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Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes
Lignin is an attractive renewable feedstock for aromatic bulk and fine chemicals production, provided that suitable depolymerization procedures are developed. Here, we describe a tandem catalysis strategy for ether linkage cleavage within lignin, involving ether hydrolysis by water‐tolerant Lewis ac...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5129541/ https://www.ncbi.nlm.nih.gov/pubmed/27440544 http://dx.doi.org/10.1002/cssc.201600683 |
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author | Jastrzebski, Robin Constant, Sandra Lancefield, Christopher S. Westwood, Nicholas J. Weckhuysen, Bert M. Bruijnincx, Pieter C. A. |
author_facet | Jastrzebski, Robin Constant, Sandra Lancefield, Christopher S. Westwood, Nicholas J. Weckhuysen, Bert M. Bruijnincx, Pieter C. A. |
author_sort | Jastrzebski, Robin |
collection | PubMed |
description | Lignin is an attractive renewable feedstock for aromatic bulk and fine chemicals production, provided that suitable depolymerization procedures are developed. Here, we describe a tandem catalysis strategy for ether linkage cleavage within lignin, involving ether hydrolysis by water‐tolerant Lewis acids followed by aldehyde decarbonylation by a Rh complex. In situ decarbonylation of the reactive aldehydes limits loss of monomers by recondensation, a major issue in acid‐catalyzed lignin depolymerization. Rate of hydrolysis and decarbonylation were matched using lignin model compounds, allowing the method to be successfully applied to softwood, hardwood, and herbaceous dioxasolv lignins, as well as poplar sawdust, to give the anticipated decarbonylation products and, rather surprisingly, 4‐(1‐propenyl)phenols. Promisingly, product selectivity can be tuned by variation of the Lewis‐acid strength and lignin source. |
format | Online Article Text |
id | pubmed-5129541 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-51295412016-11-30 Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes Jastrzebski, Robin Constant, Sandra Lancefield, Christopher S. Westwood, Nicholas J. Weckhuysen, Bert M. Bruijnincx, Pieter C. A. ChemSusChem Communications Lignin is an attractive renewable feedstock for aromatic bulk and fine chemicals production, provided that suitable depolymerization procedures are developed. Here, we describe a tandem catalysis strategy for ether linkage cleavage within lignin, involving ether hydrolysis by water‐tolerant Lewis acids followed by aldehyde decarbonylation by a Rh complex. In situ decarbonylation of the reactive aldehydes limits loss of monomers by recondensation, a major issue in acid‐catalyzed lignin depolymerization. Rate of hydrolysis and decarbonylation were matched using lignin model compounds, allowing the method to be successfully applied to softwood, hardwood, and herbaceous dioxasolv lignins, as well as poplar sawdust, to give the anticipated decarbonylation products and, rather surprisingly, 4‐(1‐propenyl)phenols. Promisingly, product selectivity can be tuned by variation of the Lewis‐acid strength and lignin source. John Wiley and Sons Inc. 2016-07-21 2016-08-23 /pmc/articles/PMC5129541/ /pubmed/27440544 http://dx.doi.org/10.1002/cssc.201600683 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Jastrzebski, Robin Constant, Sandra Lancefield, Christopher S. Westwood, Nicholas J. Weckhuysen, Bert M. Bruijnincx, Pieter C. A. Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes |
title | Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes |
title_full | Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes |
title_fullStr | Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes |
title_full_unstemmed | Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes |
title_short | Tandem Catalytic Depolymerization of Lignin by Water‐Tolerant Lewis Acids and Rhodium Complexes |
title_sort | tandem catalytic depolymerization of lignin by water‐tolerant lewis acids and rhodium complexes |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5129541/ https://www.ncbi.nlm.nih.gov/pubmed/27440544 http://dx.doi.org/10.1002/cssc.201600683 |
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