Catalytic hydrogenation of <i>N</i>-4-nitrophenyl nicotinamide in a micro-packed bed reactor

Yang, Cuixian; Teixeira, Andrew R.; Shi, Yanxiang; Born, Stephen C.; Lin, Hongkun; Song, Yunfei; Martin, Benjamin; Schenkel, Berthold; Lachegurabi, Maryam Peer; Jensen, Klavs F.

doi:10.1039/c7gc03469e

Cited by 62 publications

(43 citation statements)

References 33 publications

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“…Traditionally kinetics are obtained in batch, which while having the advantage of providing multiple data points per experiment, may be limited by heat and mass transfer. In comparison, the development of flow microreactors with superior rates of heat and mass transport and improved safety [3][4][5][6][7] enable isothermal kinetic studies. 5,[8][9][10] Flow reactors are now often combined with online analysis to provide data-rich experimental platforms.…”

Section: Introductionmentioning

confidence: 99%

An autonomous microreactor platform for the rapid identification of kinetic models

et al. 2019

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Section: Introductionmentioning

confidence: 99%

An autonomous microreactor platform for the rapid identification of kinetic models

et al. 2019

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“…The residence time distribution or RTD is an important attribute in packed-bed reactors [13][14][15]. By the rule of thumb, the wider the column, and the poorer (i.e., the broader) is the RTD.…”

Section: Introductionmentioning

confidence: 99%

Cuboid Packed-Beds as Chemical Reactors?

Ghosh

2018

Processes

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Columns are widely used as packed-bed or fixed-bed reactors in the chemical process industry. Packed columns are also used for carrying out chemical separation techniques such as adsorption, distillation, extraction and chromatography. A combination of the variability in flow path lengths, and the variability of velocity along these flow paths results in significant broadening in solute residence time distribution within columns, particularly in those having low bed height to diameter ratios. Therefore, wide packed-column reactors operate at low efficiencies. Also, for a column of a particular bed height, the ratio of heat transfer surface area to reactor volume varies inversely as the radius. Therefore, with wide columns, the available heat transfer area could become a limiting factor. In recent papers, box-shaped or cuboid packed-bed devices have been proposed as efficient alternatives to packed columns for carrying out chromatographic separations. In this paper, the use of cuboid packed-beds as reactors for carrying out chemical and biochemical reactions has been proposed. This proposition is primarily supported in terms of advantages resulting from superior system hydraulics and narrower residence time distributions. Other potential advantages, such as better heat transfer attributes, are speculated based on geometric considerations.

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“…Among numerous pharmaceutical transformations, gas-liquid reactions, such as hydrogenation, 1 aerobic oxidation, 2,3 and ozonolysis, 4 show attractive atom economy in comparison to other chemical transformations. For example, direct hydrogenation of pharmaceutical precursors with hydrogen gas outpaces other costly sacrificial reducing reagents, such as hydrides (LiAlH 4 and NaBH 4 ) or borane reagents.…”

Section: Introductionmentioning

confidence: 99%

“…5 However, concerns of process efficiency, scalability, and safety of gas-liquid systems create barriers for pharmaceutical applications and this becomes even more challenging when heterogeneous catalysts are present in gas-liquid systems. 1,6 Over the past decade, continuous flow technology has emerged as a powerful technique to produce active pharmaceutical ingredients (APIs) driven by advantages of continuous technology over conventional batch or semi-batch processes, including steady state operation, enhanced heat and mass transfer rates, reproducibility, and improved safety and process reliability. [7][8][9][10][11][12] These benefits are especially true for gas-liquid reaction systems, where the absence of high-pressure headspace gas and reduced reactor volume of continuous flow reactors significantly improve the safety profiles compared to highpressure reaction vessels.…”

Section: Introductionmentioning

confidence: 99%

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Scalable thin-layer membrane reactor for heterogeneous and homogeneous catalytic gas–liquid reactions

Imbrogno

Zhang

et al. 2018

Green Chem.

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Catalytic gas-liquid reactions have potential as environmentally benign methods for organic synthesis, particularly hydrogenation and oxidation reactions. However, safety and scalability are concerns in the application of gas-liquid reactions. In this work, we develop and demonstrate a scalable, sustainable, and safe thin-layer membrane reactor for heterogeneous Pd-catalyzed hydrogenations and homogenous Cu(I)/TEMPO alcohol oxidations. The implementation of a Teflon amorphous fluoroplastic (AF) membrane and porous carbon cloth in the membrane reactor provides sufficient gas-liquid mass transfer to afford superior performance compared to conventional packed-bed or trickle-bed reactors. The membrane separates the gas from the liquid, which avoids the formation of explosive mixtures for oxygenation reactions and simplifies the two-phase hydrodynamics to facilitate scale-up by stacking modules, while significantly reducing gas consumption. In addition, 3-dimensional simulations deliver insights into the mass transfer and hydrodynamic behavior to inform optimal membrane reactor design and operation.

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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.

Cited by 62 publications

References 33 publications

An autonomous microreactor platform for the rapid identification of kinetic models

An autonomous microreactor platform for the rapid identification of kinetic models

Cuboid Packed-Beds as Chemical Reactors?

Scalable thin-layer membrane reactor for heterogeneous and homogeneous catalytic gas–liquid reactions

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