One-Pot Process for Hydrodeoxygenation of Lignin to Alkanes Using Ru-Based Bimetallic and Bifunctional Catalysts Supported on Zeolite Y

Wang, Hongliang; Ruan, Hao; Feng, Maoqi; Qin, Yuling; Job, Heather; Luo, Langli; Wang, Chongmin; Engelhard, Mark H.; Kuhn, Erik; Chen, Xiaowen; Tucker, Melvin P.; Yang, Bin

doi:10.1002/cssc.201700160

One-Pot Process for Hydrodeoxygenation of Lignin to Alkanes Using Ru-Based Bimetallic and Bifunctional Catalysts Supported on Zeolite Y

Journal Article · Thu Mar 16 00:00:00 EDT 2017 · ChemSusChem

DOI:https://doi.org/10.1002/cssc.201700160· OSTI ID:1361984

Wang, Hongliang ^[1]; Ruan, Hao ^[1]; Feng, Maoqi ^[2]; Qin, Yuling ^[1]; Job, Heather ^[3]; Luo, Langli ^[4]; Wang, Chongmin ^[4]; Engelhard, Mark H. ^[4]; Kuhn, Erik ^[5]; Chen, Xiaowen ^[5]; Tucker, Melvin P. ^[5]; ^[1]

Department of Biological Systems Engineering, Washington State University, Richland WA 99354 USA
Chemistry & Chemical Engineering Division, Southwest Research Institute, San Antonio TX 78238 USA
Pacific Northwest National Laboratory, 902 Battelle Blvd Richland WA 99354 USA
Environmental Molecular Sciences Laboratory, 3335 Q Ave Richland WA 99354 USA
National Bioenergy Center, National Renewable Energy Laboratory, 15013 Denver West Parkway Golden CO. 80401 USA

The synthesis of high-efficiency and low-cost multifunctional catalysts for hydrodeoxygenation (HDO) of waste lignin into advanced biofuels is crucial for enhancing current biorefinery processes. Inexpensive transition metals, including Fe, Ni, Cu, Zn, were severally co-loaded with Ru on HY zeolite to form bimetallic and bifunctional catalysts. These catalysts were subsequently tested for HDO conversion of softwood lignin and several lignin model compounds. Results indicated that the inexpensive earth abundant metals could modulate the hydrogenolysis activity of Ru and decrease the yield of low molecular weight gaseous side-products. Among all the prepared catalysts, Ru-Cu/HY showed the best HDO performance, giving the highest selectivity to hydrocarbon products. The improved catalytic performance of Ru-Cu/HY was probably due to the following three factors: (1) high total and strong acid sites, (2) good dispersion of metal species and limited segregation, (3) high adsorption capacity for polar fractions, including hydroxyl groups and ether bonds. Moreover, all the bifunctional catalysts were proven to be superior over the combination catalysts of Ru/Al2O3 and HY zeolite, and this could be attributed to the “intimacy criterion”. The practical use of the designed catalysts would be promising in lignin valorization.

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1361984

Report Number(s):: PNNL-SA-120890; 48379; KP1704020

Journal Information:: ChemSusChem, Journal Name: ChemSusChem Journal Issue: 8 Vol. 10; ISSN 1864-5631

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

References (72)

