Production of Aromatic Compounds by Catalytic Depolymerization of Technical and Downstream Biorefinery Lignins.
Identifieur interne : 000180 ( Main/Exploration ); précédent : 000179; suivant : 000181Production of Aromatic Compounds by Catalytic Depolymerization of Technical and Downstream Biorefinery Lignins.
Auteurs : Alfonso Cornejo [Espagne] ; Fernando Bimbela [Espagne] ; Rui Moreira [Portugal] ; Karina Hablich [Espagne] ; Í Igo García-Yoldi [Espagne] ; Maitane Maisterra [Espagne] ; Ant Nio Portugal [Portugal] ; Luis M. Gandía [Espagne] ; Víctor Martínez-Merino [Espagne]Source :
- Biomolecules [ 2218-273X ] ; 2020.
Abstract
Lignocellulosic materials are promising alternatives to non-renewable fossil sources when producing aromatic compounds. Lignins from Populus salicaceae. Pinus radiata and Pinus pinaster from industrial wastes and biorefinery effluents were isolated and characterized. Lignin was depolymerized using homogenous (NaOH) and heterogeneous (Ni-, Cu- or Ni-Cu-hydrotalcites) base catalysis and catalytic hydrogenolysis using Ru/C. When homogeneous base catalyzed depolymerization (BCD) and Ru/C hydrogenolysis were combined on poplar lignin, the aromatics amount was ca. 11 wt.%. Monomer distributions changed depending on the feedstock and the reaction conditions. Aqueous NaOH produced cleavage of the alkyl side chain that was preserved when using modified hydrotalcite catalysts or Ru/C-catalyzed hydrogenolysis in ethanol. Depolymerization using hydrotalcite catalysts in ethanol produced monomers bearing carbonyl groups on the alkyl side chain. The analysis of the reaction mixtures was done by size exclusion chromatography (SEC) and diffusion ordered nuclear magnetic resonance spectroscopy (DOSY NMR). 31P NMR and heteronuclear single quantum coherence spectroscopy (HSQC) were also used in this study. The content in poly-(hydroxy)-aromatic ethers in the reaction mixtures decreased upon thermal treatments in ethanol. It was concluded that thermo-solvolysis is key in lignin depolymerization, and that the synergistic effect of Ni and Cu provided monomers with oxidized alkyl side chains.
DOI: 10.3390/biom10091338
PubMed: 32962141
PubMed Central: PMC7564559
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Downstream Biorefinery Lignins.</title><author><name sortKey="Cornejo, Alfonso" sort="Cornejo, Alfonso" uniqKey="Cornejo A" first="Alfonso" last="Cornejo">Alfonso Cornejo</name><affiliation wicri:level="2"><nlm:affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté forale de Navarre</region></placeName></affiliation></author><author><name sortKey="Bimbela, Fernando" sort="Bimbela, Fernando" uniqKey="Bimbela F" first="Fernando" last="Bimbela">Fernando Bimbela</name><affiliation wicri:level="2"><nlm:affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté forale de Navarre</region></placeName></affiliation></author><author><name sortKey="Moreira, Rui" sort="Moreira, Rui" uniqKey="Moreira R" first="Rui" last="Moreira">Rui Moreira</name><affiliation wicri:level="1"><nlm:affiliation>CIEPQPF, FCTUC, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II-Pinhal de Marrocos, 3030-790 Coimbra, Portugal.</nlm:affiliation><country xml:lang="fr">Portugal</country><wicri:regionArea>CIEPQPF, FCTUC, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II-Pinhal de Marrocos, 3030-790 Coimbra</wicri:regionArea><wicri:noRegion>3030-790 Coimbra</wicri:noRegion></affiliation></author><author><name sortKey="Hablich, Karina" sort="Hablich, Karina" uniqKey="Hablich K" first="Karina" last="Hablich">Karina Hablich</name><affiliation wicri:level="2"><nlm:affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté forale de Navarre</region></placeName></affiliation></author><author><name sortKey="Garcia Yoldi, I Igo" sort="Garcia Yoldi, I Igo" uniqKey="Garcia Yoldi I" first="Í Igo" last="García-Yoldi">Í Igo García-Yoldi</name><affiliation wicri:level="2"><nlm:affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté forale de Navarre</region></placeName></affiliation></author><author><name sortKey="Maisterra, Maitane" sort="Maisterra, Maitane" uniqKey="Maisterra M" first="Maitane" last="Maisterra">Maitane Maisterra</name><affiliation wicri:level="2"><nlm:affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté forale de Navarre</region></placeName></affiliation></author><author><name sortKey="Portugal, Ant Nio" sort="Portugal, Ant Nio" uniqKey="Portugal A" first="Ant Nio" last="Portugal">Ant Nio Portugal</name><affiliation wicri:level="1"><nlm:affiliation>CIEPQPF, FCTUC, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II-Pinhal de Marrocos, 3030-790 Coimbra, Portugal.