Hydrodeoxygenation of lignin model compounds to alkanes over Pd–Ni/HZSM-5 catalysts

Journal of the Energy Institute - Tập 93 Số 3 - Trang 899-910 - 2020
Yun‐Peng Zhao1,2, Fa-Peng Wu1, Qing-Lu Song1, Xing Fan1, Lijun Jin3, Ruiyu Wang2, Jing‐Pei Cao1, Xian‐Yong Wei1
1Key Laboratory of Coal Processing and Efficient Utilization, Ministry of Education, China University of Mining & Technology, Xuzhou 221116, Jiangsu, China
2Low Carbon Energy Institute, China University of Mining & Technology, Xuzhou 221008, Jiangsu, China
3State Key Laboratory of Fine Chemicals, Institute of Coal Chemical Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, China

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Tài liệu tham khảo

Vasireddy, 2011, Clean liquid fuels from direct coal liquefaction: chemistry, catalysis, technological status and challenges, Energy Environ. Sci., 4, 311, 10.1039/C0EE00097C

Huber, 2006, Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering, Chem. Rev., 106, 4044, 10.1021/cr068360d

Li, 2015, Catalytic transformation of lignin for the production of chemicals and fuels, Chem. Rev., 115, 11559, 10.1021/acs.chemrev.5b00155

Carlson, 2011, Production of green aromatics and olefins by catalytic fast pyrolysis of wood sawdust, Energy Environ. Sci., 4, 145, 10.1039/C0EE00341G

Chheda, 2007, Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals, Angew. Chem. Int. Ed., 46, 7164, 10.1002/anie.200604274

Zhai, 2017, Depolymerization of lignin via a non-precious Ni–Fe alloy catalyst supported on activated carbon, Green Chem., 19, 1895, 10.1039/C7GC00149E

Zakzeski, 2010, The catalytic valorization of lignin for the production of renewable chemicals, Chem. Rev., 110, 3552, 10.1021/cr900354u

Pandey, 2011, Lignin depolymerization and conversion: a review of thermochemical methods, Chem. Eng. Technol., 34, 29, 10.1002/ceat.201000270

Zhang, 2016, Ni/Al2O3 catalysts derived from layered double hydroxide and their applications in hydrodeoxygenation of anisole, Chem. Select, 1, 577

Parsell, 2015, A synergistic biorefinery based on catalytic conversion of lignin prior to cellulose starting from lignocellulosic biomass, Green Chem., 17, 1492, 10.1039/C4GC01911C

Zaheer, 2015, Catalytic hydrogenolysis of aryl ethers: a key step in lignin valorization to valuable chemicals, ACS Catal., 5, 1675, 10.1021/cs501498f

Zhang, 2014, Hydrodeoxygenation of lignin-derived phenolic monomers and dimers to alkane fuels over bifunctional zeolite-supported metal catalysts, ACS Sustain. Chem. Eng., 2, 683, 10.1021/sc400401n

Guo, 2017, Direct deoxygenation of lignin model compounds into aromatic hydrocarbons through hydrogen transfer reaction, Appl. Catal. A, 547, 30, 10.1016/j.apcata.2017.07.050

Besse, 2017, Reactivity of lignin model compounds through hydrogen transfer catalysis in ethanol/water mixtures, Appl. Catal. B, 209, 265, 10.1016/j.apcatb.2017.03.013

Chatterjee, 2013, An efficient cleavage of the aryl ether C-O bond in supercritical carbon dioxide-water, Chem. Commun., 49, 4567, 10.1039/c3cc41522h

Rensel, 2013, Highly selective bimetallic FeMoP catalyst for C–O bond cleavage of aryl ethers, J. Catal., 305, 256, 10.1016/j.jcat.2013.05.026

Ochoa, 2018, Carbon nanofiber supported Mo2C catalysts for hydrodeoxygenation of guaiacol: the importance of the carburization process, Appl. Catal. B, 239, 463, 10.1016/j.apcatb.2018.08.043

Sulman, 2019, Kinetic thermodynamic analysis of guaiacol hydrodeoxygenation, Catal. Lett., 149, 2453, 10.1007/s10562-019-02856-x

