Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

Title: Recent advances in oxidative valorization of lignin

Abstract

Lignin, an aromatic macromolecule synthesized by all higher plants, is one of the most intriguing natural materials for utilization across a wide range of applications. Depolymerization and fragmentation of lignin into small chemicals constituents which can either replace current market products or be used building blocks for new material synthesis is a focus of current lignin valorization strategies. And among the variety of lignin degradation chemistries, catalytic oxidation of lignin presents an energy efficient means of lignin depolymerization and generating selective reaction products. Our review provides a summary of the recent advancements in oxidative lignin valorization couched in a discussion on how these chemistries may contribute to the degradation of the lignin macromolecule through three major approaches: 1) inter-unit linkages cleavage; 2) propanyl side-chain oxidative modification; and 3) oxidation of the aromatic ring and ring cleavage reactions.

Authors:
 [1];  [1];  [2]
+ Show Author Affiliations
  1. Washington State Univ., Richland, WA (United States). Voiland School of Chemical Engineering and Bioengineering
  2. Washington State Univ., Richland, WA (United States). Voiland School of Chemical Engineering and Bioengineering; Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Publication Date:
Research Org.:
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1390581
Grant/Contract Number:  
AC05-76RL01830
Resource Type:
Accepted Manuscript
Journal Name:
Catalysis Today
Additional Journal Information:
Journal Volume: 302; Journal ID: ISSN 0920-5861
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Biomass; Lignin; Oxidation; Catalysis; Selectivity

Citation Formats

Ma, Ruoshui, Guo, Mond, and Zhang, Xiao. Recent advances in oxidative valorization of lignin. United States: N. p., 2017. Web. doi:10.1016/j.cattod.2017.05.101.
Copy to clipboard
Ma, Ruoshui, Guo, Mond, & Zhang, Xiao. Recent advances in oxidative valorization of lignin. United States. https://doi.org/10.1016/j.cattod.2017.05.101
Copy to clipboard
Ma, Ruoshui, Guo, Mond, and Zhang, Xiao. Fri . "Recent advances in oxidative valorization of lignin". United States. https://doi.org/10.1016/j.cattod.2017.05.101. https://www.osti.gov/servlets/purl/1390581.
Copy to clipboard
@article{osti_1390581,
title = {Recent advances in oxidative valorization of lignin},
author = {Ma, Ruoshui and Guo, Mond and Zhang, Xiao},
abstractNote = {Lignin, an aromatic macromolecule synthesized by all higher plants, is one of the most intriguing natural materials for utilization across a wide range of applications. Depolymerization and fragmentation of lignin into small chemicals constituents which can either replace current market products or be used building blocks for new material synthesis is a focus of current lignin valorization strategies. And among the variety of lignin degradation chemistries, catalytic oxidation of lignin presents an energy efficient means of lignin depolymerization and generating selective reaction products. Our review provides a summary of the recent advancements in oxidative lignin valorization couched in a discussion on how these chemistries may contribute to the degradation of the lignin macromolecule through three major approaches: 1) inter-unit linkages cleavage; 2) propanyl side-chain oxidative modification; and 3) oxidation of the aromatic ring and ring cleavage reactions.},
doi = {10.1016/j.cattod.2017.05.101},
journal = {Catalysis Today},
number = ,
volume = 302,
place = {United States},
year = {Fri Jul 21 00:00:00 EDT 2017},
month = {Fri Jul 21 00:00:00 EDT 2017}
}
Copy to clipboard
Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1016/j.cattod.2017.05.101
Copyright Statement
Other availability
Search WorldCat Search WorldCat to find libraries that may hold this journal
Citation Metrics:
Cited by: 111 works
Citation information provided by
Web of Science
Save / Share:
Export Metadata
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.

Works referenced in this record:

Hydrodeoxygenation of phenols as lignin models under acid-free conditions with carbon-supported platinum catalysts
journal, January 2011

  • Ohta, Hidetoshi; Kobayashi, Hirokazu; Hara, Kenji
  • Chemical Communications, Vol. 47, Issue 44
  • DOI: 10.1039/c1cc14859a

Cobalt-Schiff Base Complex Catalyzed Oxidation of Para-Substituted Phenolics. Preparation of Benzoquinones
journal, April 1995

  • Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R.
  • The Journal of Organic Chemistry, Vol. 60, Issue 8
  • DOI: 10.1021/jo00113a020

Developing Catalytic Oxygen Delignification for Kraft Pulp:  Kinetic Study of Lignin Oxidation with Polyoxometalate Anions
journal, April 2005

  • Ruuttunen, Kyösti; Vuorinen, Tapani
  • Industrial & Engineering Chemistry Research, Vol. 44, Issue 12
  • DOI: 10.1021/ie048836o

Hydroxylation of Benzene over V-HMS Catalysts with the Addition of Fe as the Second Metal Component
journal, January 2011

Autoxidation of Substituted Phenols Catalyzed by Cobalt Schiff Base Complexes in Supercritical Carbon Dioxide
journal, July 2001

  • Musie, Ghezai T.; Wei, Ming; Subramaniam, Bala
  • Inorganic Chemistry, Vol. 40, Issue 14
  • DOI: 10.1021/ic001288w

Metalloporphyrin catalysed biomimetic oxidation of aryl benzyl ethers. Implications for lignin peroxidase catalysis
journal, April 1999

Equilibrating metal-oxide cluster ensembles for oxidation reactions using oxygen in water
journal, November 2001

  • Weinstock, Ira A.; Barbuzzi, Elena M. G.; Wemple, Michael W.
  • Nature, Vol. 414, Issue 6860
  • DOI: 10.1038/35102545