Acidolysis of α-O-4 Aryl-Ether Bonds in Lignin Model Compounds: A Modeling and Experimental Study Pelzer, Adam W.; Sturgeon, Matthew R.; Yanez, Abraham J. ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 7 https://doi.org/10.1021/acssuschemeng.5b00070	journal	June 2015
Catalytic roles of metals and supports on hydrodeoxygenation of lignin monomer guaiacol Lee, Cho Rim; Yoon, Ji Sun; Suh, Young-Woong Catalysis Communications, Vol. 17 https://doi.org/10.1016/j.catcom.2011.10.011	journal	January 2012
Effect of metal–acid site balance on hydroconversion of decalin over Pt/Beta zeolite bifunctional catalysts Monteiro, Carlos A. A.; Costa, Denise; Zotin, José L. Fuel, Vol. 160 https://doi.org/10.1016/j.fuel.2015.07.054	journal	November 2015
Catalytic Hydrodeoxygenation of Guaiacol on Rh-Based and Sulfided CoMo and NiMo Catalysts Lin, Yu-Chuan; Li, Chia-Liang; Wan, Hou-Peng Energy & Fuels, Vol. 25, Issue 3 https://doi.org/10.1021/ef101521z	journal	March 2011
Conversion of Guaiacol over Supported Ru Catalysts Boonyasuwat, Sunya; Omotoso, Taiwo; Resasco, Daniel E. Catalysis Letters, Vol. 143, Issue 8 https://doi.org/10.1007/s10562-013-1033-3	journal	June 2013
Hydrodeoxygenation of lignin-derived phenolic compounds over bi-functional Ru/H-Beta under mild conditions Yao, Gang; Wu, Guangjun; Dai, Weili Fuel, Vol. 150 https://doi.org/10.1016/j.fuel.2015.02.035	journal	June 2015
Solvent Effects on the Hydrogenolysis of Diphenyl Ether with Raney Nickel and their Implications for the Conversion of Lignin Wang, Xingyu; Rinaldi, Roberto ChemSusChem, Vol. 5, Issue 8, p. 1455-1466 https://doi.org/10.1002/cssc.201200040	journal	April 2012
Selective Degradation of Organosolv Lignin over Noble Metal Catalyst in a Two-Step Process Ling-Tao, Liu; Bin, Zhang; Jing, Li Acta Physico-Chimica Sinica, Vol. 28, Issue 10 https://doi.org/10.3866/PKU.WHXB201206152	journal	January 2012
Ruthenium Nanoparticles Supported on Carbon: An Active Catalyst for the Hydrogenation of Lactic Acid to 1,2-Propanediol Iqbal, Sarwat; Kondrat, Simon A.; Jones, Daniel R. ACS Catalysis, Vol. 5, Issue 9 https://doi.org/10.1021/acscatal.5b00625	journal	July 2015
Lignin Valorization: Improving Lignin Processing in the Biorefinery Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J. Science, Vol. 344, Issue 6185, p. 1246843-1246843 https://doi.org/10.1126/science.1246843	journal	May 2014
The role of shape selectivity in catalytic fast pyrolysis of lignin with zeolite catalysts Yu, Yanqing; Li, Xiangyu; Su, Lu Applied Catalysis A: General, Vol. 447-448 https://doi.org/10.1016/j.apcata.2012.09.012	journal	December 2012
Pathways for biomass-derived lignin to hydrocarbon fuels Laskar, Dhrubojyoti D.; Yang, Bin; Wang, Huamin Biofuels, Bioproducts and Biorefining, Vol. 7, Issue 5 https://doi.org/10.1002/bbb.1422	journal	July 2013
Upgrading of lignin-derived bio-oils by catalytic hydrodeoxygenation Saidi, Majid; Samimi, Fereshteh; Karimipourfard, Dornaz Energy Environ. Sci., Vol. 7, Issue 1 https://doi.org/10.1039/C3EE43081B	journal	January 2014
Catalytic Transformation of Lignin for the Production of Chemicals and Fuels Li, Changzhi; Zhao, Xiaochen; Wang, Aiqin Chemical Reviews, Vol. 115, Issue 21, p. 11559-11624 https://doi.org/10.1021/acs.chemrev.5b00155	journal	October 2015
Catalytic Hydrotreatment of Alcell Lignin Using Supported Ru, Pd, and Cu Catalysts Kloekhorst, Arjan; Heeres, Hero Jan ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 9 https://doi.org/10.1021/acssuschemeng.5b00041	journal	August 2015
