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http://dx.doi.org/10.7464/ksct.2022.28.2.174

Catalytic Hydrodeoxygenation of Biomass-Derived Oxygenates: a Review  

Ha, Jeong-Myeong (Clean Energy Research Center, Korea Institute of Science and Technology)
Publication Information
Clean Technology / v.28, no.2, 2022 , pp. 174-181 More about this Journal
Abstract
Biomass is a sustainable alternative resource for production of liquid fuels and organic compounds that are currently produced from fossil fuels including petroleum, natural gas, and coal. Because the use of fossil fuels can increase the production of greenhouse gases, the use of carbon-neutral biomass can contribute to the reduction of global warming. Although biological and chemical processes have been proposed to produce petroleum-replacing chemicals and fuels from biomass feedstocks, it is difficult to replace completely fossil fuels because of the high oxygen content of biomass. Production of petroleum-like fuels and chemicals from biomass requires the removal of oxygen atoms or conversion of the oxygen functionalities present in biomass derivatives, which can be achieved by catalytic hydrodeoxygenation. Hydrodeoxygenation has been used to convert raw biomass-derived materials, such as biomass pyrolysis oils and lignocellulose-derived chemicals and lipids, into deoxygenated fuels and chemicals. Multifunctional catalysts composed of noble metals and transition metals supported on high surface area metal oxides and carbons, usually selected as supports of heterogeneous catalysts, have been used as efficient hydrodeoxygenation catalysts. In this review, the catalysts proposed in the literature are surveyed and hydrodeoxygenation reaction systems using these catalysts are discussed. Based on the hydrodeoxygenation methods reported in the literature, an insight for feasible hydrodeoxygenation process development is also presented.
Keywords
Biomass; Hydrodeoxygenation; Catalysts; Deoxygenated fuels;
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1 Dwiatmoko, A. A., Seo, J., Choi, J.-W., Suh, D. J., Jae, J., and Ha, J.-M., "Improved activity of a CaCO3-supported Ru catalyst for the hydrodeoxygenation of eugenol as a model lignin-derived phenolic compound," Catal. Commun., 127, 45-50 (2019).   DOI
2 Guo, Q., Wu, M., Wang, K., Zhang, L., and Xu, X., "Catalytic Hydrodeoxygenation of Algae Bio-oil over Bimetallic Ni-Cu/ZrO2 Catalysts," Ind. Eng. Chem. Res., 54(3), 890-899 (2015).   DOI
3 Jae, J., Zheng, W., Karim, A. M., Guo, W., Lobo, R. F., and Vlachos, D. G., "The Role of Ru and RuO2 in the Catalytic Transfer Hydrogenation of 5-Hydroxymethylfurfural for the Production of 2,5-Dimethylfuran," ChemCatChem, 6(3), 848-856 (2014).   DOI
4 Choi, J., Choi, J.-W., Suh, D. J., Ha, J.-M., Hwang, J. W., Jung, H. W., Lee, K.-Y., and Woo, H.-C., "Production of brown algae pyrolysis oils for liquid biofuels depending on the chemical pretreatment methods," Energy Convers. Manage., 86(0), 371-378 (2014).   DOI