Designing a Heterogeneous Catalyst for the Production of Adipic Acid by Aerial Oxidation of Cyclohexane
journal, July 2000

A Stable Polyaniline-Benzoquinone-Hydroquinone Supercapacitor
journal, June 2014

  • Vonlanthen, David; Lazarev, Pavel; See, Kimberly A.
  • Advanced Materials, Vol. 26, Issue 30
  • DOI: 10.1002/adma.201400966

Microwave assisted oxidation of a lignin model phenolic monomer using Co(salen)/SBA-15
journal, February 2009

Fe(TSPc)-Catalysed Benzylic Oxidation and Subsequent Dealkylation of a Non-Phenolic Lignin Model
journal, November 2000

  • Robinson, Murray J.; Wright, L. James; Suckling, Ian D.
  • Journal of Wood Chemistry and Technology, Vol. 20, Issue 4
  • DOI: 10.1080/02773810009351889

Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide
journal, June 2007

Hydrothermal dissolution of willow in hot compressed water as a model for biomass conversion
journal, July 2007

Production of Oxychemicals from Precipitated Hardwood Lignin
journal, January 2001

Structural Characterization and Comparison of Switchgrass Ball-milled Lignin Before and After Dilute Acid Pretreatment
journal, August 2009

  • Samuel, Reichel; Pu, Yunqiao; Raman, Babu
  • Applied Biochemistry and Biotechnology, Vol. 162, Issue 1
  • DOI: 10.1007/s12010-009-8749-y

Interaction between MnO 2 and Oxalate: Formation of a Natural and Abiotic Lignin Oxidizing System
journal, December 1998

  • Hames, Bonnie R.; Kurek, Bernard; Pollet, Brigitte
  • Journal of Agricultural and Food Chemistry, Vol. 46, Issue 12
  • DOI: 10.1021/jf9806513

Investigation of Aggregation and Assembly of Alkali Lignin Using Iodine as a Probe
journal, April 2011

  • Deng, Yonghong; Feng, Xinjia; Zhou, Mingsong
  • Biomacromolecules, Vol. 12, Issue 4
  • DOI: 10.1021/bm101449b

Chemical reactions in chlorine dioxide stages of pulp bleaching: Intermediately formed hypochlorous acid
journal, January 1983

  • Kolar, J. J.; Lindgren, B. O.; Pettersson, Birgitta
  • Wood Science and Technology, Vol. 17, Issue 2
  • DOI: 10.1007/BF00369129

Spectral Absorption and Fluorescence of Dyes in the Molecular State
journal, December 1936

Cu(II)-Catalyzed Selective Aerobic Oxidation of Alcohols under Mild Conditions
journal, September 2006

  • Jiang, Nan; Ragauskas, Arthur J.
  • The Journal of Organic Chemistry, Vol. 71, Issue 18
  • DOI: 10.1021/jo060837y

Oxidation of lignin model compounds using single-electron-transfer catalysts
journal, April 1988

  • DiCosimo, Robert; Szabo, Hsiao Chiung
  • The Journal of Organic Chemistry, Vol. 53, Issue 8
  • DOI: 10.1021/jo00243a014

Mechanism study of wood lignin pyrolysis by using TG–FTIR analysis
journal, May 2008

  • Liu, Qian; Wang, Shurong; Zheng, Yun
  • Journal of Analytical and Applied Pyrolysis, Vol. 82, Issue 1
  • DOI: 10.1016/j.jaap.2008.03.007

Graphene and Graphene Oxide: Synthesis, Properties, and Applications
journal, June 2010

  • Zhu, Yanwu; Murali, Shanthi; Cai, Weiwei
  • Advanced Materials, Vol. 22, Issue 35, p. 3906-3924
  • DOI: 10.1002/adma.201001068

Dilute acid pretreatment, enzymatic saccharification and fermentation of wheat straw to ethanol
journal, December 2005

Fermentative Production of Chemicals That Can Be Used for Polymer Synthesis
journal, March 2004

  • Lee, Sang Y.; Hong, Soon H.; Lee, Seung H.
  • Macromolecular Bioscience, Vol. 4, Issue 3
  • DOI: 10.1002/mabi.200300096

Oxidation of Spruce Wood Sawdust by MnO 2 plus Oxalate:  A Biochemical Investigation
journal, July 2000

  • Kurek, Bernard; Gaudard, François
  • Journal of Agricultural and Food Chemistry, Vol. 48, Issue 7
  • DOI: 10.1021/jf000015g

Immobilized methyltrioxo rhenium (MTO)/H2O2 systems for the oxidation of lignin and lignin model compounds
journal, August 2006

  • Crestini, Claudia; Caponi, Maria Chiara; Argyropoulos, Dimitris S.
  • Bioorganic & Medicinal Chemistry, Vol. 14, Issue 15, p. 5292-5302
  • DOI: 10.1016/j.bmc.2006.03.046

Studies of Lignin Biosynthesis Using Isotopic Carbon: vi. Formation of the side Chain of the Phenylpropane Monomer
journal, October 1958

  • Wright, D.; Brown, Stewart A.; Neish, A. C.
  • Canadian Journal of Biochemistry and Physiology, Vol. 36, Issue 10
  • DOI: 10.1139/o58-111

Bicomponent VO2-defects/MWCNT catalyst for hydroxylation of benzene to phenol: Promoter effect of defects on catalytic performance
journal, July 2011

cis,cis-Muconic acid: separation and catalysis to bio-adipic acid for nylon-6,6 polymerization
journal, January 2016

  • Vardon, Derek R.; Rorrer, Nicholas A.; Salvachúa, Davinia
  • Green Chemistry, Vol. 18, Issue 11
  • DOI: 10.1039/C5GC02844B

