Hydrogenation of Carbonyl Compounds over Granulated Ni/Al2O3 Catalyst in a Flow Reactor

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Abstract

Hydrogenation of carbonyl compounds on highly dispersed granulated Ni/Al2O3 catalyst in a flow mode was studied. The catalyst precursor was prepared from an ammonia-carbonate complex by incipient wetness impregnation with subsequent drying and calcination stages. X-ray diffraction and transmission electron microscopy methods showed the formation of nickel oxide particles less than 5 nm in size on the alumina surface. This catalyst provides highly selective hydrogenation (selectivity >99.5%) of an aliphatic ketone (2-heptanone) to the corresponding alcohol with a substrate conversion of ~99%. In the case of aliphatic aldehyde (n-octanal), which has stronger electrophilic properties, the reaction proceeds with lower selectivity (96%) due to the formation of aldol condensation products. Unlike aliphatic compounds, the hydrogenation of aromatic aldehydes and ketones occurs with very low selectivity due to the hydrogenation of the aromatic ring and hydrogenolysis of the C—O bond.

About the authors

A. L. Nuzhdin

Boreskov Institute of Catalysis SB RAS

Email: anuzhdin@catalysis.ru
Novosibirsk, Russia

M. V. Bukhtiyarova

Boreskov Institute of Catalysis SB RAS

Novosibirsk, Russia

P. V. Aleksandrov

Boreskov Institute of Catalysis SB RAS

Novosibirsk, Russia

S. O. Utyeva

Boreskov Institute of Catalysis SB RAS

Novosibirsk, Russia

G. A. Bukhtiyarova

Boreskov Institute of Catalysis SB RAS

Novosibirsk, Russia

References

  1. Jimenez-Gonzalez C., Poechlauer P., Broxterman Q.B., Yang B.-S., Ende D., Baird J., Bertsch C., Hannah R.E., Dell’Orco P., Noorman H., Yee S., Reintjens R., Wells A., Massonneau V., Manley J. // Org. Proc. Res. Dev. 2011. V. 15. P. 900–911.
  2. Ananikov V.P., Khemchyan L.L., Ivanova Yu.V., Bukhtiyarov V.I., Sorokin A.M., Prosvirin I.P., Vatsadze S.Z., Medvedko A.V., Nuriev V.N., Dilman A.D., Levin V.V., Koptyug I.V., Kovtunov K.V., Zhivonitko V.V., Likholobov V.A., Romanenko A.V., Simonov P.A., Nenajdenko V.G., Shmatova O.I., Muzalevskiy V.M., Nechaev M.S., Asachenko A.F., Morozov O.S., Dzhevakov P.B., Osipov S.N., Vorobyeva D.V., Topchiy M.A., Zotova M.A., Ponomarenko S.A., Borshchev O.V., Luponosov Yu.N., Rempel A.A., Valeeva A.A., Stakheev A.Yu., Turova O.V., Mashkovsky I.S., Sysolyatin S.V., Malykhin V.V., Bukhtiyarova G.A., Terentev A.O., Krylov I.B. // Russ. Chem. Rev. 2014. V. 83. P. 885.
  3. Sprung C., Arstad B., Olsbye U. // ChemCatChem. 2014. V. 6. P. 1969.
  4. Metaxas K.C., Papayannakos N.G. // Chem. Eng. J. 2008. V. 140. P. 352.
  5. Rahman A., S-Al-Deyab S. // Appl. Catal. A: Gen. 2014. V. 469. P. 517.
  6. Голубина Е.В., Локтева Е.С., Кавалерская Н.Е., Маслаков К.И. // Кинетика и катализ. 2020. Т. 61. № 3. С. 410.
  7. Irfan M., Glasnov T.N., Kappe C.O. // ChemSusChem. 2011. V. 4. P. 300.
  8. Cossar P.J., Hizartzidis L., Simone M.I., McCluskey A., Gordon C.P. // Org. Biomol. Chem. 2015. V. 13. P. 7119.
  9. Yu T., Jiao J., Song P., Nie W., Yi C., Zhang Q., Li P. // ChemSusChem. 2020. V. 13. P. 2876.
  10. Nuzhdin A.L., Bukhtiyarova M.V., Bukhtiyarova G.A. // Org. Biomol. Chem. 2024. V. 22. P. 7936.
  11. Bartholomew C.H., Farrauto R.J. // J. Сatal. 1976. V. 45. № 1. P. 41.
  12. Gao X., Ashok J., Kawi S. // Catal. Today. 2022. V. 397–399. P. 581.
  13. Koetsier W.T., Zwijnenburg A.C. // Catal. Today. 2011. V. 163. P. 10.
  14. Li F., Yi, X., Fang W. // Catal. Lett. 2009. V. 130. P. 335.
  15. Molina R., Poncelet G. // J. Catal. 2001. V. 199. P. 162.
  16. Partridge M.G., Vissenberg M.J., Gabrielsson A. Patent US 9387462 B2, 2016.
  17. Lok C.M., Gray G., Pogers S.D., Bailey S. Patent US 6846772 B2, 2005.
  18. Feng J.T., Lin Y.J., Evans D.G., Duan X., Li D.Q. // J. Catal. 2009. V. 266. P. 351.
  19. Rynkowski J. M., Paryjczak T., Lenik M. // Appl. Catal. A: Gen. 1993. V. 106. P. 73.
  20. Farrauto R.J. / In: Handbook of Industrial Chemistry and Biotechnology. Springer Cham, 2017. P. 1995.
  21. Déchamp N., Gamez A., Perrard A., Gallezot P. // Catal. Today. 1995. V. 24. P. 29.
  22. Nijhuis T.A., Dautzenberg F.M., Moulijn J.A. // Chem. Eng. Sci. 2003. V. 58. P. 1113.

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