Synthesis of a Renewable, Waste-Derived Nonisocyanate Polyurethane from Fish Processing Discards and Cashew Nutshell-Derived Amines.

Waste-derived fish oil (FO) can be epoxidized and reacted with CO2 to produce a cyclic carbonate containing material. Upon reaction with a bioderived amine, this leads to the formation of nonisocyanate polyurethane materials. The FO used is extracted from the by-products produced at fish processing plants, including heads, bones, skin, and viscera. Three different methods are 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. Synthesized FO epoxides are reacted with CO2 to yield FO cyclic carbonates with high conversions. The products are characterized by 1 H and 13 C NMR spectroscopy, IR spectroscopy, thermogravimetric analysis, and viscometry. Using a biomass-derived amine, nonisocyanate polyurethane materials are synthesized. This process can lead to new opportunities in waste management, producing valuable materials from a resource that is otherwise underutilized.