A simultaneous depolymerization and hydrodeoxygenation process to produce lignin-based jet fuel in continuous flow reactor

Kumar, Adarsh; Bell, David C.; Yang, Zhibin; Heyne, Joshua; Santosa, Daniel M.; Wang, Huamin; Zuo, Peng; Wang, Chongmin; Mittal, Ashutosh; Klein, Darryl P.; Manto, Michael J.; Chen, Xiaowen; Yang, Bin

doi:10.1016/j.fuproc.2024.108129

Title: A simultaneous depolymerization and hydrodeoxygenation process to produce lignin-based jet fuel in continuous flow reactor

Journal Article · Sun Sep 01 20:00:00 EDT 2024 · Fuel Processing Technology

DOI: https://doi.org/10.1016/j.fuproc.2024.108129 · OSTI ID:2440817

Kumar, Adarsh ^[1]; Bell, David C. ^[2]; Yang, Zhibin ^[2]; Heyne, Joshua ^[2];

^[3]; Wang, Huamin ^[3]; Zuo, Peng ^[3];

^[3]; Mittal, Ashutosh ^[4]; Klein, Darryl P. ^[5];

^[5]; Chen, Xiaowen ^[4]; Yang, Bin ^[6]

Washington State Univ., Richland, WA (United States); National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Washington State Univ., Richland, WA (United States)
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Advanced Refining Technologies, LLC, Baltimore, MD (United States)
Washington State Univ., Richland, WA (United States); Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Economical production of lignin-based jet fuel (LJF) can improve the sustainability of sustainable aviation fuels (SAFs) as well as can reduce the overall greenhouse gas emissions. However, the challenge lies in converting technical lignin polymer from biorefinery directly to jet fuel in a continuous operation. In this work, we demonstrate a simultaneous depolymerization and hydrodeoxygenation (SDHDO) process to produce lignin-based jet fuel from the alkali corn stover lignin (ACSL) using engineered Ru-HY-60-MI catalyst in a continuous flow reactor at first time. The maximum carbon yield of LJF of 17.9wt% was obtained, and it comprised of 60.2wt% monocycloalkanes, and 21.6wt% polycycloalkanes. Catalyst characterization of Ru-HY-60-MI suggested there was no significant change in HY zeolite structure and its crystallinity after catalyst engineering. Catalyst characterizations performed post the SDHDO experiments indicate presence of carbon and K content in the catalyst. K content presence in the spent catalyst was due to K⁺ ion was exchanged between lignin solution and HY-60 while carbon presence validated the SDHDO chemistry on the catalyst surface. Tier a fuel property testing indicates that LJF production using SDHDO chemistry can offer SAF with high compatibility, good sealing properties, low emissions, and high energy density for aircraft.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE); USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: AC05-76RL01830; EE0009257

OSTI ID:: 2440817

Report Number(s):: PNNL-SA-203423

Journal Information:: Fuel Processing Technology, Journal Name: Fuel Processing Technology Vol. 263; ISSN 0378-3820

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (67)

