Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin
Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two‐step depolymerization process. Chemoselective catalytic oxidation of β‐O‐4 linkages promoted by the DDQ/tBuONO/O2 system was achieved in model compounds, including polymeric models and in real l...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-01, Vol.54 (1), p.258-262 |
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| creator | Lancefield, Christopher S. Ojo, O. Stephen Tran, Fanny Westwood, Nicholas J. |
| description | Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two‐step depolymerization process. Chemoselective catalytic oxidation of β‐O‐4 linkages promoted by the DDQ/tBuONO/O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β‐O‐4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
Lignin depolymerization: A two‐step approach comprising the selective aerobic oxidation of the benzyl alcohols of lignin using DDQ/tBuONO/O2 followed by cleavage of the β‐O‐4 linkages of lignin through treatment with metallic zinc affords functionalized small molecules. These products will be useful building blocks for the preparation of biomass‐derived fine chemicals and materials. |
| doi_str_mv | 10.1002/anie.201409408 |
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Lignin depolymerization: A two‐step approach comprising the selective aerobic oxidation of the benzyl alcohols of lignin using DDQ/tBuONO/O2 followed by cleavage of the β‐O‐4 linkages of lignin through treatment with metallic zinc affords functionalized small molecules. These products will be useful building blocks for the preparation of biomass‐derived fine chemicals and materials.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201409408</identifier><identifier>PMID: 25377996</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Benzoquinones - chemistry ; biomass ; Bonding ; Catalysis ; Catalytic oxidation ; Cleavage ; Depolymerization ; Lignin ; Lignin - chemistry ; Linkages ; Monomers ; Oxidants - chemistry ; Oxidation ; Oxidation-Reduction ; Phenolic compounds ; Phenols ; Phenols - chemistry ; Phenols - isolation & purification ; Polymerization ; Production methods ; renewable chemicals ; Zinc</subject><ispartof>Angewandte Chemie International Edition, 2015-01, Vol.54 (1), p.258-262</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright Wiley Subscription Services, Inc. Jan 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3748-1d73c5d5ed972e4904fc6c5cb7557203c3b4d8c565bb2a868c642b1c6a1ed29c3</citedby><cites>FETCH-LOGICAL-c3748-1d73c5d5ed972e4904fc6c5cb7557203c3b4d8c565bb2a868c642b1c6a1ed29c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201409408$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201409408$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25377996$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lancefield, Christopher S.</creatorcontrib><creatorcontrib>Ojo, O. Stephen</creatorcontrib><creatorcontrib>Tran, Fanny</creatorcontrib><creatorcontrib>Westwood, Nicholas J.</creatorcontrib><title>Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two‐step depolymerization process. Chemoselective catalytic oxidation of β‐O‐4 linkages promoted by the DDQ/tBuONO/O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β‐O‐4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
Lignin depolymerization: A two‐step approach comprising the selective aerobic oxidation of the benzyl alcohols of lignin using DDQ/tBuONO/O2 followed by cleavage of the β‐O‐4 linkages of lignin through treatment with metallic zinc affords functionalized small molecules. These products will be useful building blocks for the preparation of biomass‐derived fine chemicals and materials.</description><subject>Benzoquinones - chemistry</subject><subject>biomass</subject><subject>Bonding</subject><subject>Catalysis</subject><subject>Catalytic oxidation</subject><subject>Cleavage</subject><subject>Depolymerization</subject><subject>Lignin</subject><subject>Lignin - chemistry</subject><subject>Linkages</subject><subject>Monomers</subject><subject>Oxidants - chemistry</subject><subject>Oxidation</subject><subject>Oxidation-Reduction</subject><subject>Phenolic compounds</subject><subject>Phenols</subject><subject>Phenols - chemistry</subject><subject>Phenols - isolation & purification</subject><subject>Polymerization</subject><subject>Production methods</subject><subject>renewable chemicals</subject><subject>Zinc</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1u1DAYhiNERUthyxJZYsMmU__EdrJsh0470jCD-FGXluN8M-M2Y7dxUtoue5XegAtwA67CFXCUMkJsuvIr63mfxfcmyRuCRwRjeqCdhRHFJMNFhvNnyR7hlKRMSvY85oyxVOac7CYvQziPfJ5j8SLZpTwSRSH2kvtp8LVurXfIL9Gkc6bPurZ3UKFPa3C-tgZ99M5voAmoXTe-W63RF6ghkteAFje2GvraVWj8--HnAh35Ptagr_UKem-7BvTrR7pIMzSz7iL-BmRdzCtn3atkZ6nrAK8f3_3k2-T46_g0nS1OpuPDWWqYzPKUVJIZXnGoCkkhK3C2NMJwU0rOJcXMsDKrcsMFL0uqc5EbkdGSGKEJVLQwbD95P3gvG3_VQWjVxgYDda0d-C4oIjEucsKweBqNakGY4DKi7_5Dz33XxAsGRbkQJF6c00iNBso0PoQGluqysRvd3CqCVT-k6odU2yFj4e2jtis3UG3xv8tFoBiA77aG2yd06nA-Pf5Xng5dG1q42XZ1c6GEZJKrs_mJ-nB09nk8FxM1Y38ArN66UA</recordid><startdate>20150102</startdate><enddate>20150102</enddate><creator>Lancefield, Christopher S.</creator><creator>Ojo, O. Stephen</creator><creator>Tran, Fanny</creator><creator>Westwood, Nicholas J.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150102</creationdate><title>Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin</title><author>Lancefield, Christopher S. ; Ojo, O. Stephen ; Tran, Fanny ; Westwood, Nicholas J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3748-1d73c5d5ed972e4904fc6c5cb7557203c3b4d8c565bb2a868c642b1c6a1ed29c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Benzoquinones - chemistry</topic><topic>biomass</topic><topic>Bonding</topic><topic>Catalysis</topic><topic>Catalytic oxidation</topic><topic>Cleavage</topic><topic>Depolymerization</topic><topic>Lignin</topic><topic>Lignin - chemistry</topic><topic>Linkages</topic><topic>Monomers</topic><topic>Oxidants - chemistry</topic><topic>Oxidation</topic><topic>Oxidation-Reduction</topic><topic>Phenolic compounds</topic><topic>Phenols</topic><topic>Phenols - chemistry</topic><topic>Phenols - isolation & purification</topic><topic>Polymerization</topic><topic>Production methods</topic><topic>renewable chemicals</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lancefield, Christopher S.</creatorcontrib><creatorcontrib>Ojo, O. Stephen</creatorcontrib><creatorcontrib>Tran, Fanny</creatorcontrib><creatorcontrib>Westwood, Nicholas J.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lancefield, Christopher S.</au><au>Ojo, O. 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Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
Lignin depolymerization: A two‐step approach comprising the selective aerobic oxidation of the benzyl alcohols of lignin using DDQ/tBuONO/O2 followed by cleavage of the β‐O‐4 linkages of lignin through treatment with metallic zinc affords functionalized small molecules. These products will be useful building blocks for the preparation of biomass‐derived fine chemicals and materials.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25377996</pmid><doi>10.1002/anie.201409408</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Benzoquinones - chemistry biomass Bonding Catalysis Catalytic oxidation Cleavage Depolymerization Lignin Lignin - chemistry Linkages Monomers Oxidants - chemistry Oxidation Oxidation-Reduction Phenolic compounds Phenols Phenols - chemistry Phenols - isolation & purification Polymerization Production methods renewable chemicals Zinc |
| title | Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin |
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