5 Li, C., Nakagawa, Y., Tamura, M., Nakayama, A., and Tomishige, K., "Hydrodeoxygenation of Guaiacol to Phenol over Ceria-Supported Iron Catalysts," ACS Catal., 10(24), 14624-14639 (2020).   DOI
6 Dwiatmoko, A. A., Lee, S., Ham, H. C., Choi, J.-W., Suh, D. J., and Ha, J.-M., "Effects of carbohydrates on the hydrodeoxygenation of lignin-derived phenolic compounds," ACS Catal., 5(1), 433-437 (2015).   DOI
7 Luo, W., Cao, W., Bruijnincx, P. C. A., Lin, L., Wang, A., and Zhang, T., "Zeolite-supported metal catalysts for selective hydrodeoxygenation of biomass-derived platform molecules," Green Chem., 21(14), 3744-3768 (2019).   DOI
8 Zhao, C., and Lercher, J. A., "Upgrading Pyrolysis Oil over Ni/HZSM-5 by Cascade Reactions," Angew. Chem. Int. Ed., 51(24), 5935-5940 (2012).   DOI
9 Guzman, A., Torres, J. E., Prada, L. P., and Nunez, M. L., "Hydroprocessing of crude palm oil at pilot plant scale," Catal. Today, 156(1), 38-43 (2010).   DOI
10 Dabros, T. M. H., Gaur, A., Pintos, D. G., Sprenger, P., Hoj, M., Hansen, T. W., Studt, F., Gabrielsen, J., Grunwaldt, J.-D., and Jensen, A. D., "Influence of H2O and H2S on the composition, activity, and stability of sulfided Mo, CoMo, and NiMo supported on MgAl2O4 for hydrodeoxygenation of ethylene glycol," Appl. Catal., A, 551, 106-121 (2018).   DOI
11 Luo, J., Yun, H., Mironenko, A. V., Goulas, K., Lee, J. D., Monai, M., Wang, C., Vorotnikov, V., Murray, C. B., Vlachos, D. G., Fornasiero, P., and Gorte, R. J., "Mechanisms for High Selectivity in the Hydrodeoxygenation of 5-Hydroxymethylfurfural over PtCo Nanocrystals," ACS Catal., 6(7), 4095-4104 (2016).   DOI
12 Dwiatmoko, A. A., Zhou, L., Kim, I., Choi, J.-W., Suh, D. J., and Ha, J.-M., "Hydrodeoxygenation of lignin-derived monomers and lignocellulose pyrolysis oil on the carbon-supported Ru catalysts," Catal. Today, 265, 192-198 (2016).   DOI
13 Shu, R., Lin, B., Zhang, J., Wang, C., Yang, Z., and Chen, Y., "Efficient catalytic hydrodeoxygenation of phenolic compounds and bio-oil over highly dispersed Ru/TiO2," Journal of Fuel processing and technology, 184, 12-18 (2019).   DOI
14 Wang, G.-H., Cao, Z., Gu, D., Pfander, N., Swertz, A.-C., Spliethoff, B., Bongard, H.-J., Weidenthaler, C., Schmidt, W., Rinaldi, R., and Schuth, F., "Nitrogen-Doped Ordered Mesoporous Carbon Supported Bimetallic PtCo Nanoparticles for Upgrading of Biophenolics," Angew. Chem. Int. Ed., 55(31), 8850-8855 (2016).   DOI
15 Resende, K. A., Braga, A. H., Noronha, F. B., and Hori, C. E., "Hydrodeoxygenation of phenol over Ni/Ce1-xNbxO2 catalysts," Appl. Catal., B, 245, 100-113 (2019).   DOI
16 Li, J., Zhang, J., Wang, S., Xu, G., Wang, H., and Vlachos, D. G., "Chemoselective Hydrodeoxygenation of Carboxylic Acids to Hydrocarbons over Nitrogen-Doped Carbon-Alumina Hybrid Supported Iron Catalysts," ACS Catal., 9(2), 1564-1577 (2019).   DOI
17 Saha, B., Bohn, C. M., and Abu-Omar, M. M., "Zinc-Assisted Hydrodeoxygenation of Biomass-Derived 5-Hydroxymethylfurfural to 2,5-Dimethylfuran," ChemSusChem, 7(11), 3095-3101 (2014).   DOI
18 Zhao, X., Wu, X., Wang, H., Han, J., Ge, Q., and Zhu, X., "Effect of Strong Metal-Support Interaction of Pt/TiO2 on Hydrodeoxygenation of m-Cresol," ChemistrySelect, 3(37), 10364-10370 (2018).   DOI
