Presentation Title

The Synthesis of Croconic Acid

Faculty Mentor

Douglas Smith

Start Date

17-11-2018 8:30 AM

End Date

17-11-2018 10:30 AM

Location

CREVELING 97

Session

POSTER 1

Type of Presentation

Poster

Subject Area

biological_agricultural_sciences

Abstract

Croconic acid, a confirmed ferroelectric compound (Horiuchi, et al., Nature, 2010, 463, 789-792), was synthesized from glyoxal according to the procedure of Fatiadi (Fatiadi, et al. J. Res. Nat. Bur. Stand. 1963, 67A, 153-162) in three steps with an overall yield of 2.5%. Initially, glyoxal is condensed into the disodium salt of tetrahydroxy-p-benzoquinone under oxidative conditions. Disodium salt is then further oxidatively decarbonylated and treated with barium chloride to provide barium croconate. Treating barium croconate with sulfuric acid and heat afforded croconic acid. Croconic acid’s structure was confirmed using 13C NMR spectroscopy. Croconic acid and its salts will be further converted to other croconate salts of interest in order to determine their piezo- and ferroelectric properties.

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Nov 17th, 8:30 AM Nov 17th, 10:30 AM

The Synthesis of Croconic Acid

CREVELING 97

Croconic acid, a confirmed ferroelectric compound (Horiuchi, et al., Nature, 2010, 463, 789-792), was synthesized from glyoxal according to the procedure of Fatiadi (Fatiadi, et al. J. Res. Nat. Bur. Stand. 1963, 67A, 153-162) in three steps with an overall yield of 2.5%. Initially, glyoxal is condensed into the disodium salt of tetrahydroxy-p-benzoquinone under oxidative conditions. Disodium salt is then further oxidatively decarbonylated and treated with barium chloride to provide barium croconate. Treating barium croconate with sulfuric acid and heat afforded croconic acid. Croconic acid’s structure was confirmed using 13C NMR spectroscopy. Croconic acid and its salts will be further converted to other croconate salts of interest in order to determine their piezo- and ferroelectric properties.