Laccase-mediated synthesis of lignin-core hyperbranched copolymers

Cannatelli, Mark D.; Ragauskas, Arthur J.

doi:10.1007/s00253-017-8325-2

Title: Laccase-mediated synthesis of lignin-core hyperbranched copolymers

Abstract

Lignin, one of the major chemical constituents of woody biomass, is the second most abundant biopolymer found in nature. The pulp and paper industry has long produced lignin on the scale of millions of tons annually as a by-product of the pulping process, and the dawn of cellulosic ethanol production has further contributed to this amount. Historically, lignin has been perceived as a waste material and burned as a fuel for the pulping process. But, recent research has been geared toward developing cost-effective technologies to convert lignin into valuable commodities. Attributing to the polyphenolic structure of lignin, enzymatic modification of its surface using laccases (benzenediol:oxygen oxidoreductases, EC 1.10.3.2) has demonstrated to be highly successful. The current study aims at developing lignin-core hyperbranched copolymers via the laccase-assisted copolymerization of kraft lignin with methylhydroquinone and a trithiol. Based on the physical properties of the resulting material, it is likely that crosslinking reactions have taken place during the drying process to produce a copolymeric network rather than discrete hyperbranched copolymers, with NMR data providing evidence of covalent bonding between monomers. A preliminary thermal analysis data reveals that the copolymeric material possesses a moderate glass transition temperature and exhibits good thermostability, thus may havemore »« less

Authors:

Cannatelli, Mark D. ^[1];

^[2]

Georgia Inst. of Technology, Atlanta, GA (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Georgia Inst. of Technology, Atlanta, GA (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of Tennessee, Knoxville, TN (United States)

Publication Date:: Tue Jun 06 00:00:00 EDT 2017

Research Org.:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

OSTI Identifier:: 1376587

Grant/Contract Number:: AC05-00OR22725

Resource Type:: Accepted Manuscript

Journal Name:: Applied Microbiology and Biotechnology

Additional Journal Information:: Journal Volume: 101; Journal Issue: 16; Journal ID: ISSN 0175-7598

Publisher:: Springer

Country of Publication:: United States

Language:: English

Subject:: 09 BIOMASS FUELS; biomaterials; circular economy; hyperbranched copolymer; laccase; lignin; sustainability

Citation Formats


                    Cannatelli, Mark D., and Ragauskas, Arthur J. Laccase-mediated synthesis of lignin-core hyperbranched copolymers.  United States: N. p., 2017. 
Web.  doi:10.1007/s00253-017-8325-2.

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                    Cannatelli, Mark D., & Ragauskas, Arthur J. Laccase-mediated synthesis of lignin-core hyperbranched copolymers.  United States.  https://doi.org/10.1007/s00253-017-8325-2

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                    Cannatelli, Mark D., and Ragauskas, Arthur J. Tue .  
"Laccase-mediated synthesis of lignin-core hyperbranched copolymers".  United States.  https://doi.org/10.1007/s00253-017-8325-2.  https://www.osti.gov/servlets/purl/1376587.

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@article{osti_1376587,

  title        = {Laccase-mediated synthesis of lignin-core hyperbranched copolymers},

  author       = {Cannatelli, Mark D. and Ragauskas, Arthur J.},

  abstractNote = {Lignin, one of the major chemical constituents of woody biomass, is the second most abundant biopolymer found in nature. The pulp and paper industry has long produced lignin on the scale of millions of tons annually as a by-product of the pulping process, and the dawn of cellulosic ethanol production has further contributed to this amount. Historically, lignin has been perceived as a waste material and burned as a fuel for the pulping process. But, recent research has been geared toward developing cost-effective technologies to convert lignin into valuable commodities. Attributing to the polyphenolic structure of lignin, enzymatic modification of its surface using laccases (benzenediol:oxygen oxidoreductases, EC 1.10.3.2) has demonstrated to be highly successful. The current study aims at developing lignin-core hyperbranched copolymers via the laccase-assisted copolymerization of kraft lignin with methylhydroquinone and a trithiol. Based on the physical properties of the resulting material, it is likely that crosslinking reactions have taken place during the drying process to produce a copolymeric network rather than discrete hyperbranched copolymers, with NMR data providing evidence of covalent bonding between monomers. A preliminary thermal analysis data reveals that the copolymeric material possesses a moderate glass transition temperature and exhibits good thermostability, thus may have potential application as a lignin-based thermoplastic. Scanning electron microscopy images confirm the smooth, glossy surface of the material and that it is densely packed. Our results are a sustainable, ecofriendly, economic method to create an exciting novel biomaterial from a renewable feedstock while further enhancing lignin valorization.},

  doi          = {10.1007/s00253-017-8325-2},

  journal      = {Applied Microbiology and Biotechnology},

  number       = 16,

  volume       = 101,

  place        = {United States},

  year         = {Tue Jun 06 00:00:00 EDT 2017},

  month        = {Tue Jun 06 00:00:00 EDT 2017}

}

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Works referencing / citing this record:

Immobilized Cerrena sp. laccase: preparation, thermal inactivation, and operational stability in malachite green decolorization
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Abejón, Ricardo; Pérez-Acebo, Heriberto; Clavijo, Leonardo
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Title: Laccase-mediated synthesis of lignin-core hyperbranched copolymers

Abstract

Citation Formats

2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane, a Reagent for the Accurate Determination of the Uncondensed and Condensed Phenolic Moieties in Lignins journal, June 1995

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

N-Hydroxy Compounds as New Internal Standards for the 31P-NMR Determination of Lignin Hydroxy Functional Groups journal, April 2001

Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones journal, September 2015

