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Issue 4, 2018
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Catalytic hydrogenation of N-4-nitrophenyl nicotinamide in a micro-packed bed reactor

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Abstract

Recent advancements in micro-flow technologies and a drive toward more efficient, greener and safer processes have led to a renaissance in flow-chemistry for pharmaceutical production. In this work, we demonstrate the use of a stabilized Pd nanoparticle-organic-silica catalyst to selectively catalyze the hydrogenation of N-4-nitrophenyl nicotinamide, a functionalized active pharmaceutical ingredient (API) surrogate. Extensive catalyst and reactor characterization is provided to establish an in-depth understanding of the unique multiphase dynamics within the micro-packed bed reactor, including the identification of a large liquid holdup (74ā€“84%), rapid multiphase mass transfer (kma > 1 sāˆ’1), and liquid residence time distributions. A kinetic analysis has revealed that the surface catalyzed hydrogenation progresses through a condensation mechanism whereby an azo dimer intermediate is formed and rapidly consumed. Finally, a parametric study was performed at various pressures, temperatures, residence times and flow regimes to achieve quantitative chemoselective conversion of the nitroarene to the corresponding primary amine.

Graphical abstract: Catalytic hydrogenation of N-4-nitrophenyl nicotinamide in a micro-packed bed reactor

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Publication details

The article was received on 17 Nov 2017, accepted on 19 Jan 2018 and first published on 19 Jan 2018


Article type: Paper
DOI: 10.1039/C7GC03469E
Citation: Green Chem., 2018,20, 886-893
  • Open access: Creative Commons BY license
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    Catalytic hydrogenation of N-4-nitrophenyl nicotinamide in a micro-packed bed reactor

    C. Yang, A. R. Teixeira, Y. Shi, S. C. Born, H. Lin, Y. Li Song, B. Martin, B. Schenkel, M. Peer Lachegurabi and K. F. Jensen, Green Chem., 2018, 20, 886
    DOI: 10.1039/C7GC03469E

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