Presentation Title

Towards the Synthesis of Fatty Acid Methyl Esters Containing Amines

Start Date

November 2016

End Date

November 2016

Location

HUB 302-#147

Type of Presentation

Poster

Abstract

Petroleum is a finite resource used ubiquitously as a fuel and in the manufacture of plastic materials. Due to the growing concerns regarding the environmental impact and future of petroleum as a chemical feedstock, extensive efforts have focused on curtailing the world’s dependence on oil. Previously, in the Page group, seed oils have been chemically modified and cross-linked using diisocyanate to form carbamates. Diisocyanate, however, is acutely toxic and exposure often causes severe respiratory problems in addition to being a detriment to the environment.

The goal of this current project is to synthesize a 100% green polyurethane that is diisocyanate-free. This methodology involves the synthesis of a fatty acid methyl ester (FAME) derivative with two amine moieties. In the first step towards synthesizing the amine, the alkenes on the fatty acid chain are converted to diols, which display a key 13C NMR resonance at 71.9 ppm. In the subsequent step, the diols are oxidized to ketones using Dess-Martin periodinane, which display a key 13C NMR resonance at 211.6 ppm. In the future, the ketones will undergo a reductive amination in the presence of Raney-Nickel as a catalyst, to arrive at the desired monomer. Following characterization, the diamine will be polymerized with a cyclic carbamate to ultimately yield a green material based on renewable starting materials.

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Nov 12th, 4:00 PM Nov 12th, 5:00 PM

Towards the Synthesis of Fatty Acid Methyl Esters Containing Amines

HUB 302-#147

Petroleum is a finite resource used ubiquitously as a fuel and in the manufacture of plastic materials. Due to the growing concerns regarding the environmental impact and future of petroleum as a chemical feedstock, extensive efforts have focused on curtailing the world’s dependence on oil. Previously, in the Page group, seed oils have been chemically modified and cross-linked using diisocyanate to form carbamates. Diisocyanate, however, is acutely toxic and exposure often causes severe respiratory problems in addition to being a detriment to the environment.

The goal of this current project is to synthesize a 100% green polyurethane that is diisocyanate-free. This methodology involves the synthesis of a fatty acid methyl ester (FAME) derivative with two amine moieties. In the first step towards synthesizing the amine, the alkenes on the fatty acid chain are converted to diols, which display a key 13C NMR resonance at 71.9 ppm. In the subsequent step, the diols are oxidized to ketones using Dess-Martin periodinane, which display a key 13C NMR resonance at 211.6 ppm. In the future, the ketones will undergo a reductive amination in the presence of Raney-Nickel as a catalyst, to arrive at the desired monomer. Following characterization, the diamine will be polymerized with a cyclic carbamate to ultimately yield a green material based on renewable starting materials.