Levulinic acid is produced from the acidic aqueous degradation of 5-hydroxymethylfurfural, with potential applications in bio-value added chemicals synthesis. Here, we report for the first time, the Baeyer-Villiger oxidation of levulinic acid to succinic acid, with hydrogen peroxide and tungstic acid at mild conditions and without any organic solvent. We investigated the effects of time, amount of reagent-to-catalyst molar ratio and H2O2-to-levulinic acid molar ratio. The maximum succinic acid selectivity was 75% with a levulinic acid conversion as high as 48%, after 6 h at 90 °C. We propose a reaction mechanism based on results obtained from the reactivity of the intermediates. The catalyst interacts with the substrate, forming a cyclic species that enhances the formation of succinic acid versus 3-hydroxypropanoic acid.
Levulinic acid upgrade to succinic acid with hydrogen peroxide / Carnevali, Davide; Rigamonti, Marco G.; Tabanelli, Tommaso; Patience, Gregory S.; Cavani, Fabrizio*. - In: APPLIED CATALYSIS A: GENERAL. - ISSN 0926-860X. - STAMPA. - 563:(2018), pp. 98-104. [10.1016/j.apcata.2018.06.034]
Levulinic acid upgrade to succinic acid with hydrogen peroxide
Carnevali, Davide;Tabanelli, Tommaso;Cavani, Fabrizio
2018
Abstract
Levulinic acid is produced from the acidic aqueous degradation of 5-hydroxymethylfurfural, with potential applications in bio-value added chemicals synthesis. Here, we report for the first time, the Baeyer-Villiger oxidation of levulinic acid to succinic acid, with hydrogen peroxide and tungstic acid at mild conditions and without any organic solvent. We investigated the effects of time, amount of reagent-to-catalyst molar ratio and H2O2-to-levulinic acid molar ratio. The maximum succinic acid selectivity was 75% with a levulinic acid conversion as high as 48%, after 6 h at 90 °C. We propose a reaction mechanism based on results obtained from the reactivity of the intermediates. The catalyst interacts with the substrate, forming a cyclic species that enhances the formation of succinic acid versus 3-hydroxypropanoic acid.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