19 Yoon, J. S., Lee, T., Choi, J.-W., Suh, D. J., Lee, K., Ha, J.-M., and Choi, J., "Layered MWW zeolite-supported Rh catalysts for the hydrodeoxygenation of lignin model compounds," Catal. Today, 293, 142-150 (2017).   DOI
20 Gamliel, D. P., Baillie, B. P., Augustine, E., Hall, J., Bollas, G. M., and Valla, J. A., "Nickel impregnated mesoporous USY zeolites for hydrodeoxygenation of anisole," Journal of Microporous and Mesoporous Materials, 261, 18-28 (2018).   DOI
21 Balakrishnan, M., Sacia, E. R., and Bell, A. T., "Selective hydrogenation of furan-containing condensation products as a source of biomass-derived diesel additives," ChemSusChem, 7(10), 2796-2800 (2014).   DOI
22 Ishigaki, A., and Shono, T., "The cationic oligomerization of 2-methylfuran and the characteristics of the oligomers," Bull. Chem. Soc. Jpn., 47(6), 1467-1470 (1974).   DOI
23 Eftax, D. S. P., and Dunlop, A. P., "Hydrolysis of simple furans. Products of secondary condensation," J. Org. Chem., 30(4), 1317-1319 (1965).   DOI
24 Corma, A., de la Torre, O., and Renz, M., "High-quality diesel from hexose- and pentose-derived biomass platform molecules," ChemSusChem, 4(11), 1574-1577 (2011).   DOI
25 Knothe, G., "Biodiesel and renewable diesel: A comparison," Prog. Energy Combust. Sci., 36(3), 364-373 (2010).   DOI
26 Yati, I., Yeom, M., Choi, J.-W., Choo, H., Suh, D. J., and Ha, J.-M., "Water-promoted selective heterogeneous catalytic trimerization of xylose-derived 2-methylfuran to diesel precursors," Appl. Catal., A, 495(0), 200-205 (2015).   DOI
27 Kim, Y., Shim, J., Choi, J.-W., Jin Suh, D., Park, Y.-K., Lee, U., Choi, J., and Ha, J.-M., "Continuous-flow production of petroleum-replacing fuels from highly viscous Kraft lignin pyrolysis oil using its hydrocracked oil as a solvent," Energy Convers. Manage., 213, 112728 (2020).   DOI
28 Liu, G., Robertson, A. W., Li, M. M.-J., Kuo, W. C., Darby, M. T., Muhieddine, M. H., Lin, Y.-C., Suenaga, K., Stamatakis, M., and Warner, J. H., "MoS 2 monolayer catalyst doped with isolated Co atoms for the hydrodeoxygenation reaction," Nat. Chem., 9(8), 810 (2017).   DOI
29 Zhang, F., Zheng, S., Xiao, Q., Zhong, Y., Zhu, W., Lin, A., and Samy El-Shall, M., "Synergetic catalysis of palladium nanoparticles encaged within amine-functionalized UiO-66 in the hydrodeoxygenation of vanillin in water," Green Chem., 18(9), 2900-2908 (2016).   DOI
30 Xu, X., Li, Y., Gong, Y., Zhang, P., Li, H., and Wang, Y., "Synthesis of palladium nanoparticles supported on mesoporous N-doped carbon and their catalytic ability for biofuel upgrade," Journal of the American Chemical Society, 134(41), 16987-16990 (2012).   DOI
31 Fu, L., Ba, W., Li, Y., Li, X., Zhao, J., Zhang, S., and Liu, Y., "Hydrodeoxygenation of non-edible bio-lipids to renewable hydrocarbons over mesoporous SiO2-TiO2 supported NiMo bimetallic catalyst," Appl. Catal., A, 633, 118475 (2022).   DOI