Hydrodeoxygenation of Lignin-Derived Phenolic Monomers and Dimers to Alkane Fuels over Bifunctional Zeolite-Supported Metal Catalysts Zhang, Wei; Chen, Jinzhu; Liu, Ruliang ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 4 https://doi.org/10.1021/sc400401n	journal	January 2014
Effect of post-synthesis hydrogen-treatment on the nature of iron species in Fe-BEA as NH ₃ -SCR catalyst Shwan, Soran; Jansson, Jonas; Olsson, Louise Catal. Sci. Technol., Vol. 4, Issue 9 https://doi.org/10.1039/C4CY00236A	journal	January 2014
In situ trapping of enol intermediates with alcohol during acid-catalysed de-polymerisation of lignin in a nonpolar solvent Kaiho, Atsushi; Kogo, Makiko; Sakai, Ryo Green Chemistry, Vol. 17, Issue 5 https://doi.org/10.1039/C5GC00130G	journal	January 2015
n-Hexadecane hydroisomerization over Pt-HBEA catalysts. Quantification and effect of the intimacy between metal and protonic sites Batalha, N.; Pinard, L.; Bouchy, C. Journal of Catalysis, Vol. 307 https://doi.org/10.1016/j.jcat.2013.07.014	journal	November 2013
Monolayer bimetallic surfaces: Experimental and theoretical studies of trends in electronic and chemical properties Chen, Jingguang G.; Menning, Carl A.; Zellner, Michael B. Surface Science Reports, Vol. 63, Issue 5 https://doi.org/10.1016/j.surfrep.2008.02.001	journal	May 2008
One-Pot Catalytic Conversion of Raw Lignocellulosic Biomass into Gasoline Alkanes and Chemicals over LiTaMoO ₆ and Ru/C in Aqueous Phosphoric Acid Liu, Yong; Chen, Lungang; Wang, Tiejun ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 8 https://doi.org/10.1021/acssuschemeng.5b00256	journal	July 2015
ZnCl ₂ induced catalytic conversion of softwood lignin to aromatics and hydrocarbons Wang, Hongliang; Zhang, Libing; Deng, Tiansheng Green Chemistry, Vol. 18, Issue 9 https://doi.org/10.1039/C5GC02967H	journal	January 2016
Role of Strain and Ligand Effects in the Modification of the Electronic and Chemical Properties of Bimetallic Surfaces Kitchin, J. R.; Nørskov, J. K.; Barteau, M. A. Physical Review Letters, Vol. 93, Issue 15 https://doi.org/10.1103/PhysRevLett.93.156801	journal	October 2004
Zeolite supported mono- and bimetallic systems: structure and performance as CO hydrogenation catalysts Guczi, László; Kiricsi, Imre Applied Catalysis A: General, Vol. 186, Issue 1-2 https://doi.org/10.1016/S0926-860X(99)00156-8	journal	October 1999
Torn between two sites Donoeva, Baira; de Jong, Krijn P. Nature Materials, Vol. 19, Issue 1 https://doi.org/10.1038/s41563-019-0568-0	journal	December 2019
XPS and reactivity study of bimetallic nanoparticles containing Ru and Pt supported on a gold disk Lewera, A.; Zhou, W. P.; Vericat, C. Electrochimica Acta, Vol. 51, Issue 19 https://doi.org/10.1016/j.electacta.2005.11.009	journal	May 2006
Hydrogen adsorption, absorption and diffusion on and in transition metal surfaces: A DFT study Ferrin, Peter; Kandoi, Shampa; Nilekar, Anand Udaykumar Surface Science, Vol. 606, Issue 7-8 https://doi.org/10.1016/j.susc.2011.12.017	journal	April 2012
Polyol conversions into furanic derivatives on bimetallic catalysts: CuRu, CuPt and RuCu Montassier, C.; Ménézo, J. C.; Moukolo, J. Journal of Molecular Catalysis, Vol. 70, Issue 1 https://doi.org/10.1016/0304-5102(91)85006-N	journal	November 1991
