Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor
Author(s)
Li Song, Yunfei; Martin, Benjamin; Schenkel, Berthold; Yang, Cuixian; Teixeira, Andrew; Shi, Yanxiang; Born, Stephen C; Lin, Hongkun; Peer Lachegurabi, Maryam; Jensen, Klavs F; ... Show more Show less
Downloadc7gc03469e.pdf (1.498Mb)
PUBLISHER_CC
Publisher with Creative Commons License
Creative Commons Attribution
Terms of use
Metadata
Show full item recordAbstract
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.
Date issued
2018-01Department
Massachusetts Institute of Technology. Department of Chemical EngineeringJournal
Green Chemistry
Publisher
Royal Society of Chemistry (RSC)
Citation
Yang, Cuixian, et al. “Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor.” Green Chemistry 20, 4 (2018): 886–893 © 2018 The Royal Society of Chemistry
Version: Final published version
ISSN
1463-9262
1463-9270