Recent Trends, Opportunities and Challenges of Sustainable Aviation Fuel Zhang, Libing; Butler, Terri L.; Yang*,, Bin Green Energy to Sustainability: Strategies for Global Industries https://doi.org/10.1002/9781119152057.ch5	book	January 2020
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
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
Vapor-Phase Hydrodeoxygenation of Guaiacol to Aromatics over Pt/HBeta: Identification of the Role of Acid Sites and Metal Sites on the Reaction Pathway Nie, Lei; Peng, Bo; Zhu, Xinli ChemCatChem, Vol. 10, Issue 5 https://doi.org/10.1002/cctc.201701413	journal	February 2018
Green Diesel from Kraft Lignin in Three Steps Löfstedt, Joakim; Dahlstrand, Christian; Orebom, Alexander ChemSusChem, Vol. 9, Issue 12, p. 1392-1396 https://doi.org/10.1002/cssc.201600172	journal	June 2016
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 ChemSusChem, Vol. 10, Issue 8 https://doi.org/10.1002/cssc.201700160	journal	March 2017
Production of Jet Fuel-Range Hydrocarbons from Hydrodeoxygenation of Lignin over Super Lewis Acid Combined with Metal Catalysts Wang, Hongliang; Wang, Huamin; Kuhn, Eric ChemSusChem, Vol. 11, Issue 1 https://doi.org/10.1002/cssc.201701567	journal	November 2017
Effects of Sugars, Furans, and their Derivatives on Hydrodeoxygenation of Biorefinery Lignin‐Rich Wastes to Hydrocarbons Wang, Hongliang; Duan, Yuhua; Zhang, Qian ChemSusChem, Vol. 11, Issue 15 https://doi.org/10.1002/cssc.201801401	journal	July 2018
Flexibilization of Biorefineries: Tuning Lignin Hydrogenation by Hydrogen Partial Pressure Cao, Zhengwen; Xu, Yun; Lyu, Pengbo ChemSusChem, Vol. 14, Issue 1 https://doi.org/10.1002/cssc.202002248	journal	November 2020
Debottlenecking a Pulp Mill by Producing Biofuels from Black Liquor in Three Steps Di Francesco, Davide; Dahlstrand, Christian; Löfstedt, Joakim ChemSusChem, Vol. 14, Issue 11, p. 2414-2425 https://doi.org/10.1002/cssc.202100496	journal	May 2021
Elucidating the Reaction Pathways of Veratrylglycero‐β‐Guaiacyl Ether Degradation over Metal‐Free Solid Acid Catalyst with Hydrogen** Ruan, Hao; Xu, Zhangyang; Kumar, Adarsh ChemSusChem, Vol. 16, Issue 6 https://doi.org/10.1002/cssc.202202001	journal	January 2023
Partial oxidation of methane over supported ruthenium catalysts Lanza, R.; Järås, S. G.; Canu, P. Applied Catalysis A: General, Vol. 325, Issue 1 https://doi.org/10.1016/j.apcata.2007.03.005	journal	May 2007
Engineered Ru on HY zeolite catalyst for continuous and selective hydrodeoxygenation of lignin phenolics to cycloalkanes under moderate conditions Kumar, Adarsh; Kumar, Abhishek; Santosa, Daniel M. Applied Catalysis A: General, Vol. 676 https://doi.org/10.1016/j.apcata.2024.119649 119649	journal	April 2024
Hydrodeoxygenation of guaiacol via in situ H2 generated through a water gas shift reaction over dispersed NiMoS catalysts from oil-soluble precursors: Tuning the selectivity towards cyclohexene Vutolkina, A. V.; Baigildin, I. G.; Glotov, A. P. Applied Catalysis B: Environmental, Vol. 312 https://doi.org/10.1016/j.apcatb.2022.121403	journal	September 2022
Transportation fuels from co-processing of waste vegetable oil and gas oil mixtures Rana, Bharat S.; Kumar, Rohit; Tiwari, Rashmi Biomass and Bioenergy, Vol. 56 https://doi.org/10.1016/j.biombioe.2013.04.029	journal	September 2013
Hydrothermal conversion of lignin to substituted phenols and aromatic ethers Singh, Rawel; Prakash, Aditya; Dhiman, Shashi Kumar Bioresource Technology, Vol. 165 https://doi.org/10.1016/j.biortech.2014.02.076	journal	August 2014
From lignin to valuable products–strategies, challenges, and prospects Wang, Hongliang; Pu, Yunqiao; Ragauskas, Arthur Bioresource Technology, Vol. 271 https://doi.org/10.1016/j.biortech.2018.09.072	journal	January 2019
