Catalytic Aldol Condensation of 5-Hydroxymethylfurfural and its Synthesis from Concentrated Feed of Carbohydrates

Ramdani, Wahiba, Rabadán González, Inés, Benbakoura, Nora, Ahmar, Mohammed, Verrier, Charlie, Queneau, Yves, Pera Titus, Marc, Jérôme, François and De Oliveira Vigier, Karine 2023. Catalytic Aldol Condensation of 5-Hydroxymethylfurfural and its Synthesis from Concentrated Feed of Carbohydrates. ChemCatChem 15 (11) , e202300044. 10.1002/cctc.202300044

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Abstract

1-(5-(Hydroxymethyl)furan-2-yl)-5-methylhex-1-en-3-one was prepared from cellulose or glucose by a sequence of depolymerization/dehydration/aldol condensation reactions. The synthesis of HMF was first performed starting from a highly concentrated feed of glucose and cellulose (31 wt.%) using choline chloride in MIBK/water biphasic media via the formation of a glucoside intermediate. Next, the aldol condensation of HMF with MIBK was investigated over alkaline metal oxides. Among the catalysts used, commercial BaO was highly efficient with a yield of aldol product above 90 %. Under air, BaO instantaneously transformed into Ba(OH)2, H2O and BaO2 which are regarded as active phases for the reaction. The catalyst basicity and solvent were key parameters to govern the selectivity of the reaction by limiting secondary reactions.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Publisher:	Wiley
ISSN:	1867-3880
Funders:	ANR
Date of First Compliant Deposit:	15 June 2023
Date of Acceptance:	29 March 2023
Last Modified:	10 Nov 2024 18:00
URI:	https://orca.cardiff.ac.uk/id/eprint/160402

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