Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor
Name
c7gc03469e.pdf
Size
1.5 MB
Format
Adobe PDF
Checksum (MD5)
da98790385c7bc544c5735298d5b9323
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
Date Issued
January 2018
Journal
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Terms of Use
Creative Commons Attribution 3.0 Unported license
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1039/C7GC03469E
