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Title: Supercritical methanol depolymerization and hydrodeoxygenation of lignin and biomass over reduced copper porous metal oxides

Abstract

Supercritical methanol upgrading with a CuMgAlO x catalyst is effective at depolymerizing and hydrodeoxygenating lignin into monomers and oligomers.

Authors:
 [1]; ORCiD logo [1];  [2];  [3]; ORCiD logo [4];  [3]; ORCiD logo [2]; ORCiD logo [1]
  1. Department of Chemical and Biological Engineering, University of Wisconsin–Madison, Madison, USA
  2. Department of Chemical and Biological Engineering, University of Wisconsin–Madison, Madison, USA, Great Lakes Bioenergy Research Center
  3. ExxonMobil Research and Engineering, Annandale, USA
  4. Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, Madison, USA, Department of Biochemistry
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1514763
Grant/Contract Number:  
DOE BER Office of Science DE-SC0018409
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Name: Green Chemistry Journal Volume: 21 Journal Issue: 11; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

McClelland, Daniel J., Galebach, Peter H., Motagamwala, Ali Hussain, Wittrig, Ashley M., Karlen, Steven D., Buchanan, J. Scott, Dumesic, James A., and Huber, George W. Supercritical methanol depolymerization and hydrodeoxygenation of lignin and biomass over reduced copper porous metal oxides. United Kingdom: N. p., 2019. Web. doi:10.1039/C9GC00589G.
McClelland, Daniel J., Galebach, Peter H., Motagamwala, Ali Hussain, Wittrig, Ashley M., Karlen, Steven D., Buchanan, J. Scott, Dumesic, James A., & Huber, George W. Supercritical methanol depolymerization and hydrodeoxygenation of lignin and biomass over reduced copper porous metal oxides. United Kingdom. https://doi.org/10.1039/C9GC00589G
McClelland, Daniel J., Galebach, Peter H., Motagamwala, Ali Hussain, Wittrig, Ashley M., Karlen, Steven D., Buchanan, J. Scott, Dumesic, James A., and Huber, George W. Tue . "Supercritical methanol depolymerization and hydrodeoxygenation of lignin and biomass over reduced copper porous metal oxides". United Kingdom. https://doi.org/10.1039/C9GC00589G.
@article{osti_1514763,
title = {Supercritical methanol depolymerization and hydrodeoxygenation of lignin and biomass over reduced copper porous metal oxides},
author = {McClelland, Daniel J. and Galebach, Peter H. and Motagamwala, Ali Hussain and Wittrig, Ashley M. and Karlen, Steven D. and Buchanan, J. Scott and Dumesic, James A. and Huber, George W.},
abstractNote = {Supercritical methanol upgrading with a CuMgAlO x catalyst is effective at depolymerizing and hydrodeoxygenating lignin into monomers and oligomers.},
doi = {10.1039/C9GC00589G},
journal = {Green Chemistry},
number = 11,
volume = 21,
place = {United Kingdom},
year = {Tue Jun 04 00:00:00 EDT 2019},
month = {Tue Jun 04 00:00:00 EDT 2019}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C9GC00589G

Citation Metrics:
Cited by: 45 works
Citation information provided by
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Works referenced in this record:

Catalytic disassembly of an organosolv lignin via hydrogen transfer from supercritical methanol
journal, January 2010

  • Barta, Katalin; Matson, Theodore D.; Fettig, Makayla L.
  • Green Chemistry, Vol. 12, Issue 9
  • DOI: 10.1039/c0gc00181c

Formic-acid-induced depolymerization of oxidized lignin to aromatics
journal, November 2014

  • Rahimi, Alireza; Ulbrich, Arne; Coon, Joshua J.
  • Nature, Vol. 515, Issue 7526, p. 249-252
  • DOI: 10.1038/nature13867

Production of Alcohols from Cellulose by Supercritical Methanol Depolymerization and Hydrodeoxygenation
journal, February 2018

  • Galebach, Peter H.; McClelland, Daniel J.; Eagan, Nathaniel M.
  • ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 3
  • DOI: 10.1021/acssuschemeng.7b04820

