Methods for lignin depolymerization using thiols

Hegg, Eric Linke; Jackson, James E.; Klinger, Grace Elizabeth

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Title: Methods for lignin depolymerization using thiols

Abstract

The disclosure relates to a method for depolymerizing lignin. The method includes reacting a lignin compound with a thiol compound to depolymerize the lignin compound and to form a depolymerized lignin product having a reduced molecular weight relative to the lignin compound prior to reacting. The method can further include forming an oxidized thiol reaction product between two thiol groups from one or more thiol compounds, and then reducing the oxidized thiol reaction product to re-form or regenerate the thiol compound for further lignin depolymerization.

Inventors:: Hegg, Eric Linke; Jackson, James E.; Klinger, Grace Elizabeth

Issue Date:: 2022-03-08

Research Org.:: Michigan State Univ., East Lansing, MI (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1892680

Patent Number(s):: 11267838

Application Number:: 16/603,328

Assignee:: Board of Trustees of Michigan State University (East Lansing, MI)

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07G - COMPOUNDS OF UNKNOWN CONSTITUTION

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C319/14 - of sulfides
C07C323/22 - containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
C07C37/055 - the substituted group being bound to oxygen, e.g. ether group
C07C37/54 - by hydrolysis of lignin or sulfite waste liquor
C07C39/04 - Phenol
C07C41/01 - Preparation of ethers
C07C45/65 - by splitting-off hydrogen atoms or functional groups
C07C49/78 - Acetophenone

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07G - COMPOUNDS OF UNKNOWN CONSTITUTION
C07G1/00 - Lignin

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
Y02E50/10 - Biofuels

Show less

DOE Contract Number:: FC02-07ER64494

Resource Type:: Patent

Resource Relation:: Patent File Date: 04/17/2018

Country of Publication:: United States

Language:: English

Subject:: 09 BIOMASS FUELS

Citation Formats


                    Hegg, Eric Linke, Jackson, James E., and Klinger, Grace Elizabeth. Methods for lignin depolymerization using thiols.  United States: N. p., 2022. 
        Web.

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                    Hegg, Eric Linke, Jackson, James E., & Klinger, Grace Elizabeth. Methods for lignin depolymerization using thiols.  United States.

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                    Hegg, Eric Linke, Jackson, James E., and Klinger, Grace Elizabeth. Tue .  
        "Methods for lignin depolymerization using thiols".  United States.  https://www.osti.gov/servlets/purl/1892680.

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@article{osti_1892680,

  title        = {Methods for lignin depolymerization using thiols},

  author       = {Hegg, Eric Linke and Jackson, James E. and Klinger, Grace Elizabeth},

  abstractNote = {The disclosure relates to a method for depolymerizing lignin. The method includes reacting a lignin compound with a thiol compound to depolymerize the lignin compound and to form a depolymerized lignin product having a reduced molecular weight relative to the lignin compound prior to reacting. The method can further include forming an oxidized thiol reaction product between two thiol groups from one or more thiol compounds, and then reducing the oxidized thiol reaction product to re-form or regenerate the thiol compound for further lignin depolymerization.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2022},

  month        = {3}

}

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Works referenced in this record:

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Similar Records

Title: Methods for lignin depolymerization using thiols

Abstract

Citation Formats

Lignin Oxidation and Products Thereof patent-application, May 2012

Electrochemical reduction of disulfide bonds in proteinaceous substances and electrochemical cell for carrying out such reduction patent-application, March 2014

Electrochemical routes for industrial synthesis journal, January 2009

Organic solvent pretreatment of biomass to enhance enzymatic saccharification patent, November 2012

Methods for Detecting and Determining Levels of Monolignol Ester Conjugates Incorporated into Lignin and Compounds Relating Thereto patent-application, June 2016

Characterization and analysis of the molecular weight of lignin for biorefining studies journal, June 2014

Methods of reducing the inhibitory effect of a redox active metal ion on the enzymatic hydrolysis of cellulosic material patent-application, May 2009