32 Nie, R., Yang, H., Zhang, H., Yu, X., Lu, X., Zhou, D., and Xia, Q., "Mild-temperature hydrodeoxygenation of vanillin over porous nitrogen-doped carbon black supported nickel nanoparticles," Green Chem., 19(13), 3126-3134 (2017).   DOI
33 Chaiwong, K., Kiatsiriroat, T., Vorayos, N., and Thararax, C., "Study of bio-oil and bio-char production from algae by slow pyrolysis," Biomass Bioenergy, 56, 600-606 (2013).   DOI
34 Fang, H., Zheng, J., Luo, X., Du, J., Roldan, A., Leoni, S., and Yuan, Y., "Product tunable behavior of carbon nanotubessupported Ni-Fe catalysts for guaiacol hydrodeoxygenation," Appl. Catal., A, 529, 20-31 (2017).   DOI
35 Koike, N., Hosokai, S., Takagaki, A., Nishimura, S., Kikuchi, R., Ebitani, K., Suzuki, Y., and Oyama, S. T., "Upgrading of pyrolysis bio-oil using nickel phosphide catalysts," J. Catal., 333, 115-126 (2016).   DOI
36 Kim, H., Yang, S., Lim, Y. H., Ha, J.-M., and Kim, D. H., "Upgrading bio-oil model compound over bifunctional Ru/HZSM-5 catalysts in biphasic system: Complete hydrodeoxygenation of vanillin," J. Hazard. Mater., 423, 126525 (2022).   DOI
37 Tan, Q., Wang, G., Long, A., Dinse, A., Buda, C., Shabaker, J., and Resasco, D. E., "Mechanistic analysis of the role of metal oxophilicity in the hydrodeoxygenation of anisole," J. Catal., 347, 102-115 (2017).   DOI
38 Yang, F., Libretto, N. J., Komarneni, M. R., Zhou, W., Miller, J. T., Zhu, X., and Resasco, D. E., "Enhancement of m-Cresol Hydrodeoxygenation Selectivity on Ni Catalysts by Surface Decoration of MoOx Species," ACS Catal., 9(9), 7791-7800 (2019).   DOI
39 de Souza, P. M., Rabelo-Neto, R. C., Borges, L. E. P., Jacobs, G., Davis, B. H., Sooknoi, T., Resasco, D. E., and Noronha, F. B., "Role of Keto Intermediates in the Hydrodeoxygenation of Phenol over Pd on Oxophilic Supports," ACS Catal., 5(2), 1318-1329 (2015).   DOI
40 Romero, Y., Richard, F., and Brunet, S., "Hydrodeoxygenation of 2-ethylphenol as a model compound of bio-crude over sulfided Mo-based catalysts: Promoting effect and reaction mechanism," Appl. Catal., B, 98(3), 213-223 (2010).   DOI
41 Li, Y., Zhang, C., Liu, Y., Tang, S., Chen, G., Zhang, R., and Tang, X., "Coke formation on the surface of Ni/HZSM-5 and Ni-Cu/HZSM-5 catalysts during bio-oil hydrodeoxygenation," Fuel, 189, 23-31 (2017).   DOI
42 Lee, E. H., Park, R.-s., Kim, H., Park, S. H., Jung, S.-C., Jeon, J.-K., Kim, S. C., and Park, Y.-K., "Hydrodeoxygenation of guaiacol over Pt loaded zeolitic materials," J. Ind. Eng. Chem., 37, 18-21 (2016).   DOI
43 Nimmanwudipong, T., Aydin, C., Lu, J., Runnebaum, R., Brodwater, K., Browning, N., Block, D., and Gates, B., "Selective Hydrodeoxygenation of Guaiacol Catalyzed by Platinum Supported on Magnesium Oxide," Catal. Lett., 142(10), 1190-1196 (2012).   DOI
44 Tian, S., Wang, Z., Gong, W., Chen, W., Feng, Q., Xu, Q., Chen, C., Chen, C., Peng, Q., Gu, L., Zhao, H., Hu, P., Wang, D., and Li, Y., "Temperature-Controlled Selectivity of Hydrogenation and Hydrodeoxygenation in the Conversion of Biomass Molecule by the Ru1/mpg-C3N4 Catalyst," Journal of the American Chemical Society, 140(36), 11161-11164 (2018).   DOI
