Electrochemical Aminoxyl-Mediated Oxidation of Primary Alcohols in Lignin to Carboxylic Acids: Polymer Modification and Depolymerization.
Identifieur interne : 000993 ( Main/Exploration ); précédent : 000992; suivant : 000994Electrochemical Aminoxyl-Mediated Oxidation of Primary Alcohols in Lignin to Carboxylic Acids: Polymer Modification and Depolymerization.
Auteurs : Mohammad Rafiee [États-Unis] ; Manar Alherech [États-Unis] ; Steven D. Karlen [États-Unis] ; Shannon S. Stahl [États-Unis]Source :
- Journal of the American Chemical Society [ 1520-5126 ] ; 2019.
Descripteurs français
- KwdFr :
- MESH :
- composition chimique : Acides carboxyliques, Alcools, Lignine, Polymères.
- synthèse chimique : Acides carboxyliques.
- Oxydoréduction, Polymérisation, Structure moléculaire, Techniques électrochimiques.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Carboxylic Acids.
- chemical , chemistry : Alcohols, Carboxylic Acids, Lignin, Polymers.
- Electrochemical Techniques, Molecular Structure, Oxidation-Reduction, Polymerization.
Abstract
An electrochemical process has been developed for chemoselective oxidation of primary alcohols in lignin to the corresponding carboxylic acids. The electrochemical oxidation reactions proceed under mildly basic conditions and employ 2,2,6,6-tetramethyl-1-piperidine N-oxyl (TEMPO) and 4-acetamido-TEMPO (ACT) as catalytic mediators. Lignin model compounds and related alcohols are used to conduct structure-reactivity studies that provide insights into the origin of the reaction selectivity. The method is applied to the oxidation of lignin extracted from poplar wood chips via a mild acidolysis method, and the reaction affords a novel polyelectrolyte material. Gel permeation chromatography data for the oxidized lignin shows that this material has a molecular weight and molecular weight distribution very similar to that of the extracted lignin, but notable differences are also evident. Base titration reveals a significant increase in the acid content, and the oxidized lignin has much higher water solubility relative to the extracted lignin. Treatment of the oxidized lignin under acidic conditions results in depolymerization of the material into characterized aromatic monomers in nearly 30 wt% yield.
DOI: 10.1021/jacs.9b07243
PubMed: 31483640
PubMed Central: PMC7641471
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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Karlen</name><affiliation wicri:level="1"><nlm:affiliation>Department of Energy Great Lakes Bioenergy Research Center, the Wisconsin Energy Institute , University of Wisconsin-Madison , Madison , Wisconsin 53726 , United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Energy Great Lakes Bioenergy Research Center, the Wisconsin Energy Institute , University of Wisconsin-Madison , Madison , Wisconsin 53726 </wicri:regionArea><wicri:noRegion>Wisconsin 53726 </wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:affiliation>Department of Biochemistry , University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Biochemistry , University of Wisconsin-Madison , Madison , Wisconsin 53706 </wicri:regionArea><wicri:noRegion>Wisconsin 53706 </wicri:noRegion></affiliation></author><author><name sortKey="Stahl, Shannon S" sort="Stahl, Shannon S" uniqKey="Stahl S" first="Shannon S" last="Stahl">Shannon S. Stahl</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 </wicri:regionArea><wicri:noRegion>Wisconsin 53706 </wicri:noRegion></affiliation></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="eISSN">1520-5126</idno><imprint><date when="2019" type="published">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alcohols (chemistry)</term><term>Carboxylic Acids (chemical synthesis)</term><term>Carboxylic Acids (chemistry)</term><term>Electrochemical Techniques (MeSH)</term><term>Lignin (chemistry)</term><term>Molecular Structure (MeSH)</term><term>Oxidation-Reduction (MeSH)</term><term>Polymerization (MeSH)</term><term>Polymers (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acides carboxyliques (composition chimique)</term><term>Acides carboxyliques (synthèse chimique)</term><term>Alcools (composition chimique)</term><term>Lignine (composition chimique)</term><term>Oxydoréduction (MeSH)</term><term>Polymères (composition chimique)</term><term>Polymérisation (MeSH)</term><term>Structure moléculaire (MeSH)</term><term>Techniques électrochimiques (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Carboxylic Acids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alcohols</term><term>Carboxylic Acids</term><term>Lignin</term><term>Polymers</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Acides carboxyliques</term><term>Alcools</term><term>Lignine</term><term>Polymères</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Acides carboxyliques</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Electrochemical Techniques</term><term>Molecular Structure</term><term>Oxidation-Reduction</term><term>Polymerization</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Oxydoréduction</term><term>Polymérisation</term><term>Structure moléculaire</term><term>Techniques électrochimiques</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">An electrochemical process has been developed for chemoselective oxidation of primary