Polyoxometalate (POM) oxidation of lignin model compounds
journal, January 2008

  • Kim, Yong Sik; Chang, Hou-min; Kadla, John F.
  • Holzforschung, Vol. 62, Issue 1
  • DOI: 10.1515/HF.2008.006

Metal-free organocatalysis through explicit hydrogen bonding interactions
journal, January 2003

  • Schreiner, Peter R.
  • Chemical Society Reviews, Vol. 32, Issue 5
  • DOI: 10.1039/b107298f

Chemistry of delignification: Part 2: Reactions of lignins during bleaching
journal, January 1986

Iron porphyrin catalyzed oxidation of lignin model compounds: oxidation of phenylpropane and phenylpropene model compounds
journal, December 1995

  • Cui, Futong; Dolphin, David
  • Canadian Journal of Chemistry, Vol. 73, Issue 12
  • DOI: 10.1139/v95-267

Highly Selective Catalytic Conversion of Phenolic Bio-Oil to Alkanes
journal, May 2009

  • Zhao, Chen; Kou, Yuan; Lemonidou, Angeliki A.
  • Angewandte Chemie, Vol. 121, Issue 22
  • DOI: 10.1002/ange.200900404

Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin
journal, April 2013

  • Rahimi, Alireza; Azarpira, Ali; Kim, Hoon
  • Journal of the American Chemical Society, Vol. 135, Issue 17, p. 6415-6418
  • DOI: 10.1021/ja401793n

Efficient Cobalt-Catalyzed Oxidative Conversion of Lignin Models to Benzoquinones
journal, May 2013

  • Biannic, Berenger; Bozell, Joseph J.
  • Organic Letters, Vol. 15, Issue 11
  • DOI: 10.1021/ol401065r

Aggregation of Lignin Derivatives under Alkaline Conditions. Kinetics and Aggregate Structure
journal, April 2002

  • Norgren, Magnus; Edlund, Håkan; Wågberg, Lars
  • Langmuir, Vol. 18, Issue 7
  • DOI: 10.1021/la011627d

Kinetic Evaluation and Modeling of Lignin Catalytic Wet Oxidation to Selective Production of Aromatic Aldehydes
journal, September 2006

  • Sales, Fernando G.; Maranhão, Laísse C. A.; Lima Filho, Nelson M.
  • Industrial & Engineering Chemistry Research, Vol. 45, Issue 20
  • DOI: 10.1021/ie0601697

Catalytic Oxidation of Biorefinery Lignin to Value-added Chemicals to Support Sustainable Biofuel Production
journal, October 2014

Characterization of Lignin by Gas Chromatography and Mass Spectrometry Using a Simplified CuO Oxidation Method
journal, December 2011

  • Kaiser, Karl; Benner, Ronald
  • Analytical Chemistry, Vol. 84, Issue 1
  • DOI: 10.1021/ac202004r

Aerobic Oxidation Reactions Catalyzed by Vanadium Complexes of Bis(Phenolate) Ligands
journal, June 2012

  • Zhang, Guoqi; Scott, Brian L.; Wu, Ruilian
  • Inorganic Chemistry, Vol. 51, Issue 13
  • DOI: 10.1021/ic3007525

A Mechanistic Investigation of Acid-Catalyzed Cleavage of Aryl-Ether Linkages: Implications for Lignin Depolymerization in Acidic Environments
journal, November 2013

  • Sturgeon, Matthew R.; Kim, Seonah; Lawrence, Kelsey
  • ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 3, p. 472-485
  • DOI: 10.1021/sc400384w

Efficacy of Fresh and Used Supported Copper-Based Catalysts for Ferulic Acid Degradation by Wet Air Oxidation Process
journal, November 2012

  • Yadav, Bholu R.; Garg, Anurag
  • Industrial & Engineering Chemistry Research, Vol. 51, Issue 48
  • DOI: 10.1021/ie301787g

Copper-Catalyzed Highly Efficient Aerobic Oxidation of Alcohols under Ambient Conditions
journal, October 2008

C-C or C-O Bond Cleavage in a Phenolic Lignin Model Compound: Selectivity Depends on Vanadium Catalyst
journal, January 2012

  • Hanson, Susan K.; Wu, Ruilian; Silks, Louis A. “Pete”
  • Angewandte Chemie International Edition, Vol. 51, Issue 14, p. 3410-3413
  • DOI: 10.1002/anie.201107020

Functionalization of Graphene: Covalent and Non-Covalent Approaches, Derivatives and Applications
journal, September 2012

  • Georgakilas, Vasilios; Otyepka, Michal; Bourlinos, Athanasios B.
  • Chemical Reviews, Vol. 112, Issue 11
  • DOI: 10.1021/cr3000412

Electrocatalytically Active Graphene–Porphyrin MOF Composite for Oxygen Reduction Reaction
journal, April 2012

  • Jahan, Maryam; Bao, Qiaoliang; Loh, Kian Ping
  • Journal of the American Chemical Society, Vol. 134, Issue 15
  • DOI: 10.1021/ja211433h

Lignin Degradation in Oxygen Delignification Catalysed by [PMo7V5O40]8- Polyanion. Part I. Study on Wood Lignin
journal, July 2000

  • Evtuguin, D. V.; Neto, C. Pascoal; Rocha, J.
  • Holzforschung, Vol. 54, Issue 4
  • DOI: 10.1515/HF.2000.065

The effect of reaction conditions on the oxidation of veratryl alcohol catalyzed by cobalt salen-complexes
journal, July 2002

Computational design of molecules for an all-quinone redox flow battery
journal, January 2015

