Chapter 7: Reactions of Mixed Natural Acids and Esters in Acidic Media
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Published:22 Dec 2023
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Special Collection: 2023 ebook collectionSeries: Green Chemistry Series
W. J. Bradley, Y. Qu, Z. Crandall, T. L. Windus, and G. A. Kraus, in Green Chemistry and Green Materials from Plant Oils and Natural Acids, ed. Z. Liu and G. Kraus, Royal Society of Chemistry, 2023, vol. 83, ch. 7, pp. 135-143.
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Citric acid and malic acid are renewable organic acids with considerable market size. The reaction between the two acids in sulfuric acid at 80 °C gave an unexpected pyrone diacid. A mixture of dimethyl malate and trimethyl citrate gave a pyrone diester. These pyrones were produced in good yields on a multigram scale. The pyrone diacid represents a potentially useful monomer. Molecular electrostatic potential surfaces and dipole moments were calculated for ethyl butyrate and 4-hydroxy-6-methyl-alpha-pyrone.