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Aerobic oxidation of alcohols using ruthenium supported on DD3 kaolin

  • B. Zadam
  • D. Obaid
  • A. Mayoufi
  • P. Beaunier
  • F. Launay
  • F. Z. El Berrichi
Article
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Abstract

Supported ruthenium nanoparticles were prepared through the chemical reduction of aqueous Ru(III) species previously loaded (1 or 5 wt%) onto DD3 kaolin through an ion-exchanged pathway. Resulting nanoporous materials were characterized by XRF, XRD, TEM, EDX, and N2 sorption measurements, and then used as catalysts in the liquid phase aerobic oxidation of benzyl alcohol. Benzaldehyde was obtained as the main product with a 97% yield at 100% alcohol conversion at 100 °C in the presence of Ru-DD3 (5%) using 10 mL/min O2 flow and 10 mol% of tert-butyl hydroperoxide with respect to the substrate. Oxidation tests were more efficient in the case of Ru-DD3 (5%) than with other Ru-based solids such as Ru-HZSM-5 (5%). It was also shown that, in the presence of Ru-DD3 (5%), the aerobic oxidation of benylalcohol in the presence of an amine (aniline) gives rise to the imine instead of the aldehyde through a one-pot oxidation and condensation process.

Keywords

Aerobic oxidation Benzyl alcohol Ru nanoparticles DD3 ZSM-5 SBA-15 

Notes

Acknowledgements

One of us, Besma Zadam thanks the Algerian government and her university for allowing her to spend a 2-month scientific stay in France at the Laboratoire de Réactivité de Surface. We are also grateful to Dr. Christophe Methivier for carrying out XPS experiments and the analysis of the data.