  • Er, Süleyman; Suh, Changwon; Marshak, Michael P.
  • Chemical Science, Vol. 6, Issue 2, p. 885-893
  • DOI: 10.1039/C4SC03030C

H- and J-Aggregate Behavior in Polymeric Semiconductors
journal, April 2014

Metallophthalocyanines as possible lignin peroxidase models
journal, May 1995

Arene and Phenol oxidation with hydrogen peroxide using ‘sandwich’ type substituted polyoxometalates as catalysts
journal, January 2008

  • Egusquiza, María G.; Romanelli, Gustavo P.; Cabello, Carmen I.
  • Catalysis Communications, Vol. 9, Issue 1
  • DOI: 10.1016/j.catcom.2007.04.026

Novel Polyaniline-Supported Molybdenum-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones
journal, December 2004

  • Velusamy, Subbarayan; Ahamed, Muneer; Punniyamurthy, T.
  • Organic Letters, Vol. 6, Issue 26
  • DOI: 10.1021/ol048195t

Selective Conversion of Biorefinery Lignin into Dicarboxylic Acids
journal, January 2014

Photochemical bleaching of chemical pulps catalyzed by titanium dioxide
journal, May 1998

  • da Silva Perez, Denilson; Castellan, Alain; Grelier, Stephane
  • Journal of Photochemistry and Photobiology A: Chemistry, Vol. 115, Issue 1
  • DOI: 10.1016/S1010-6030(98)00233-0

Biomimetic Fenton-Catalyzed Lignin Depolymerization to High-Value Aromatics and Dicarboxylic Acids
journal, February 2015

Chemistry of softwood lignin degradation byStreptomyces viridosporus
journal, March 1982

  • Crawford, Don L.; Barder, Michael J.; Pometto, Anthony L.
  • Archives of Microbiology, Vol. 131, Issue 2
  • DOI: 10.1007/BF01053996

Lignin aerobic oxidation promoted by molybdovanadophosphate polyanion [PMo7V5O40]8−. Study on the oxidative cleavage of β-O-4 aryl ether structures using model compounds
journal, March 2000

  • Evtuguin, Dmitry V.; Daniel, Ana I. D.; Silvestre, Armando J. D.
  • Journal of Molecular Catalysis A: Chemical, Vol. 154, Issue 1-2
  • DOI: 10.1016/S1381-1169(99)00383-0

Methyltrioxorhenium: a new catalyst for the activation of hydrogen peroxide to the oxidation of lignin and lignin model compounds
journal, April 2005

  • Crestini, Claudia; Pro, Paola; Neri, Veronica
  • Bioorganic & Medicinal Chemistry, Vol. 13, Issue 7
  • DOI: 10.1016/j.bmc.2005.01.049

Photocatalytic degradation of lignin using Pt/TiO2 as the catalyst
journal, March 2008

Alternatives for lignocellulosic pulp delignification using polyoxometalates and oxygen: a review
journal, January 2007

  • Gaspar, Armindo R.; Gamelas, Jos? A. F.; Evtuguin, Dmitry V.
  • Green Chemistry, Vol. 9, Issue 7
  • DOI: 10.1039/b607824a

Oxidative degradation of monomeric and dimeric phenylpropanoids: reactivity and mechanistic investigation
journal, July 2002

  • Canevali, Carmen; Orlandi, Marco; Pardi, Luca
  • Journal of the Chemical Society, Dalton Transactions, Issue 15
  • DOI: 10.1039/b203386k

About Supramolecular Assemblies of π-Conjugated Systems
journal, April 2005

  • Hoeben, Freek J. M.; Jonkheijm, Pascal; Meijer, E. W.
  • Chemical Reviews, Vol. 105, Issue 4
  • DOI: 10.1021/cr030070z

Peracetic Acid Depolymerization of Biorefinery Lignin for Production of Selective Monomeric Phenolic Compounds
journal, July 2016

  • Ma, Ruoshui; Guo, Mond; Lin, Kuan-ting
  • Chemistry - A European Journal, Vol. 22, Issue 31
  • DOI: 10.1002/chem.201600546

Nb2O5·nH2O as a Heterogeneous Catalyst with Water-Tolerant Lewis Acid Sites
journal, March 2011

  • Nakajima, Kiyotaka; Baba, Yusuke; Noma, Ryouhei
  • Journal of the American Chemical Society, Vol. 133, Issue 12, p. 4224-4227
  • DOI: 10.1021/ja110482r

Transition-Metal-Free:  A Highly Efficient Catalytic Aerobic Alcohol Oxidation Process
journal, April 2004

  • Liu, Renhua; Liang, Xinmiao; Dong, Chunyan
  • Journal of the American Chemical Society, Vol. 126, Issue 13
  • DOI: 10.1021/ja031765k

Hydrogen Bonding in Lignin:  A Fourier Transform Infrared Model Compound Study
journal, September 2005

  • Kubo, Satoshi; Kadla, John F.
  • Biomacromolecules, Vol. 6, Issue 5
  • DOI: 10.1021/bm050288q

Manganese(III) acetate-catalyzed synthesis of polyguaiacol
journal, September 2008

  • Hwang, Sangpill; Lee, Yong-Woo; Lee, Chang-Ha
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 46, Issue 18
  • DOI: 10.1002/pola.22902

From graphene to graphite: Electronic structure around the K point
journal, August 2006

A metal-free organic–inorganic aqueous flow battery
journal, January 2014

  • Huskinson, Brian; Marshak, Michael P.; Suh, Changwon
  • Nature, Vol. 505, Issue 7482, p. 195-198
  • DOI: 10.1038/nature12909

