Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes.
Identifieur interne : 001700 ( Main/Corpus ); précédent : 001699; suivant : 001701Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes.
Auteurs : Robin Jastrzebski ; Sandra Constant ; Christopher S. Lancefield ; Nicholas J. Westwood ; Bert M. Weckhuysen ; Pieter C A. BruijnincxSource :
- ChemSusChem [ 1864-564X ] ; 2016.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Lewis Acids, Lignin, Organometallic Compounds, Rhodium, Styrene, Water.
- Catalysis, Polymerization.
Abstract
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.
DOI: 10.1002/cssc.201600683
PubMed: 27440544
PubMed Central: PMC5129541
Links to Exploration step
pubmed:27440544Le document en format XML
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Lancefield</name><affiliation><nlm:affiliation>School of Chemistry and Biomedical Science Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.</nlm:affiliation></affiliation></author><author><name sortKey="Westwood, Nicholas J" sort="Westwood, Nicholas J" uniqKey="Westwood N" first="Nicholas J" last="Westwood">Nicholas J. Westwood</name><affiliation><nlm:affiliation>School of Chemistry and Biomedical Science Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.</nlm:affiliation></affiliation></author><author><name sortKey="Weckhuysen, Bert M" sort="Weckhuysen, Bert M" uniqKey="Weckhuysen B" first="Bert M" last="Weckhuysen">Bert M. 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Lancefield</name><affiliation><nlm:affiliation>School of Chemistry and Biomedical Science Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.</nlm:affiliation></affiliation></author><author><name sortKey="Westwood, Nicholas J" sort="Westwood, Nicholas J" uniqKey="Westwood N" first="Nicholas J" last="Westwood">Nicholas J. Westwood</name><affiliation><nlm:affiliation>School of Chemistry and Biomedical Science Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.</nlm:affiliation></affiliation></author><author><name sortKey="Weckhuysen, Bert M" sort="Weckhuysen, Bert M" uniqKey="Weckhuysen B" first="Bert M" last="Weckhuysen">Bert M. Weckhuysen</name><affiliation><nlm:affiliation>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.</nlm:affiliation></affiliation></author><author><name sortKey="Bruijnincx, Pieter C A" sort="Bruijnincx, Pieter C A" uniqKey="Bruijnincx P" first="Pieter C A" last="Bruijnincx">Pieter C A. Bruijnincx</name><affiliation><nlm:affiliation>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands. p.c.a.bruijnincx@uu.nl.</nlm:affiliation></affiliation></author></analytic><series><title level="j">ChemSusChem</title><idno type="eISSN">1864-564X</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Catalysis (MeSH)</term><term>Lewis Acids (chemistry)</term><term>Lignin (chemistry)</term><term>Organometallic Compounds (chemistry)</term><term>Polymerization (MeSH)</term><term>Rhodium (chemistry)</term><term>Styrene (chemistry)</term><term>Water (chemistry)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Lewis Acids</term><term>Lignin</term><term>Organometallic Compounds</term><term>Rhodium</term><term>Styrene</term><term>Water</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Polymerization</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">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.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">27440544</PMID><DateCompleted><Year>2017</Year><Month>06</Month><Day>13</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1864-564X</ISSN><JournalIssue CitedMedium="Internet"><Volume>9</Volume><Issue>16</Issue><PubDate><Year>2016</Year><Month>08</Month><Day>23</Day></PubDate></JournalIssue><Title>ChemSusChem</Title><ISOAbbreviation>ChemSusChem</ISOAbbreviation></Journal><ArticleTitle>Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes.</ArticleTitle><Pagination><MedlinePgn>2074-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/cssc.201600683</ELocationID><Abstract><AbstractText>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.</AbstractText><CopyrightInformation>© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Jastrzebski</LastName><ForeName>Robin</ForeName><Initials>R</Initials><AffiliationInfo><Affiliation>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Constant</LastName><ForeName>Sandra</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lancefield</LastName><ForeName>Christopher S</ForeName><Initials>CS</Initials><AffiliationInfo><Affiliation>School of Chemistry and Biomedical Science Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Westwood</LastName><ForeName>Nicholas J</ForeName><Initials>NJ</Initials><AffiliationInfo><Affiliation>School of Chemistry and Biomedical Science Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Weckhuysen</LastName><ForeName>Bert M</ForeName><Initials>BM</Initials><AffiliationInfo><Affiliation>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bruijnincx</LastName><ForeName>Pieter C A</ForeName><Initials>PC</Initials><Identifier Source="ORCID">0000-0001-8134-0530</Identifier><AffiliationInfo><Affiliation>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands. p.c.a.bruijnincx@uu.nl.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>07</Month><Day>21</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>ChemSusChem</MedlineTA><NlmUniqueID>101319536</NlmUniqueID><ISSNLinking>1864-5631</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D058116">Lewis Acids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009942">Organometallic Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>059QF0KO0R</RegistryNumber><NameOfSubstance 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