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

Abstract

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 1H and 13C 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.

CO2-derived non-isocyanate polyurethanes (NIPUs) and their potential applications

“…Epoxidized FO can react with CO 2 to produce cyclic carbonates. 79 Three different methods are used for the epoxidation of FO: (i) oxidation with 3-chloroperoxybenzoic acid, (ii) oxidation with hydrogen peroxide and acetic acid, catalyzed by sulphuric acid, and (iii) oxidation with hydrogen peroxide and acetic acid and (iv) oxidation with hydrogen peroxide catalyzed by formic acid. The synthesized FO epoxides are reacted with CO 2 in the presence of TBAB as the catalyst and ascorbic acid to produce cyclic FO carbonates with high conversions (Fig.…”

Click chemistry for the synthesis of biobased polymers and networks derived from vegetable oils

“…55 Furthermore, many non-isocyanate polyurethanes routes to achieving polyurethanes using vegetable oils and derivatives that have been explored. [56][57][58] Polyamides are a class of polymers commonly used as fibers for different applications, such as electric and electronic applications, or in the automotive or textile industry. They show great performance regarding heat and chemical resistance as well as toughness.…”

Silicon Oxycarbide (SiOC)-Supported Ionic Liquids: Heterogeneous Catalysts for Cyclic Carbonate Formation

“…This high demand highlights the necessity to develop synthetic routes utilizing bio-based feedstocks including terpenes, such as limonene, and vegetable oils, such as linseed oil, to become independent from crude oil as a limited fossil feedstock. The homogeneous catalysis of such bio-based cyclic carbonates is well-established, but only a few examples of heterogeneous catalysts exist in the literature. − Supports based on carboxymethyl cellulose and polyethylene have been reported. However, silica is the most used support. ,− …”