Strategies for synthesis of epoxy resins from oleic acid derived from food wastes

The use of biomass-sourced chemical feedstocks creates a conflict over land use between food and fuel/chemical production. Such conflict could be reduced by making use of the annual 1.3 Pg food waste resource. Oleic acid is available from seed oils such as pumpkin, grape, avocado and mango. Its esterification with diols 1,3-propanediol, resorcinol and orcinol was used to form diesters and the naturally occurring norspermidine was used to prepare a diamide, all under ambient conditions. These compounds were then epoxidized and polymerized. When esterification was followed by epoxidation and subsequent curing at elevated temperature with p-phenylenediamine or diethylenetriamine, hard insoluble resins were formed. When the sequence was changed such that the epoxidized oleic acid was first reacted with cis-1,2-cyclohexanedicarboxylic anhydride and then esterified with orcinol and resorcinol, insoluble crosslinked polymers were also obtained. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3159–3170