Pre-methylation of lignin to improve storage stability of oil produced by solvent liquefaction

dc.contributor.author Cady, Sarah
dc.contributor.author Kim, Jae-Young
dc.contributor.author Hafezi-Sefat, Parinaz
dc.contributor.author Cady, Sarah
dc.contributor.author Smith, Ryan
dc.contributor.author Brown, Robert
dc.contributor.author Brown, Robert
dc.contributor.department Mechanical Engineering
dc.contributor.department Chemical and Biological Engineering
dc.contributor.department Chemistry
dc.contributor.department Agricultural and Biosystems Engineering
dc.contributor.department Bioeconomy Institute (BEI)
dc.date 2019-02-16T13:09:52.000
dc.date.accessioned 2020-06-30T06:04:51Z
dc.date.available 2020-06-30T06:04:51Z
dc.date.copyright Tue Jan 01 00:00:00 UTC 2019
dc.date.issued 2019-01-29
dc.description.abstract <p>In this study, we methylated hydroxyl groups (phenolic hydroxyl: Phe-OH and aliphatic hydroxyl: Aliph-OH) in soda lignin (SL) prior to solvent liquefaction to improve storage stability of the resulting oil. We investigated two methylating reagents, dimethyl sulfate (DMS) and dimethyl carbonate (DMC), for selective Phe-OH and total hydroxyl group (Phe-OH and Aliph-OH) blocking. Samples of SL, DMS-SL, and DMC-SL were depolymerized into oils under supercritical ethanol (350 °C). Both methylated lignins produced higher amounts of oils and smaller amounts of char compared to untreated SL due to suppressed charring reactions. Oil produced from SL had relatively higher functional group contents than other oils from methylated lignins. Simulated one-year aging of oils was carried out and this revealed Mw increase of oil was the highest in SL (11.8 %), followed by DMC-SL (6.8 %) and DMC-SL (4.6 %). Interestingly, these increases showed linear correlation with decrease in Phe-OH after accelerated aging. Meanwhile, compositional difference in monomeric phenols in the oils were observed by GC/MS analysis. For example, methoxylated aromatics such as 4-ethylveratrole, 4-vinylveratrole, methylisoeugenol, and veratryl-2-propanone were detected only in oils from DMS-SL, and DMC-SL. Interestingly, there was no significant difference in monomeric compounds yields before and after accelerated aging among the oils, which suggests that repolymerization mainly occurred between oligomeric lignin fragments.</p>
dc.description.comments <p>This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in <em>Energy and Fuels</em>, copyright © American Chemical Society after peer review. To access the final edited and published work see DOI: <a href="http://dx.doi.org/10.1021/acs.energyfuels.8b03894" target="_blank">10.1021/acs.energyfuels.8b03894</a>.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/me_pubs/324/
dc.identifier.articleid 1326
dc.identifier.contextkey 13758062
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath me_pubs/324
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/55192
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/me_pubs/324/2019_BrownRobert_PremethylationLignin.pdf|||Fri Jan 14 23:36:00 UTC 2022
dc.source.uri 10.1021/acs.energyfuels.8b03894
dc.subject.disciplines Mechanical Engineering
dc.subject.disciplines Petroleum Engineering
dc.subject.disciplines Polymer Chemistry
dc.subject.keywords Lignin
dc.subject.keywords Methylation
dc.subject.keywords Solvent liquefaction
dc.subject.keywords Repolymerization
dc.subject.keywords Hydroxyl group
dc.title Pre-methylation of lignin to improve storage stability of oil produced by solvent liquefaction
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication bdd61196-0f0a-4ec2-9723-b7edddf99843
relation.isAuthorOfPublication 06f45e8f-14d0-42f9-90df-c902e3049987
relation.isOrgUnitOfPublication 6d38ab0f-8cc2-4ad3-90b1-67a60c5a6f59
relation.isOrgUnitOfPublication 86545861-382c-4c15-8c52-eb8e9afe6b75
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
relation.isOrgUnitOfPublication 8eb24241-0d92-4baf-ae75-08f716d30801
File
Original bundle
Now showing 1 - 1 of 1
Name:
2019_BrownRobert_PremethylationLignin.pdf
Size:
660.32 KB
Format:
Adobe Portable Document Format
Description:
Collections