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

Abstract

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.

Authors:
 [1];  [2];  [3];  [3]; ORCiD logo [1]
+ Show Author Affiliations
  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)
Publication Date:
Research Org.:
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
OSTI Identifier:
1411326
Alternate Identifier(s):
OSTI ID: 1409447
Report Number(s):
NREL/JA-5100-70587
Journal ID: ISSN 1864-5631; TRN: US1800208
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
ChemSusChem
Additional Journal Information:
Journal Volume: 11; Journal Issue: 1; Journal ID: ISSN 1864-5631
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; biomass conversion; fuels; hydrocarbons; hydrodeoxygenation; metal triflates

Citation Formats

Wang, Hongliang, Wang, Huamin, Kuhn, Eric, Tucker, Melvin P., and Yang, Bin. Production of Jet Fuel-Range Hydrocarbons from Hydrodeoxygenation of Lignin over Super Lewis Acid Combined with Metal Catalysts. United States: N. p., 2017. Web. doi:10.1002/cssc.201701567.
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Wang, Hongliang, Wang, Huamin, Kuhn, Eric, Tucker, Melvin P., & Yang, Bin. Production of Jet Fuel-Range Hydrocarbons from Hydrodeoxygenation of Lignin over Super Lewis Acid Combined with Metal Catalysts. United States. https://doi.org/10.1002/cssc.201701567
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Wang, Hongliang, Wang, Huamin, Kuhn, Eric, Tucker, Melvin P., and Yang, Bin. Tue . "Production of Jet Fuel-Range Hydrocarbons from Hydrodeoxygenation of Lignin over Super Lewis Acid Combined with Metal Catalysts". United States. https://doi.org/10.1002/cssc.201701567. https://www.osti.gov/servlets/purl/1411326.
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@article{osti_1411326,
title = {Production of Jet Fuel-Range Hydrocarbons from Hydrodeoxygenation of Lignin over Super Lewis Acid Combined with Metal Catalysts},
author = {Wang, Hongliang and Wang, Huamin and Kuhn, Eric and Tucker, Melvin P. and Yang, Bin},
abstractNote = {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.},
doi = {10.1002/cssc.201701567},
journal = {ChemSusChem},
number = 1,
volume = 11,
place = {United States},
year = {Tue Nov 14 00:00:00 EST 2017},
month = {Tue Nov 14 00:00:00 EST 2017}
}
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Journal Article:
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Publisher's Version of Record
https://doi.org/10.1002/cssc.201701567
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Cited by: 67 works
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Figures / Tables:

Table 1 Table 1: HDO conversion of guaiacol with different metal triflate/supported noble metal catalyst systems[a]
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    Works referencing / citing this record:

    Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst
    journal, May 2020

    • Moos, Gilles; Emondts, Meike; Bordet, Alexis
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    • DOI: 10.1002/anie.201916385

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    Effects of Sugars, Furans, and their Derivatives on Hydrodeoxygenation of Biorefinery Lignin‐Rich Wastes to Hydrocarbons
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    Tandem Hydrogenolysis–Hydrogenation of Lignin‐Derived Oxygenates over Integrated Dual Catalysts with Optimized Interoperations
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    Electrochemical Generation of ROS in Ionic Liquid for the Degradation of Lignin Model Compound
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    Valorization of Lignin as an Immobilizing Agent for Bioinoculant Production using Azospirillum brasilense as a Model Bacteria
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    Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst
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    • Moos, Gilles; Emondts, Meike; Bordet, Alexis
    • Angewandte Chemie, Vol. 132, Issue 29
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    Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst
    text, January 2020

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