Zeolite Catalysis: Water Can Dramatically Increase or Suppress Alkane C–H Bond Activation Chen, Kuizhi; Damron, Joshua; Pearson, Carlie ACS Catalysis, Vol. 4, Issue 9 https://doi.org/10.1021/cs500858d	journal	August 2014
Biomass-derived lignin to jet fuel range hydrocarbons via aqueous phase hydrodeoxygenation Wang, Hongliang; Ruan, Hao; Pei, Haisheng Green Chemistry, Vol. 17, Issue 12 https://doi.org/10.1039/C5GC01534K	journal	January 2015
Preparation of Pd-Co-Based Nanocatalysts and Their Superior Applications in Formic Acid Decomposition and Methanol Oxidation Qin, Yu-ling; Liu, Ya-cheng; Liang, Fei ChemSusChem, Vol. 8, Issue 2 https://doi.org/10.1002/cssc.201402926	journal	December 2014
Mechanisms of selective cleavage of C–O bonds in di-aryl ethers in aqueous phase He, Jiayue; Zhao, Chen; Mei, Donghai Journal of Catalysis, Vol. 309 https://doi.org/10.1016/j.jcat.2013.09.012	journal	January 2014
Historical Developments in Hydroprocessing Bio-oils Elliott, Douglas C. Energy & Fuels, Vol. 21, Issue 3, p. 1792-1815 https://doi.org/10.1021/ef070044u	journal	May 2007
Relevance of sulfiding pretreatment on the performance of Re/ZrO2 and Re/ZrO2-sulfated catalysts for the hydrodeoxygenation of guayacol Ruiz, P. E.; Leiva, K.; Garcia, R. Applied Catalysis A: General, Vol. 384, Issue 1-2 https://doi.org/10.1016/j.apcata.2010.06.009	journal	August 2010
Novel MoP/HY catalyst for the selective conversion of naphthalene to tetralin Usman, Muhammad; Li, Dan; Razzaq, Rauf Journal of Industrial and Engineering Chemistry, Vol. 23 https://doi.org/10.1016/j.jiec.2014.08.033	journal	March 2015
Noble-metal catalyzed hydrodeoxygenation of biomass-derived lignin to aromatic hydrocarbons Laskar, Dhrubojyoti D.; Tucker, Melvin P.; Chen, Xiaowen Green Chemistry, Vol. 16, Issue 2 https://doi.org/10.1039/c3gc42041h	journal	January 2014
Catalytic hydrodeoxygenation Furimsky, Edward Applied Catalysis A: General, Vol. 199, Issue 2, p. 147-190 https://doi.org/10.1016/S0926-860X(99)00555-4	journal	June 2000
n-Heptane hydroisomerization over Pt/MFI zeolite nanosheets: Effects of zeolite crystal thickness and platinum location Kim, Jeongnam; Kim, Wookdong; Seo, Yongbeom Journal of Catalysis, Vol. 301 https://doi.org/10.1016/j.jcat.2013.02.015	journal	May 2013
Unlocking the potential of a sleeping giant: lignins as sustainable raw materials for renewable fuels, chemicals and materials Bruijnincx, Pieter C. A.; Rinaldi, Roberto; Weckhuysen, Bert M. Green Chemistry, Vol. 17, Issue 11 https://doi.org/10.1039/C5GC90055G	journal	January 2015
Activity, selectivity and stability of Ni and bimetallic Ni–Pt supported on zeolite Y catalysts for hydrogenation of acetophenone and its substituted derivatives Malyala, R. V.; Rode, C. V.; Arai, M. Applied Catalysis A: General, Vol. 193, Issue 1-2 https://doi.org/10.1016/S0926-860X(99)00442-1	journal	February 2000
Catalytic Hydrogenolysis of Aryl Ethers: A Key Step in Lignin Valorization to Valuable Chemicals Zaheer, Muhammad; Kempe, Rhett ACS Catalysis, Vol. 5, Issue 3 https://doi.org/10.1021/cs501498f	journal	February 2015
Hydropyrolysis of Lignin Using Pd/HZSM-5 Jan, Oliver; Marchand, Ryan; Anjos, Luiz C. A. Energy & Fuels, Vol. 29, Issue 3 https://doi.org/10.1021/ef502779s	journal	February 2015
Selective Degradation of Wood Lignin over Noble‐Metal Catalysts in a Two‐Step Process Yan, Ning; Zhao, Chen; Dyson, Paul J. ChemSusChem, Vol. 1, Issue 7 https://doi.org/10.1002/cssc.200800080	journal	July 2008
