The aim of this project was to develop a renewable polyurethane from a dihydrocarvide- and menthide-based polyamine. Synthesis of dihydrocarvide presented difficulties due to unwanted side products. Previously published procedures for the Baeyer-Villiger oxidation of dihydrocarvone to dihydrocarvide produced a mixture: 60% desired lactone and 40% epoxide. Optimal synthesis of dihydrocarvide was studied through the addition of various salts, Lewis acids, and oxidants. Superior results were ultimately obtained through the use of catalytic amounts of oxidants including sodium molybdate, potassium permanganate, and Dess-Martin periodinane. These conditions led to lactone in 96-98% purity by <sup>1</sup>H NMR and an isolated yield of 85%. Subsequent copolymerization of menthide and dihydrocarvide was successful with good control of polymer molar masses determined from <sup>1</sup>H NMR spectra. Polyamine synthesis studies are ongoing.

Synthesis of sustainable monomers for a polyurethane

249th National Meeting (2015)

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