</nlm:affiliation><country xml:lang="fr">Portugal</country><wicri:regionArea>CIEPQPF, FCTUC, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II-Pinhal de Marrocos, 3030-790 Coimbra</wicri:regionArea><wicri:noRegion>3030-790 Coimbra</wicri:noRegion></affiliation></author><author><name sortKey="Gandia, Luis M" sort="Gandia, Luis M" uniqKey="Gandia L" first="Luis M" last="Gandía">Luis M. Gandía</name><affiliation wicri:level="2"><nlm:affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté forale de Navarre</region></placeName></affiliation></author><author><name sortKey="Martinez Merino, Victor" sort="Martinez Merino, Victor" uniqKey="Martinez Merino V" first="Víctor" last="Martínez-Merino">Víctor Martínez-Merino</name><affiliation wicri:level="2"><nlm:affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté forale de Navarre</region></placeName></affiliation></author></analytic><series><title level="j">Biomolecules</title><idno type="eISSN">2218-273X</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Lignocellulosic materials are promising alternatives to non-renewable fossil sources when producing aromatic compounds. Lignins from <i>Populus salicaceae</i>. <i>Pinus radiata</i> and <i>Pinus pinaster</i> from industrial wastes and biorefinery effluents were isolated and characterized. Lignin was depolymerized using homogenous (NaOH) and heterogeneous (Ni-, Cu- or Ni-Cu-hydrotalcites) base catalysis and catalytic hydrogenolysis using Ru/C. When homogeneous base catalyzed depolymerization (BCD) and Ru/C hydrogenolysis were combined on poplar lignin, the aromatics amount was ca. 11 wt.%. Monomer distributions changed depending on the feedstock and the reaction conditions. Aqueous NaOH produced cleavage of the alkyl side chain that was preserved when using modified hydrotalcite catalysts or Ru/C-catalyzed hydrogenolysis in ethanol. Depolymerization using hydrotalcite catalysts in ethanol produced monomers bearing carbonyl groups on the alkyl side chain. The analysis of the reaction mixtures was done by size exclusion chromatography (SEC) and diffusion ordered nuclear magnetic resonance spectroscopy (DOSY NMR). <sup>31</sup>P NMR and heteronuclear single quantum coherence spectroscopy (HSQC) were also used in this study. The content in poly-(hydroxy)-aromatic ethers in the reaction mixtures decreased upon thermal treatments in ethanol. It was concluded that thermo-solvolysis is key in lignin depolymerization, and that the synergistic effect of Ni and Cu provided monomers with oxidized alkyl side chains.</div></front></TEI><pubmed><MedlineCitation Status="In-Data-Review" Owner="NLM"><PMID Version="1">32962141</PMID><DateRevised><Year>2020</Year><Month>10</Month><Day>30</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">2218-273X</ISSN><JournalIssue CitedMedium="Internet"><Volume>10</Volume><Issue>9</Issue><PubDate><Year>2020</Year><Month>Sep</Month><Day>18</Day></PubDate></JournalIssue><Title>Biomolecules</Title><ISOAbbreviation>Biomolecules</ISOAbbreviation></Journal><ArticleTitle>Production of Aromatic Compounds by Catalytic Depolymerization of Technical and Downstream Biorefinery Lignins.</ArticleTitle><ELocationID EIdType="pii" ValidYN="Y">E1338</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.3390/biom10091338</ELocationID><Abstract><AbstractText>Lignocellulosic materials are promising alternatives to non-renewable fossil sources when producing aromatic compounds. Lignins from <i>Populus salicaceae</i>. <i>Pinus radiata</i> and <i>Pinus pinaster</i> from industrial wastes and biorefinery effluents were isolated and characterized. Lignin was depolymerized using homogenous (NaOH) and heterogeneous (Ni-, Cu- or Ni-Cu-hydrotalcites) base catalysis and catalytic hydrogenolysis using Ru/C. When homogeneous base catalyzed depolymerization (BCD) and Ru/C hydrogenolysis were combined on poplar lignin, the aromatics amount was ca. 11 wt.