Review of Pt-Based Bimetallic Catalysis: From Model Surfaces to Supported Catalysts Yu, Weiting; Porosoff, Marc D.; Chen, Jingguang G. Chemical Reviews, Vol. 112, Issue 11, p. 5780-5817 https://doi.org/10.1021/cr300096b	journal	August 2012
Following Solid-Acid-Catalyzed Reactions by MAS NMR Spectroscopy in Liquid Phase-Zeolite-Catalyzed Conversion of Cyclohexanol in Water Vjunov, Aleksei; Hu, Mary Y.; Feng, Ju Angewandte Chemie International Edition, Vol. 53, Issue 2 https://doi.org/10.1002/anie.201306673	journal	November 2013
Why Is Ruthenium an Efficient Catalyst for the Aqueous-Phase Hydrogenation of Biosourced Carbonyl Compounds? Michel, Carine; Gallezot, Pierre ACS Catalysis, Vol. 5, Issue 7 https://doi.org/10.1021/acscatal.5b00707	journal	June 2015
A Series of NiM (M = Ru, Rh, and Pd) Bimetallic Catalysts for Effective Lignin Hydrogenolysis in Water Zhang, Jiaguang; Teo, Jason; Chen, Xi ACS Catalysis, Vol. 4, Issue 5 https://doi.org/10.1021/cs401199f	journal	April 2014
Understanding the role of TiO ₂ crystal structure on the enhanced activity and stability of Ru/TiO ₂ catalysts for the conversion of lignin-derived oxygenates Omotoso, Taiwo; Boonyasuwat, Sunya; Crossley, Steven P. Green Chem., Vol. 16, Issue 2 https://doi.org/10.1039/C3GC41377B	journal	January 2014
One step thermal conversion of lignin to the gasoline range liquid products by using zeolites as additives Ben, Haoxi; Ragauskas, Arthur J. RSC Advances, Vol. 2, Issue 33 https://doi.org/10.1039/c2ra22616b	journal	January 2012
Methylation of phenol over high-silica beta zeolite: Effect of zeolite acidity and crystal size on catalyst behaviour Bregolato, M.; Bolis, V.; Busco, C. Journal of Catalysis, Vol. 245, Issue 2 https://doi.org/10.1016/j.jcat.2006.10.024	journal	January 2007
Selective production of 1,2-propanediol by hydrogenolysis of glycerol over bimetallic Ru–Cu nanoparticles supported on TiO2 Salazar, Joyce B.; Falcone, Derek D.; Pham, Hien N. Applied Catalysis A: General, Vol. 482 https://doi.org/10.1016/j.apcata.2014.06.002	journal	July 2014
Conversion of Kraft Lignin Over Hierarchical MFI Zeolite Kim, Seong-Soo; Lee, Hyung Won; Ryoo, Ryong Journal of Nanoscience and Nanotechnology, Vol. 14, Issue 3 https://doi.org/10.1166/jnn.2014.8545	journal	March 2014
Large-pore mesoporous RuNi-doped TiO2–Al2O3 nanocomposites for highly efficient selective CO methanation in hydrogen-rich reformate gases Dai, Xiaoping; Liang, Ji; Ma, Ding Applied Catalysis B: Environmental, Vol. 165 https://doi.org/10.1016/j.apcatb.2014.10.069	journal	April 2015
Aromatic Monomers by in Situ Conversion of Reactive Intermediates in the Acid-Catalyzed Depolymerization of Lignin Deuss, Peter J.; Scott, Martin; Tran, Fanny Journal of the American Chemical Society, Vol. 137, Issue 23 https://doi.org/10.1021/jacs.5b03693	journal	June 2015
Theoretical surface science and catalysis—calculations and concepts Hammer, B.; Nørskov, J. K. Impact of Surface Science on Catalysis, p. 71-129 https://doi.org/10.1016/S0360-0564(02)45013-4	book	January 2000
Influence of water in the deactivation of a sulfided NiMo/γ-Al2O3 catalyst during hydrodeoxygenation Laurent, E.; Delmon, B. Journal of Catalysis, Vol. 146, Issue 1 https://doi.org/10.1016/0021-9517(94)90032-9	journal	March 1994
Fe/HY zeolite as an effective catalyst for levulinic acid production from glucose: Characterization and catalytic performance Ramli, Nur Aainaa Syahirah; Amin, Nor Aishah Saidina Applied Catalysis B: Environmental, Vol. 163 https://doi.org/10.1016/j.apcatb.2014.08.031	journal	February 2015
