Fast and efficient DMSO-mediated dehydration of carbohydrates into 5-hydroxymethylfurfural

Dehydration of monoaldoses and aldoketoses under catalyst-free conditions has been studied varying the solvent nature, the concentration and the heating mode (conventional or microwaves). Best results were obtained in dimethylsulfoxide (DMSO) indicating that DMSO has a dual role: solvent and reactio...

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Bibliographic Details
Published in:Catalysis communications 2014-06, Vol.51, p.5-9
Main Authors: Despax, Solenne, Maurer, Carole, Estrine, Boris, Le Bras, Jean, Hoffmann, Norbert, Marinkovic, Sinisa, Muzart, Jacques
Format: Article
Language:English
Subjects:
Carbohydrates
Chemical Sciences
Dehydration
HMF
Microwave chemistry
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Summary:Dehydration of monoaldoses and aldoketoses under catalyst-free conditions has been studied varying the solvent nature, the concentration and the heating mode (conventional or microwaves). Best results were obtained in dimethylsulfoxide (DMSO) indicating that DMSO has a dual role: solvent and reaction mediator. Thus, d-fructose provided 5-hydroxymethylfurfural (HMF) in up to 92% yield after only 4min under microwave irradiation. Under similar experimental conditions, inulin and l-sorbose afforded HMF in yields up to 47% and 76%, respectively, while d-xylose yielded up to 25% of furfural under conventional heating. [Display omitted] •Dehydration of monoaldoses and aldoketoses under catalyst-free conditions.•Dimethylsulfoxide has a dual role, solvent and reaction mediator.•Up to 92 % yield of HMF from D-fructose after 4min.•Other 6 and 5 atom carbon carbohydrates tested in cyclodehydration.
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2014.03.009