Functionality and molecular weight distribution of red oak lignin before and after pyrolysis and hydrogenation
Three red oak derived lignin samples: 1. lignin extracted from red oak chips using gamma -valerolactone (GVL lignin), 2. lignin extracted from the pyrolysis oil of red oak chips by fractionation and water extraction (pyrolytic lignin) and 3. pyrolytic lignin hydrogenated over Ru/C (hydrogenated pyro...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2017, Vol.19 (5), p.1378-1389 |
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| creator | McClelland, Daniel J Motagamwala, Ali Hussain Li, Yanding Rover, Marjorie R Wittrig, Ashley M Wu, Chunping Buchanan, JScott Brown, Robert C Ralph, John Dumesic, James A Huber, George W |
| description | Three red oak derived lignin samples: 1. lignin extracted from red oak chips using gamma -valerolactone (GVL lignin), 2. lignin extracted from the pyrolysis oil of red oak chips by fractionation and water extraction (pyrolytic lignin) and 3. pyrolytic lignin hydrogenated over Ru/C (hydrogenated pyrolytic lignin), were analyzed by FT-ICR MS, NMR, and GPC. More than 1100 distinct molecular weights were observed by FT-ICR MS of the lignin streams while changes in the O/C and H/C ratios suggested the dehydration of hydroxylated sidechains from pyrolysis and partial saturation of the compounds from hydrogenation. The relative average molecular weight of the lignin determined by GPC decreased five-fold after pyrolysis. Quantitative 13C, HSQC, and HMBC NMR revealed a decrease in the C-O aliphatics from pyrolysis potentially forming alkane, alkene, and carbonyl functionalities. The aldehydes and ketones were highly reactive during hydrogenation and may potentially be responsible for coke formation. |
| doi_str_mv | 10.1039/c6gc03515a |
| format | Article |
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More than 1100 distinct molecular weights were observed by FT-ICR MS of the lignin streams while changes in the O/C and H/C ratios suggested the dehydration of hydroxylated sidechains from pyrolysis and partial saturation of the compounds from hydrogenation. The relative average molecular weight of the lignin determined by GPC decreased five-fold after pyrolysis. Quantitative 13C, HSQC, and HMBC NMR revealed a decrease in the C-O aliphatics from pyrolysis potentially forming alkane, alkene, and carbonyl functionalities. 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More than 1100 distinct molecular weights were observed by FT-ICR MS of the lignin streams while changes in the O/C and H/C ratios suggested the dehydration of hydroxylated sidechains from pyrolysis and partial saturation of the compounds from hydrogenation. The relative average molecular weight of the lignin determined by GPC decreased five-fold after pyrolysis. Quantitative 13C, HSQC, and HMBC NMR revealed a decrease in the C-O aliphatics from pyrolysis potentially forming alkane, alkene, and carbonyl functionalities. The aldehydes and ketones were highly reactive during hydrogenation and may potentially be responsible for coke formation.</description><subject>Aldehydes</subject><subject>Aliphatic compounds</subject><subject>Chips</subject><subject>Hydrogenation</subject><subject>INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</subject><subject>Molecular weight</subject><subject>Nuclear magnetic resonance</subject><subject>Oak</subject><subject>Pyrolysis</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNkU9LxDAQxYMouP65-AmCJxGqSdMm7XFZ3FVY8KLnkKbTbjSbrEmK9Nu73RXPzmWGx-_NMDyEbih5oITVj5r3mrCSluoEzWjBWVbngpz-zTw_RxcxfhBCqeDFDLnl4HQy3ilr0oiVa_HWW9CDVQF_g-k3CbcmpmCaYcKw73CAFnv1ia3pnXG4gc4HOFhVlyDg3Ri8HaOJB20ztsH34NRkv0JnnbIRrn_7JXpfPr0tnrP16-plMV9nmtUiZYKrUrQVU03HQbGqJV1TlFxN1ZGyIkqTumBA9r-2ZaUIr7UWot6rkAtasEt0e9zrYzIyapNAb7R3DnSStBBlkbM9dHeEdsF_DRCT3JqowVrlwA9R0qpmVcUF_Q8qRFVQlk-n74-oDj7GAJ3cBbNVYZSUyCkkueCrxSGkOfsBfXOFqw</recordid><startdate>2017</startdate><enddate>2017</enddate><creator>McClelland, Daniel J</creator><creator>Motagamwala, Ali Hussain</creator><creator>Li, Yanding</creator><creator>Rover, Marjorie R</creator><creator>Wittrig, Ashley M</creator><creator>Wu, Chunping</creator><creator>Buchanan, JScott</creator><creator>Brown, Robert C</creator><creator>Ralph, John</creator><creator>Dumesic, James A</creator><creator>Huber, George W</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7ST</scope><scope>7U6</scope><scope>C1K</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>OIOZB</scope><scope>OTOTI</scope><orcidid>https://orcid.org/0000-0003-0847-9557</orcidid><orcidid>https://orcid.org/0000-0002-7838-6893</orcidid><orcidid>https://orcid.org/0000000278386893</orcidid><orcidid>https://orcid.org/0000000308479557</orcidid></search><sort><creationdate>2017</creationdate><title>Functionality and molecular weight distribution of red oak lignin before and after pyrolysis and hydrogenation</title><author>McClelland, Daniel J ; 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| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2017, Vol.19 (5), p.1378-1389 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes Aliphatic compounds Chips Hydrogenation INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Molecular weight Nuclear magnetic resonance Oak Pyrolysis |
| title | Functionality and molecular weight distribution of red oak lignin before and after pyrolysis and hydrogenation |
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