45 Sitthisa, S., Sooknoi, T., Ma, Y., Balbuena, P. B., and Resasco, D. E., "Kinetics and mechanism of hydrogenation of furfural on Cu/SiO2 catalysts," J. Catal., 277(1), 1-13 (2011).   DOI
46 Corma, A., de la Torre, O., and Renz, M., "Production of high quality diesel from cellulose and hemicellulose by the Sylvan process: Catalysts and process variables," Energy Environ. Sci., 5(4), 6328-6344 (2012).   DOI
47 Corma, A., de la Torre, O., Renz, M., and Villandier, N., "Production of high-quality diesel from biomass waste products," Angew. Chem. Int. Ed., 50(10), 2375-2378 (2011).   DOI
48 Kim, G., Seo, J., Choi, J.-W., Jae, J., Ha, J.-M., Suh, D. J., Lee, K.-Y., Jeon, J.-K., and Kim, J.-K., "Two-step continuous upgrading of sawdust pyrolysis oil to deoxygenated hydrocarbons using hydrotreating and hydrodeoxygenating catalysts," Catal. Today, 303, 130-135 (2018).   DOI
49 Kwon, J. S., Choo, H., Choi, J.-W., Jae, J., Jin Suh, D., Young Lee, K., and Ha, J.-M., "Condensation of pentose-derived furan compounds to C15 fuel precursors using supported phosphotungstic acid catalysts: Strategy for designing heterogeneous acid catalysts based on the acid strength and pore structures," Appl. Catal., A, 570, 238-244 (2019).   DOI
50 Roldugina, E. A., Naranov, E. R., Maximov, A. L., and Karakhanov, E. A., "Hydrodeoxygenation of guaiacol as a model compound of bio-oil in methanol over mesoporous noble metal catalysts," Appl. Catal., A, 553, 24-35 (2018).   DOI
51 Masoumi, S., and Dalai, A. K., "NiMo carbide supported on algal derived activated carbon for hydrodeoxygenation of algal biocrude oil," Energy Convers. Manage., 231, 113834 (2021).   DOI
52 Dwiatmoko, A. A., Kim, I., Zhou, L., Choi, J.-W., Suh, D. J., Jae, J., and Ha, J.-M., "Hydrodeoxygenation of guaiacol on tungstated zirconia supported Ru catalysts," Appl. Catal., A, 543, 10-16 (2017).   DOI
53 Jafarian, S., Tavasoli, A., and Nikkhah, H., "Catalytic hydrotreating of pyro-oil derived from green microalgae spirulina the (Arthrospira) plantensis over NiMo catalysts impregnated over a novel hybrid support," Int. J. Hydrogen Energy, 44(36), 19855-19867 (2019).   DOI
54 Sitthisa, S., and Resasco, D. E., "Hydrodeoxygenation of Furfural Over Supported Metal Catalysts: A Comparative Study of Cu, Pd and Ni," Catal. Lett., 141(6), 784-791 (2011).   DOI
55 Lee, C. R., Yoon, J. S., Suh, Y.-W., Choi, J.-W., Ha, J.-M., Suh, D. J., and Park, Y.-K., "Catalytic roles of metals and supports on hydrodeoxygenation of lignin monomer guaiacol," Catal. Commun., 17, 54-58 (2012).   DOI
56 Elliott, D. C., Hart, T. R., Neuenschwander, G. G., Rotness, L. J., Olarte, M. V., Zacher, A. H., and Solantausta, Y., "Catalytic hydroprocessing of fast pyrolysis bio-oil from pine sawdust," Energy Fuels, 26(6), 3891-3896 (2012).   DOI
57 Kim, I., Dwiatmoko, A. A., Choi, J.-W., Suh, D. J., Jae, J., Ha, J.-M., and Kim, J.-K., "Upgrading of sawdust pyrolysis oil to hydrocarbon fuels using tungstate-zirconia-supported Ru catalysts with less formation of cokes," J. Ind. Eng. Chem., 56(Supplement C), 74-81 (2017).   DOI