Thioaldehyde Diels-Alder reactions journal, May 1986

Bioconversion process for the production of vanillin patent, July 1992

Process for Increasing the Enzymatic Accessibility of a Thermally Treated Ligno-cellulosic Biomass Feedstock patent-application, August 2016

Stereochemical Features of Glutathione-dependent Enzymes in the Sphingobium sp. Strain SYK-6 β-Aryl Etherase Pathway journal, February 2014

Chemical Groups and Structural Characterization of Lignin via Thiol-Mediated Demethylation journal, December 2013

High Purity Lignin, Lignin Compositions, and Higher Structured Lignin patent-application, September 2014

Compositions Comprising a Polypeptide Having Cellulolytic Enhancing Activity and a Sulfur-Containing Compound and Uses Thereof patent-application, July 2013

A bacterial enzyme degrading the model lignin compound β-etherase is a member of the glutathione- S -transferase superfamily journal, May 1993

LigF-type systems for bioconversion of lignin-derived compounds patent-application, August 2012

Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols journal, September 2019

Structure and Action Mechanism of Ligninolytic Enzymes journal, June 2008

Renewable Aromatics from Lignocellulosic Lignin patent-application, November 2015

Method of Depolymerizing Lignin patent-application, June 2017

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

Electrochemical production of organic thiols patent, February 1978

Methods of increasing the cellulolytic enhancing activity of a polypeptide patent, October 2015

Demethylation of thiolignin by reaction with potassium dichromate ? a kinetic study journal, January 1985

Selective C—O bond cleavage of oxidized lignin and lignin-type materials into simple aromatic compounds patent, June 2016

Organic solvent pretreatment of biomass to enhance enzymatic saccharification patent-application, June 2010

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

Thioacidolysis book, January 1992

Processes for Pretreating Cellulosic Material and Improving Hydrolysis Thereof patent-application, May 2014

Recovery of Vanillin and Syringaldehyde from Lignin Oxidation: A Review of Separation and Purification Processes journal, August 2015

Delignification and bleaching of wood pulp with oxygen in the presence of triethanolamine patent, April 1976

Apparatus and process for preparing reactive lignin with high yield from plant biomass for production of fuels and chemicals patent-application, April 2015

From gene to biorefinery: microbial β-etherases as promising biocatalysts for lignin valorization journal, September 2015

Electrochemical Manufacturing in the Chemical Industry journal, January 2014

Oxidative upgrade of lignin – Recent routes reviewed journal, June 2013

Equilibrium and kinetic constants for the thiol-disulfide interchange reaction between glutathione and dithiothreitol. journal, September 1992

Process for Isolating Cellulose from Cellulosic Biomass, Isolated Cellulose of Type I and Composite Materials Comprising Same patent-application, December 2015

AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading journal, January 2009

Thiol-mediated Oxidation of Nonphenolic Lignin Model Compounds by Manganese Peroxidase of Phanerochaete chrysosporium journal, August 1989

Structural Basis of Stereospecificity in the Bacterial Enzymatic Cleavage of β-Aryl Ether Bonds in Lignin journal, December 2015

A Comparison of Energy Densities of Prevalent Energy Sources in Units of Joules Per Cubic Meter journal, December 2008

Generation of Chemical Building Blocks From Plant Biomass by Selective Depolymerization patent-application, January 2009

One pot and single step hydrolytic process for the conversion of lignocellulose into value added chemicals patent-application, August 2012

Biomimetic metalloporphines and metalloporphyrins as potential tools for delignification: Molecular mechanisms and application perspectives journal, July 2014

Process for Obtaining Low Molecular Lignin (LML) patent-application, September 2014

Lignin Oxidation and Products Thereof
patent-application, May 2012

Electrochemical reduction of disulfide bonds in proteinaceous substances and electrochemical cell for carrying out such reduction
patent-application, March 2014

Electrochemical routes for industrial synthesis
journal, January 2009

Organic solvent pretreatment of biomass to enhance enzymatic saccharification
patent, November 2012

Methods for Detecting and Determining Levels of Monolignol Ester Conjugates Incorporated into Lignin and Compounds Relating Thereto
patent-application, June 2016

