Synthesis and Characterization of Furanic Compounds

Report No. ARL-TR-6668
Authors: LaShonda T. Cureton; John J. La Scala
Date/Pages: September 2013; 24 pages
Abstract: Furans have been investigated in many chemical syntheses for specialty chemicals and polymers. Furans are attractive compounds because they are chemically obtainable through the catalytic decarbonylation of furfural, which is obtain through chemical modification of hemicelluloses (xylose). We seek to further develop biobased furanic materials with the goal of obtaining polymers with high Tg and mechanical properties. This report details the synthesis of monomers necessary for the production of high-performance furan-based polymers analogous to Kevlar, nylon, epoxies, and other high-performance polymers. We used conventional synthetic organic chemistry to prepare monomers including furan-2-carbonyl azide; 2-furanamine; 2,2'-Methylenedifuran; di(2-furyl)methanone; 2,5-furan dicarboxylic acid; 2,5-furan dicarboxylic acid chloride; and 2,5-furan diamide. The monomers were purified using extraction methods and characterized using nuclear magnetic resonance spectroscopy. The monomers were produced at high purity and in good yields.
Distribution: Approved for public release
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Last Update / Reviewed: September 1, 2013