%. Monomer distributions changed depending on the feedstock and the reaction conditions. Aqueous NaOH produced cleavage of the alkyl side chain that was preserved when using modified hydrotalcite catalysts or Ru/C-catalyzed hydrogenolysis in ethanol. Depolymerization using hydrotalcite catalysts in ethanol produced monomers bearing carbonyl groups on the alkyl side chain. The analysis of the reaction mixtures was done by size exclusion chromatography (SEC) and diffusion ordered nuclear magnetic resonance spectroscopy (DOSY NMR). <sup>31</sup>P NMR and heteronuclear single quantum coherence spectroscopy (HSQC) were also used in this study. The content in poly-(hydroxy)-aromatic ethers in the reaction mixtures decreased upon thermal treatments in ethanol. It was concluded that thermo-solvolysis is key in lignin depolymerization, and that the synergistic effect of Ni and Cu provided monomers with oxidized alkyl side chains.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Cornejo</LastName><ForeName>Alfonso</ForeName><Initials>A</Initials><Identifier Source="ORCID">0000-0001-8810-0062</Identifier><AffiliationInfo><Affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bimbela</LastName><ForeName>Fernando</ForeName><Initials>F</Initials><Identifier Source="ORCID">0000-0002-8588-2350</Identifier><AffiliationInfo><Affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Moreira</LastName><ForeName>Rui</ForeName><Initials>R</Initials><Identifier Source="ORCID">0000-0003-0426-7506</Identifier><AffiliationInfo><Affiliation>CIEPQPF, FCTUC, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II-Pinhal de Marrocos, 3030-790 Coimbra, Portugal.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hablich</LastName><ForeName>Karina</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>García-Yoldi</LastName><ForeName>Íñigo</ForeName><Initials>Í</Initials><AffiliationInfo><Affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Maisterra</LastName><ForeName>Maitane</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Portugal</LastName><ForeName>António</ForeName><Initials>A</Initials><Identifier Source="ORCID">0000-0002-7520-4767</Identifier><AffiliationInfo><Affiliation>CIEPQPF, FCTUC, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II-Pinhal de Marrocos, 3030-790 Coimbra, Portugal.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gandía</LastName><ForeName>Luis M</ForeName><Initials>LM</Initials><Identifier Source="ORCID">0000-0002-3954-4609</Identifier><AffiliationInfo><Affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Martínez-Merino</LastName><ForeName>Víctor</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>Institute for Advanced Materials and Mathematics (InaMat2) and Department of Sciences, Universidad Pública de Navarra, E31006 Pamplona, Spain.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>LCF/PR/PR15/511000007</GrantID><Agency>UNED-Fundación LaCaixa</Agency><Country></Country></Grant><Grant><GrantID>PC036-37 Biovalorización</GrantID><Agency>Economy Development Department, Navarre Government</Agency><Country></Country></Grant><Grant><GrantID>POCI-01-0145-FEDER-016403</GrantID><Agency>Portuguese Foundation for Science and Technology (FCT) - European Development Regional Fund</Agency><Country></Country></Grant><Grant><GrantID>Programa de Intensificación de la Investigación 2018</GrantID><Agency>Banco de Santander - Universidad Pública de Navarra</Agency><Country></Country></Grant><Grant><GrantID>OUT_2018_1700</GrantID><Agency>Erasmus + Programme of the European Union</Agency><Country></Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>09</Month><Day>18</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Biomolecules</MedlineTA><NlmUniqueID>101596414</NlmUniqueID><ISSNLinking>2218-273X</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">bio-based aromatic compounds</Keyword><Keyword MajorTopicYN="N">depolymerization</Keyword><Keyword MajorTopicYN="N">homogeneous and heterogeneous catalysis</Keyword><Keyword MajorTopicYN="N">lignin</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>07</Month><Day>31</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>08</Month><Day>19</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>09</Month><Day>11</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>9</Month><Day>23</Day><Hour>1</Hour><Minute>3</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>9</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>9</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>epublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32962141</ArticleId><ArticleId IdType="pii">biom10091338</ArticleId><ArticleId IdType="doi">10.3390/biom10091338</ArticleId><ArticleId IdType="pmc">PMC7564559</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>Bioresour 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