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Synthesizing α,β- and β-Unsaturated Acids and Hydroxy Acids via Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol-Derivatives.

07:00 EST 13th February 2020 | BioPortfolio

Summary of "Synthesizing α,β- and β-Unsaturated Acids and Hydroxy Acids via Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol-Derivatives."

We report a reaction platform for the synthesis of three different high-value specialty chemical building blocks starting from bio-ethanol, which might have an important impact in the implementation of biorefineries. First, oxidative dehydrogenation of ethanol to acetaldehyde generates an aldehyde-containing stream active for the production of C4 aldehydes via base-catalyzed aldol-condensation. Then, the resulting C4 adduct is selectively converted into crotonic acid via catalytic aerobic oxidation (90 % yield). Using a sequential epoxidation and hydrogenation of crotonic acid leads to 70 % yield of β-hydroxy acid (3-hydroxybutanoic acid). By controlling the pH of the reaction media, it is possible to hydrolyze the oxirane moiety leading to 34 % yield of α,β-dihydroxy acid (2,3-dihydroxybutanoic acid). Crotonic acid, 3-hydroxybutanoic acid, and 2,3-dihydroxybutanoic acid are archetypal specialty chemicals used in the synthesis of polyvinyl-co-unsaturated acids resins, pharmaceutics, and bio- degradable/-compatible polymers, respectively.

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This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
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