Catalytic Static Mixers for the Continuous Flow Hydrogenation of a Key Intermediate of Linezolid (Zyvox)

Gardiner, James; Nguyen, Xuan; Genet, Charlotte; Horne, Michael D.; Hornung, Christian H.; Tsanaktsidis, John

doi:10.1021/acs.oprd.8b00153

Cited by 40 publications

(35 citation statements)

References 32 publications

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“…A relevant outcome regarding these results is that high catalytic activity and high selectivity towards hydrogenation to anilines were achieved by the (x)Au/ANW systems, despite their low metal content. In this context, our catalyst shows better performance than previous reports from Gardiner et al that used Pd immobilized to hydrogenated NFMF reaching to 30% of yield to the amine-arene desire [46]. With respect to selectivity, one intermediate reaction was detected, namely N-(substituted-phenyl)-hydroxylamine derivate (<1%), with no evidence of condensation byproducts.…”

Section: Effect Of Au Loadingmentioning

confidence: 53%

“…Only a few report exploring molecules with pharmaceutical applications has been published. Gardiner et al used catalytic static mixers coated with Pd to obtain 3-fluoro-4-morpholinoaniline (Yield prod < 30%) [46]. Bustamante et al employ Pd-Co catalysts to study a series of halonitroarenes under soft hydrogenation conditions (ethanol as solvent, 80 • C and 20 bar of H 2 pressure) with selectivity to the desired aniline greater than 95% [47].…”

Section: Introductionmentioning

confidence: 99%

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Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

et al. 2020

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In this work, Au nanoparticles, supported in Al2O3 nanowires (ANW) modified with (3-aminopropyl)trimethoxysilane were synthetized, for their use as catalysts in the hydrogenation reaction of 4-(2-fluoro-4-nitrophenyl)-morpholine and 4-(4-nitrophenyl)morpholin-3-one. ANW was obtained by hydrothermal techniques and the metal was incorporated by the reduction of the precursor with NaBH4 posterior to superficial modification. The catalysts were prepared at different metal loadings and were characterized by different techniques. The characterization revealed structured materials in the form of nanowires and a successful superficial modification. All catalysts show that Au is in a reduced state and the shape of the nanoparticles is spherical, with high metal dispersion and size distributions from 3.7 to 4.6 nm. The different systems supported in modified-ANW were active and selective in the hydrogenation reaction of both substrates, finding for all catalytic systems a selectivity of almost 100% to the aromatic amine. Catalytic data showed pseudo first-order kinetics with respect to the substrate for all experimental conditions used in this work. The solvent plays an important role in the activity and selectivity of the catalyst, where the highest efficiency and operational stability was achieved when ethanol was used as the solvent.

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Section: Effect Of Au Loadingmentioning

confidence: 53%

Section: Introductionmentioning

confidence: 99%

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

et al. 2020

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“…Recently, Gardiner et al. discussed a new technique for the synthesis of the key intermediate of linezolid . Their novel continuous‐flow hydrogenation reactor contains a series of 3D‐printed catalytic static mixers (CSMs), which were coated with Pd catalysts via electroplating.…”

Section: Continuous‐flow Hydrogenation Using Heterogeneous Catalystsmentioning

confidence: 99%

Recent Progress in Continuous‐Flow Hydrogenation

Jiao

Song

et al. 2020

ChemSusChem

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To achieve a safe, efficient, and sustainable (even fully automated) production for the continuous‐flow hydrogenation reactions, which is among the most often used reactions in chemical synthesis, new catalyst types and immobilization methods as well as flow reactors and technologies have been developed over the last years; in addition, these approaches have been combined with new and transformational technologies in other fields such as artificial intelligence. Thus, attention from academic and industry practitioners has increasingly focused on improving the performance of hydrogenation in flow mode by reducing the reaction times, increasing selectivities, and achieve safe operation. This Minireview aims to summarize the most recent research results on this topic with focus on the advantages, current limitations, and future directions of flow chemistry.

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“…Another research team proposed manufacturing of static mixers by Electron Beam Melting from the alloys of Ti6Al4V, CoCr [ 80 ], 316L stainless-steel [ 81 , 82 , 83 ]. Layers of catalytically active metals were deposited on the static mixers.…”

Section: 3d Printing Applications In Heterogeneous Catalysismentioning

confidence: 99%

“…Layers of catalytically active metals were deposited on the static mixers. Various catalytic systems of the static mixers were fitted inside steel tubular flow reactors [ 80 , 81 , 82 , 83 ]. The catalytic mixers coated with Pt and Ni were tested in a series of processes of alkenes and carbonyl hydrogenation.…”

Section: 3d Printing Applications In Heterogeneous Catalysismentioning

confidence: 99%

3D Printing in Heterogeneous Catalysis—The State of the Art

Богдан

Michorczyk

2020

Materials

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This paper describes the process of additive manufacturing and a selection of three-dimensional (3D) printing methods which have applications in chemical synthesis, specifically for the production of monolithic catalysts. A review was conducted on reference literature for 3D printing applications in the field of catalysis. It was proven that 3D printing is a promising production method for catalysts.

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Catalytic Static Mixers for the Continuous Flow Hydrogenation of a Key Intermediate of Linezolid (Zyvox)

Cited by 40 publications

References 32 publications

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

Recent Progress in Continuous‐Flow Hydrogenation

3D Printing in Heterogeneous Catalysis—The State of the Art

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