58 Choi, W., Jo, H., Choi, J.-W., Suh, D. J., Lee, H., Kim, C., Kim, K. H., Lee, K.-Y., and Ha, J.-M., "Stabilization of acid-rich bio-oil by catalytic mild hydrotreating," Environ. Pollut., 272, 116180 (2021).   DOI
59 Luque, R., Herrero-Davila, L., Campelo, J. M., Clark, J. H., Hidalgo, J. M., Luna, D., Marinas, J. M., and Romero, A. A., "Biofuels: a technological perspective," Energy Environ. Sci., 1(5), 542-564 (2008).   DOI
60 Furimsky, E., "Catalytic hydrodeoxygenation," Appl. Catal., A, 199, 147-190 (2000).   DOI
61 Seo, J., Kwon, J. S., Choo, H., Choi, J.-W., Jae, J., Suh, D. J., Kim, S., and Ha, J.-M., "Production of deoxygenated high carbon number hydrocarbons from furan condensates: Hydrodeoxygenation of biomass-based oxygenates," Chem. Eng. J., 377, 119985 (2019).   DOI
62 Zhou, M., Ye, J., Liu, P., Xu, J., and Jiang, J., "Water-Assisted Selective Hydrodeoxygenation of Guaiacol to Cyclohexanol over Supported Ni and Co Bimetallic Catalysts," ACS Sustain. Chem. Eng., 5(10), 8824-8835 (2017).   DOI
63 Xia, Q., Xia, Y., Xi, J., Liu, X., Zhang, Y., Guo, Y., and Wang, Y., "Selective one-pot production of high-grade diesel-range alkanes from furfural and 2-Methylfuran over Pd/NbOPO4," ChemSusChem, 10(4), 747-753 (2017).   DOI
64 Yeletsky, P. M., Kukushkin, R. G., Yakovlev, V. A., and Chen, B. H., "Recent advances in one-stage conversion of lipid-based biomass-derived oils into fuel components - aromatics and isomerized alkanes," Fuel, 278, 118255 (2020).   DOI
65 Liu, X., Xu, L., Xu, G., Jia, W., Ma, Y., and Zhang, Y., "Selective Hydrodeoxygenation of Lignin-Derived Phenols to Cyclohexanols or Cyclohexanes over Magnetic CoNx@NC Catalysts under Mild Conditions," ACS Catal., 6(11), 7611-7620 (2016).   DOI
66 Elliott, D. C., "Review of recent reports on process technology for thermochemical conversion of whole algae to liquid fuels," Algal Research, 13, 255-263 (2016).   DOI
67 Park, S., Kannapu, H. P. R., Jeong, C., Kim, J., and Suh, Y.-W., "Highly Active Mesoporous Cu-Al2O3 Catalyst for the Hydrodeoxygenation of Furfural to 2-methylfuran," ChemCat Chem, 12(1), 105-111 (2020).   DOI
68 Nimmanwudipong, T., Runnebaum, R., Block, D., and Gates, B., "Catalytic Reactions of Guaiacol: Reaction Network and Evidence of Oxygen Removal in Reactions with Hydrogen," Catal. Lett., 141(6), 779-783 (2011).   DOI
69 Vikar, A., Solt, H. E., Novodarszki, G., Mihalyi, M. R., Barthos, R., Domjan, A., Hancsok, J., Valyon, J., and Lonyi, F., "A study of the mechanism of triglyceride hydrodeoxygenation over alumina-supported and phosphatized-alumina-supported Pd catalysts," J. Catal., 404, 67-79 (2021).   DOI
70 Long, J. X., Shu, S. Y., Wu, Q. Y., Yuan, Z. Q., Wang, T. J., Xu, Y., Zhang, X. H., Zhang, Q., and Ma, L. L., "Selective cyclohexanol production from the renewable lignin derived phenolic chemicals catalyzed by Ni/MgO," Energy Convers. Manage., 105, 570-577 (2015).   DOI
71 Bergvall, N., Sandstrom, L., Weiland, F., and Ohrman, O. G. W., "Corefining of Fast Pyrolysis Bio-Oil with Vacuum Residue and Vacuum Gas Oil in a Continuous Slurry Hydrocracking Process," Energy Fuels, 34(7), 8452-8465 (2020).   DOI