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Russian Chemical Bulletin

, Volume 64, Issue 5, pp 1069–1073 | Cite as

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

  • V. P. Kashparova
  • E. A. Khokhlova
  • K. I. Galkin
  • V. M. Chernyshev
  • V. P. Ananikov
Full Articles

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.

Keywords

2,5-diformylfuran ionic liquids carbohydrates biomass NMR monitoring 5-hydroxymethylfurfural 

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References

  1. 1.
    C. Chatterjee, F. Pong, A. Sen, Green Chem., 2015, 17, 40.CrossRefGoogle Scholar
  2. 2.
    E. L. Kunkes, D. A. Simonetti, R. M. West, J. C. SerranoRuiz, C. A. Gartner, J. A. Dumesic, Science, 2008, 322, 417.CrossRefGoogle Scholar
  3. 3.
    J. N. Chheda, J. A. Dumesic, Catal. Today, 2007, 123, 59.CrossRefGoogle Scholar
  4. 4.
    P. Gallezort, Chem. Soc. Rev., 2012, 41, 1538.CrossRefGoogle Scholar
  5. 5.
    H. W. Blanch, B. A. Simmons, D. Klein-Marcuschamer, Biotechnol. J., 2011, 6, 1086.CrossRefGoogle Scholar
  6. 6.
    P. N. R. Vennestrm, C. M. Osmundsen, C. H. Christensen, E. Taarning, Angew. Chem., Int. Ed. Engl., 2011, 50, 10502.CrossRefGoogle Scholar
  7. 7.
    M. E. Zakrzewska, E. Bogel-Lukasik, R. Bogel-Lukasik, Chem. Rev., 2011, 111, 397.CrossRefGoogle Scholar
  8. 8.
    M. Chidambaram, A. Bell, Green Chem., 2010, 12, 1253.CrossRefGoogle Scholar
  9. 9.
    E. A. Khokhlova, V. V. Kachala, V. P. Ananikov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 830 [Izv. Akad. Nauk, Ser. Khim., 2013, 829].CrossRefGoogle Scholar
  10. 10.
    S. Lima, P. Neves, M. M. Antunes, M. Pillinger, N. Ignatyev, A. A. Valente, Appl. Catal., A, 2009, 363, 93.CrossRefGoogle Scholar
  11. 11.
    X. Qu, M. Watanabe, T. M. Smith, R. L. Smith, Green Chem., 2009, 11, 1327.CrossRefGoogle Scholar
  12. 12.
    R.-J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra, H. J. Heeres, J. G. de Vries, Chem. Rev., 2013, 113, 1499.CrossRefGoogle Scholar
  13. 13.
    M. Dashtban, A. Gilbert, P. Fatehi, RSC Adv., 2014, 4, 2037.CrossRefGoogle Scholar
  14. 14.
    A. S. Amarasekara, in Renewable Polymers: Synthesis, Processing, and Technology, Ed. V. Mittal, John Wiley and Sons, Inc., Hoboken, 2011, p. 398.Google Scholar
  15. 15.
    T. Xiang, X. Liu, P. Yi, M. Guo, Y. Chen, C. Wesdemiotis, J. Xu, Y. Pang, Polym. Int., 2013, 62, 1517.CrossRefGoogle Scholar
  16. 16.
    T. S. Hansen, I. Sádaba, E. J. García-Suárez, A. Riisager, Appl. Catal., A, 2013, 456, 44.CrossRefGoogle Scholar
  17. 17.
    A. Takagaki, M. Takahashi, S. Nishimura, K. Ebitani, ACS Catal., 2011, 1, 1562.CrossRefGoogle Scholar
  18. 18.
    J. Nie, J. Xie, H. Liu, J. Catal., 2013, 301, 83.CrossRefGoogle Scholar
  19. 19.
    Y. Zhu, M. Shen, Y. Xia, M. Lu, Catal. Commun., 2015, 64, 37.CrossRefGoogle Scholar
  20. 20.
    X. Tong, Y. Sun, X. Bai, Y. Li, RSC Adv., 2014, 4, 44307.CrossRefGoogle Scholar
  21. 21.
