Synthesis of α,β- and β-Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives

Daniel Santhanaraj, Maria P. Ruiz, Mallik R. Komarneni, Tu Pham, Gengnan Li, Daniel E. Resasco, Jimmy Faria*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)
63 Downloads (Pure)

Abstract

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 (62 % yield). Using a sequential epoxidation and hydrogenation of crotonic acid leads to 29 % 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 21 % 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.

Original languageEnglish
Pages (from-to)7456-7460
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number19
Early online date13 Feb 2020
DOIs
Publication statusPublished - 4 May 2020

Keywords

  • UT-Hybrid-D
  • Chemical building blocks
  • Polyhydroxyalkanoates
  • Tandem chemistry
  • Unsaturated acids
  • Bioethanol

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