Syntheses of 5-hydroxymethylfurfural and levoglucosan by selective dehydration of glucose using solid acid and base catalysts

Mika Ohara, Atsushi Takagaki, Shun Nishimura, Kohki Ebitani

Research output: Contribution to journalArticle

138 Citations (Scopus)

Abstract

Selective dehydration of glucose, the most abundant monosaccharide, was examined using a solid acid catalyst individually or a combination of solid acid and base catalysts to form anhydroglucose (levoglucosan) or 5-hydroxymethylfurfural (HMF), respectively. Glucose was dehydrated to anhydroglucose by acid catalysis in polar aprotic solvents including N,N-dimethylformamide. Amberlyst-15, a strongly acidic ion-exchange resin, functioned as an efficient solid acid catalyst for anhydroglucose production with high selectivity. In the presence of solid base, aldose-ketose isomerization of glucose to fructose preferentially occurred by base catalysis, even in coexistence with the solid acid, resulting in successive dehydration of fructose to 5-hydroxymethylfurfural by acid catalysis with high yield in a one-pot reaction. A combination of Amberlyst-15 and hydrotalcite, an anionic layered clay, afforded high HMF selectivity under a moderate reaction temperature, owing to prevention of anhydroglucose formation.

Original languageEnglish
Pages (from-to)149-155
Number of pages7
JournalApplied Catalysis A: General
Volume383
Issue number1-2
DOIs
Publication statusPublished - Jul 31 2010
Externally publishedYes

Fingerprint

Dehydration
Glucose
Catalysts
Acids
Catalysis
Fructose
hydrotalcite
Ketoses
Ion Exchange Resins
Dimethylformamide
Ion exchange resins
Monosaccharides
Catalyst selectivity
Isomerization
5-hydroxymethylfurfural
1,6-anhydro-beta-glucopyranose
Clay
Temperature

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Process Chemistry and Technology

Cite this

Syntheses of 5-hydroxymethylfurfural and levoglucosan by selective dehydration of glucose using solid acid and base catalysts. / Ohara, Mika; Takagaki, Atsushi; Nishimura, Shun; Ebitani, Kohki.

In: Applied Catalysis A: General, Vol. 383, No. 1-2, 31.07.2010, p. 149-155.

Research output: Contribution to journalArticle

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