A Unique Aliphatic Tertiary Amine Chromophore: Fluorescence, Polymer Structure, and Application in Cell Imaging journal, December 2012

O2 Reduction to H2O by the multicopper oxidases journal, January 2008

Residual lignin studies of laccase-delignified kraft pulps journal, November 1998

Laccase-assisted surface functionalization of lignocellulosics journal, April 2014

An enzymatic approach to develop a lignin-based adhesive for wool floor coverings journal, January 2014

The structure and function of fungal laccases journal, January 1994

Hyperbranched polymers: advances from synthesis to applications journal, January 2015

Modification of lignin for the production of new compounded materials journal, May 2001

The circular economy journal, March 2016

Value Added Biomaterials via Laccase-Mediated Surface Functionalization journal, January 2015

Conversion of lignin into value-added materials and chemicals via laccase-assisted copolymerization journal, September 2016

Turning renewable resources into value-added polymer: development of lignin-based thermoplastic journal, January 2012

Development of Lignin Supramolecular Hydrogels with Mechanically Responsive and Self-Healing Properties journal, August 2015

The Path Forward for Biofuels and Biomaterials journal, January 2006

Two Decades of Laccases: Advancing Sustainability in the Chemical Industry journal, August 2016

Lignins as macromonomers for polyurethane synthesis: A comparative study on hydroxyl group determination journal, January 2008

Recent Industrial Applications of Lignin: A Sustainable Alternative to Nonrenewable Materials journal, April 2002

Lignin valorization by forming toughened lignin-co-polymers: Development of hyperbranched prepolymers for cross-linking journal, December 2012

Lignin-Derived Carbon Fiber as a Co-Product of Refining Cellulosic Biomass journal, January 2014

Production and properties of adhesives formulated from laccase modified Kraft lignin journal, February 2013

Enzymatic co-polymerization of lignin with low-molecular mass compounds journal, January 1994

Lignin Biosynthesis and Structure journal, May 2010

Dioxomolybdenum(VI) Complexes Stabilized by Polydentate Ligands with NO3, N2O2, and NS2 Donor-Atom Sets journal, July 1994

Immobilized Cerrena sp. laccase: preparation, thermal inactivation, and operational stability in malachite green decolorization journal, November 2017

Alternatives for Chemical and Biochemical Lignin Valorization: Hot Topics from a Bibliometric Analysis of the Research Published During the 2000–2016 Period journal, July 2018

Immobilized Cerrena sp. laccase: preparation, thermal inactivation, and operational stability in malachite green decolorization journal, November 2017

Alternatives for Chemical and Biochemical Lignin Valorization: Hot Topics from a Bibliometric Analysis of the Research Published During the 2000–2016 Period journal, July 2018

2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane, a Reagent for the Accurate Determination of the Uncondensed and Condensed Phenolic Moieties in Lignins
journal, June 1995

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

N-Hydroxy Compounds as New Internal Standards for the 31P-NMR Determination of Lignin Hydroxy Functional Groups
journal, April 2001

Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones
journal, September 2015

A Unique Aliphatic Tertiary Amine Chromophore: Fluorescence, Polymer Structure, and Application in Cell Imaging
journal, December 2012

O2 Reduction to H2O by the multicopper oxidases
journal, January 2008

Residual lignin studies of laccase-delignified kraft pulps
journal, November 1998

Laccase-assisted surface functionalization of lignocellulosics
journal, April 2014

An enzymatic approach to develop a lignin-based adhesive for wool floor coverings
journal, January 2014

The structure and function of fungal laccases
journal, January 1994

Hyperbranched polymers: advances from synthesis to applications
journal, January 2015

Modification of lignin for the production of new compounded materials
journal, May 2001

The circular economy
journal, March 2016

Value Added Biomaterials via Laccase-Mediated Surface Functionalization
journal, January 2015

Conversion of lignin into value-added materials and chemicals via laccase-assisted copolymerization
journal, September 2016

Turning renewable resources into value-added polymer: development of lignin-based thermoplastic
journal, January 2012

Development of Lignin Supramolecular Hydrogels with Mechanically Responsive and Self-Healing Properties
journal, August 2015

The Path Forward for Biofuels and Biomaterials
journal, January 2006

Two Decades of Laccases: Advancing Sustainability in the Chemical Industry
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Lignins as macromonomers for polyurethane synthesis: A comparative study on hydroxyl group determination
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Recent Industrial Applications of Lignin: A Sustainable Alternative to Nonrenewable Materials
journal, April 2002

Lignin valorization by forming toughened lignin-co-polymers: Development of hyperbranched prepolymers for cross-linking
journal, December 2012

Lignin-Derived Carbon Fiber as a Co-Product of Refining Cellulosic Biomass
journal, January 2014

Production and properties of adhesives formulated from laccase modified Kraft lignin
journal, February 2013

Enzymatic co-polymerization of lignin with low-molecular mass compounds
journal, January 1994

Lignin Biosynthesis and Structure
journal, May 2010

Dioxomolybdenum(VI) Complexes Stabilized by Polydentate Ligands with NO3, N2O2, and NS2 Donor-Atom Sets
journal, July 1994

Immobilized Cerrena sp. laccase: preparation, thermal inactivation, and operational stability in malachite green decolorization
journal, November 2017

Alternatives for Chemical and Biochemical Lignin Valorization: Hot Topics from a Bibliometric Analysis of the Research Published During the 2000–2016 Period
journal, July 2018

Immobilized Cerrena sp. laccase: preparation, thermal inactivation, and operational stability in malachite green decolorization
journal, November 2017

Alternatives for Chemical and Biochemical Lignin Valorization: Hot Topics from a Bibliometric Analysis of the Research Published During the 2000–2016 Period
journal, July 2018