Advanced Model Compounds for Understanding Acid-Catalyzed Lignin Depolymerization: Identification of Renewable Aromatics and a Lignin-Derived Solvent

The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly simplified model compounds often lack relevance to the chemistry of lignin, the direct use of lignin streams poses significant analytical challenges t...

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Veröffentlicht in:	Journal of the American Chemical Society Jg. 138; H. 28; S. 8900 - 8911
Hauptverfasser:	Lahive, Ciaran W., Deuss, Peter J., Lancefield, Christopher S., Sun, Zhuohua, Cordes, David B., Young, Claire M., Tran, Fanny, Slawin, Alexandra M. Z., de Vries, Johannes G., Kamer, Paul C. J., Westwood, Nicholas J., Barta, Katalin
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	WASHINGTON Amer Chemical Soc 20.07.2016
Schlagworte:	Acetals - chemistry Catalysis Chemistry Chemistry, Multidisciplinary Dimerization Formaldehyde - chemistry Hydrogen-Ion Concentration Lignin - chemistry Physical Sciences Polymerization Science & Technology Solvents - chemistry SELECTIVE OXIDATION ENANTIOSELECTIVE SYNTHESIS BETA-O-4 BOND-CLEAVAGE PRODUCTS CONVERSION C-O BONDS DEGRADATION IONIC LIQUID ACIDOLYSIS MOLECULAR-WEIGHT PHENOLS
ISSN:	0002-7863, 1520-5126, 1520-5126
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Abstract	The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly simplified model compounds often lack relevance to the chemistry of lignin, the direct use of lignin streams poses significant analytical challenges to methodology development. Ideally, new methods should be tested on model compounds that are complex enough to mirror the structural diversity in lignin but still of sufficiently low molecular weight to enable facile analysis. In this contribution, we present a new class of advanced (beta-O-4)-(beta-5) dilinkage models that are highly realistic representations of a lignin fragment. Together with selected beta-O-4, beta-5, and beta-beta structures, these compounds provide a detailed understanding of the reactivity of various types of lignin linkages in acid catalysis in conjunction with stabilization of reactive intermediates using ethylene glycol. The use of these new models has allowed for identification of novel reaction pathways and intermediates and led to the characterization of new dimeric products in subsequent lignin depolymerization studies. The excellent correlation between model and lignin experiments highlights the relevance of this new class of model compounds for broader use in catalysis studies. Only by understanding the reactivity of the linkages in lignin at this level of detail can fully optimized lignin depolymerization strategies be developed.
AbstractList	The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly simplified model compounds often lack relevance to the chemistry of lignin, the direct use of lignin streams poses significant analytical challenges to methodology development. Ideally, new methods should be tested on model compounds that are complex enough to mirror the structural diversity in lignin but still of sufficiently low molecular weight to enable facile analysis. In this contribution, we present a new class of advanced (beta-O-4)-(beta-5) dilinkage models that are highly realistic representations of a lignin fragment. Together with selected beta-O-4, beta-5, and beta-beta structures, these compounds provide a detailed understanding of the reactivity of various types of lignin linkages in acid catalysis in conjunction with stabilization of reactive intermediates using ethylene glycol. The use of these new models has allowed for identification of novel reaction pathways and intermediates and led to the characterization of new dimeric products in subsequent lignin depolymerization studies. The excellent correlation between model and lignin experiments highlights the relevance of this new class of model compounds for broader use in catalysis studies. Only by understanding the reactivity of the linkages in lignin at this level of detail can fully optimized lignin depolymerization strategies be developed. The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly simplified model compounds often lack relevance to the chemistry of lignin, the direct use of lignin streams poses significant analytical challenges to methodology development. Ideally, new methods should be tested on model compounds that are complex enough to mirror the structural diversity in lignin but still of sufficiently low molecular weight to enable facile analysis. In this contribution, we present a new class of advanced (β-O-4)-(β-5) dilinkage models that are highly realistic representations of a lignin fragment. Together with selected β-O-4, β-5, and β-β structures, these compounds provide a detailed understanding of the reactivity of various types of lignin linkages in acid catalysis in conjunction with stabilization of reactive intermediates using ethylene glycol. The use of these new models has allowed for identification of novel reaction pathways and intermediates and led to the characterization of new dimeric products in subsequent lignin depolymerization studies. The excellent correlation between model and lignin experiments highlights the relevance of this new class of model compounds for broader use in catalysis studies. Only by understanding the reactivity of the linkages in lignin at this level of detail can fully optimized lignin depolymerization strategies be developed. The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly simplified model compounds often lack relevance to the chemistry of lignin, the direct use of lignin streams poses significant analytical challenges to methodology development. Ideally, new methods should be tested on model compounds that are complex enough to mirror the structural diversity in lignin but still of sufficiently low molecular weight to enable facile analysis. In this contribution, we present a new class of advanced (β-O-4)-(β-5) dilinkage models that are highly realistic representations of a lignin fragment. Together with selected β-O-4, β-5, and β-β structures, these compounds provide a detailed understanding of the reactivity of various types of lignin linkages in acid catalysis in conjunction with stabilization of reactive intermediates using ethylene glycol. The use of these new models has allowed for identification of novel reaction pathways and intermediates and led to the characterization of new dimeric products in subsequent lignin depolymerization studies. The excellent correlation between model and lignin experiments highlights the relevance of this new class of model compounds for broader use in catalysis studies. Only by understanding the reactivity of the linkages in lignin at this level of detail can fully optimized lignin depolymerization strategies be developed.The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly simplified model compounds often lack relevance to the chemistry of lignin, the direct use of lignin streams poses significant analytical challenges to methodology development. Ideally, new methods should be tested on model compounds that are complex enough to mirror the structural diversity in lignin but still of sufficiently low molecular weight to enable facile analysis. In this contribution, we present a new class of advanced (β-O-4)-(β-5) dilinkage models that are highly realistic representations of a lignin fragment. Together with selected β-O-4, β-5, and β-β structures, these compounds provide a detailed understanding of the reactivity of various types of lignin linkages in acid catalysis in conjunction with stabilization of reactive intermediates using ethylene glycol. The use of these new models has allowed for identification of novel reaction pathways and intermediates and led to the characterization of new dimeric products in subsequent lignin depolymerization studies. The excellent correlation between model and lignin experiments highlights the relevance of this new class of model compounds for broader use in catalysis studies. Only by understanding the reactivity of the linkages in lignin at this level of detail can fully optimized lignin depolymerization strategies be developed.
Author	Lancefield, Christopher S. Lahive, Ciaran W. Kamer, Paul C. J. Cordes, David B. Deuss, Peter J. Tran, Fanny Barta, Katalin Slawin, Alexandra M. Z. de Vries, Johannes G. Westwood, Nicholas J. Young, Claire M. Sun, Zhuohua
Author_xml	– sequence: 1 givenname: Ciaran W. orcidid: 0000-0002-1794-2921 surname: Lahive fullname: Lahive, Ciaran W. organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 2 givenname: Peter J. orcidid: 0000-0002-2254-2500 surname: Deuss fullname: Deuss, Peter J. organization: Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands – sequence: 3 givenname: Christopher S. orcidid: 0000-0001-9134-5589 surname: Lancefield fullname: Lancefield, Christopher S. organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 4 givenname: Zhuohua orcidid: 0000-0001-5876-8918 surname: Sun fullname: Sun, Zhuohua organization: Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands – sequence: 5 givenname: David B. orcidid: 0000-0002-5366-9168 surname: Cordes fullname: Cordes, David B. organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 6 givenname: Claire M. orcidid: 0000-0002-2923-4228 surname: Young fullname: Young, Claire M. organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 7 givenname: Fanny surname: Tran fullname: Tran, Fanny organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 8 givenname: Alexandra M. Z. orcidid: 0000-0002-9527-6418 surname: Slawin fullname: Slawin, Alexandra M. Z. organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 9 givenname: Johannes G. orcidid: 0000-0001-5245-7748 surname: de Vries fullname: de Vries, Johannes G. organization: Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands – sequence: 10 givenname: Paul C. J. surname: Kamer fullname: Kamer, Paul C. J. organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 11 givenname: Nicholas J. orcidid: 0000-0003-0630-0138 surname: Westwood fullname: Westwood, Nicholas J. email: njw3@st-andrews.ac.uk organization: Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland – sequence: 12 givenname: Katalin surname: Barta fullname: Barta, Katalin email: k.barta@rug.nl organization: Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/27310182$$D View this record in MEDLINE/PubMed
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Snippet	The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly...
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SubjectTerms	Acetals - chemistry Catalysis Chemistry Chemistry, Multidisciplinary Dimerization Formaldehyde - chemistry Hydrogen-Ion Concentration Lignin - chemistry Physical Sciences Polymerization Science & Technology Solvents - chemistry
Title	Advanced Model Compounds for Understanding Acid-Catalyzed Lignin Depolymerization: Identification of Renewable Aromatics and a Lignin-Derived Solvent
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