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The “one-pot” synthesis of 2,5-diformylfuran, a promising synthon for organic materials in the conversion of biomass

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Abstract

The organic ionic oxidant 4-acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate, [Pip*(O)][BF4], was found to be compatible with both classical organic solvents and the ionic liquids [BMIm][Cl]/[BMIm][BF4] (BMIm is 1-butyl-3-methylimidazolium), which are essential in the conversion of cellulose biomass. A unique NMR monitoring procedure developed in our group was used to study the conversion of fructose to 2,5-diformylfuran in ionic liquids. This process can successfully be carried out in a “one-pot” fashion; [Pip*(O)][BF4] efficiently oxidizes intermediate 5-hydroxymethylfurfural. The reaction is highly selective, giving 2,5-diformylfuran in 95% yield.

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Authors and Affiliations

  1. M. I. Platov South-Russian State Polytechnic University (NPI), 132 ul. Prosveshcheniya, 346428, Novocherkassk, Russian Federation

    V. P. Kashparova & V. M. Chernyshev

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    E. A. Khokhlova, K. I. Galkin & V. P. Ananikov

Authors
  1. V. P. Kashparova
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  2. E. A. Khokhlova
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  3. K. I. Galkin
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  4. V. M. Chernyshev
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  5. V. P. Ananikov
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Corresponding author

Correspondence to V. P. Ananikov.

Additional information

On the occasion of the 100th anniversary of the birth of Academician N. K. Kochetkov (1915—2005).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1069—1073, May, 2015.

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Kashparova, V.P., Khokhlova, E.A., Galkin, K.I. et al. The “one-pot” synthesis of 2,5-diformylfuran, a promising synthon for organic materials in the conversion of biomass. Russ Chem Bull 64, 1069–1073 (2015). https://doi.org/10.1007/s11172-015-0979-2

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  • DOI: https://doi.org/10.1007/s11172-015-0979-2

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