Synthesis of α,β‐ and β‐Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives
[1];
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- School of Chemical, Biological and Materials Engineering University of Oklahoma Norman OK 73019 USA, Present address: Department of Chemistry Loyola College Chennai 600-034 India
- Faculty of Science and Technology Sustainable Process Technology group University of Twente Enschede 7522 NB The Netherlands
- School of Chemical, Biological and Materials Engineering University of Oklahoma Norman OK 73019 USA
- Faculty of Science and Technology Catalytic Processes and Materials group MESA+ Institute for Nanotechnology University of Twente Enschede 7522 NB The Netherlands
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 C 4 aldehydes via base‐catalyzed aldol‐condensation. Then, the resulting C 4 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.
- Sponsoring Organization:
- USDOE
- Grant/Contract Number:
- SC0018284
- OSTI ID:
- 1638531
- Journal Information:
- Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 19 Vol. 132; ISSN 0044-8249
- Publisher:
- Wiley Blackwell (John Wiley & Sons)Copyright Statement
- Country of Publication:
- Germany
- Language:
- English
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