C, Ruan T, Ouyang X. . 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

[88] Miao F, Luo Z, Zhou Q. . Study on the reaction mechanism of C8+ aliphatic hydrocarbons obtained directly from biomass by hydropyrolysis vapor upgrading. Chemical Engineering Journal, 2023, 464: 142639

[89] Khromova S A, Smirnov A A, Bulavchenko O A. . Anisole hydrodeoxygenation over Ni–Cu bimetallic catalysts: The effect of Ni/Cu ratio on selectivity. Applied Catalysis A, General, 2014, 470: 261–270

[90] Liu M, Zhang J, Zheng L. . 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

[91] Blanco E, Carrales-Alvarado D, Belen Dongil A. . 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

[92] Zhang Y, Wang W, Fan G. . Defect-decorated NiFe bimetallic nanocatalysts for the enhanced hydrodeoxygenation of guaiacol. ChemCatChem, 2022, 14(19): e202200585

[93] Zhang Y, Fan G, Yang L. . 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

[94] Han Q, Rehman M U, Wang J. . 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

[95] Lei X, Du X, Xin H. . Chemical-switching strategy for the production of green biofuel on NiCo/MCM-41 catalysts by tuning atmosphere. Fuel, 2022, 315: 123118

[96] Jaswal A, Singh P P, Kar A K. . 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

[97] Lu K L, Yin F, Wei X Y. . Promotional effect of metallic Co and Fe on Ni-based catalysts for p-cresol deoxygenation. Fuel, 2022, 321: 124033

[98] Zhou M H, Xue Y Q, Ge F. MOF-derived NiM@C catalysts (M = Co, Mo, La) for in-situ hydrogenation/hydrodeoxygenation of lignin-derived phenols to cycloalkanes/COL. Fuel, 2022, 329: 125446

[99] 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

[100] LiL, NieX, ChenY, et al. Computational insights into the hydrodeoxygenation of phenolic compounds over Pt–Fe catalysts. Journal of Physical Chemistry, 2021, 125, 26: 14239–14252

[101] Liu X, An W, Wang Y. . 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

[102] Konadu D, Kwawu C R, Tia R. . Mechanism of guaiacol hydrodeoxygenation on Cu(111): Insights from density functional theory studies. Catalysts, 2021, 11(4): 523

[103] Fraga G, Yin Y, Konarova M. . Hydrocarbon hydrogen carriers for catalytic transfer hydrogenation of guaiacol. International Journal of Hydrogen Energy, 2020, 45(51): 27381–27391

[104] Gao M, Tan H, Zhu P. . Why phenol is selectively hydrogenated to cyclohexanol on Ru(0001): An experimental and theoretical study. Applied Surface Science, 2021, 558: 149880

[105] Zhou J, An W, Wang Z. . Hydrodeoxygenation of phenol over Ni-based bimetallic single-atom surface alloys: Mechanism, kinetics and descriptor. Catalysis Science & Technology, 2019, 9(16): 4314–4326

[106] Nie X, Zhang Z, Wang H. . Effect of surface structure and Pd doping of Fe catalysts on the selective hydrodeoxygenation of phenol. Catalysis Today, 2021, 371: 189–203

[107] Wu B, Li L, Wang H. . Role of MoO_x/Ni(111) interfacial sites in direct deoxygenation of phenol toward benzene. Catalysis Science & Technology, 2023, 13(7): 2201–2211

[108] Tan H, Rong S, Zhao R. . Targeted conversion of model phenolics in pyrolysis bio-oils to arenes via hydrodeoxygenation over MoO_x/BaO@SBA-15 catalyst. Chemical Engineering Journal, 2022, 438: 135577

[109] Itthibenchapong V, Chakthranont P, Sattayanon C. . Understanding the promoter effect of bifunctional (Pt, Ni, Cu)-MoO_3–x/TiO₂ catalysts for the hydrodeoxygenation of p-cresol: A combined DFT and experimental study. Applied Surface Science, 2021, 547: 149170

[110] Khan T S, Singh D, Samal P P. . 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