Liu, 2017, Selective hydrodeoxygenation of lignin-derived phenols to cyclohexanols over Co-based catalysts, ACS Sustain. Chem. Eng., 5, 8594, 10.1021/acssuschemeng.7b01047

Qi, 2017, Integrated study on the role of solvent, catalyst and reactant in the hydrodeoxygenation of eugenol over nickel-based catalysts, Appl. Catal. A, 535, 24, 10.1016/j.apcata.2017.01.020

Song, 2015, Synergistic effects of Ni and acid sites for hydrogenation and C–O bond cleavage of substituted phenols, Green Chem., 17, 1204, 10.1039/C4GC01798F

Zhao, 2010, Hydrodeoxygenation of bio-derived phenols to hydrocarbons using RANEY Ni and Nafion/SiO2 catalysts, Chem. Commun., 46, 412, 10.1039/B916822B

Zhao, 2012, Upgrading pyrolysis oil over Ni/HZSM-5 by cascade reactions, Angew. Chem., 51, 5935, 10.1002/anie.201108306

Gao, 2016, Chemo- and regioselective hydrogenolysis of diaryl ether C-O bonds by a robust heterogeneous Ni/C catalyst: applications to the cleavage of complex lignin-related fragments, Angew. Chem., 55, 1474, 10.1002/anie.201509133

Tieuli, 2019, Hydrodeoxyhenation of isoeugenol over Ni-SBA-15: kinetics and modelling, Appl. Catal. A, 580, 1, 10.1016/j.apcata.2019.04.028

Alda-Onggar, 2019, Hydrodeoxygenation of phenolic model compounds over zirconia supported Ir and Ni-catalysts, React. Kinet. Mech. Catal., 126, 737, 10.1007/s11144-018-1502-1

Ma, 2015, Ni nanoparticles encapsulated into mesoporous single-crystalline HBEA: application for drainage oil hydrodeoxygenation to diesel, Green Chem., 17, 4610, 10.1039/C5GC01199J

Zhang, 2014, A series of NiM (M = Ru, Rh, and Pd) bimetallic catalysts for effective lignin hydrogenolysis in water, ACS Catal., 4, 1574, 10.1021/cs401199f

Kim, 2015, Selective cleavage of C-O bond in benzyl phenyl ether to aromatics over Pd–Fe bimetallic catalyst supported on ordered mesoporous carbon, Appl. Catal. A, 498, 142, 10.1016/j.apcata.2015.03.034

Zhang, 2016, Facile and selective hydrogenolysis of β-O-4 linkages in lignin catalyzed by Pd–Ni bimetallic nanoparticles supported on ZrO2, Green Chem., 18, 6229, 10.1039/C6GC02265K

Hong, 2010, Hydrodeoxygenation and coupling of aqueous phenolics over bifunctional zeolite-supported metal catalysts, Chem. Commun., 46, 1038, 10.1039/B918209H

Zhou, 2017, Highly selective catalytic hydroconversion of benzyloxybenzene to bicyclic cyclanes over bifunctional nickel catalysts, Catal. Commun., 98, 38, 10.1016/j.catcom.2017.04.042

Yao, 2015, Hydrodeoxygenation of lignin-derived phenolic compounds over bi-functional Ru/H-Beta under mild conditions, Fuel, 150, 175, 10.1016/j.fuel.2015.02.035

Zhang, 2018, Hydrodeoxygenation of lignin-derived phenoic compounds to hydrocarbon fuel over supported Ni-based catalysts, Appl. Energy, 227, 73, 10.1016/j.apenergy.2017.08.078

Luo, 2016, Hydrothermally stable Ru/HZSM-5-catalyzed selective hydrogenolysis of lignin-derived substituted phenols to bio-arenes in water, Green Chem., 18, 5845, 10.1039/C6GC01971D

Frisch, 2009

Zhao, 2008, Density functionals with broad applicability in chemistry, Acc. Chem. Res., 41, 157, 10.1021/ar700111a

Kendall, 1992, Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions, J. Chem. Phys., 96, 6796, 10.1063/1.462569

Tang, 2010, Effect of Fe state on electrocatalytic activity of Pd–Fe/C catalyst for oxygen reduction, Appl. Surf. Sci., 256, 4196, 10.1016/j.apsusc.2010.01.124

