Synthesis of non-isocyanate polyurethanes from waste-derived fish oil

Laprise, Courtney M. (2019) Synthesis of non-isocyanate polyurethanes from waste-derived fish oil. Masters thesis, Memorial University of Newfoundland.

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Abstract

Waste-derived fish oil (FO) can be epoxidized, reacted with CO₂ to produce cyclic carbonates, then reacted with an amine to form non-isocyanate polyurethane materials. The FO used was previously extracted from the by-products produced at fish processing plants, including heads, bones, skin and viscera. Extracting oil from these waste products and using it as a feedstock reduces the amount of waste generated by fish processing plants. Three different methods were used for the epoxidation of the FO: (i) oxidation by 3-chloroperoxybenzoic acid, (ii) oxidation by hydrogen peroxide and acetic acid, catalyzed by sulfuric acid, and (iii) oxidation by hydrogen peroxide catalyzed by formic acid. A gate-to-gate life cycle assessment of the epoxidation methods was performed, showing the formic acid reaction is the greenest route to the formation of FO epoxides. Synthesized FO epoxides were reacted with CO₂ to yield FO cyclic carbonates. The optimum conditions used 3.9 mol% tetrabutylammonium bromide and 2.0 mol% ascorbic acid (vitamin C) with respect to epoxy-groups in the starting material to form cyclic carbonates with a conversion of 90%. The products were characterized by ¹H and ¹³C NMR spectroscopy, IR spectroscopy, and TGA. The FO carbonates were used to produce sustainable, bio-sourced polyurethanes. Using a biomass-derived amine, non-isocyanate polyurethane materials were synthesized and preliminary studies towards their degradation in aqueous solutions was performed. This process could lead to new opportunities in waste management, producing valuable materials from a resource that is otherwise underutilized.

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