Characterization and analysis of the molecular weight of lignin for biorefining studies
journal, June 2014

Methods of reducing the inhibitory effect of a redox active metal ion on the enzymatic hydrolysis of cellulosic material
patent-application, May 2009

Thioaldehyde Diels-Alder reactions
journal, May 1986

Bioconversion process for the production of vanillin
patent, July 1992

Process for Increasing the Enzymatic Accessibility of a Thermally Treated Ligno-cellulosic Biomass Feedstock
patent-application, August 2016

Stereochemical Features of Glutathione-dependent Enzymes in the Sphingobium sp. Strain SYK-6 β-Aryl Etherase Pathway
journal, February 2014

Chemical Groups and Structural Characterization of Lignin via Thiol-Mediated Demethylation
journal, December 2013

High Purity Lignin, Lignin Compositions, and Higher Structured Lignin
patent-application, September 2014

Compositions Comprising a Polypeptide Having Cellulolytic Enhancing Activity and a Sulfur-Containing Compound and Uses Thereof
patent-application, July 2013

A bacterial enzyme degrading the model lignin compound β-etherase is a member of the glutathione- S -transferase superfamily
journal, May 1993

LigF-type systems for bioconversion of lignin-derived compounds
patent-application, August 2012

Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols
journal, September 2019

Structure and Action Mechanism of Ligninolytic Enzymes
journal, June 2008

Renewable Aromatics from Lignocellulosic Lignin
patent-application, November 2015

Method of Depolymerizing Lignin
patent-application, June 2017

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

Electrochemical production of organic thiols
patent, February 1978

Methods of increasing the cellulolytic enhancing activity of a polypeptide
patent, October 2015

Demethylation of thiolignin by reaction with potassium dichromate ? a kinetic study
journal, January 1985

Selective C—O bond cleavage of oxidized lignin and lignin-type materials into simple aromatic compounds
patent, June 2016

Organic solvent pretreatment of biomass to enhance enzymatic saccharification
patent-application, June 2010

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

Thioacidolysis
book, January 1992

Processes for Pretreating Cellulosic Material and Improving Hydrolysis Thereof
patent-application, May 2014

Recovery of Vanillin and Syringaldehyde from Lignin Oxidation: A Review of Separation and Purification Processes
journal, August 2015

Delignification and bleaching of wood pulp with oxygen in the presence of triethanolamine
patent, April 1976

Apparatus and process for preparing reactive lignin with high yield from plant biomass for production of fuels and chemicals
patent-application, April 2015

From gene to biorefinery: microbial β-etherases as promising biocatalysts for lignin valorization
journal, September 2015

Electrochemical Manufacturing in the Chemical Industry
journal, January 2014

Oxidative upgrade of lignin – Recent routes reviewed
journal, June 2013

Equilibrium and kinetic constants for the thiol-disulfide interchange reaction between glutathione and dithiothreitol.
journal, September 1992

Process for Isolating Cellulose from Cellulosic Biomass, Isolated Cellulose of Type I and Composite Materials Comprising Same
patent-application, December 2015

AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading
journal, January 2009

Thiol-mediated Oxidation of Nonphenolic Lignin Model Compounds by Manganese Peroxidase of Phanerochaete chrysosporium
journal, August 1989

Structural Basis of Stereospecificity in the Bacterial Enzymatic Cleavage of β-Aryl Ether Bonds in Lignin
journal, December 2015

A Comparison of Energy Densities of Prevalent Energy Sources in Units of Joules Per Cubic Meter
journal, December 2008

Generation of Chemical Building Blocks From Plant Biomass by Selective Depolymerization
patent-application, January 2009

One pot and single step hydrolytic process for the conversion of lignocellulose into value added chemicals
patent-application, August 2012

Biomimetic metalloporphines and metalloporphyrins as potential tools for delignification: Molecular mechanisms and application perspectives
journal, July 2014

Process for Obtaining Low Molecular Lignin (LML)
patent-application, September 2014