Xia, 2016, Hydrogenation of nitrophenols catalyzed by carbon black-supported nickel nanoparticles under mild conditions, Appl. Catal. B, 180, 408, 10.1016/j.apcatb.2015.06.043

Park, 2002, Chemical and electronic effects of Ni in Pt/Ni and Pt/Ru/Ni alloy nanoparticles in methanol electrooxidation, J. Phys. Chem. B, 106, 10.1021/jp013168v

Lin, 2012, Deactivation of Ni/TiO2 catalyst in the hydrogenation of nitrobenzene in water and improvement in its stability by coating a layer of hydrophobic carbon, J. Catal., 291, 149, 10.1016/j.jcat.2012.04.020

Luo, 2017, Bimetallic Ru–Ni catalyzed aqueous-phase guaiacol hydrogenolysis at low H2 pressures, ACS Catal., 7, 8304, 10.1021/acscatal.7b02317

Bourikas, 2006, The role of the liquid-solid interface in the preparation of supported catalysts, Catal. Rev., 48, 363, 10.1080/01614940600962321

Jin, 2016, Hydrodeoxygenation of lignin-derived diaryl ethers to aromatics and alkanes using nickel on Zr-doped niobium phosphate, Chem. Select, 1, 4949

Saidi, 2014, Upgrading of lignin-derived bio-oils by catalytic hydrodeoxygenation, Energy Environ. Sci., 7, 103, 10.1039/C3EE43081B

Nava, 2009, Upgrading of bio-liquids on different mesoporous silica-supported CoMo catalysts, Appl. Catal. B, 92, 154, 10.1016/j.apcatb.2009.07.014

Ghampson, 2017, Catalytic hydrodeoxygenation of anisole over Re-MoOx/TiO2 and Re-VO x/TiO2 catalysts, Appl. Catal. B, 208, 60, 10.1016/j.apcatb.2017.02.047

Zuo, 2012, Hydrodeoxygenation of methyl palmitate over supported Ni catalysts for diesel-like fuel production, Energy Fuels, 26, 3747, 10.1021/ef300063b

Li, 2015, A theoretical study on bond dissociation enthalpies of coal based model compounds, Fuel, 153, 70, 10.1016/j.fuel.2015.02.088

Kim, 2015, Catalytic decomposition of phenethyl phenyl ether to aromatics over Pd–Fe bimetallic catalysts supported on ordered mesoporous carbon, J. Mol. Catal. A, 410, 184, 10.1016/j.molcata.2015.09.023

Hu, 2018, Hydrogenolysis of lignin model compounds into aromatics with bimetallic Ru-Ni supported onto nitrogen-doped activated carbon catalyst, Mol. Catal., 445, 316, 10.1016/j.mcat.2017.12.009

Jin, 2015, Cleavage of lignin-Derived 4-O-5 aryl ethers over nickel nanoparticles supported on niobic acid-activated carbon composites, Ind. Eng. Chem. Res., 54, 2302, 10.1021/ie504600f

Chen, 2013, Hydrodeoxygenation of phenol and derivatives over an ionic liquid-like copolymer stabilized nanocatalyst in aqueous media, ChemCatChem, 5, 1598, 10.1002/cctc.201200582

Zhao, 2011, Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes, J. Catal., 280, 8, 10.1016/j.jcat.2011.02.001

Ohta, 2011, Hydrodeoxygenation of phenols as lignin models under acid-free conditions with carbon-supported platinum catalysts, Chem. Commun., 47, 12209, 10.1039/c1cc14859a

Zhu, 2011, Bifunctional transalkylation and hydrodeoxygenation of anisole over a Pt/HBeta catalyst, J. Catal., 281, 21, 10.1016/j.jcat.2011.03.030

He, 2012, Ni-catalyzed cleavage of aryl ethers in the aqueous phase, J. Am. Chem. Soc., 134, 20768, 10.1021/ja309915e

Liu, 2017, Difunctional nickel/microfiber attapulgite modified with an acidic ionic liquid for catalytic hydroconversion of lignite-related model compounds, Fuel, 204, 236, 10.1016/j.fuel.2017.05.039