Supported Metal Clusters: Synthesis, Structure, and Catalysis Gates, B. C. Chemical Reviews, Vol. 95, Issue 3 https://doi.org/10.1021/cr00035a003	journal	May 1995
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals Zakzeski, Joseph; Bruijnincx, Pieter C. A.; Jongerius, Anna L. Chemical Reviews, Vol. 110, Issue 6, p. 3552-3599 https://doi.org/10.1021/cr900354u	journal	June 2010
Selective Hydrodeoxygenation of Lignin-Derived Phenolic Monomers and Dimers to Cycloalkanes on Pd/C and HZSM-5 Catalysts Zhao, Chen; Lercher, Johannes A. ChemCatChem, Vol. 4, Issue 1 https://doi.org/10.1002/cctc.201100273	journal	November 2011
Size-dependent catalytic activity of supported metal clusters Xu, Z.; Xiao, F. -S.; Purnell, S. K. Nature, Vol. 372, Issue 6504 https://doi.org/10.1038/372346a0	journal	November 1994
Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps Van den Bosch, S.; Schutyser, W.; Vanholme, R. Energy & Environmental Science, Vol. 8, Issue 6 https://doi.org/10.1039/C5EE00204D	journal	January 2015
Effect of Acidic Properties of Mesoporous Zeolites Supporting Pt Nanoparticles on Hydrogenative Conversion of Methylcyclopentane Na, Kyungsu; Alayoglu, Selim; Ye, Rong Journal of the American Chemical Society, Vol. 136, Issue 49 https://doi.org/10.1021/ja509273h	journal	November 2014
Following Solid-Acid-Catalyzed Reactions by MAS NMR Spectroscopy in Liquid Phase-Zeolite-Catalyzed Conversion of Cyclohexanol in Water Vjunov, Aleksei; Hu, Mary Y.; Feng, Ju Angewandte Chemie, Vol. 126, Issue 2 https://doi.org/10.1002/ange.201306673	journal	November 2013
Comprehensive Handbook of Chemical Bond Energies Luo, Yu-Ran https://doi.org/10.1201/9781420007282	book	March 2007
Calculation of Flame Ionization Detector Relative Response Factors Using the Effective Carbon Number Concept Scanlon, J. T.; Willis, D. E. Journal of Chromatographic Science, Vol. 23, Issue 8 https://doi.org/10.1093/chromsci/23.8.333	journal	August 1985
Precise oxygen scission of lignin derived aryl ethers to quantitatively produce aromatic hydrocarbons in water Luo, Zhicheng; Wang, Yimeng; He, Mingyuan Green Chemistry, Vol. 18, Issue 2 https://doi.org/10.1039/C5GC01790D	journal	January 2016
Lignin Depolymerization into Aromatic Monomers over Solid Acid Catalysts Deepa, Ayillath K.; Dhepe, Paresh L. ACS Catalysis, Vol. 5, Issue 1 https://doi.org/10.1021/cs501371q	journal	November 2014
A study of ruthenium in zeolite-Y by X-ray photoelectron spectroscopy Pedersen, L. Journal of Catalysis, Vol. 61, Issue 1 https://doi.org/10.1016/0021-9517(80)90337-1	journal	January 1980
Carbon-supported bimetallic Pd–Fe catalysts for vapor-phase hydrodeoxygenation of guaiacol Sun, Junming; Karim, Ayman M.; Zhang, He Journal of Catalysis, Vol. 306 https://doi.org/10.1016/j.jcat.2013.05.020	journal	October 2013
Catalytic depolymerisation of isolated lignins to fine chemicals using a Pt/alumina catalyst: part 1—impact of the lignin structure Bouxin, Florent P.; McVeigh, Ashley; Tran, Fanny Green Chemistry, Vol. 17, Issue 2 https://doi.org/10.1039/C4GC01678E	journal	January 2015
Nanoscale intimacy in bifunctional catalysts for selective conversion of hydrocarbons Zecevic, Jovana; Vanbutsele, Gina; de Jong, Krijn P. Nature, Vol. 528, Issue 7581 https://doi.org/10.1038/nature16173	journal	December 2015