[111] Yan P, Tian X, Kennedy E M. . 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

[112] 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

[113] Tan Q, Wang G, Long A. . Mechanistic analysis of the role of metal oxophilicity in the hydrodeoxygenation of anisole. Journal of Catalysis, 2017, 347: 102–115

[114] Chia M, Pagán-Torres Y J, Hibbitts D. . 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

[115] Tan Q, Wang G, Nie L. . Different product distributions and mechanistic aspects of the hydrodeoxygenation of m-cresol over platinum and ruthenium catalysts. ACS Catalysis, 2015, 5(11): 6271–6283

[116] Deepa A K, Dhepe P L. Function of metals and supports on the hydrodeoxygenation of phenolic compounds. ChemPlusChem, 2014, 79(11): 1573–1583

[117] Runnebaum R C, Nimmanwudipong T, Block D E. . 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

[118] Furimsky E. Catalytic hydrodeoxygenation. Applied Catalysis A, General, 2000, 199(2): 147–190

[119] Kanchan D R, Banerjee A. Linear scaling relationships for furan hydrodeoxygenation over transition metal and bimetallic surfaces. ChemSusChem, 2023, 16(18): e202300491

[120] 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

[121] Chen L, Shi Y, Chen C. . 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

[122] Zhang Z, Zhang Z, Zhang X. . Single pot selective conversion of furfural into 2-methylfuran over a Co-CoO_x/AC bifunctional catalyst. Applied Surface Science, 2023, 612: 155871

[123] Hamid A H, Ali L, Shittu T. . Transformation of levoglucosan into liquid fuel via catalytic upgrading over Ni-CeO₂ catalysts. Molecular Catalysis, 2023, 547: 113382

[124] Asada D, Ikeda T, Muraoka K. . 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

[125] 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

[126] Wang X B, Xie Z Z, Guo L. . Mechanism of dibenzofuran hydrodeoxygenation on the surface of Pt(111): A DFT study. Catalysis Today, 2021, 364: 220–228

[127] Chen H, Liu J, Li W. . Mechanism insights into the decarbonylation of furfural to furan over Ni/MgO: A molecular simulation study. Energy & Fuels, 2023, 37(14): 10594–10602

[128] Zhang J, Jia Z, Yu S. . Regulating the Cu⁰–Cu⁺ ratio to enhance metal-support interaction for selective hydrogenation of furfural under mild conditions. Chemical Engineering Journal, 2023, 468: 143755

[129] Pino N, Sitthisa S, Tan Q. . 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

[130] Lin W, Chen Y, Zhang Y. . Surface synergetic effects of Ni–ReO_x for promoting the mild hydrogenation of furfural to tetrahydrofurfuryl alcohol. ACS Catalysis, 2023, 13(17): 11256–11267

[131] Luo J, Cheng Y, Niu H. . Efficient Cu/FeO_x catalyst with developed structure for catalytic transfer hydrogenation of furfural. Journal of Catalysis, 2022, 413: 575–587

[132] Zhao H, Liao X, Cui H. . Efficient Cu–Co bimetallic catalysts for the selective hydrogenation of furfural to furfuryl alcohol. Fuel, 2023, 351: 128887

[133] Yuan E, Wang C, Wu C. . 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

[134] Šivec R, Huš M, Likozar B. . 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

[135] Xue J, Wang Y, Meng Y. . Theoretical investigation of decarbonylation mechanism of furfural on Pd(111) and M/Pd(111) (M = Ru, Ni, Ir) surfaces. Molecular Catalysis, 2020, 493: 111054

[136] Liu W, Yang Y, Chen L. . Atomically-ordered active sites in NiMo intermetallic compound toward low-pressure hydrodeoxygenation of furfural. Applied Catalysis B: Environmental, 2021, 282: 119569

[137] 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

[138] Gunawan R, Cahyadi H S, Insyani R. . 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

[139] Hsiao Y W, Zong X, Zhou J. . 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

