Issue 4, 2018

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

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 (74–84%), rapid multiphase mass transfer (kma > 1 s−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

Supplementary files

Article information

Article type
Paper
Submitted
17 Nov 2017
Accepted
19 Jan 2018
First published
19 Jan 2018
This article is Open Access
Creative Commons BY license

Green Chem., 2018,20, 886-893

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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