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Selective Hydrogenation

The selective hydrogenation of multiple unsaturated compounds by heterogenous catalysis is a field of great importance for both the scientific impact for our knowledge in heterogeneous catalysis as well as its industrial application. The efficient synthesis of valuable fine chemicals by selective hydrogenation of organic compounds containing multifunctional groups involves frequently complex problems of chemo-, regio- and stereoselectivity, and represents a challenging task in heterogeneous catalysis. Our group focus currently in three research lines in this field, dealing with the selective hydrogenations of nitriles to amines, 5-hydroxymethylfurfural to 2,5-bis(hydroxymethyl)furan, and mono and disaccharides to sugar alcohols, respectively.

Reactions

  • Hydrogenation of carbohydrates to polyols
    Our group studies the selective hydrogenation of mono and disaccharides (D-fructose to D-mannitol, glucose to sorbitol, lactose to lactilol) over supported mono- and bimetallic catalysts based on noble (Pt, Pd) and nonnoble (Cu, Ni, Co) metals. Catalysts are prepared by using different methods (impregnation, precipitation-deposition, adsorption) and supports (SiO2, Al2O3, SiO2-Al2O3, zeolites).

  • Selective synthesis of amines e imines by nitrile hydrogenation
    We investigate the development of efficient metal-supported catalysts to selectively hydrogenate saturated and saturated nitriles to imines or amines amines. The selective hydrogenation of the C≡N group in unsaturated nitriles to obtain unsaturated amines is still a challenging objective in heterogeneous catalysis. Besides, increasing research efforts have been devoted to selectively convert saturated nitriles to a given saturated primary, secondary or tertiary amine. Both saturated and unsaturated amines are valuable intermediates in agrochemical, pharmaceutical, and fine chemicals industries. In the same way secondary imines are valuable products that can be used to selectively obtain intermediates for industry or prochiral precursors (via asymmetric, prochiral secondary imines).

  • Hydrogenation of 5-hydroxymethylfurfural (HMF) to 2,5-bis(hydroxymethyl)furan (BHMF)
    HMF may be obtained by dehydration of biomass-derived hexoses, such as glucose and fructose. Our objective is to selectively hydrogenate the aldehydic group of HMF to obtain BHM, and thereby avoiding the hydrogenolysis of HMF C-OH groups that leads to the formation of undesired 2,5-dimethylfuran. Mono and bimetallic catalysts (Cu, Ni and Cu-Ni) supported on different single or mixed oxides such as SiO2, Al2O3 and SiO2-Al2O3 are used.

Recent Publications:

  • Effect of the catalyst preparation method on the performance of Ni supported catalysts for the synthesis of saturated amines from nitrile hydrogenation, D.J. Segobia, A.F. Trasarti, C.R. Apesteguia, Chin. J. Catal., in press 2019.

  • Selective liquid-phase hydrogenation of fructose to D-mannitol over copper-supported metallic nanoparticles, J. Zelin, C.I. Meyer, S.A. Regenhardt, V. Sebastian, T.F. Garetto, A.J. Marchi, Chem. Eng. J., 319, 48-56 (2017).

  • Impact of solvent on Co/SiO2 activity and selectivity for the synthesis of n-butylamine from butyronitrile hydrogenation, D.J. Segobia, A.F. Trasarti, C.R. Apesteguía, Catal. Comm., 62, 62-66 (2015).

  • Chemoselective hydrogenation of unsaturated nitriles to unsaturated primary amines: Conversion of cinnamonitrile on metal-supported catalysts, D.J. Segobia, A.F. Trasarti, C.R. Apesteguía, Appl. Catal. A: General, 494, 41-47 (2015).

  • Conversion of butyronitrile to butyilamines on noble metals: Effect of solvent on catalyst activity and selectivity, D.J. Segobia, A.F. Trasarti, C.R. Apesteguía, Catal. Sci. Technol., 4, 4075-4083 (2014).

  • Synthesis of n-butylamine from butyronitrile on Ni/SiO2: Effect of solvent, D.J. Segobia, A.F. Trasarti, C.R. Apesteguía, J. Braz. Chem. Soc., 25(12), 2272-2279 (2014).

  • Selective liquid-phase hydrogenation of furfural to furfuryl alcohol over Cu-based catalysts, M.M. Villaverde, N.M. Bertero, T.F. Garetto, A.J. Marchi, Catal. Today 213, 87-92 (2013).

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