Hydrocracking, hydrogenation and hydro-deoxygenation of fatty acids, esters and glycerides: Mechanisms, kinetics and transport phenomena Žula, Matej; Grilc, Miha; Likozar, Blaž Chemical Engineering Journal, Vol. 444 https://doi.org/10.1016/j.cej.2022.136564	journal	September 2022
Production of liquid fuels via catalytic transfer hydrogenation promoting lignin depolymerization on modified Y zeolite: Formic acid as a continuous hydrogen source Zhang, Xia; Jiang, Yihang; Li, Wenzhi Energy Conversion and Management, Vol. 302 https://doi.org/10.1016/j.enconman.2024.118144 118144	journal	February 2024
The capability of organic compounds to swell acrylonitrile butadiene O-rings and their effects on O-ring mechanical properties Romanczyk, Mark; Ramirez Velasco, Jorge H.; Xu, Lan Fuel, Vol. 238 https://doi.org/10.1016/j.fuel.2018.10.103	journal	February 2019
Chemical compositions and properties of lignin-based jet fuel range hydrocarbons Ruan, Hao; Qin, Yulin; Heyne, Joshua Fuel, Vol. 256 https://doi.org/10.1016/j.fuel.2019.115947	journal	November 2019
A machine learning framework for drop-in volume swell characteristics of sustainable aviation fuel Kosir, Shane; Heyne, Joshua; Graham, John Fuel, Vol. 274 https://doi.org/10.1016/j.fuel.2020.117832	journal	August 2020
High-performance jet fuel optimization and uncertainty analysis Kosir, Shane; Stachler, Robert; Heyne, Joshua Fuel, Vol. 281 https://doi.org/10.1016/j.fuel.2020.118718	journal	December 2020
Cetane number, derived cetane number, and cetane index: When correlations fail to predict combustibility Luning Prak, Dianne; Cooke, Jay; Dickerson, Terrence Fuel, Vol. 289 https://doi.org/10.1016/j.fuel.2020.119963	journal	April 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
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
Lignin-based jet fuel and its blending effect with conventional jet fuel Yang, Zhibin; Xu, Zhangyang; Feng, Maoqi Fuel, Vol. 321 https://doi.org/10.1016/j.fuel.2022.124040	journal	August 2022
Effect of space velocity on the hydrocracking of Light Cycle Oil over a Pt–Pd/HY zeolite catalyst Gutiérrez, Alazne; Arandes, José M.; Castaño, Pedro Fuel Processing Technology, Vol. 95 https://doi.org/10.1016/j.fuproc.2011.11.003	journal	March 2012
Efficient conversion of lignin-derived phenols to cycloalkanes over bifunctional catalysts with low loading of ruthenium Xiang, Zhiyu; Wang, Weichen; Zhou, Fangyuan Fuel Processing Technology, Vol. 256 https://doi.org/10.1016/j.fuproc.2024.108073	journal	June 2024
Effect of traditional solvent on thermal decomposition mechanism of lignin: A density functional theory study Luo, Xiaosong; Li, Qibin Fuel Processing Technology, Vol. 258 https://doi.org/10.1016/j.fuproc.2024.108093 108093	journal	July 2024
Towards functionalized lignin and its derivatives for high-value material applications Yu, Xiaona; Yang, Bin; Zhu, Wanbin Industrial Crops and Products, Vol. 200 https://doi.org/10.1016/j.indcrop.2023.116824	journal	September 2023
Relationship between acidity and catalytic reactivity of faujasite zeolite: A periodic DFT study Liu, Chong; Li, Guanna; Hensen, Emiel J. M. Journal of Catalysis, Vol. 344 https://doi.org/10.1016/j.jcat.2016.10.027	journal	December 2016
Characterization of deactivated and regenerated zeolite ZSM-5-based catalyst extrudates used in catalytic pyrolysis of biomass Heracleous, E.; Pachatouridou, E.; Hernández-Giménez, A. M. Journal of Catalysis, Vol. 380 https://doi.org/10.1016/j.jcat.2019.10.019	journal	December 2019
Continuous hydrodeoxygenation of lignin to jet-range aromatic hydrocarbons Stone, Michael L.; Webber, Matthew S.; Mounfield, William P. Joule, Vol. 6, Issue 10 https://doi.org/10.1016/j.joule.2022.08.005	journal	October 2022
Shape selectivity of zeolite catalysts for the hydrodeoxygenation of biocrude oil and its model compounds Yan, Penghui; Bryant, Glenn; Li, Molly Meng-Jung Microporous and Mesoporous Materials, Vol. 309 https://doi.org/10.1016/j.micromeso.2020.110561	journal	December 2020
