Identification of a diagnostic structural motif reveals a new reaction intermediate and condensation pathway in kraft lignin formation
Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little...
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| Published in: | Chemical science (Cambridge) Vol. 9; no. 30; pp. 6348 - 6360 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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England
Royal Society of Chemistry
2018
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| ISSN: | 2041-6520, 2041-6539 |
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| Abstract | Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little is known about the nature of those bonds and linkages in kraft lignin, information that is essential for its efficient valorization to renewable fuels, materials or chemicals. Here, we provide detailed new insights into the structure of softwood kraft lignin, identifying and quantifying the major native as well as kraft pulping-derived units as a function of molecular weight.
De novo
synthetic kraft lignins, generated from (isotope labelled) dimeric and advanced polymeric models, provided key mechanistic understanding of kraft lignin formation, revealing different process dependent reaction pathways to be operating. The discovery of a novel kraft-derived lactone condensation product proved diagnostic for the identification of a previously unknown homovanillin based condensation pathway. The lactone marker is found in various different soft- and hardwood kraft lignins, suggesting the general pertinence of this new condensation mechanism for kraft pulping. These novel structural and mechanistic insights will aid the development of future biomass and lignin valorization technologies. |
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| AbstractList | Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little is known about the nature of those bonds and linkages in kraft lignin, information that is essential for its efficient valorization to renewable fuels, materials or chemicals. Here, we provide detailed new insights into the structure of softwood kraft lignin, identifying and quantifying the major native as well as kraft pulping-derived units as a function of molecular weight.
De novo
synthetic kraft lignins, generated from (isotope labelled) dimeric and advanced polymeric models, provided key mechanistic understanding of kraft lignin formation, revealing different process dependent reaction pathways to be operating. The discovery of a novel kraft-derived lactone condensation product proved diagnostic for the identification of a previously unknown homovanillin based condensation pathway. The lactone marker is found in various different soft- and hardwood kraft lignins, suggesting the general pertinence of this new condensation mechanism for kraft pulping. These novel structural and mechanistic insights will aid the development of future biomass and lignin valorization technologies. Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little is known about the nature of those bonds and linkages in kraft lignin, information that is essential for its efficient valorization to renewable fuels, materials or chemicals. Here, we provide detailed new insights into the structure of softwood kraft lignin, identifying and quantifying the major native as well as kraft pulping-derived units as a function of molecular weight. De novo synthetic kraft lignins, generated from (isotope labelled) dimeric and advanced polymeric models, provided key mechanistic understanding of kraft lignin formation, revealing different process dependent reaction pathways to be operating. The discovery of a novel kraft-derived lactone condensation product proved diagnostic for the identification of a previously unknown homovanillin based condensation pathway. The lactone marker is found in various different soft- and hardwood kraft lignins, suggesting the general pertinence of this new condensation mechanism for kraft pulping. These novel structural and mechanistic insights will aid the development of future biomass and lignin valorization technologies.Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little is known about the nature of those bonds and linkages in kraft lignin, information that is essential for its efficient valorization to renewable fuels, materials or chemicals. Here, we provide detailed new insights into the structure of softwood kraft lignin, identifying and quantifying the major native as well as kraft pulping-derived units as a function of molecular weight. De novo synthetic kraft lignins, generated from (isotope labelled) dimeric and advanced polymeric models, provided key mechanistic understanding of kraft lignin formation, revealing different process dependent reaction pathways to be operating. The discovery of a novel kraft-derived lactone condensation product proved diagnostic for the identification of a previously unknown homovanillin based condensation pathway. The lactone marker is found in various different soft- and hardwood kraft lignins, suggesting the general pertinence of this new condensation mechanism for kraft pulping. These novel structural and mechanistic insights will aid the development of future biomass and lignin valorization technologies. Detailed structural analysis of industrial and model kraft lignins reveals an important new reaction intermediate and condensation pathway operating during kraft pulping. Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little is known about the nature of those bonds and linkages in kraft lignin, information that is essential for its efficient valorization to renewable fuels, materials or chemicals. Here, we provide detailed new insights into the structure of softwood kraft lignin, identifying and quantifying the major native as well as kraft pulping-derived units as a function of molecular weight. De novo synthetic kraft lignins, generated from (isotope labelled) dimeric and advanced polymeric models, provided key mechanistic understanding of kraft lignin formation, revealing different process dependent reaction pathways to be operating. The discovery of a novel kraft-derived lactone condensation product proved diagnostic for the identification of a previously unknown homovanillin based condensation pathway. The lactone marker is found in various different soft- and hardwood kraft lignins, suggesting the general pertinence of this new condensation mechanism for kraft pulping. These novel structural and mechanistic insights will aid the development of future biomass and lignin valorization technologies. Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little is known about the nature of those bonds and linkages in kraft lignin, information that is essential for its efficient valorization to renewable fuels, materials or chemicals. Here, we provide detailed new insights into the structure of softwood kraft lignin, identifying and quantifying the major native as well as kraft pulping-derived units as a function of molecular weight. De novo synthetic kraft lignins, generated from (isotope labelled) dimeric and advanced polymeric models, provided key mechanistic understanding of kraft lignin formation, revealing different process dependent reaction pathways to be operating. The discovery of a novel kraft-derived lactone condensation product proved diagnostic for the identification of a previously unknown homovanillin based condensation pathway. The lactone marker is found in various different soft- and hardwood kraft lignins, suggesting the general pertinence of this new condensation mechanism for kraft pulping. These novel structural and mechanistic insights will aid the development of future biomass and lignin valorization technologies. Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the lignin undergoes extensive structural modification, with many labile native bonds being replaced by new, more recalcitrant ones. Currently little is known about the nature of those bonds and linkages in kraft lignin, information that is essential for its efficient valorization to renewable fuels, materials or chemicals. Here, we provide detailed new insights into the structure of softwood kraft lignin, identifying and quantifying the major native as well as kraft pulping-derived units as a function of molecular weight. synthetic kraft lignins, generated from (isotope labelled) dimeric and advanced polymeric models, provided key mechanistic understanding of kraft lignin formation, revealing different process dependent reaction pathways to be operating. The discovery of a novel kraft-derived lactone condensation product proved diagnostic for the identification of a previously unknown homovanillin based condensation pathway. The lactone marker is found in various different soft- and hardwood kraft lignins, suggesting the general pertinence of this new condensation mechanism for kraft pulping. These novel structural and mechanistic insights will aid the development of future biomass and lignin valorization technologies. |
| Author | Boelens, Rolf Lancefield, Christopher S. Weckhuysen, Bert M. Wienk, Hans L. J. Bruijnincx, Pieter C. A. |
| AuthorAffiliation | b NMR Spectroscopy , Bijvoet Center for Biomolecular Research , Utrecht University , Padualaan 8 , 3584 CH Utrecht , The Netherlands a Inorganic Chemistry and Catalysis , Debye Institute for Nanomaterials Science , Utrecht University , Universiteitsweg 99 , 3584 CG Utrecht , The Netherlands . Email: p.c.a.bruijnincx@uu.nl c Organic Chemistry and Catalysis , Debye Institute for Nanomaterials Science , Utrecht University , Universiteitsweg 99 , 3584 CG Utrecht , The Netherlands |
| AuthorAffiliation_xml | – name: c Organic Chemistry and Catalysis , Debye Institute for Nanomaterials Science , Utrecht University , Universiteitsweg 99 , 3584 CG Utrecht , The Netherlands – name: b NMR Spectroscopy , Bijvoet Center for Biomolecular Research , Utrecht University , Padualaan 8 , 3584 CH Utrecht , The Netherlands – name: a Inorganic Chemistry and Catalysis , Debye Institute for Nanomaterials Science , Utrecht University , Universiteitsweg 99 , 3584 CG Utrecht , The Netherlands . Email: p.c.a.bruijnincx@uu.nl |
| Author_xml | – sequence: 1 givenname: Christopher S. orcidid: 0000-0001-9134-5589 surname: Lancefield fullname: Lancefield, Christopher S. organization: Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, 3584 CG Utrecht, The Netherlands – sequence: 2 givenname: Hans L. J. surname: Wienk fullname: Wienk, Hans L. J. organization: NMR Spectroscopy, Bijvoet Center for Biomolecular Research, Utrecht University, 3584 CH Utrecht, The Netherlands – sequence: 3 givenname: Rolf surname: Boelens fullname: Boelens, Rolf organization: NMR Spectroscopy, Bijvoet Center for Biomolecular Research, Utrecht University, 3584 CH Utrecht, The Netherlands – sequence: 4 givenname: Bert M. orcidid: 0000-0001-5245-1426 surname: Weckhuysen fullname: Weckhuysen, Bert M. organization: Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, 3584 CG Utrecht, The Netherlands – sequence: 5 givenname: Pieter C. A. orcidid: 0000-0001-8134-0530 surname: Bruijnincx fullname: Bruijnincx, Pieter C. A. organization: Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, 3584 CG Utrecht, The Netherlands |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30310563$$D View this record in MEDLINE/PubMed |
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| Snippet | Kraft lignin, the main by-product of the pulping industry, is an abundant, yet highly underutilized renewable aromatic polymer. During kraft pulping, the... Detailed structural analysis of industrial and model kraft lignins reveals an important new reaction intermediate and condensation pathway operating during... |
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| SubjectTerms | Chemistry Condensates Diagnostic systems Lignin Organic chemistry Pulping Reaction intermediates |
| Title | Identification of a diagnostic structural motif reveals a new reaction intermediate and condensation pathway in kraft lignin formation |
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