Cited By (20)

Efficient hydrodeoxygenation of lignin-derived phenols and dimeric ethers with synergistic [Bmim]PF ₆ -Ru/SBA-15 catalysis under acid free conditions Yang, Shaoqi; Lu, Xingmei; Yao, Haoyu Green Chemistry, Vol. 21, Issue 3 https://doi.org/10.1039/c8gc03775b	journal	January 2019
Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading Schutyser, W.; Renders, T.; Van den Bosch, S. Chemical Society Reviews, Vol. 47, Issue 3 https://doi.org/10.1039/c7cs00566k	journal	January 2018
Effect of HCOOK/Ethanol on Fe/HUSY, Ni/HUSY, and Ni–Fe/HUSY Catalysts on Lignin Depolymerization to Benzyl Alcohols and Bioaromatics Wanmolee, Wanwitoo; Beltramini, Jorge N.; Atanda, Luqman ACS Omega, Vol. 4, Issue 16 https://doi.org/10.1021/acsomega.9b02413	journal	September 2019
Tandem Hydrogenolysis–Hydrogenation of Lignin‐Derived Oxygenates over Integrated Dual Catalysts with Optimized Interoperations Fang, Huihuang; Chen, Weikun; Li, Shuang ChemSusChem, Vol. 12, Issue 23 https://doi.org/10.1002/cssc.201902029	journal	November 2019
Development of Bifunctional Hydrodeoxygenation Catalyst Rh‐HY for the Generation of Biomass‐Derived High‐Energy‐Density Fuels Granados Fócil, Andrés A.; Granados Fócil, Sergio; Conde Sotelo, Víctor M. Energy Technology, Vol. 7, Issue 6 https://doi.org/10.1002/ente.201801112	journal	April 2019
Catalytic Strategies Towards Lignin-Derived Chemicals Van den Bosch, S.; Koelewijn, S. -F.; Renders, T. Topics in Current Chemistry, Vol. 376, Issue 5 https://doi.org/10.1007/s41061-018-0214-3	journal	August 2018
Lignin Valorizations with Ni Catalysts for Renewable Chemicals and Fuels Productions Chen, Xiao; Guan, Weixiang; Tsang, Chi-Wing Catalysts, Vol. 9, Issue 6 https://doi.org/10.3390/catal9060488	journal	May 2019
Techno‐economic analysis of jet‐fuel production from biorefinery waste lignin Shen, Rongchun; Tao, Ling; Yang, Bin Biofuels, Bioproducts and Biorefining, Vol. 13, Issue 3 https://doi.org/10.1002/bbb.1952	journal	December 2018
Promising Techniques for Depolymerization of Lignin into Value-added Chemicals Ren, Tianyu; Qi, Wei; Su, Rongxin ChemCatChem, Vol. 11, Issue 2 https://doi.org/10.1002/cctc.201900021	journal	January 2019
Bright Side of Lignin Depolymerization: Toward New Platform Chemicals Sun, Zhuohua; Fridrich, Bálint; de Santi, Alessandra Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00588	journal	January 2018
Recent advances in the selective catalytic hydrodeoxygenation of lignin-derived oxygenates to arenes Zhang, Jianghao; Sun, Junming; Wang, Yong Green Chemistry, Vol. 22, Issue 4 https://doi.org/10.1039/c9gc02762a	journal	January 2020
State-of-the-art catalytic hydrogenolysis of lignin for the production of aromatic chemicals Cheng, Chongbo; Shen, Dekui; Gu, Sai Catalysis Science & Technology, Vol. 8, Issue 24 https://doi.org/10.1039/c8cy00845k	journal	January 2018
Economic feasibility of gasoline production from lignocellulosic wastes in Hong Kong Guan, Weixiang; Chua, Sim-Ying; Tsang, Chi-Wing BMC Chemical Engineering, Vol. 1, Issue 1 https://doi.org/10.1186/s42480-019-0024-6	journal	December 2019
NiMoS on alumina-USY zeolites for hydrotreating lignin dimers: effect of support acidity and cleavage of C–C bonds Salam, Muhammad Abdus; Arora, Prakhar; Ojagh, Houman Sustainable Energy & Fuels, Vol. 4, Issue 1 https://doi.org/10.1039/c9se00507b	journal	January 2020
Zeolite-supported metal catalysts for selective hydrodeoxygenation of biomass-derived platform molecules Luo, Wenhao; Cao, Wenxiu; Bruijnincx, Pieter C. A. Green Chemistry, Vol. 21, Issue 14 https://doi.org/10.1039/c9gc01216h	journal	January 2019
Two-step catalytic conversion of lignocellulose to alkanes Sun, Zhuohua; Buwalda, Daniel; Barta, Katalin RSC Advances, Vol. 9, Issue 41 https://doi.org/10.1039/c9ra03174j	journal	January 2019
Solvation effect on binding modes of model lignin dimer compounds on MWW 2D-zeolite Jain, Varsha; Wilson, Woodrow N.; Rai, Neeraj The Journal of Chemical Physics, Vol. 151, Issue 11 https://doi.org/10.1063/1.5112101	journal	September 2019
Promising Techniques for Depolymerization of Lignin into Value-added Chemicals Ren, Tianyu; Qi, Wei; Su, Rongxin ChemCatChem, Vol. 11, Issue 2 https://doi.org/10.1002/cctc.201801428	journal	December 2018
Additional file 2 of Understanding of bacterial lignin extracellular degradation mechanisms by Pseudomonas putida KT2440 via secretomic analysis Xu, Zhangyang; Peng, Bo; Kitata, Reta Birhanu figshare https://doi.org/10.6084/m9.figshare.21443760.v1	dataset	January 2022
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 Liu, Xiaoyang; An, Wei; Wang, Yixing Catalysis Science & Technology, Vol. 8, Issue 8 https://doi.org/10.1039/c8cy00282g	journal	January 2018

Similar Records

One-pot process for hydrodeoxygenation of lignin to alkanes using Ru-based bimetallic and bifunctional catalysts supported on zeolite Y

Journal Article · Tue Feb 21 23:00:00 EST 2017 · ChemSusChem · OSTI ID:1353424

Hydrodeoxygenation of lignin to hydrocarbons using bimetallic catalysts

Patent · Tue Aug 03 00:00:00 EDT 2021 · OSTI ID:1840305

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Environmental Molecular Sciences Laboratory

One-Pot Process for Hydrodeoxygenation of Lignin to Alkanes Using Ru-Based Bimetallic and Bifunctional Catalysts Supported on Zeolite Y

Citation Formats

References (72)

Cited By (20)

Similar Records

Related Subjects