Synthesis and characterization of zeolite W and its ion-exchange properties to K+ in seawater Hou, Jin; Yuan, Junsheng; Shang, Ru Powder Technology, Vol. 226 https://doi.org/10.1016/j.powtec.2012.04.046	journal	August 2012
A comprehensive review on the pyrolysis of lignocellulosic biomass Dhyani, Vaibhav; Bhaskar, Thallada Renewable Energy, Vol. 129 https://doi.org/10.1016/j.renene.2017.04.035	journal	December 2018
Hydrodeoxygenation of m-Cresol over Ru based catalysts: Influence of catalyst support on m-Cresol conversion and methylcyclohexane selectivity Kumar, Adarsh; Kumar, Avnish; Biswas, Bijoy Renewable Energy, Vol. 151 https://doi.org/10.1016/j.renene.2019.11.076	journal	May 2020
Catalytic routes for the conversion of lignocellulosic biomass to aviation fuel range hydrocarbons Wang, Hongliang; Yang, Bin; Zhang, Qian Renewable and Sustainable Energy Reviews, Vol. 120 https://doi.org/10.1016/j.rser.2019.109612	journal	March 2020
Global biorenewable development strategies for sustainable aviation fuel production Ng, Kok Siew; Farooq, Danial; Yang, Aidong Renewable and Sustainable Energy Reviews, Vol. 150 https://doi.org/10.1016/j.rser.2021.111502	journal	October 2021
Breaking C─C Bonds and Preserving C─O Bonds in Aromatic Plastics and Lignin via a Reversing Bond Energy Cleavage Strategy Jing, Yaxuan; Shakouri, Mohsen; Liu, Xiaohui ACS Catalysis, Vol. 12, Issue 17, p. 10690-10699 https://doi.org/10.1021/acscatal.2c02924	journal	August 2022
Characterization of Coke on a Pt-Re/γ-Al ₂ O ₃ Re-Forming Catalyst: Experimental and Theoretical Study Bare, Simon R.; Vila, F. D.; Charochak, Meghan E. ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b02785	journal	January 2017
Synthesis of High-Density Components of Jet Fuel from Lignin-Derived Aromatics via Alkylation and Subsequent Hydrodeoxygenation Bai, Jing; Zhang, Yang; Zhang, Xinghua ACS Sustainable Chemistry & Engineering, Vol. 9, Issue 20 https://doi.org/10.1021/acssuschemeng.1c01339	journal	May 2021
Effects of Lignin Structure on Hydrodeoxygenation Reactivity of Pine Wood Lignin to Valuable Chemicals Wang, Hongliang; Ben, Haoxi; Ruan, Hao ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 2 https://doi.org/10.1021/acssuschemeng.6b02563	journal	December 2016
Lipid Production from Dilute Alkali Corn Stover Lignin by Rhodococcus Strains He, Yucai; Li, Xiaolu; Ben, Haoxi ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 3 https://doi.org/10.1021/acssuschemeng.6b02627	journal	January 2017
Swelling of Nitrile Rubber by Selected Aromatics Blended in a Synthetic Jet Fuel Graham, John L.; Striebich, Richard C.; Myers, Kevin J. Energy & Fuels, Vol. 20, Issue 2 https://doi.org/10.1021/ef050191x	journal	January 2006
Hydrocarbon Liquid Production from Biomass via Hot-Vapor-Filtered Fast Pyrolysis and Catalytic Hydroprocessing of the Bio-oil Elliott, Douglas C.; Wang, Huamin; French, Richard Energy & Fuels, Vol. 28, Issue 9 https://doi.org/10.1021/ef501536j	journal	August 2014
Hydrodeoxygenation of water-insoluble bio-oil to alkanes using a highly dispersed Pd–Mo catalyst Duan, Haohong; Dong, Juncai; Gu, Xianrui Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/s41467-017-00596-3	journal	September 2017
Solvent-free microwave synthesis of ultra-small Ru-Mo2C@CNT with strong metal-support interaction for industrial hydrogen evolution Wu, Xueke; Wang, Zuochao; Zhang, Dan Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-24322-2	journal	June 2021
Ambient-pressure and low-temperature upgrading of lignin bio-oil to hydrocarbons using a hydrogen buffer catalytic system Liu, Wei; You, Wenqin; Sun, Wei Nature Energy, Vol. 5, Issue 10 https://doi.org/10.1038/s41560-020-00680-x	journal	September 2020