Oxidation of veratryl alcohol by molecular oxygen in aqueous solution catalyzed by cobalt salen-type complexes: the effect of reaction conditions
journal, September 2003

  • Kervinen, Kaisa; Korpi, Heikki; Leskelä, Markku
  • Journal of Molecular Catalysis A: Chemical, Vol. 203, Issue 1-2
  • DOI: 10.1016/S1381-1169(03)00156-0

Non-Oxidative Vanadium-Catalyzed C-O Bond Cleavage: Application to Degradation of Lignin Model Compounds
journal, April 2010

  • Son, Sunghee; Toste, F. Dean
  • Angewandte Chemie International Edition, Vol. 49, Issue 22, p. 3791-3794
  • DOI: 10.1002/anie.201001293

Lignin Biosynthesis
journal, June 2003

Raman spectroscopy of graphene and graphite: Disorder, electron–phonon coupling, doping and nonadiabatic effects
journal, July 2007

Nanostructured Rutile TiO 2 for Selective Photocatalytic Oxidation of Aromatic Alcohols to Aldehydes in Water
journal, February 2008

  • Yurdakal, Sedat; Palmisano, Giovanni; Loddo, Vittorio
  • Journal of the American Chemical Society, Vol. 130, Issue 5
  • DOI: 10.1021/ja709989e

Poly(ethylene glycol)-Supported TEMPO:  An Efficient, Recoverable Metal-Free Catalyst for the Selective Oxidation of Alcohols
journal, January 2004

  • Pozzi, Gianluca; Cavazzini, Marco; Quici, Silvio
  • Organic Letters, Vol. 6, Issue 3
  • DOI: 10.1021/ol036398w

Recyclable ionic liquid tagged Co(salen) catalysts for the oxidation of lignin model compounds
journal, December 2013

  • Ambrose, Kenson; Hurisso, Bitu B.; Singer, Robert D.
  • Canadian Journal of Chemistry, Vol. 91, Issue 12
  • DOI: 10.1139/cjc-2013-0336

On the mechanism of vanillin formation in the catalytic oxidation of lignin with oxygen
journal, April 1995

  • Tarabanko, V. E.; Fomova, N. A.; Kuznetsov, B. N.
  • Reaction Kinetics & Catalysis Letters, Vol. 55, Issue 1
  • DOI: 10.1007/BF02075847

Aerobic Oxidation of Lignin Models Using a Base Metal Vanadium Catalyst
journal, June 2010

  • Hanson, Susan K.; Baker, R. Tom; Gordon, John C.
  • Inorganic Chemistry, Vol. 49, Issue 12, p. 5611-5618
  • DOI: 10.1021/ic100528n

Oxalic acid: a microbial metabolite of interest for the pulping industry
journal, September 2004

  • Meyer-Pinson, Valérie; Ruel, Katia; Gaudard, François
  • Comptes Rendus Biologies, Vol. 327, Issue 9-10
  • DOI: 10.1016/j.crvi.2004.07.007

Biomimetic degradation of lignin
journal, July 1993

Characteristics of hemicellulose, cellulose and lignin pyrolysis
journal, August 2007

Lignin Degradation in Oxygen Delignification Catalysed by [PMo7V5O40]8- Polyanion. Part II. Study on Lignin Monomeric Model Compounds
journal, September 2000

  • Evtuguin, D. V.; Neto, C. Pascoal; Carapuça, H.
  • Holzforschung, Vol. 54, Issue 5
  • DOI: 10.1515/HF.2000.087

Catalytic oxidation of aromatic oxygenates by the heterogeneous catalyst Co-ZIF-9
journal, February 2011

  • Zakzeski, Joseph; Dębczak, Agnieszka; Bruijnincx, Pieter C. A.
  • Applied Catalysis A: General, Vol. 394, Issue 1-2
  • DOI: 10.1016/j.apcata.2010.12.026

Polyoxometalate oxidation of non-phenolic lignin subunits in water: Effect of substrate structure on reaction kinetics
journal, March 2004

  • Yokoyama, T.; Chang, H. -M.; Reiner, R. S.
  • Holzforschung, Vol. 58, Issue 2
  • DOI: 10.1515/HF.2004.016

Degradation of Pulp-Mill Effluent by Oxygen and Na 5 [PV 2 Mo 10 O 40 ], a Multipurpose Delignification and Wet Air Oxidation Catalyst
journal, October 1997

  • Sonnen, Daniel M.; Reiner, Richard S.; Atalla, Rajai H.
  • Industrial & Engineering Chemistry Research, Vol. 36, Issue 10
  • DOI: 10.1021/ie970150r

Characterization and molecular weight distribution of carbohydrates isolated from the autohydrolysis extract of mixed southern hardwoods
journal, January 2011

Processable aqueous dispersions of graphene nanosheets
journal, January 2008

Catalytic Lignin Valorization Process for the Production of Aromatic Chemicals and Hydrogen
journal, June 2012

  • Zakzeski, Joseph; Jongerius, Anna L.; Bruijnincx, Pieter C. A.
  • ChemSusChem, Vol. 5, Issue 8
  • DOI: 10.1002/cssc.201100699

Biomass Recalcitrance: Engineering Plants and Enzymes for Biofuels Production
journal, February 2007

  • Himmel, M. E.; Ding, S.-Y.; Johnson, D. K.
  • Science, Vol. 315, Issue 5813, p. 804-807
  • DOI: 10.1126/science.1137016

Noble-metal catalyzed hydrodeoxygenation of biomass-derived lignin to aromatic hydrocarbons
journal, January 2014

