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Olefin cross-metathesis, a mild, modular approach to functionalized cellulose esters

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dc.contributorMacromolecules Innovation Instituteen
dc.contributorSustainable Biomaterialsen
dc.contributorChemistryen
dc.contributor.authorMeng, Xiangtaoen
dc.contributor.authorMatson, John B.en
dc.contributor.authorEdgar, Kevin J.en
dc.date.accessed2015-04-15en
dc.date.accessioned2015-04-21T14:01:43Zen
dc.date.available2015-04-21T14:01:43Zen
dc.date.issued2014-09-02en
dc.description.abstractOlefin cross-metathesis has been demonstrated to be a modular pathway for synthesis of a series of functionalized cellulose esters. As a proof of concept, cellulose acetate was acylated with two terminally olefinic acid chlorides, pent-4-enoyl chloride and undec-10-enoyl chloride, providing olefin-terminated cellulose esters with different side-chain lengths. These ω-unsaturated cellulose esters were then reacted with a variety of cross-metathesis partners, including acrylic acid, methyl acrylate, 2-hydroxyethyl acrylate, poly(ethylene glycol) methyl ether acrylate, and allyl alcohols, using Hoveyda–Grubbs’ 2nd generation catalyst. Complete conversion to cross-metathesis products was achieved in reactions with acrylic acid or acrylates using 3–5 mol% catalyst at 40 °C within 1 h. We further demonstrate successful hydrogenation of these α,β-unsaturated esters and acids, thereby eliminating the potential for radical-induced crosslinking during storage.en
dc.description.notesSupplementary information is included in a separate fileen
dc.description.sponsorshipEastman Chemical Companyen
dc.description.sponsorshipNational Science Foundation (U.S.) - Grant DMR-1308276en
dc.description.sponsorshipVirginia Tech. Institute for Critical Technologies and Applied Scienceen
dc.description.sponsorshipMacromolecules and Interfaces Institute at Virginia Techen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationMeng, X., Matson, J. B., & Edgar, K. J. (2014). Olefin cross-metathesis, a mild, modular approach to functionalized cellulose esters. Polymer Chemistry, 5(24), 7021-7033. doi: 10.1039/C4PY01102Cen
dc.identifier.doihttps://doi.org/10.1039/C4PY01102Cen
dc.identifier.issn1759-9954en
dc.identifier.urihttp://hdl.handle.net/10919/51733en
dc.identifier.urlhttp://pubs.rsc.org/en/content/articlelanding/2014/py/c4py01102cen
dc.language.isoen_USen
dc.publisherThe Royal Society of Chemistryen
dc.rightsCreative Commons Attribution-NonCommercial 3.0 Unporteden
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/en
dc.subjectOlefin cross-metathesisen
dc.subjectPolysaccharidesen
dc.subjectCellulose estersen
dc.titleOlefin cross-metathesis, a mild, modular approach to functionalized cellulose estersen
dc.title.serialPolymer Chemistryen
dc.typeArticle - Refereeden
dc.typeDataseten
dc.type.dcmitypeTexten
dc.type.dcmitypeDataseten

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