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Olefin cross-metathesis as a source of polysaccharide derivatives: Cellulose ω-carboxyalkanoates

Biomacromolecules, ISSN: 1525-7797, Vol: 15, Issue: 1, Page: 177-187
2014
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Article Description

Cross-metathesis has been shown for the first time to be a useful method for the synthesis of polysaccharide derivatives, focusing herein on preparation of cellulose ω-carboxyalkanoates. Commercially available cellulose esters were first acylated with 10-undecenoyl chloride, providing esters with olefin-terminated side chains. Subsequent cross-metathesis of these terminal olefin moieties with acrylic acid was performed in solvents including acrylic acid, THF, and CHCl. Complete conversion to discrete, soluble cross-metathesis products was achieved by using the Hoveyda-Grubbs second generation ruthenium catalyst and an excess of acrylic acid. Oligomerization during storage, caused by a free radical mechanism, was observed and successfully suppressed by the addition of a free radical scavenger (BHT). Furthermore, the cross-metathesis products exhibited glass transition temperatures (T) that were at least 50 C higher than ambient temperature, supporting the potential for application of these polymers as amorphous solid dispersion matrices for enhancing drug aqueous solubility. © 2013 American Chemical Society.

Bibliographic Details

Meng, Xiangtao; Matson, John B; Edgar, Kevin J

American Chemical Society (ACS)

Chemical Engineering; Materials Science

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