    G. A. Halliday, R. J. Young, V. V. Grushin, Org. Lett., 2003, 5, 2003.CrossRefGoogle Scholar
  22. 22.
    Z.-Z. Yang, J. Deng, T. Pan, Q.-X. Guo, Y. Fu, Green Chem., 2012, 14, 2986.CrossRefGoogle Scholar
  23. 23.
    F. L. Grasset, B. Katryniok, S. Paul, V. Nardello-Rataj, M. Pera-Titus, J.-M. Clacens, F. De Campo, F. Dumeignil, RSC Adv., 2013, 3, 9942.CrossRefGoogle Scholar
  24. 24.
    L. Cottier, G. Descotes, E. Viollet, J. Lewkowski, R. Skowrosski, J. Heterocycl. Chem., 1995, 32, 927.CrossRefGoogle Scholar
  25. 25.
    B. Karimi, H. M. Mirzaei, E. Farhangi, ChemCatChem, 2014, 6, 758.CrossRefGoogle Scholar
  26. 26.
    M. Krystof, M. Pérez-Sánchez, P. Domínguez de María, ChemSusChem, 2013, 6, 826.CrossRefGoogle Scholar
  27. 27.
    J. Nie, H. Liu, J. Catal., 2014, 316, 57.CrossRefGoogle Scholar
  28. 28.
    H. Mehdi, A. Bodor, D. Lantos, I. T. Horváth, D. E. De Vos, K. Binnemans, J. Org. Chem., 2007, 72, 517.CrossRefGoogle Scholar
  29. 29.
    Y. Yan, X. Tong, K. Wang, X. Bai, Catal. Commun., 2014, 43, 112.CrossRefGoogle Scholar
  30. 30.
    K. K. Yadav, S. Ahmad, S. M. S. Chauhan, J. Mol. Catal. A: Chem., 2014, 394, 170.CrossRefGoogle Scholar
  31. 31.
    R. A. Miller, R. S. Hoerrer, Org. Lett., 2003, 5, 285.CrossRefGoogle Scholar
  32. 32.
    Z. Ma, J. M. Bobbitt, J. Org. Chem., 1991, 56, 6110.CrossRefGoogle Scholar
  33. 33.
    J. M. Bobbitt, Chem. Eng. News, 1999, 4, 6.Google Scholar
  34. 34.
    J. M. Bobbitt, N. Merbough, Org. Synth., 2005, 82, 80.CrossRefGoogle Scholar
  35. 35.
    W. F. Bailey, J. M. Bobbitt, K. B. Wieberg, J. Org. Chem., 2007, 72, 4504.CrossRefGoogle Scholar
  36. 36.
    J. C. Qiu, P. P. Pradhan, J. M. Bobbitt, W. F. Bailey, Org. Lett., 2012, 14, 350.CrossRefGoogle Scholar
  37. 37.
    M. M. Mercadante, C. B. Kelly, J. M. Bobbitt, L. J. Tilley, N. E. Leadbeater, Nat. Protoc., 2013, 8, 666.CrossRefGoogle Scholar
  38. 38.
    E. A. Khokhlova, V. V. Kachala, V. P. Ananikov, ChemSusChem, 2012, 5, 783.CrossRefGoogle Scholar
  39. 39.
    V. P. Ananikov, Chem. Rev., 2011, 111, 418.CrossRefGoogle Scholar
  40. 40.
    R. Ciriminna, J. Blum, D. Avnir, M. Pagliaro, Chem. Commun., 2000, 1441.Google Scholar
  41. 41.
    C. Bolm, T. Fey, Chem. Commun., 1999, 1795.Google Scholar
  42. 42.
    V. P. Ananikov, E. A. Khokhlova, M. P. Egorov, A. M. Sakharov, S. G. Zlotin, A. V. Kucherov, L. M. Kustov, M. L. Gening, N. E. Nifantiev, Mendeleev Commun., 2015, 25, 75.CrossRefGoogle Scholar
  43. 43.
    N. Mittal, G. M. Nisola, L. B. Malihan, J. G. Seo, S.-P. Lee, W.-J. Chung, Korean J. Chem. Eng., 2014, 31, 1362.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • V. P. Kashparova
    • 1
  • E. A. Khokhlova
    • 2
  • K. I. Galkin
    • 2
  • V. M. Chernyshev
    • 1
  • V. P. Ananikov
    • 2
  1. 1.M. I. Platov South-Russian State Polytechnic University (NPI)NovocherkasskRussian Federation
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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