skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Production of Jet Fuel-Range Hydrocarbons from Hydrodeoxygenation of Lignin over Super Lewis Acid Combined with Metal Catalysts

Journal Article · · ChemSusChem
 [1];  [2];  [3];  [3]; ORCiD logo [1]
  1. Washington State Univ., Pullman, WA (United States)
  2. Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
  3. National Renewable Energy Lab. (NREL), Golden, CO (United States)

Abstract Super Lewis acids containing the triflate anion [e.g., Hf(OTf) 4 , Ln(OTf) 3 , In(OTf) 3 , Al(OTf) 3 ] and noble metal catalysts (e.g., Ru/C, Ru/Al 2 O 3 ) formed efficient catalytic systems to generate saturated hydrocarbons from lignin in high yields. In such catalytic systems, the metal triflates mediated rapid ether bond cleavage through selective bonding to etheric oxygens while the noble metal catalyzed subsequent hydrodeoxygenation (HDO) reactions. Near theoretical yields of hydrocarbons were produced from lignin model compounds by the combined catalysis of Hf(OTf) 4 and ruthenium‐based catalysts. When a technical lignin derived from a pilot‐scale biorefinery was used, more than 30 wt % of the hydrocarbons produced with this catalytic system were cyclohexane and alkylcyclohexanes in the jet fuel range. Super Lewis acids are postulated to strongly interact with lignin substrates by protonating hydroxyl groups and ether linkages, forming intermediate species that enhance hydrogenation catalysis by supported noble metal catalysts. Meanwhile, the hydrogenation of aromatic rings by the noble metal catalysts can promote deoxygenation reactions catalyzed by super Lewis acids.

Research Organization:
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
Grant/Contract Number:
AC36-08GO28308
OSTI ID:
1411326
Alternate ID(s):
OSTI ID: 1409447
Report Number(s):
NREL/JA-5100-70587; TRN: US1800208
Journal Information:
ChemSusChem, Vol. 11, Issue 1; ISSN 1864-5631
Publisher:
ChemPubSoc EuropeCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 67 works
Citation information provided by
Web of Science

References (40)

Lignin Valorization: Improving Lignin Processing in the Biorefinery journal May 2014
Reductive fractionation of woody biomass into lignin monomers and cellulose by tandem metal triflate and Pd/C catalysis journal January 2017
Bifunctional transalkylation and hydrodeoxygenation of anisole over a Pt/HBeta catalyst journal July 2011
Pathways for biomass-derived lignin to hydrocarbon fuels journal July 2013
Overcoming lignin heterogeneity: reliably characterizing the cleavage of technical lignin journal January 2016
Catalytic hydrodeoxygenation of anisole: an insight into the role of metals in transalkylation reactions in bio-oil upgrading journal January 2017
Formic-acid-induced depolymerization of oxidized lignin to aromatics journal November 2014
Selective Degradation of Wood Lignin over Noble‐Metal Catalysts in a Two‐Step Process journal July 2008
Catalytic Ethanolysis of Kraft Lignin into High‐Value Small‐Molecular Chemicals over a Nanostructured α‐Molybdenum Carbide Catalyst journal June 2014
Direct hydrodeoxygenation of raw woody biomass into liquid alkanes journal March 2016
Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin journal November 2014
Catalytic Ethanolysis of Kraft Lignin into High-Value Small-Molecular Chemicals over a Nanostructured α-Molybdenum Carbide Catalyst journal June 2014
Highly selective hydrogenation of arenes using nanostructured ruthenium catalysts modified with a carbon–nitrogen matrix journal April 2016
Biomass-derived lignin to jet fuel range hydrocarbons via aqueous phase hydrodeoxygenation journal January 2015
Cleavage and hydrodeoxygenation (HDO) of C–O bonds relevant to lignin conversion using Pd/Zn synergistic catalysis journal January 2013
Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps journal January 2015
Alkanes from Bioderived Furans by using Metal Triflates and Palladium-Catalyzed Hydrodeoxygenation of Cyclic Ethers journal November 2015
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals journal June 2010
Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes journal July 2016
Advanced Model Compounds for Understanding Acid-Catalyzed Lignin Depolymerization: Identification of Renewable Aromatics and a Lignin-Derived Solvent journal July 2016
Rapid Ether and Alcohol C–O Bond Hydrogenolysis Catalyzed by Tandem High-Valent Metal Triflate + Supported Pd Catalysts journal December 2013
Catalytic Transformation of Lignin for the Production of Chemicals and Fuels journal October 2015
Reaction Pathways and Energetics of Etheric C–O Bond Cleavage Catalyzed by Lanthanide Triflates journal July 2013
Aromatic Monomers by in Situ Conversion of Reactive Intermediates in the Acid-Catalyzed Depolymerization of Lignin journal June 2015
A Route for Lignin and Bio-Oil Conversion: Dehydroxylation of Phenols into Arenes by Catalytic Tandem Reactions journal September 2013
Thermodynamic Strategies for C–O Bond Formation and Cleavage via Tandem Catalysis journal April 2016
Methanol Fractionation of Softwood Kraft Lignin: Impact on the Lignin Properties journal November 2013
Towards Quantitative Catalytic Lignin Depolymerization journal April 2011
Why Is Ruthenium an Efficient Catalyst for the Aqueous-Phase Hydrogenation of Biosourced Carbonyl Compounds? journal June 2015
Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process journal January 2013
Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization journal October 2016
A Route for Lignin and Bio-Oil Conversion: Dehydroxylation of Phenols into Arenes by Catalytic Tandem Reactions journal September 2013
Hydrolytic Cleavage of C–O Linkages in Lignin Model Compounds Catalyzed by Water-Tolerant Lewis Acids journal February 2014
Lignin depolymerization/repolymerization and its critical role for delignification of aspen wood by steam explosion journal November 2007
Development of Novel Lewis Acid Catalysts for Selective Organic Reactions in Aqueous Media journal April 2002
ZnCl 2 induced catalytic conversion of softwood lignin to aromatics and hydrocarbons journal January 2016
Metal Triflates for the Production of Aromatics from Lignin journal September 2016
A Series of NiM (M = Ru, Rh, and Pd) Bimetallic Catalysts for Effective Lignin Hydrogenolysis in Water journal April 2014
Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin journal November 2014
Overcoming lignin heterogeneity : reliably characterizing the cleavage of technical lignin text January 2016

Cited By (9)

Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst journal May 2020
Techno‐economic analysis of jet‐fuel production from biorefinery waste lignin journal December 2018
Biotransformation of lignin: Mechanisms, applications and future work journal October 2019
Effects of Sugars, Furans, and their Derivatives on Hydrodeoxygenation of Biorefinery Lignin‐Rich Wastes to Hydrocarbons journal July 2018
Tandem Hydrogenolysis–Hydrogenation of Lignin‐Derived Oxygenates over Integrated Dual Catalysts with Optimized Interoperations journal November 2019
Electrochemical Generation of ROS in Ionic Liquid for the Degradation of Lignin Model Compound journal January 2018
Valorization of Lignin as an Immobilizing Agent for Bioinoculant Production using Azospirillum brasilense as a Model Bacteria journal December 2019
Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst journal May 2020
Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst text January 2020

Figures / Tables (5)