title: Singlet-oxygen oxidation of 5-hydroxymethylfurfural in continuous flow.
abstract: Singlet-oxygen oxidation of 5-hydroxymethylfurfural (5-HMF) was performed in continuous flow mode using rose Bengal as photosensitizer. The resulting butenolide (H(2) MF) was formed selectively in high yield. The procedure proved to be scalable and applicable to related bio-based furfurals. Furthermore, preliminary data show that H(2) MF can be readily isomerized thermally to 5-hydroxy-4-keto-pentenoic acid oligomers.
authors.affiliation: Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria).
authors.forename: Thomas S A
authors.initials: TS
authors.lastname: Heugebaert
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, GhentUniversity, Coupure Links 653, 9000 Ghent (Belgium).
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
authors.affiliation: Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria). oliver.kappe@uni-graz.at.
authors.forename: C Oliver
authors.initials: CO
authors.lastname: Kappe
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D008027:Light; D010084:Oxidation-Reduction; D017319:Photosensitizing Agents / Q000737:chemistry; D012395:Rose Bengal / Q000737:chemistry; D026082:Singlet Oxygen / Q000737:chemistry*
chemical_list: D017319:Photosensitizing Agents; D026082:Singlet Oxygen; D012395:Rose Bengal; C008046:5-hydroxymethylfurfural; C004511:butenolide; D005662:Furaldehyde; D015107:4-Butyrolactone
keywords: 5-HMF; continuous flow; oxidation; photochemistry; singlet oxygen