  • Laskar, Dhrubojyoti D.; Tucker, Melvin P.; Chen, Xiaowen
  • Green Chemistry, Vol. 16, Issue 2
  • DOI: 10.1039/c3gc42041h

The nature of .pi.-.pi. interactions
journal, July 1990

  • Hunter, Christopher A.; Sanders, Jeremy K. M.
  • Journal of the American Chemical Society, Vol. 112, Issue 14
  • DOI: 10.1021/ja00170a016

Demonstration of a Process for the Conversion of Kraft Lignin into Vanillin and Methyl Vanillate by Acidic Oxidation in Aqueous Methanol
journal, January 2010

  • Voitl, Tobias; Rohr, Philipp Rudolf von
  • Industrial & Engineering Chemistry Research, Vol. 49, Issue 2
  • DOI: 10.1021/ie901293p

Novel cobalt(II)-catalyzed oxidative cleavage of a carbon-carbon double bond
journal, April 1986

  • Drago, R. S.; Corden, B. B.; Barnes, C. W.
  • Journal of the American Chemical Society, Vol. 108, Issue 9
  • DOI: 10.1021/ja00269a057

New Mechanism for the Catalytic Oxidation of Lignin to Vanillin
journal, July 2004

Enhanced succinic acid production in Aspergillus saccharolyticus by heterologous expression of fumarate reductase from Trypanosoma brucei
journal, October 2015

  • Yang, Lei; Lübeck, Mette; Ahring, Birgitte K.
  • Applied Microbiology and Biotechnology, Vol. 100, Issue 4
  • DOI: 10.1007/s00253-015-7086-z

Routes to Potential Bioproducts from Lignocellulosic Biomass Lignin and Hemicelluloses
journal, August 2011

A review of catalytic hydrodeoxygenation of lignin-derived phenols from biomass pyrolysis
journal, November 2012

Oxidative Degradation of in Situ and Isolated Spruce Lignins by Water-Soluble Hydrogen Peroxide Resistant Pentafluorophenylporphyrin
journal, January 1996

  • Kurek, Bernard; Artaud, Isabelle; Pollet, Brigitte
  • Journal of Agricultural and Food Chemistry, Vol. 44, Issue 7
  • DOI: 10.1021/jf950612g

Macromolecular replication during lignin biosynthesis
journal, March 2010

Aerobic Epoxidation of Olefins Catalyzed by the Cobalt-Based Metal-Organic Framework STA-12(Co)
journal, December 2011

  • Beier, Matthias J.; Kleist, Wolfgang; Wharmby, Michael T.
  • Chemistry - A European Journal, Vol. 18, Issue 3
  • DOI: 10.1002/chem.201101223

Graphene goes undercover
journal, May 2009

Oxidation of Organosolv Lignins in Acetic Acid: Influence of Oxygen Pressure
journal, January 1999

  • Gonçalves, Adilson R.; Schuchardt, Ulf
  • Applied Biochemistry and Biotechnology, Vol. 77, Issue 1-3
  • DOI: 10.1385/ABAB:77:1-3:127

Synthetic strategy for Fe-MCM-41 catalyst: a key factor for homogeneous or heterogeneous phenol oxidation
journal, January 2011

  • Sirotin, Sergey V.; Moskovskaya, Irina F.; Romanovsky, Boris V.
  • Catalysis Science & Technology, Vol. 1, Issue 6
  • DOI: 10.1039/c1cy00107h

Lignin Valorization: Improving Lignin Processing in the Biorefinery
journal, May 2014

  • Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.
  • Science, Vol. 344, Issue 6185, p. 1246843-1246843
  • DOI: 10.1126/science.1246843

Oxidative strategies in lignin chemistry: A new environmental friendly approach for the functionalisation of lignin and lignocellulosic fibers
journal, October 2010

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

Analysis of products from the oxidation of technical lignins by oxygen and H3PMo12O40 in water and aqueous methanol by size-exclusion chromatography
journal, January 2010

  • Voitl, Tobias; Nagel, Marina V.; von Rohr, Philipp Rudolf
  • Holzforschung, Vol. 64, Issue 1
  • DOI: 10.1515/hf.2010.006

Photocatalysis on TiO2 Surfaces: Principles, Mechanisms, and Selected Results
journal, May 1995

  • Linsebigler, Amy L.; Lu, Guangquan.; Yates, John T.
  • Chemical Reviews, Vol. 95, Issue 3
  • DOI: 10.1021/cr00035a013

5,10,15,20-Tetrakis(4-sulfonato-phenyl)porphine-Mn(III) immobilized on imidazole-activated silica as a novel lignin-peroxidase-like biomimetic catalyst
journal, December 2007

  • Zucca, Paolo; Mocci, Giuseppe; Rescigno, Antonio
  • Journal of Molecular Catalysis A: Chemical, Vol. 278, Issue 1-2, p. 220-227
  • DOI: 10.1016/j.molcata.2007.09.017

Oxidation of lignin model compounds in water with dioxygen and hydrogen peroxide catalysed by metallophthalocyanines
journal, February 1993

Wet oxidation properties of process waste waters of fine chemical and pharmaceutical origin
journal, April 2011

  • Hosseini, A. M.; Tungler, A.; Bakos, V.
  • Reaction Kinetics, Mechanisms and Catalysis, Vol. 103, Issue 2
  • DOI: 10.1007/s11144-011-0315-2

Reactions of Metal Ion Complexes with Lignin Model Compounds, Part II. Fe(TSPC) Catalyzed Formation of Oxidized Products in the Absence of Oxygen
journal, September 1993

  • Watson, Paul A.; Wright, L. James; Fullerton, Terry J.
  • Journal of Wood Chemistry and Technology, Vol. 13, Issue 3
  • DOI: 10.1080/02773819308020524