Catalytic Depolymerization of Lignin in Supercritical Ethanol
journal, May 2014

  • Huang, Xiaoming; Korányi, Tamás I.; Boot, Michael D.
  • ChemSusChem, Vol. 7, Issue 8
  • DOI: 10.1002/cssc.201402094

Synergy in Lignin Upgrading by a Combination of Cu-Based Mixed Oxide and Ni-Phosphide Catalysts in Supercritical Ethanol
journal, March 2017

  • Korányi, Tamás I.; Huang, Xiaoming; Coumans, Alessandro E.
  • ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 4
  • DOI: 10.1021/acssuschemeng.7b00239

Comparative Studies on Cellulolytic Enzyme Lignin and Milled Wood Lignin of Sweetgum and Spruce
journal, January 1975


Monolignol ferulate conjugates are naturally incorporated into plant lignins
journal, October 2016

  • Karlen, Steven D.; Zhang, Chengcheng; Peck, Matthew L.
  • Science Advances, Vol. 2, Issue 10
  • DOI: 10.1126/sciadv.1600393

Temperature Tuning the Catalytic Reactivity of Cu-Doped Porous Metal Oxides with Lignin Models
journal, December 2017

  • Bernt, Christopher M.; Manesewan, Hussaya; Chui, Megan
  • ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 2
  • DOI: 10.1021/acssuschemeng.7b03969

Probing the Lignin Disassembly Pathways with Modified Catalysts Based on Cu-Doped Porous Metal Oxides
journal, March 2017

  • Chui, Megan; Metzker, Gustavo; Bernt, Christopher M.
  • ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 4
  • DOI: 10.1021/acssuschemeng.6b02954

Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps
journal, January 2015

  • Van den Bosch, S.; Schutyser, W.; Vanholme, R.
  • Energy & Environmental Science, Vol. 8, Issue 6
  • DOI: 10.1039/C5EE00204D

Flowthrough Reductive Catalytic Fractionation of Biomass
journal, November 2017


Integrating lignin valorization and bio-ethanol production: on the role of Ni-Al 2 O 3 catalyst pellets during lignin-first fractionation
journal, January 2017

  • Van den Bosch, S.; Renders, T.; Kennis, S.
  • Green Chemistry, Vol. 19, Issue 14
  • DOI: 10.1039/C7GC01324H

Lignin monomer production integrated into the γ-valerolactone sugar platform
journal, January 2015

  • Luterbacher, Jeremy S.; Azarpira, Ali; Motagamwala, Ali H.
  • Energy & Environmental Science, Vol. 8, Issue 9
  • DOI: 10.1039/C5EE01322D

Liquid fuels, hydrogen and chemicals from lignin A critical review
journal, May 2013

  • Azadi, Pooya; Inderwildi, Oliver R.; Farnood, Ramin
  • Renewable and Sustainable Energy Reviews, Vol. 21, p. 506-523
  • DOI: 10.1016/j.rser.2012.12.022

Catalytic Transformation of Lignin for the Production of Chemicals and Fuels
journal, October 2015


A Convergent Approach for a Deep Converting Lignin-First Biorefinery Rendering High-Energy-Density Drop-in Fuels
journal, June 2018


Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6/pyridine-d5
journal, January 2010

  • Kim, Hoon; Ralph, John
  • Org. Biomol. Chem., Vol. 8, Issue 3
  • DOI: 10.1039/B916070A

PVT measurements for pure methanol in the near-critical and supercritical regions
journal, June 2007


Catalytic Conversion of Nonfood Woody Biomass Solids to Organic Liquids
journal, April 2014

  • Barta, Katalin; Ford, Peter C.
  • Accounts of Chemical Research, Vol. 47, Issue 5, p. 1503-1512
  • DOI: 10.1021/ar4002894

Lignin Conversion to Low-Molecular-Weight Aromatics via an Aerobic Oxidation-Hydrolysis Sequence: Comparison of Different Lignin Sources
journal, January 2018