[140] Zhang Y, Zhan S, Liu K. . Heterogeneous hydrogenation with hydrogen spillover enabled by nitrogen vacancies on boron nitride-supported Pd nanoparticles. Angewandte Chemie International Edition 62, 2023, 62(9): e202217191

[141] Kim H, Yang S, Lim Y H. . 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

[142] Redina E A, Vikanova K V, Kapustin G I. . 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

[143] Kasabe M M, Kotkar V R, Dongare M K. . Phenol hydrogenation to COL catalysed by palladium supported on CuO/CeO₂. Chemistry, an Asian Journal, 2023, 18(11): e202300119

[144] 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

[145] Rong S, Tan H, Pang Z. . Synergetic effect between Pd clusters and oxygen vacancies in hierarchical Nb₂O₅ for lignin-derived phenol hydrodeoxygenation into benzene. Renewable Energy, 2022, 187: 271–281

[146] Rios-Escobedo R, Ortiz-Santos E, Colín-Luna J A. . 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

[147] Zanuttini M S, Gross M, Marchetti G. . Furfural hydrodeoxygenation on iron and platinum catalysts. Applied Catalysis A, General, 2019, 587: 117217

[148] Guo L, Tian Y, He X. . Hydrodeoxygenation of phenolics over uniformly dispersed Pt–Ni alloys supported by self-pillared ZSM-5 nanosheets. Fuel, 2022, 322: 124082

[149] Wu X, Liu C, Wang H. . 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

[150] Li T, Miao K, Zhao Z. . Understanding cellulose pyrolysis under hydrogen atmosphere. Energy Conversion and Management, 2022, 254: 115195

[151] Wang H, Li T, Su J. . Noncatalytic hydropyrolysis of lignin in a high pressure micro-pyrolyzer. Fuel Processing Technology, 2022, 233: 107289

[152] Geng Y, Li H. Hydrogen spillover-enhanced heterogeneously catalyzed hydrodeoxygenation for biomass upgrading, ChemSusChem, 2022, 15(8): e202102495

[153] Alayoglu S, An K, Melaet G. . 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

[154] Ahmed F, Alam M K, Muira R. . 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

[155] Messou D, Bernardin V, Meunier F. . Origin of the synergistic effect between TiO₂ crystalline phases in the Ni/TiO₂-catalyzed CO₂ methanation reaction. Journal of Catalysis, 2021, 398: 14–28

[156] Zhang S, Xia Z, Zhang M. . Boosting selective hydrogenation through hydrogen spillover on supported-metal catalysts at room temperature. Applied Catalysis B: Environmental, 2021, 297: 120418

[157] 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

[158] Newman C, Zhou X, Goundie B. . Effects of support identity and metal dispersion in supported ruthenium hydrodeoxygenation catalysts. Applied Catalysis A, General, 2014, 477: 64–74

[159] Moogi S, Jae J, Kannapu H P R. . Enhancement of aromatics from catalytic pyrolysis of yellow poplar: Role of hydrogen and methane decomposition. Bioresource Technology, 2020, 315: 123835

[160] Moogi S, Pyo S, Farooq A. . 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

[161] Austin D, Wang A, He P. . Catalytic valorization of biomass derived glycerol under methane: Effect of catalyst synthesis method. Fuel, 2018, 216: 218–226

[162] Peng H, Wang A, He P. . Solvent-free catalytic conversion of xylose with methane to aromatics over Zn–Cr modified zeolite catalyst. Fuel, 2019, 253: 988–996

[163] 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

[164] He P, Shan W, Xiao Y. . Performance of Zn/ZSM-5 for in situ catalytic upgrading of pyrolysis bio-oil by methane. Topics in Catalysis, 2016, 59(1): 86–93

[165] Wang A, Austin D, Qian H. . Catalytic valorization of furfural under methane environment. ACS Sustainable Chemistry & Engineering, 2018, 6(7): 8891–8903

[166] Tshikesho R S, Kumar A, Huhnke R L. . Catalytic co-pyrolysis of red cedar with methane to produce upgraded bio-oil. Bioresource Technology, 2019, 285: 121299

