Cyclobutane tetracarboxylic acids (CBTAs) and their derivatives (e.g., anhydride) are versatile precursors that can be used in making polyimides, polyamides, polyesters, metal organic frameworks, and in the synthesis of energetic materials. Herein, two ecofriendly methods have been used to synthesize cyclobutane-1,2,3,4-tetracarboxylic acid (CBTA-1) and its anhydride derivative directly from maleic and fumaric acids. We further demonstrated that the cyclobutane ring in all these molecules have desirable physical properties, such as good thermostability for materials synthesis. The photo energy used to fuse the olefin molecules to form the four-membered carbon ring were from germicidal lamps, which represent an ECO-UV (Energy-efficient, Cost-effective, and Operator-friendly) source.  Meanwhile, several studies have already described the synthesis of maleic and fumaric acids from biomass derived carbohydrates and other lignocellulosic biomass via furfural. Fumaric acid produced by fermentation of biomass, has been listed as one of the top value-added chemicals from biomass by the US Department of Energy (DOE). Thus, these cyclobutane-containing compounds may serve as potential building blocks for the production of a variety of green materials, especially polymeric products.

Ecofriendly methods to synthesize cyclobutane-1,2,3,4-tetracarboxylic acid and its derivatives from maleic and fumaric acids

ACS Fall 2021

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