Kinetic Studies of Lignin Solvolysis and Reduction by Reductive Catalytic Fractionation Decoupled in Flow-Through Reactors
journal, April 2018

  • Anderson, Eric M.; Stone, Michael L.; Hülsey, Max J.
  • ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 6
  • DOI: 10.1021/acssuschemeng.8b01256

Exploring, Tuning, and Exploiting the Basicity of Hydrotalcites for Applications in Heterogeneous Catalysis
journal, April 2009

  • Debecker, Damien P.; Gaigneaux, Eric M.; Busca, Guido
  • Chemistry - A European Journal, Vol. 15, Issue 16, p. 3920-3935
  • DOI: 10.1002/chem.200900060

Catalytic Biorefining of Plant Biomass to Non-Pyrolytic Lignin Bio-Oil and Carbohydrates through Hydrogen Transfer Reactions
journal, June 2014

  • Ferrini, Paola; Rinaldi, Roberto
  • Angewandte Chemie International Edition, Vol. 53, Issue 33
  • DOI: 10.1002/anie.201403747

Enhancing Aromatic Production from Reductive Lignin Disassembly: in Situ O-Methylation of Phenolic Intermediates
journal, September 2016


Aspects of the mechanism of the flame ionization detector
journal, May 1999


Role of Cu–Mg–Al Mixed Oxide Catalysts in Lignin Depolymerization in Supercritical Ethanol
journal, November 2015


One-Pot Catalytic Conversion of Cellulose and of Woody Biomass Solids to Liquid Fuels
journal, September 2011

  • Matson, Theodore D.; Barta, Katalin; Iretskii, Alexei V.
  • Journal of the American Chemical Society, Vol. 133, Issue 35, p. 14090-14097
  • DOI: 10.1021/ja205436c

Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization
journal, October 2016

  • Shuai, Li; Amiri, Masoud Talebi; Questell-Santiago, Ydna M.
  • Science, Vol. 354, Issue 6310
  • DOI: 10.1126/science.aaf7810

Isolation and Structural Characterization of the Milled Wood Lignin, Dioxane Lignin, and Cellulolytic Lignin Preparations from Brewer’s Spent Grain
journal, January 2015

  • Rencoret, Jorge; Prinsen, Pepijn; Gutiérrez, Ana
  • Journal of Agricultural and Food Chemistry, Vol. 63, Issue 2
  • DOI: 10.1021/jf505808c

Low temperature hydrogenation of pyrolytic lignin over Ru/TiO 2 : 2D HSQC and 13 C NMR study of reactants and products
journal, January 2016

  • Chen, Wen; McClelland, Daniel J.; Azarpira, Ali
  • Green Chemistry, Vol. 18, Issue 1
  • DOI: 10.1039/C5GC02286J

Promising bulk production of a potentially benign bisphenol A replacement from a hardwood lignin platform
journal, January 2018

  • Koelewijn, S. -F.; Cooreman, C.; Renders, T.
  • Green Chemistry, Vol. 20, Issue 5
  • DOI: 10.1039/C7GC02989F

Selective C-alkylation of phenol with methanol over catalysts derived from copper-aluminium hydrotalcite-like compounds
journal, October 1996


Depolymerization of concentrated sulfuric acid hydrolysis lignin to high-yield aromatic monomers in basic sub- and supercritical fluids
journal, June 2017


Designer lignins: harnessing the plasticity of lignification
journal, February 2016


Structural Characterization of Wheat Straw Lignin as Revealed by Analytical Pyrolysis, 2D-NMR, and Reductive Cleavage Methods
journal, December 2011

  • del Río, José C.; Rencoret, Jorge; Prinsen, Pepijn
  • Journal of Agricultural and Food Chemistry, Vol. 60, Issue 23
  • DOI: 10.1021/jf301002n

Protection Group Effects During α,γ-Diol Lignin Stabilization Promote High-Selectivity Monomer Production
journal, January 2018

  • Lan, Wu; Amiri, Masoud Talebi; Hunston, Christopher M.
  • Angewandte Chemie International Edition, Vol. 57, Issue 5
  • DOI: 10.1002/anie.201710838