Get access
Advertisement

NaBr/DMSO-Induced Synthesis of 2,5-Diformylfuran from Fructose or 5-(Hydroxymethyl)furfural

Authors

  • Dr. Caroline Laugel,

    1. Green Chemistry Department, Agro-industrie Recherches et Développements, Route de Bazancourt, Pomacle 51110 (France)
    2. Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS-Université de Reims Champagne-Ardenne, UFR des Sciences Exactes et Naturelles, Reims 51100 (France)
    Search for more papers by this author
  • Dr. Boris Estrine,

    Corresponding author
    1. Green Chemistry Department, Agro-industrie Recherches et Développements, Route de Bazancourt, Pomacle 51110 (France)
    • Boris Estrine, Green Chemistry Department, Agro-industrie Recherches et Développements, Route de Bazancourt, Pomacle 51110 (France)===

      Jean Le Bras, Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS-Université de Reims Champagne-Ardenne, UFR des Sciences Exactes et Naturelles, Reims 51100 (France)===

    Search for more papers by this author
  • Dr. Jean Le Bras,

    Corresponding author
    1. Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS-Université de Reims Champagne-Ardenne, UFR des Sciences Exactes et Naturelles, Reims 51100 (France)
    • Boris Estrine, Green Chemistry Department, Agro-industrie Recherches et Développements, Route de Bazancourt, Pomacle 51110 (France)===

      Jean Le Bras, Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS-Université de Reims Champagne-Ardenne, UFR des Sciences Exactes et Naturelles, Reims 51100 (France)===

    Search for more papers by this author
  • Dr. Norbert Hoffmann,

    1. Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS-Université de Reims Champagne-Ardenne, UFR des Sciences Exactes et Naturelles, Reims 51100 (France)
    Search for more papers by this author
  • Dr. Sinisa Marinkovic,

    1. Green Chemistry Department, Agro-industrie Recherches et Développements, Route de Bazancourt, Pomacle 51110 (France)
    Search for more papers by this author
  • Dr. Jacques Muzart

    1. Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS-Université de Reims Champagne-Ardenne, UFR des Sciences Exactes et Naturelles, Reims 51100 (France)
    Search for more papers by this author

Abstract

2,5-Diformylfuran (DFF) was obtained by heating a solution of 5-(hydroxymethyl)furfural in DMSO. The addition of acids or salts improved the selectivity, especially if bromides were employed. Good yields of DFF were obtained with HBr or NaBr as the catalyst. One-pot procedures were developed from fructose, which led to DFF in medium yields. This transformation occurs through the formation of 5-(bromomethyl)furan-2-carbaldehyde followed by a Kornblum-type reaction. In the presence of bromide salts, the in situ formation of the catalyst involves the thermolysis of DMSO and the association of the resulting strong acids with the bromides.

Get access to the full text of this article

Ancillary