The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
journal, June 2010

  • Zakzeski, Joseph; Bruijnincx, Pieter C. A.; Jongerius, Anna L.
  • Chemical Reviews, Vol. 110, Issue 6, p. 3552-3599
  • DOI: 10.1021/cr900354u

Preventing Graphene Sheets from Restacking for High-Capacitance Performance
journal, October 2011

  • Wang, Yan; Wu, Yingpeng; Huang, Yi
  • The Journal of Physical Chemistry C, Vol. 115, Issue 46
  • DOI: 10.1021/jp206444e

Polyelectrolyte expansion of a lignin sulfonate microgel
journal, October 1960

Adipic acid production from lignin
journal, January 2015

  • Vardon, Derek R.; Franden, Mary Ann; Johnson, Christopher W.
  • Energy & Environmental Science, Vol. 8, Issue 2
  • DOI: 10.1039/C4EE03230F

MnO 2 and Oxalate: An Abiotic Route for the Oxidation of Aromatic Components in Wheat Straw
journal, September 1998

  • Lequart, Christelle; Kurek, Bernard; Debeire, Philippe
  • Journal of Agricultural and Food Chemistry, Vol. 46, Issue 9
  • DOI: 10.1021/jf980324v

Propensity of Lignin to Associate: Light Scattering Photometry Study with Native Lignins
journal, December 2008

  • Contreras, Sofía; Gaspar, Armindo R.; Guerra, Anderson
  • Biomacromolecules, Vol. 9, Issue 12
  • DOI: 10.1021/bm800673a

Catalysis of Cu-Doped Co-Based Perovskite-Type Oxide in Wet Oxidation of Lignin To Produce Aromatic Aldehydes
journal, September 2010

  • Deng, Haibo; Lin, Lu; Liu, Shijie
  • Energy & Fuels, Vol. 24, Issue 9
  • DOI: 10.1021/ef100768e

The formation of hydroxy monocarboxylic acids and dicarboxylic acids by alkaline thermochemical degradation of cellulose
journal, January 1990

  • Niemelä, Klaus
  • Journal of Chemical Technology & Biotechnology, Vol. 48, Issue 1
  • DOI: 10.1002/jctb.280480103

Evaluation of CuO oxidation parameters for determining the source and stage of lignin degradation in soil
journal, June 2006

Fractionation of Forest Residues of Douglas-fir for Fermentable Sugar Production by SPORL Pretreatment
journal, May 2012

Aromatic interactions
journal, January 2001

  • Hunter, Christopher A.; Lawson, Kevin R.; Perkins, Julie
  • Journal of the Chemical Society, Perkin Transactions 2, Issue 5
  • DOI: 10.1039/b008495f

Selective Aerobic Oxidation of Activated Alcohols into Acids or Aldehydes in Ionic Liquids
journal, August 2007

  • Jiang, Nan; Ragauskas, Arthur J.
  • The Journal of Organic Chemistry, Vol. 72, Issue 18
  • DOI: 10.1021/jo0707737

Oxidation of Lignin Using Aqueous Polyoxometalates in the Presence of Alcohols
journal, September 2008

Chemical Transformations of Buddleja davidii Lignin during Ethanol Organosolv Pretreatment
journal, April 2010

  • Hallac, Bassem B.; Pu, Yunqiao; Ragauskas, Arthur J.
  • Energy & Fuels, Vol. 24, Issue 4
  • DOI: 10.1021/ef901556u

Polyoxometalate-Catalyzed Oxygen Delignification of Kraft Pulp:  A Pilot-Plant Experience
journal, November 2004

  • Gaspar, Armindo R.; Evtuguin, Dmitry V.; Neto, Carlos Pascoal
  • Industrial & Engineering Chemistry Research, Vol. 43, Issue 24
  • DOI: 10.1021/ie040061w

Vanadium-catalyzed selective aerobic alcohol oxidation in ionic liquid [bmim]PF6
journal, January 2007

Hydrothermal Conversion of Catechol into Four-Carbon Dicarboxylic Acids
journal, December 2014

  • Yin, Guodong; Jin, Fangming; Yao, Guodong
  • Industrial & Engineering Chemistry Research, Vol. 54, Issue 1
  • DOI: 10.1021/ie5036447

Co(salen)/SBA-15 catalysed oxidation of a β-O-4 phenolic dimer under microwave irradiation
journal, June 2011

  • Badamali, Sushanta K.; Luque, Rafael; Clark, James H.
  • Catalysis Communications, Vol. 12, Issue 11, p. 993-995
  • DOI: 10.1016/j.catcom.2011.02.025

Ruthenium Complexation in an Aluminium Metal-Organic Framework and Its Application in Alcohol Oxidation Catalysis
journal, October 2012

  • Carson, Fabian; Agrawal, Santosh; Gustafsson, Mikaela
  • Chemistry - A European Journal, Vol. 18, Issue 48
  • DOI: 10.1002/chem.201200885

Efficient electrosynthesis of highly active Cu3(BTC)2-MOF and its catalytic application to chemical reduction
journal, March 2013

Piperylene Sulfone:  A Recyclable Dimethyl Sulfoxide Substitute for Copper-Catalyzed Aerobic Alcohol Oxidation
journal, February 2008

  • Jiang, Nan; Vinci, Daniele; Liotta, Charles L.
  • Industrial & Engineering Chemistry Research, Vol. 47, Issue 3
  • DOI: 10.1021/ie070616y

Mechanistic Insights into the Oxidation of Veratryl Alcohol with Co(salen) and Oxygen in Aqueous Media: An in-situ Spectroscopic Study
journal, July 2005