Solar energy-driven lignin-first approach to full utilization of lignocellulosic biomass under mild conditions Wu, Xuejiao; Fan, Xueting; Xie, Shunji Nature Catalysis, Vol. 1, Issue 10 https://doi.org/10.1038/s41929-018-0148-8	journal	October 2018
Metal–support cooperation in Al(PO3)3-supported platinum nanoparticles for the selective hydrogenolysis of phenols to arenes Jin, Xiongjie; Tsukimura, Rio; Aihara, Takeshi Nature Catalysis, Vol. 4, Issue 4 https://doi.org/10.1038/s41929-021-00598-x	journal	April 2021
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
Size effects in Atomic-Level Epitaxial Redistribution Process of RuO2 over TiO2 Xiang, Guolei; Shi, Xuejun; Wu, Yulong Scientific Reports, Vol. 2, Issue 1 https://doi.org/10.1038/srep00801	journal	November 2012
Ruthenium nanoparticles confined in SBA-15 as highly efficient catalyst for hydrolytic dehydrogenation of ammonia borane and hydrazine borane Yao, Qilu; Lu, Zhang-Hui; Yang, Kangkang Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep15186	journal	October 2015
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
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
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
Catalytic hydrodeoxygenation of anisole: an insight into the role of metals in transalkylation reactions in bio-oil upgrading Wang, Hongliang; Feng, Maoqi; Yang, Bin Green Chemistry, Vol. 19, Issue 7 https://doi.org/10.1039/C6GC03198F	journal	January 2017
Integrated production of bio-jet fuel containing lignin-derived arenes via lipid deoxygenation Lu, Yijian; Ma, Bing; Zhao, Chen Chemical Communications, Vol. 54, Issue 70 https://doi.org/10.1039/C8CC04969F	journal	January 2018
Structure sensitivity in Pt-catalyzed hydrodeoxygenation of multi-oxygenated lignol model compounds Marlowe, Justin; Ford, Peter C.; Abu-Omar, Mahdi M. Catalysis Science & Technology, Vol. 13, Issue 19 https://doi.org/10.1039/D3CY00757J	journal	January 2023
Boosting the catalytic performance of Ru nanoparticles in the cleavage of β-O-4 linkages in lignin by doping Mo Lei, Puyi; Zhang, Jiali; Shen, Wenzhuo Green Chemistry, Vol. 26, Issue 11, p. 6616-6624 https://doi.org/10.1039/D4GC00294F	journal	January 2024
Aviation fuel production from lipids by a single-step route using hierarchical mesoporous zeolites Verma, Deepak; Kumar, Rohit; Rana, Bharat S. Energy & Environmental Science, Vol. 4, Issue 5 https://doi.org/10.1039/c0ee00744g	journal	January 2011
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
An “ideal lignin” facilitates full biomass utilization Li, Yanding; Shuai, Li; Kim, Hoon Science Advances, Vol. 4, Issue 9 https://doi.org/10.1126/sciadv.aau2968	journal	September 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
The Exchange Mechanism of Alkaline and Alkaline-Earth Ions in Zeolite N Khosravi, Monireh; Murthy, Vinuthaa; D. R. Mackinnon, Ian Molecules, Vol. 24, Issue 20 https://doi.org/10.3390/molecules24203652	journal	October 2019

Similar Records

Engineered $\mathrm{Ru}$ on $\mathrm{HY}$ zeolite catalyst for continuous and selective hydrodeoxygenation of lignin phenolics to cycloalkanes under moderate conditions

Journal Article · Thu Feb 29 19:00:00 EST 2024 · Applied Catalysis. A, General · OSTI ID:2322501

Adarsh Kumar, Fnu; Kumar, Abhishek; Santosa, Daniel M.; +8 more

Biomass-derived Lignin to Jet Fuel Range Hydrocarbons via Aqueous Phase Hydrodeoxygenation

Journal Article · Mon Sep 14 00:00:00 EDT 2015 · Green Chemistry · OSTI ID:1243279

Wang, Hongliang; Ruan, Hao; Pei, Haisheng; +5 more

2.3.4.104 - Lignin Conversion to Sustainable Aviation Fuel Blendstocks

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

Beckham, Gregg T.; Benavides, Thathiana; Heyne, Joshua; +1 more

Related Subjects

09 BIOMASS FUELS

Title: A simultaneous depolymerization and hydrodeoxygenation process to produce lignin-based jet fuel in continuous flow reactor

Citation Formats

References (67)

Similar Records

Related Subjects