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- Title
Synthesis of α,β‐ and β‐Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives.
- Authors
Santhanaraj, Daniel; Ruiz, Maria P.; Komarneni, Mallik R.; Pham, Tu; Li, Gengnan; Resasco, Daniel E.; Faria, Jimmy
- 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.
- Subjects
HYDROXY acids; CROTONIC acid; ETHANOL as fuel; EPOXIDATION; SPECIALTY chemicals; OXIDATIVE dehydrogenation
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 19, p7526
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202002049