  • Kervinen, Kaisa; Korpi, Heikki; Gerbrand Mesu, J.
  • European Journal of Inorganic Chemistry, Vol. 2005, Issue 13
  • DOI: 10.1002/ejic.200500042

PbO2-SnO2 composite anode with interconnected structure for the electrochemical incineration of phenol
journal, December 2011

Bis(o-phenanthroline)copper-catalysed oxidation of lignin model compounds for oxygen bleaching of pulp
journal, February 2005

Bio-fuels from thermochemical conversion of renewable resources: A review
journal, February 2008

  • Goyal, H. B.; Seal, Diptendu; Saxena, R. C.
  • Renewable and Sustainable Energy Reviews, Vol. 12, Issue 2
  • DOI: 10.1016/j.rser.2006.07.014

Effects of fungal degradation on the CuO oxidation products of lignin: A controlled laboratory study
journal, November 1988

  • Hedges, John I.; Blanchette, Robert A.; Weliky, Karen
  • Geochimica et Cosmochimica Acta, Vol. 52, Issue 11
  • DOI: 10.1016/0016-7037(88)90040-3

Methyltrioxorhenium: oxidative cleavage of CC-double bonds and its application in a highly efficient synthesis of vanillin from biological waste
journal, March 2000

  • Herrmann, Wolfgang A.; Weskamp, Thomas; Zoller, Jochen P.
  • Journal of Molecular Catalysis A: Chemical, Vol. 153, Issue 1-2, p. 49-52
  • DOI: 10.1016/S1381-1169(99)00370-2

Oxidation of hardwood kraft-lignin to phenolic derivatives with oxygen as oxidant
journal, June 2001

  • Villar, J. C.; Caperos, A.; García-Ochoa, F.
  • Wood Science and Technology, Vol. 35, Issue 3
  • DOI: 10.1007/s002260100089

Chemistry of delignification
journal, December 1985

Oxidation of substituted phenols with metal dioxygen carrier, Co(salen) pyridinate: solvent effects
journal, January 1986

  • Satish, S.; Ganeshpure, P. A.
  • Proceedings / Indian Academy of Sciences, Vol. 96, Issue 1-2
  • DOI: 10.1007/BF02863297
    Sort by:
    [ × clear filter / sort ]

    Works referencing / citing this record:

    Chemo-enzymatically prepared lignin nanoparticles for value-added applications
    journal, July 2019

    • Henn, Alexander; Mattinen, Maija-Liisa
    • World Journal of Microbiology and Biotechnology, Vol. 35, Issue 8
    • DOI: 10.1007/s11274-019-2697-7

    Electrochemical Generation of ROS in Ionic Liquid for the Degradation of Lignin Model Compound
    journal, January 2018

    • Wang, Lei; Liu, Shuangyan; Jiang, Haomin
    • Journal of The Electrochemical Society, Vol. 165, Issue 11
    • DOI: 10.1149/2.0801811jes

    Attapulgite-supported magnetic dual acid-base catalyst for the catalytic conversion of lignin to phenolic monomers: Attapulgite-supported magnetic dual acid-base
    journal, January 2019

    • Wu, Zhen; Zhang, Jun; Zhao, Xinxu
    • Journal of Chemical Technology & Biotechnology, Vol. 94, Issue 4
    • DOI: 10.1002/jctb.5881

    The sustainable heterogeneous catalytic reductive amination of lignin models to produce aromatic tertiary amines
    journal, January 2018

    • Zhang, Haigang; Tong, Xinli; Liu, Zonghui
    • Catalysis Science & Technology, Vol. 8, Issue 21
    • DOI: 10.1039/c8cy01480a

    Enzymatic Oxidation of Lignin: Challenges and Barriers Toward Practical Applications
    journal, November 2019

    Chemo-enzymatically prepared lignin nanoparticles for value-added applications
    journal, July 2019

    • Henn, Alexander; Mattinen, Maija-Liisa
    • World Journal of Microbiology and Biotechnology, Vol. 35, Issue 8
    • DOI: 10.1007/s11274-019-2697-7

    Promising Techniques for Depolymerization of Lignin into Value-added Chemicals
    journal, January 2019

    New Insights Toward Quantitative Relationships between Lignin Reactivity to Monomers and Their Structural Characteristics
    journal, June 2018

    Comparative study of solvolysis of technical lignins in flow reactor
    journal, May 2019

    • Sebhat, Woldemichael; El-Roz, Ayman; Crepet, Agnès
    • Biomass Conversion and Biorefinery, Vol. 10, Issue 2
    • DOI: 10.1007/s13399-019-00435-z

    Oxidative Depolymerisation of Lignosulphonate Lignin into Low-Molecular-Weight Products with Cu–Mn/δ-Al2O3
    journal, March 2019

    Promising Techniques for Depolymerization of Lignin into Value-added Chemicals
    journal, December 2018

    Catalytic Scissoring of Lignin into Aryl Monomers
    journal, July 2019

    Hydrogen peroxide as an oxidant in biomass-to-chemical processes of industrial interest
    journal, January 2019

    • Teong, Siew Ping; Li, Xiukai; Zhang, Yugen
    • Green Chemistry, Vol. 21, Issue 21
    • DOI: 10.1039/c9gc02445j

    Mechanistic studies of milled and Kraft lignin oxidation by radical species
    journal, January 2020

    • Davaritouchaee, Maryam; Hiscox, William C.; Terrell, Evan
    • Green Chemistry, Vol. 22, Issue 4
    • DOI: 10.1039/c9gc04162a
      Sort by:
      [ × clear filter / sort ]

      Similar Records in DOE PAGES and OSTI.GOV collections: