Continuous Hydrodeoxygenation of Lignin to Jet-Range Aromatic Hydrocarbons

Stone, Michael L; Webber, Matthew S; Mounfield III, William P; Bell, David C.; Christensen, Earl; Morais, Ana R. C.; Li, Yanding; Anderson, Eric M.; Heyne, Joshua S.; Beckham, Gregg T.; Roman-Leshkov, Yuriy

doi:10.1016/j.joule.2022.08.005

Continuous Hydrodeoxygenation of Lignin to Jet-Range Aromatic Hydrocarbons

Journal Article · Thu Sep 22 04:00:00 EDT 2022 · Joule

DOI:https://doi.org/10.1016/j.joule.2022.08.005· OSTI ID:1900006

Stone, Michael L; Webber, Matthew S; Mounfield III, William P; Bell, David C.; ; Morais, Ana R. C.; Li, Yanding; Anderson, Eric M.; Heyne, Joshua S.; ; Roman-Leshkov, Yuriy

Sustainable aviation fuel (SAF) is essential to decrease the carbon footprint of the aviation industry. Although many strategies have been developed to provide the linear and branched aliphatic components of SAF, few viable strategies have been demonstrated to supply the aromatic and cycloalkane fraction of the SAF at the necessary scale from bio-based feedstocks. Lignin is the largest natural source of renewable aromatic compounds; however, major challenges in deoxygenation have prevented its use as a feedstock for SAFs. Here, we report a continuous, two-stage catalytic process using molybdenum carbide to deoxygenate lignin from poplar into aromatic hydrocarbons with 87.5% selectivity toward aromatic hydrocarbons at 86% of the theoretical carbon recovery. Tier a fuel property testing indicates that the SAF-range lignin-derived aromatic compounds are likely performance-advantaged across multiple properties relative to conventional jet fuel aromatic compounds. This work demonstrates an effective approach to convert lignin into aromatic SAF blendstocks.

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B); USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)

DOE Contract Number:: AC36-08GO28308

OSTI ID:: 1900006

Report Number(s):: NREL/JA-2A00-82012; MainId:82785; UUID:01c0cc85-2a70-4c38-90e4-3f73c234af9c; MainAdminID:68062

Journal Information:: Joule, Journal Name: Joule Journal Issue: 10 Vol. 6

Country of Publication:: United States

Language:: English

References (58)

Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization Shuai, Li; Amiri, Masoud Talebi; Questell-Santiago, Ydna M. Science, Vol. 354, Issue 6310 https://doi.org/10.1126/science.aaf7810	journal	October 2016
A review on the catalytic hydrodeoxygenation of lignin-derived phenolic compounds and the conversion of raw lignin to hydrocarbon liquid fuels Shu, Riyang; Li, Rongxuan; Lin, Biqin Biomass and Bioenergy, Vol. 132 https://doi.org/10.1016/j.biombioe.2019.105432	journal	January 2020
Chemical Titration and Transient Kinetic Studies of Site Requirements in Mo ₂ C-Catalyzed Vapor Phase Anisole Hydrodeoxygenation Lee, Wen-Sheng; Kumar, Anurag; Wang, Zhenshu ACS Catalysis, Vol. 5, Issue 7 https://doi.org/10.1021/acscatal.5b00713	journal	June 2015
Synergistic Interaction within Bifunctional Ruthenium Nanoparticle/SILP Catalysts for the Selective Hydrodeoxygenation of Phenols Luska, Kylie L.; Migowski, Pedro; El Sayed, Sami Angewandte Chemie International Edition, Vol. 54, Issue 52 https://doi.org/10.1002/anie.201508513	journal	November 2015
Hydrodeoxygenation of guaiacol over Ni/carbon catalysts: effect of the support and Ni loading Dongil, A. B.; Ghampson, I. T.; García, R. RSC Advances, Vol. 6, Issue 4 https://doi.org/10.1039/C5RA22540J	journal	January 2016
Catalytic deoxygenation on transition metal carbide catalysts Sullivan, Mark M.; Chen, Cha-Jung; Bhan, Aditya Catalysis Science & Technology, Vol. 6, Issue 3 https://doi.org/10.1039/C5CY01665G	journal	January 2016
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
Cleaner burning aviation fuels can reduce contrail cloudiness Voigt, Christiane; Kleine, Jonas; Sauer, Daniel Communications Earth & Environment, Vol. 2, Issue 1 https://doi.org/10.1038/s43247-021-00174-y	journal	June 2021
Bifunctional Molybdenum Polyoxometalates for the Combined Hydrodeoxygenation and Alkylation of Lignin-Derived Model Phenolics Anderson, Eric; Crisci, Anthony; Murugappan, Karthick ChemSusChem, Vol. 10, Issue 10 https://doi.org/10.1002/cssc.201700297	journal	April 2017
Progress in utilisation of waste cooking oil for sustainable biodiesel and biojet fuel production Goh, Brandon Han Hoe; Chong, Cheng Tung; Ge, Yuqi Energy Conversion and Management, Vol. 223 https://doi.org/10.1016/j.enconman.2020.113296	journal	November 2020
Oxygen content as a variable to control product selectivity in hydrodeoxygenation reactions on molybdenum carbide catalysts Kumar, Anurag; Bhan, Aditya Chemical Engineering Science, Vol. 197 https://doi.org/10.1016/j.ces.2018.12.027	journal	April 2019
Liquid-phase reforming and hydrodeoxygenation as a two-step route to aromatics from lignin Jongerius, Anna L.; Bruijnincx, Pieter C. A.; Weckhuysen, Bert M. Green Chemistry, Vol. 15, Issue 11 https://doi.org/10.1039/c3gc41150h	journal	January 2013
Stabilization strategies in biomass depolymerization using chemical functionalization Questell-Santiago, Ydna M.; Galkin, Maxim V.; Barta, Katalin Nature Reviews Chemistry, Vol. 4, Issue 6 https://doi.org/10.1038/s41570-020-0187-y	journal	May 2020
A sustainable wood biorefinery for low–carbon footprint chemicals production Liao, Yuhe; Koelewijn, Steven-Friso; Van den Bossche, Gil Science, Vol. 367, Issue 6484 https://doi.org/10.1126/science.aau1567	journal	February 2020
Producing jet fuel from biomass lignin: Potential pathways to alkyl-benzenes and cycloalkanes Cheng, Feng; Brewer, Catherine E. Renewable and Sustainable Energy Reviews, Vol. 72 https://doi.org/10.1016/j.rser.2017.01.030	journal	May 2017
Alternative jet fuel feasibility Hileman, J. I.; Stratton, R. W. Transport Policy, Vol. 34 https://doi.org/10.1016/j.tranpol.2014.02.018	journal	July 2014
Reductive catalytic fractionation of pine wood: elucidating and quantifying the molecular structures in the lignin oil Van Aelst, K.; Van Sinay, E.; Vangeel, T. Chemical Science, Vol. 11, Issue 42 https://doi.org/10.1039/D0SC04182C	journal	January 2020
Drop‐in biofuel production via conventional (lipid/fatty acid) and advanced (biomass) routes. Part I Karatzos, Sergios; van Dyk, J. Susan; McMillan, James D. Biofuels, Bioproducts and Biorefining, Vol. 11, Issue 2 https://doi.org/10.1002/bbb.1746	journal	January 2017
Effects of support identity and metal dispersion in supported ruthenium hydrodeoxygenation catalysts Newman, Cody; Zhou, Xiaobo; Goundie, Ben Applied Catalysis A: General, Vol. 477 https://doi.org/10.1016/j.apcata.2014.02.030	journal	May 2014
Condensation of lignin during heating of wood Funaoka, M.; Kako, T.; Abe, I. Wood Science and Technology, Vol. 24, Issue 3 https://doi.org/10.1007/BF01153560	journal	July 1990
A Mechanistic Investigation of Acid-Catalyzed Cleavage of Aryl-Ether Linkages: Implications for Lignin Depolymerization in Acidic Environments Sturgeon, Matthew R.; Kim, Seonah; Lawrence, Kelsey ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 3, p. 472-485 https://doi.org/10.1021/sc400384w	journal	November 2013
Bimetallic effects in the hydrodeoxygenation of meta-cresol on γ-Al2O3 supported Pt–Ni and Pt–Co catalysts Do, Phuong T. M.; Foster, Andrew J.; Chen, Jingguang Green Chemistry, Vol. 14, Issue 5 https://doi.org/10.1039/c2gc16544a	journal	January 2012
Mo ₂ C Modification by CO ₂ , H ₂ O, and O ₂ : Effects of Oxygen Content and Oxygen Source on Rates and Selectivity of m -Cresol Hydrodeoxygenation Chen, Cha-Jung; Bhan, Aditya ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b02762	journal	January 2017
Insights into the catalytic activity and surface modification of MoO ₃ during the hydrodeoxygenation of lignin-derived model compounds into aromatic hydrocarbons under low hydrogen pressures Prasomsri, Teerawit; Shetty, Manish; Murugappan, Karthick Energy Environ. Sci., Vol. 7, Issue 8 https://doi.org/10.1039/C4EE00890A	journal	January 2014
Behaviour of lignin during thermal treatments of wood Windeisen, Elisabeth; Wegener, Gerd Industrial Crops and Products, Vol. 27, Issue 2 https://doi.org/10.1016/j.indcrop.2007.07.015	journal	March 2008
Hydrodeoxygenation of solvolysed lignocellulosic biomass by unsupported MoS2, MoO2, Mo2C and WS2 catalysts Grilc, M.; Veryasov, G.; Likozar, B. Applied Catalysis B: Environmental, Vol. 163 https://doi.org/10.1016/j.apcatb.2014.08.032	journal	February 2015
Techno-economic analysis and life cycle assessment of a biorefinery utilizing reductive catalytic fractionation Bartling, Andrew; Stone, Michael L.; Hanes, Rebecca J. Energy & Environmental Science https://doi.org/10.1039/D1EE01642C	journal	January 2021
A GC × GC Tier α combustor operability prescreening method for sustainable aviation fuel candidates Yang, Zhibin; Kosir, Shane; Stachler, Robert Fuel, Vol. 292 https://doi.org/10.1016/j.fuel.2021.120345	journal	May 2021
Selective Hydrodeoxygenation of Lignin-Derived Phenols to Cyclohexanols or Cyclohexanes over Magnetic CoNx@NC Catalysts under Mild Conditions Liu, Xiaohao; Xu, Lujiang; Xu, Guangyue ACS Catalysis, Vol. 6, Issue 11 https://doi.org/10.1021/acscatal.6b01785	journal	October 2016
Mo2C catalyzed vapor phase hydrodeoxygenation of lignin-derived phenolic compound mixtures to aromatics under ambient pressure Chen, Cha-Jung; Lee, Wen-Sheng; Bhan, Aditya Applied Catalysis A: General, Vol. 510 https://doi.org/10.1016/j.apcata.2015.10.043	journal	January 2016
Selective Conversion of Lignin-Derivable 4-Alkylguaiacols to 4-Alkylcyclohexanols over Noble and Non-Noble-Metal Catalysts Schutyser, Wouter; Van den Bossche, Gil; Raaffels, Anton ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 10 https://doi.org/10.1021/acssuschemeng.6b01580	journal	August 2016
Renewable Aromatics from Kraft Lignin with Molybdenum-Based Catalysts Cattelan, Lisa; Yuen, Alexander K. L.; Lui, Matthew Y. ChemCatChem, Vol. 9, Issue 14 https://doi.org/10.1002/cctc.201700374	journal	June 2017
Mesoporous ZSM-5 Zeolite-Supported Ru Nanoparticles as Highly Efficient Catalysts for Upgrading Phenolic Biomolecules Wang, Liang; Zhang, Jian; Yi, Xianfeng ACS Catalysis, Vol. 5, Issue 5 https://doi.org/10.1021/acscatal.5b00083	journal	March 2015
Atmospheric Hydrodeoxygenation of Guaiacol over Alumina-, Zirconia-, and Silica-Supported Nickel Phosphide Catalysts Wu, Shin-Kuan; Lai, Po-Chen; Lin, Yu-Chuan ACS Sustainable Chemistry & Engineering, Vol. 1, Issue 3 https://doi.org/10.1021/sc300157d	journal	February 2013
Sustainable aviation fuel prescreening tools and procedures Heyne, Joshua; Rauch, Bastian; Le Clercq, Patrick Fuel, Vol. 290 https://doi.org/10.1016/j.fuel.2020.120004	journal	April 2021
Flowthrough Reductive Catalytic Fractionation of Biomass Anderson, Eric M.; Stone, Michael L.; Katahira, Rui Joule, Vol. 1, Issue 3 https://doi.org/10.1016/j.joule.2017.10.004	journal	November 2017
Highly selective bimetallic FeMoP catalyst for C–O bond cleavage of aryl ethers Rensel, Dallas J.; Rouvimov, Sergei; Gin, Megan E. Journal of Catalysis, Vol. 305 https://doi.org/10.1016/j.jcat.2013.05.026	journal	September 2013
Flow-through solvolysis enables production of native-like lignin from biomass Brandner, David G.; Kruger, Jacob S.; Thornburg, Nicholas E. Green Chemistry, Vol. 23, Issue 15 https://doi.org/10.1039/D1GC01591E	journal	January 2021
Operando NAP-XPS unveils differences in MoO3 and Mo2C during hydrodeoxygenation Murugappan, Karthick; Anderson, Eric M.; Teschner, Detre Nature Catalysis, Vol. 1, Issue 12 https://doi.org/10.1038/s41929-018-0171-9	journal	November 2018
Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes Zhao, Chen; He, Jiayue; Lemonidou, Angeliki A. Journal of Catalysis, Vol. 280, Issue 1 https://doi.org/10.1016/j.jcat.2011.02.001	journal	May 2011
Towards fuel composition and properties from Two-dimensional gas chromatography with flame ionization and vacuum ultraviolet spectroscopy Heyne, Joshua; Bell, David; Feldhausen, John Fuel, Vol. 312 https://doi.org/10.1016/j.fuel.2021.122709	journal	March 2022
Synthetic aromatic kerosene property prediction improvements with isomer specific characterization via GCxGC and vacuum ultraviolet spectroscopy Feldhausen, John; Bell, David C.; Yang, Zhibin Fuel, Vol. 326 https://doi.org/10.1016/j.fuel.2022.125002	journal	October 2022
Guidelines for performing lignin-first biorefining Abu-Omar, Mahdi M.; Barta, Katalin; Beckham, Gregg T. Energy & Environmental Science, Vol. 14, Issue 1 https://doi.org/10.1039/D0EE02870C	journal	January 2021
Influence on nickel particle size on the hydrodeoxygenation of phenol over Ni/SiO 2 Mortensen, Peter M.; Grunwaldt, Jan-Dierk; Jensen, Peter A. Catalysis Today, Vol. 259 https://doi.org/10.1016/j.cattod.2015.08.022	journal	January 2016
Deoxygenation of guaiacol and woody tar over reduced catalysts Mochizuki, Takehisa; Chen, Shih-Yuan; Toba, Makoto Applied Catalysis B: Environmental, Vol. 146 https://doi.org/10.1016/j.apcatb.2013.05.040	journal	March 2014
Differences in S/G ratio in natural poplar variants do not predict catalytic depolymerization monomer yields Anderson, Eric M.; Stone, Michael L.; Katahira, Rui Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09986-1	journal	May 2019
Downstream processing of lignin derived feedstock into end products Wong, Sie Shing; Shu, Riyang; Zhang, Jiaguang Chemical Society Reviews, Vol. 49, Issue 15 https://doi.org/10.1039/D0CS00134A	journal	January 2020
Effective hydrodeoxygenation of biomass-derived oxygenates into unsaturated hydrocarbons by MoO₃ using low H₂ pressures Prasomsri, Teerawit; Nimmanwudipong, Tarit; Román-Leshkov, Yuriy Energy & Environmental Science, Vol. 6, Issue 6, p. 1732-1738 https://doi.org/10.1039/c3ee24360e	journal	January 2013
Selective vapor-phase hydrodeoxygenation of anisole to benzene on molybdenum carbide catalysts Lee, Wen-Sheng; Wang, Zhenshu; Wu, Ryan J. Journal of Catalysis, Vol. 319 https://doi.org/10.1016/j.jcat.2014.07.025	journal	November 2014
Hydrodeoxygenation of mono- and dimeric lignin model compounds on noble metal catalysts Güvenatam, Burcu; Kurşun, Osman; Heeres, Erik H. J. Catalysis Today, Vol. 233 https://doi.org/10.1016/j.cattod.2013.12.011	journal	September 2014
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
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
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
Kinetic Studies of Lignin Solvolysis and Reduction by Reductive Catalytic Fractionation Decoupled in Flow-Through Reactors Anderson, Eric M.; Stone, Michael L.; Hülsey, Max J. ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 6 https://doi.org/10.1021/acssuschemeng.8b01256	journal	April 2018
Protection Group Effects During α,γ-Diol Lignin Stabilization Promote High-Selectivity Monomer Production Lan, Wu; Amiri, Masoud Talebi; Hunston, Christopher M. Angewandte Chemie, Vol. 130, Issue 5 https://doi.org/10.1002/ange.201710838	journal	January 2018
Perspectives on Fully Synthesized Sustainable Aviation Fuels: Direction and Opportunities Kramer, Stephen; Andac, Gurhan; Heyne, Joshua Frontiers in Energy Research, Vol. 9 https://doi.org/10.3389/fenrg.2021.782823	journal	January 2022
Identification and quantification of lignin monomers and oligomers from reductive catalytic fractionation of pine wood with GC × GC – FID/MS Dao Thi, Hang; Van Aelst, Korneel; Van den Bosch, Sander Green Chemistry, Vol. 24, Issue 1 https://doi.org/10.1039/D1GC03822B	journal	January 2022
Hydrodeoxygenation of phenol over niobia supported Pd catalyst Barrios, Adriana M.; Teles, Camila A.; de Souza, Priscilla M. Catalysis Today, Vol. 302 https://doi.org/10.1016/j.cattod.2017.03.034	journal	March 2018

Similar Records

Continuous hydrodeoxygenation of lignin to jet-range aromatic hydrocarbons

Journal Article · Wed Sep 21 20:00:00 EDT 2022 · Joule · OSTI ID:1957789

2.3.4.104 - Lignin Conversion to Sustainable Aviation Fuel Blendstocks

Conference · Mon Apr 17 20:00:00 EDT 2023 · OSTI ID:1971863

Drop-in sustainable aviation fuels enabled by feedstock-agnostic lignin deoxygenation

Journal Article · Sun Jul 06 20:00:00 EDT 2025 · Cell Reports Physical Science · OSTI ID:2574735

Related Subjects

BIOMASS FUELS,INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
blendstock
lignin deoxygenation
molybdenum carbide
sustainable aviation fuel

Continuous Hydrodeoxygenation of Lignin to Jet-Range Aromatic Hydrocarbons

Citation Formats

References (58)

Similar Records

Related Subjects