Decarboxylative Ketonization of Aliphatic Carboxylic Acids in a Continuous Flow Reactor Catalysed by Manganese Oxide on Silica.

Autor: Goebel JF; Chair of Organic Chemistry I, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, 44801, Bochum, Germany., Belitz F; Chair of Organic Chemistry I, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, 44801, Bochum, Germany., Prendes DS; Chair of Organic Chemistry I, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, 44801, Bochum, Germany., Haver Y; Laboratory of Industrial Chemistry, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, 44801, Bochum, Germany., Diehl P; Laboratory of Industrial Chemistry, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, 44801, Bochum, Germany., Muhler M; Laboratory of Industrial Chemistry, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, 44801, Bochum, Germany., Gooßen LJ; Chair of Organic Chemistry I, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, 44801, Bochum, Germany.
Jazyk: angličtina
Zdroj: ChemSusChem [ChemSusChem] 2024 Jul 22; Vol. 17 (14), pp. e202400094. Date of Electronic Publication: 2024 May 18.
DOI: 10.1002/cssc.202400094
Abstrakt: The sustainable synthesis of long carbon chain molecules from carbon dioxide, water and electricity relies on the development of waste-free, highly selective C-C bond forming reactions. An example for such a power-to-chemicals process is the industrial-scale fermentation for the production of hexanoic acid. Herein, we describe how this product is transformed into 6-undecanone via decarboxylative ketonization using a heterogeneous manganese oxide/silica catalyst. The reaction reaches full conversion with near-complete selectivity when carried out in a continuous flow reactor, requires no solvent or carrier gas, and releases carbon dioxide and water as the only by-products. The reactor was operated for several weeks with no loss of reactivity, producing 7 kg of 6-undecanone from 10 g of catalyst and achieving a productivity of 1.135 kg per litre of reactor volume per hour. 6-Undecanone and other long-chain ketones accessible this way can be hydrogenated to industrially meaningful alkanes, or converted into valuable fatty acids via a hydrogenation/elimination/isomerizing hydrocarboxylation sequence.
(© 2024 The Authors. ChemSusChem published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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