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Issue 24, 2014
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Olefin cross-metathesis, a mild, modular approach to functionalized cellulose esters

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Abstract

Olefin 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.

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

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Publication details

The article was received on 11 Aug 2014, accepted on 01 Sep 2014 and first published on 02 Sep 2014


Article type: Paper
DOI: 10.1039/C4PY01102C
Citation: Polym. Chem., 2014,5, 7021-7033
  • Open access: Creative Commons BY-NC license
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    Olefin cross-metathesis, a mild, modular approach to functionalized cellulose esters

    X. Meng, J. B. Matson and K. J. Edgar, Polym. Chem., 2014, 5, 7021
    DOI: 10.1039/C4PY01102C

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