Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes.
Identifieur interne : 001648 ( Main/Exploration ); précédent : 001647; suivant : 001649Tandem Catalytic Depolymerization of Lignin by Water-Tolerant Lewis Acids and Rhodium Complexes.
Auteurs : Robin Jastrzebski [Pays-Bas] ; Sandra Constant [Pays-Bas] ; Christopher S. Lancefield [Royaume-Uni] ; Nicholas J. Westwood [Royaume-Uni] ; Bert M. Weckhuysen [Pays-Bas] ; Pieter C A. Bruijnincx [Pays-Bas]Source :
- ChemSusChem [ 1864-564X ] ; 2016.
Descripteurs français
- KwdFr :
- MESH :
- composition chimique : Acides de Lewis, Composés organométalliques, Eau, Lignine, Rhodium, Styrène.
- Catalyse, Polymérisation.
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
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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Westwood</name><affiliation wicri:level="1"><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><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>School of Chemistry and Biomedical Science Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife, KY16 9ST</wicri:regionArea><wicri:noRegion>KY16 9ST</wicri:noRegion></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 wicri:level="4"><nlm:affiliation>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.</nlm:affiliation><country xml:lang="fr">Pays-Bas</country><wicri:regionArea>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht</wicri:regionArea><placeName><settlement type="city">Utrecht</settlement><region nuts="2" type="province">Utrecht (province)</region></placeName><orgName type="university">Université d'Utrecht</orgName></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 wicri:level="4"><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><country xml:lang="fr">Pays-Bas</country><wicri:regionArea>Inorganic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht</wicri:regionArea><placeName><settlement type="city">Utrecht</settlement><region nuts="2" type="province">Utrecht (province)</region></placeName><orgName type="university">Université d'Utrecht</orgName></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="KwdFr" xml:lang="fr"><term>Acides de Lewis (composition chimique)</term><term>Catalyse (MeSH)</term><term>Composés organométalliques (composition chimique)</term><term>Eau (composition chimique)</term><term>Lignine (composition chimique)</term><term>Polymérisation (MeSH)</term><term>Rhodium (composition chimique)</term><term>Styrène (composition chimique)</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" qualifier="composition chimique" xml:lang="fr"><term>Acides de Lewis</term><term>Composés organométalliques</term><term>Eau</term><term>Lignine</term><term>Rhodium</term><term>Styrène</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Polymerization</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Catalyse</term><term>Polymérisation</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 UI="D014867">Water</NameOfSubstance></Chemical><Chemical><RegistryNumber>44LJ2U959V</RegistryNumber><NameOfSubstance UI="D020058">Styrene</NameOfSubstance></Chemical><Chemical><RegistryNumber>9005-53-2</RegistryNumber><NameOfSubstance UI="D008031">Lignin</NameOfSubstance></Chemical><Chemical><RegistryNumber>DMK383DSAC</RegistryNumber><NameOfSubstance UI="D012238">Rhodium</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D002384" MajorTopicYN="N">Catalysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D058116" MajorTopicYN="N">Lewis Acids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008031" MajorTopicYN="N">Lignin</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009942" MajorTopicYN="N">Organometallic Compounds</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D058105" MajorTopicYN="Y">Polymerization</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D012238" MajorTopicYN="N">Rhodium</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D020058" MajorTopicYN="N">Styrene</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014867" MajorTopicYN="N">Water</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">biomass</Keyword><Keyword MajorTopicYN="Y">decarbonylation</Keyword><Keyword MajorTopicYN="Y">lewis acid</Keyword><Keyword MajorTopicYN="Y">lignin</Keyword><Keyword MajorTopicYN="Y">tandem 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