[167] 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

[168] Tang P, Zhu Q, Wu Z. . Methane activation: The past and future. Energy & Environmental Science, 2014, 7(8): 2580–2591

[169] 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

[170] Xu Y, Liu S, Guo X. . Methane activation without using oxidants over Mo/HZSM-5 zeolite catalysts. Catalysis Letters, 1995, 30(1–4): 135–149

[171] Xu J, Zheng A, Wang X. . 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

[172] Luzgin M V, Rogov V A, Arzumanov S S. . Understanding methane aromatization on a Zn-modified high-silica zeolite. Angewandte Chemie International Edition, 2008, 47(24): 4559–4562

[173] Gabrienko A A, Arzumanov S S, Luzgin M V. . Methane activation on Zn²⁺-exchanged ZSM-5 zeolites. The effect of molecular oxygen addition. Journal of Physical Chemistry C, 2015, 119(44): 24910–24918

[174] Wang A, Song H. Maximizing the production of aromatic hydrocarbons from lignin conversion by coupling methane activation. Bioresource Technology, 2018, 268: 505–513

[175] He P, Wang A, Meng S. . Impact of Al sites on the methane co-aromatization with alkanes over Zn/HZSM-5. Catalysis Today, 2019, 323: 94–104

[176] Wang A, Austin D, Karmakar A. . 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

[177] Du L, Luo Z, Wang K. . 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

[178] Li S, Liu B, Truong J. . One-pot hydrodeoxygenation (HDO) of lignin monomers to C9 hydrocarbons co-catalysed by Ru/C and Nb₂O₅. Green Chemistry, 2020, 22(21): 7406–7416

[179] 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

[180] 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

[181] Kim Y M, Jae J, Kim B S. . 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

[182] Ahmed M H M, Batalha N, Mahmudul H M D. . 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

[183] Wu P, Zhao D, Lu G. . 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

[184] 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

[185] Shafaghat H, Lee I G, Jae J. . Pd/C catalyzed transfer hydrogenation of pyrolysis oil using 2-propanol as hydrogen source. Chemical Engineering Journal, 2019, 377: 119986

[186] 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

[187] Boscagli C, Yang C, Welle A. . Effect of pyrolysis oil components on the activity and selectivity of nickel-based catalysts during hydrotreatment. Applied Catalysis A, General, 2017, 544: 161–172

[188] Ambursa M M, Juan J C, Yahaya Y. . A review on catalytic hydrodeoxygenation of lignin to transportation fuels by using nickel-based catalysts. Renewable & Sustainable Energy Reviews, 2021, 138: 110667

[189] 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

[190] Khanh TranQVu Ly HAnh VoT, . 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: () 10018410.1016/j.ecmx.2022.100184

[191] Tian Y, Guo L, Qiao C. . Dynamics-driven tailoring of sub-nanometric Pt–Ni bimetals confined in hierarchical zeolite for catalytic hydrodeoxygenation. Applied Catalysis B: Environmental, 2023, 336: 122945

[192] Chen S, Yan P, Yu X. . Conversion of lignin to high yields of aromatics over Ru–ZnO/SBA-15 bifunctional catalysts. Renewable Energy, 2023, 215: 118919

[193] Hita I, Cordero-Lanzac T, Kekäläinen T. . 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

[194] Cordero-Lanzac T, Palos R, Hita I. . Revealing the pathways of catalyst deactivation by coke during the hydrodeoxygenation of raw bio-oil. Applied Catalysis B: Environmental, 2018, 239: 513–524

[195] Wu T, Dang Q, Wu Y. . Catalytic hydropyrolysis of biomass over NiMo bimetallic carbon-based catalysts. Journal of Environmental Chemical Engineering, 2023, 11(3): 110024

[196] Wang J, Jiang J, Li D. . 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

[197] Liu Y, Chen L, Chen Y. . Pilot study on production of aviation fuel from catalytic conversion of corn stover. Bioresource Technology, 2023, 372: 128653

[198] Ma D, Lu S, Liu X. . 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

[199] Li R, Zhao Z, Zhang B. . 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

[200] 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

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