The Preparation of Croconic and Rhodizonic Acid

Event Center A&B

Ferroelectric molecules are electro-active materials that can store and switch their polarities. It has been determined that croconic acid, in its crystallized form, is ferroelectric. Croconic acid is a dihydroxy triketone having a five-carbon ring. It is hypothesized that the similar six-carbon ring, rhodizonic acid, may also be ferroelectric. The purpose of our research is to synthesize and crystallize croconic acid to confirm its ferroelectric properties, and then synthesize and crystallize rhodizonic acid to determine if it has ferroelectric properties as well. Croconic acid is prepared through a multi-step synthesis: Glyoxal is used to prepare the disodium salt of tetrahydroxy-p-benzoquinone; the disodium salt is then converted into barium croconate which is then converted to croconic acid. Rhodizonic acid, whose structure is similar to that of croconic acid, is synthesized starting from the disodium salt of tetrahydroxyp-benzoquinone, by a series of oxidation reactions. If rhodizonic acid is determined to be ferroelectric, then rhodizonic acid and croconic acid may prove to have some interesting commercial applications.