alcohols in lignin to the corresponding carboxylic acids. The electrochemical oxidation reactions proceed under mildly basic conditions and employ 2,2,6,6-tetramethyl-1-piperidine N-oxyl (TEMPO) and 4-acetamido-TEMPO (ACT) as catalytic mediators. Lignin model compounds and related alcohols are used to conduct structure-reactivity studies that provide insights into the origin of the reaction selectivity. The method is applied to the oxidation of lignin extracted from poplar wood chips via a mild acidolysis method, and the reaction affords a novel polyelectrolyte material. Gel permeation chromatography data for the oxidized lignin shows that this material has a molecular weight and molecular weight distribution very similar to that of the extracted lignin, but notable differences are also evident. Base titration reveals a significant increase in the acid content, and the oxidized lignin has much higher water solubility relative to the extracted lignin. Treatment of the oxidized lignin under acidic conditions results in depolymerization of the material into characterized aromatic monomers in nearly 30 wt% yield.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31483640</PMID><DateCompleted><Year>2020</Year><Month>10</Month><Day>20</Day></DateCompleted><DateRevised><Year>2020</Year><Month>11</Month><Day>06</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5126</ISSN><JournalIssue CitedMedium="Internet"><Volume>141</Volume><Issue>38</Issue><PubDate><Year>2019</Year><Month>09</Month><Day>25</Day></PubDate></JournalIssue><Title>Journal of the American Chemical Society</Title><ISOAbbreviation>J Am Chem Soc</ISOAbbreviation></Journal><ArticleTitle>Electrochemical Aminoxyl-Mediated Oxidation of Primary Alcohols in Lignin to Carboxylic Acids: Polymer Modification and Depolymerization.</ArticleTitle><Pagination><MedlinePgn>15266-15276</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jacs.9b07243</ELocationID><Abstract><AbstractText>An electrochemical process has been developed for chemoselective oxidation of primary alcohols in lignin to the corresponding carboxylic acids. The electrochemical oxidation reactions proceed under mildly basic conditions and employ 2,2,6,6-tetramethyl-1-piperidine N-oxyl (TEMPO) and 4-acetamido-TEMPO (ACT) as catalytic mediators. Lignin model compounds and related alcohols are used to conduct structure-reactivity studies that provide insights into the origin of the reaction selectivity. The method is applied to the oxidation of lignin extracted from poplar wood chips via a mild acidolysis method, and the reaction affords a novel polyelectrolyte material. Gel permeation chromatography data for the oxidized lignin shows that this material has a molecular weight and molecular weight distribution very similar to that of the extracted lignin, but notable differences are also evident. Base titration reveals a significant increase in the acid content, and the oxidized lignin has much higher water solubility relative to the extracted lignin. Treatment of the oxidized lignin under acidic conditions results in depolymerization of the material into characterized aromatic monomers in nearly 30 wt% yield.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Rafiee</LastName><ForeName>Mohammad</ForeName><Initials>M</Initials><Identifier Source="ORCID">0000-0002-5325-5387</Identifier><AffiliationInfo><Affiliation>Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Alherech</LastName><ForeName>Manar</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Karlen</LastName><ForeName>Steven D</ForeName><Initials>SD</Initials><Identifier Source="ORCID">0000-0002-2044-8895</Identifier><AffiliationInfo><Affiliation>Department of Energy Great Lakes Bioenergy Research Center, the Wisconsin Energy Institute , University of Wisconsin-Madison , Madison , Wisconsin 53726 , United States.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Biochemistry , University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Stahl</LastName><ForeName>Shannon S</ForeName><Initials>SS</Initials><Identifier Source="ORCID">0000-0002-9000-7665</Identifier><AffiliationInfo><Affiliation>Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>S10 OD020022</GrantID><Acronym>OD</Acronym><Agency>NIH HHS</Agency><Country>United 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MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010084" MajorTopicYN="N">Oxidation-Reduction</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D058105" MajorTopicYN="N">Polymerization</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011108" MajorTopicYN="N">Polymers</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2019</Year><Month>9</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>10</Month><Day>21</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2019</Year><Month>9</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId 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Karlen</name><name sortKey="Karlen, Steven D" sort="Karlen, Steven D" uniqKey="Karlen S" first="Steven D" last="Karlen">Steven D. Karlen</name><name sortKey="Stahl, Shannon S" sort="Stahl, Shannon S" uniqKey="Stahl S" first="Shannon S" last="Stahl">Shannon S. Stahl</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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