References

  1. 1.
    J.I. Kroschwitz, K. Othmer, Encyclopedia of Chemical Technology, vol. 4, 4th edn. (Wiley-Interscience Publication, New York, 1992)Google Scholar
  2. 2.
    T. Mallat, A. Baiker, Chem. Rev. 104, 3037 (2004)CrossRefGoogle Scholar
  3. 3.
    F. Adam, E.A. Sugiarmawan, J. Porous Mater. 16, 321 (2009)CrossRefGoogle Scholar
  4. 4.
    G. Cainelli, G. Cardillo, Chromium Oxidants in Organic Chemistry (Springer, Berlin, 1984)CrossRefGoogle Scholar
  5. 5.
    D.G. Lee, U.A. Spitzer, J. Org. Chem. 35, 3589 (1970)CrossRefGoogle Scholar
  6. 6.
    B.M. Choudary, M.L. Kantam, P.L. Santhi, Catal. Today 57, 17 (2000)CrossRefGoogle Scholar
  7. 7.
    M. Besson, P. Gallezot, Catal. Today 57, 127 (2000)CrossRefGoogle Scholar
  8. 8.
    I.W.C.E. Arends, R.A. Sheldon, in Modern Oxidation Methods of Alcohols Using Environmentally Benign Oxidants, ed. by E. Bäckvall (Wiley-VCH, Weinheim, 2004), p. 147Google Scholar
  9. 9.
    B.Z. Zhan, A. Thompson, Tetrahedron 60, 2917 (2004)CrossRefGoogle Scholar
  10. 10.
    T. Mallat, A. Baiker, Catal. Today 19, 247 (1994)CrossRefGoogle Scholar
  11. 11.
    R.A. Sheldon, I.W.C.E. Arends, A. Dijksman, Catal. Today 57, 157 (2000)CrossRefGoogle Scholar
  12. 12.
    A.P. Markusse, B.F.M. Kuster, J.C. Schouten, J. Mol. Catal. A 158, 215 (2000)CrossRefGoogle Scholar
  13. 13.
    J. Muzart, Tetrahedron 59, 5789 (2003)CrossRefGoogle Scholar
  14. 14.
    S. Rostamnia, S. Kholdi, Adv. Powder Technol. 29, 1167 (2018)CrossRefGoogle Scholar
  15. 15.
    E. Doustkhah, S. Rostamnia, B. Gholipour, B. Zeynizadeh, A. Baghban, R. Luque, Mol. Catal. 434, 7 (2017)CrossRefGoogle Scholar
  16. 16.
    S. Rostamnia, E. Doustkhah, Z. Karimi, S. Amini, R. Luque, ChemCatChem 1678, 7 (2015)Google Scholar
  17. 17.
    E.J. García-Suárez, M. Tristany, A.B. García, V. Collière, K. Philippot, Microporous Mesoporous Mater. 153, 155 (2012)CrossRefGoogle Scholar
  18. 18.
    B.-Z. Zhan, M.A. White, T.-K. Sham, J.A. Pincock, R.J. Doucet, K.V. Ramana Rao, K.N. Robertson, T.S. Cameron, J. Am. Chem. Soc. 125, 2195 (2003)CrossRefGoogle Scholar
  19. 19.
    V.V. Costa, M.J. Jacinto, L.M. Rossi, R. Landers, E.V. Gusevskaya, J. Catal. 282, 209 (2011)CrossRefGoogle Scholar
  20. 20.
    S.G. Peng, M.R. Weng, J.G. Han, Y.K. Guo, Y.G. Zhang, Acta Pet. Sin. 25, 80 (2009)Google Scholar
  21. 21.
    M.J. Jacinto, O.H.C.F. Santos, R.F. Jardim, R. Landers, L.M. Rossi, Appl. Catal. A Gen. 360, 177 (2009)CrossRefGoogle Scholar
  22. 22.
    B.J. Borah, D. Dutta, P.P. Saikia, N.C. Baruah, D.K. Dutta, Green Chem. 13, 3453 (2011)CrossRefGoogle Scholar
  23. 23.
    G. Nagendrappa, Appl. Clay Sci. 53, 106 (2011)CrossRefGoogle Scholar
  24. 24.
    G. Nagendrappa, Resonance 7, 64 (2002)Google Scholar
  25. 25.
    R.S. Varma, Tetrahedron 58, 1235 (2002)CrossRefGoogle Scholar
  26. 26.
    A. Amari, M. Chlendi, A. Gannouni, A. Bellagi, Appl. Clay Sci. 47, 457 (2010)CrossRefGoogle Scholar
  27. 27.
    A. Boulmokh, Y. Berredjem, K. Guerfi, A. Gheid, Res. J. Appl. Sci. 2, 435 (2007)Google Scholar
  28. 28.
    S.P. Dubey, K. Gopal, J.L. Bersillon, J. Environ. Biol. 30, 327 (2009)PubMedGoogle Scholar
  29. 29.
    V.K. Gupta, N. Suhas, J. Environ. Manag. 90, 2313 (2009)CrossRefGoogle Scholar
  30. 30.
    G. Rodney Harris, D. Wells John, B. Johnson Bruce, Colloids Surf. A 180, 131 (2001)CrossRefGoogle Scholar
  31. 31.
    P. Liu, L. Zhang, Sep. Purif. Technol. 58, 32 (2007)CrossRefGoogle Scholar
  32. 32.
    B. Rabehi, K. Boumchedda, Y. Ghernouti, Int. J. Phys. Sci. 7, 5179 (2012)CrossRefGoogle Scholar
  33. 33.
    S. Mellouk, S. Cherifi, M. Sassi, K. Marouf-Khelifa, K.A. Bengueddach, J. Schott, A. Khelifa, Appl. Clay Sci. 44, 230 (2009)CrossRefGoogle Scholar
  34. 34.
    D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998)CrossRefGoogle Scholar
  35. 35.
    R. Ghezini, M. Sassi, A. Bengueddach, Microporous Mesoporous Mater. 113, 370 (2008)CrossRefGoogle Scholar
  36. 36.
    S. Zen, F. Zohra El Berrichi, Desalin. Water Treat. 57, 6024 (2016)CrossRefGoogle Scholar
  37. 37.
    N. Thi Bich Hien, H. Young Kim, M. Jeon, J. Hee Lee, M. Ridwan, R. Tamarany, C. Won Yoon, Materials 8, 3442 (2015)CrossRefGoogle Scholar
  38. 38.
    C. Leterme, C. Fernández, P. Eloy, E.M. Gaigneaux, P. Ruiz, Catal. Today 286, 85 (2017)CrossRefGoogle Scholar
  39. 39.
    V. Veselovskaya, J.D. Parunin, P.V. Netskina, O.S.L. Kibis, I.A. Lysikov, G.A. Okunev, Energy 159, 766 (2018)CrossRefGoogle Scholar
  40. 40.
    R. Bavand, A. Yelon, E. Sacher, Appl. Surf. Sci. 355, 279 (2015)CrossRefGoogle Scholar
  41. 41.
    D.J. Morgan, Surf. Interface Anal. 47, 1072 (2015)CrossRefGoogle Scholar
  42. 42.
    Y. Zhang, F. Lu, H.-Y. Zhang, J. Zhao, Catal. Lett. 147, 20 (2017)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • B. Zadam
    • 1
    • 2
  • D. Obaid
    • 2
  • A. Mayoufi
    • 2
  • P. Beaunier
    • 2
  • F. Launay
    • 2
  • F. Z. El Berrichi
    • 3
  1. 1.Laboratoire de Chimie AppliquéeUniversité 08 Mai 1945GuelmaAlgeria
  2. 2.Laboratoire de Réactivité de Surface, LRS, CNRSSorbonne UniversitéParisFrance
  3. 3.Laboratoire de Chimie PhysiqueUniversité 08 Mai 1945GuelmaAlgeria

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