Synthesis of α,β- and β-Unsaturated Acids and Hydroxy Acids by Tandem Oxidation,Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives |
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Authors: | Dr Daniel Santhanaraj Prof Maria P Ruiz Dr Mallik R Komarneni Dr Tu Pham Dr Gengnan Li Prof Daniel E Resasco Prof Jimmy Faria |
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Institution: | 1. School of Chemical, Biological and Materials Engineering, University of Oklahoma, Norman, OK, 73019 USA;2. Faculty of Science and Technology, Sustainable Process Technology group, University of Twente, Enschede, 7522 NB, The Netherlands;3. Faculty of Science and Technology, Catalytic Processes and Materials group, MESA+ Institute for Nanotechnology, University of Twente, Enschede, 7522 NB, The Netherlands |
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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. |
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Keywords: | Bioethanol Chemische Bausteine Polyhydroxyalkanoate Tandemchemie Ungesättigte Säuren |
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