Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor
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 catalyz...
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| Format: | Article |
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Royal Society of Chemistry (RSC)
2018
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| Online Access: | http://hdl.handle.net/1721.1/116913 https://orcid.org/0000-0003-2889-9102 https://orcid.org/0000-0002-9211-7972 https://orcid.org/0000-0001-7266-9350 https://orcid.org/0000-0002-4362-2876 https://orcid.org/0000-0001-7192-580X |
| _version_ | 1811071508380909568 |
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| author | Li Song, Yunfei Martin, Benjamin Schenkel, Berthold Yang, Cuixian Teixeira, Andrew Shi, Yanxiang Born, Stephen C Lin, Hongkun Peer Lachegurabi, Maryam Jensen, Klavs F |
| author2 | Massachusetts Institute of Technology. Department of Chemical Engineering |
| author_facet | Massachusetts Institute of Technology. Department of Chemical Engineering Li Song, Yunfei Martin, Benjamin Schenkel, Berthold Yang, Cuixian Teixeira, Andrew Shi, Yanxiang Born, Stephen C Lin, Hongkun Peer Lachegurabi, Maryam Jensen, Klavs F |
| author_sort | Li Song, Yunfei |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T08:52:17Z |
| format | Article |
| id | mit-1721.1/116913 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T08:52:17Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry (RSC) |
| record_format | dspace |
| spelling | mit-1721.1/1169132022-09-26T08:52:06Z Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor Li Song, Yunfei Martin, Benjamin Schenkel, Berthold Yang, Cuixian Teixeira, Andrew Shi, Yanxiang Born, Stephen C Lin, Hongkun Peer Lachegurabi, Maryam Jensen, Klavs F Massachusetts Institute of Technology. Department of Chemical Engineering Yang, Cuixian Teixeira, Andrew Shi, Yanxiang Born, Stephen C Lin, Hongkun Peer Lachegurabi, Maryam Jensen, Klavs F 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. 2018-07-11T18:47:25Z 2018-07-11T18:47:25Z 2018-01 2017-11 2018-07-11T14:38:52Z Article http://purl.org/eprint/type/JournalArticle 1463-9262 1463-9270 http://hdl.handle.net/1721.1/116913 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 https://orcid.org/0000-0003-2889-9102 https://orcid.org/0000-0002-9211-7972 https://orcid.org/0000-0001-7266-9350 https://orcid.org/0000-0002-4362-2876 https://orcid.org/0000-0001-7192-580X http://dx.doi.org/10.1039/C7GC03469E Green Chemistry Creative Commons Attribution 3.0 Unported license http://creativecommons.org/licenses/by/3.0/ application/pdf Royal Society of Chemistry (RSC) Royal Society of Chemistry |
| spellingShingle | Li Song, Yunfei Martin, Benjamin Schenkel, Berthold Yang, Cuixian Teixeira, Andrew Shi, Yanxiang Born, Stephen C Lin, Hongkun Peer Lachegurabi, Maryam Jensen, Klavs F Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor |
| title | Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor |
| title_full | Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor |
| title_fullStr | Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor |
| title_full_unstemmed | Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor |
| title_short | Catalytic Hydrogenation of N-4-Nitrophenyl Nicotinamide in a Micro-Packed Bed Reactor |
| title_sort | catalytic hydrogenation of n 4 nitrophenyl nicotinamide in a micro packed bed reactor |
| url | http://hdl.handle.net/1721.1/116913 https://orcid.org/0000-0003-2889-9102 https://orcid.org/0000-0002-9211-7972 https://orcid.org/0000-0001-7266-9350 https://orcid.org/0000-0002-4362-2876 https://orcid.org/0000-0001-7192-580X |
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