Palladium-mediated organic synthesis using porous polymer monolith formed in situ as a continuous catalyst support structure for application in microfluidic devices

Gömann, Anissa; Deverell, Jeremy A.; Munting, Katrina F.; Jones, Roderick C.; Rodemann, Thomas; Canty, Allan J.; Smith, Jason A.; Guijt, Rosanne M.

doi:10.1016/j.tet.2008.12.007

Cited by 78 publications

(47 citation statements)

References 45 publications

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“…The synthesis in situ of a porous polymer for the immobilization of covalently bound catalysts has been proposed [68]. Heterogenised Pd-NHC catalysts have been compared under batch and flow conditions, although life tests have not been reported [69].…”

Section: Methodsmentioning

confidence: 99%

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Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

Rossetti

Compagnoni

2016

Chemical Engineering Journal

203

103

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Flow chemistry has been proposed in modern organic chemistry as a mean for process intensification, to improve the control over reaction performance and to achieve higher yield. However, many open issues can be evidenced regarding the true possibility of scale-up, as well as currently lacking information for process design and economical evaluation. This review proposes some recent examples of flow synthesis deepening in particular the scale-up and engineering issues. Required information is evidenced, as well as some transport and kinetic data required for the practical implementation of the results.

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Section: Methodsmentioning

confidence: 99%

“…Additionally, nanoconfinement of asymmetric catalysts in multiwalled carbon nanotubes was also accomplished [72,73]. Pd supported over 8 monoliths has been considered for continuous flow reactions [50,68,[74][75][76][77]. The comparison of homogeneous and heterogeneous paths for the ligandless Mizoroki-Heck reactions are also overviewed [78].…”

Section: Methodsmentioning

confidence: 99%

Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

Rossetti

Compagnoni

2016

Chemical Engineering Journal

203

103

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“…[92][93][94][95][96][97][98] Molecular organic transformations with heterogeneous catalystimmobilized flow microreactors are representative examples of these systems, where the efficiency of various organic transformations has been found to increase due to the vast interfacial area and the close distance of the molecular diffusion path in the narrow space of the flow microreactor. [99][100][101][102][103][104][105][106][107][108][109][110] If a heterogeneous catalyst was immobilized as a membranous composite at the interface of an organic layer and aqueous layer (the center of the microchannel), two reactants could be oppositely charged into and flow through the divided channel, all the while in contact with the vast interfacial surface of the catalytic membrane from both front and back sides, thereby realizing an instantaneous chemical reaction. This concept is shown schematically in Fig.…”

Section: Development Of Catalytic Membrane-installed Microflow Reactomentioning

confidence: 99%

Development of Batch and Flow Immobilized Catalytic Systems with High Catalytic Activity and Reusability

Yamada

2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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My mission in catalysis research is to develop highly active and reusable supported catalytic systems in terms of fundamental chemistry and industrial application. For this purpose, I developed three types of highly active and reusable supported catalytic systems. The first type involves polymeric base-supported metal catalysts: Novel polymeric imidazole-Pd and Cu complexes were developed that worked at the mol ppm level for a variety of organic transformations. The second involves catalytic membrane-installed microflow reactors: Membranous polymeric palladium and copper complex/nanoparticle catalysts were installed at the center of a microtube to produce novel catalytic membrane-immobilized flow microreactor devices. These catalytic devices mediated a variety of organic transformations to afford the corresponding products in high yield within 1-38 s. The third is a silicon nanowire array-immobilized palladium nanoparticle catalyst. This device promoted a variety of organic transformations as a heterogeneous catalyst. The Mizoroki-Heck reaction proceeded with 280 mol ppb (0.000028 mol%) of the catalyst, affording the corresponding products in high yield.

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“…[115,129] Guijt et al also used p-chloromethylstyrene-and divinylbenzene-containing monoliths in 250 mm capillaries for Pd immobilization. [130] Either 5-amino-1,10-phenanthroline or 1-methylimidazole was grafted to the monolith through reaction with benzyl chloride groups, and Pd was loaded through reaction with PdCl 2 (NCMe) 2 solutions. Imidazolium-based monoliths were believed to contain both NHC-grafted Pd and [PdCl 3 (NCMe)] À counterions and possessed Pd loadings around 0.4 wt % compared with 0.3 wt % loadings for the phenanthroline-containing monoliths.…”

Section: Pd-based Catalysts For Càc Coupling Reactionsmentioning

confidence: 99%

Catalysts Immobilized on Organic Polymeric Monolithic Supports: From Molecular Heterogeneous Catalysis to Biocatalysis

Anderson

Buchmeiser

2011

ChemCatChem

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This review describes the synthetic routes to various types of organic polymeric monoliths. Significant concentration is applied to the role of these continuous, porous structures in both heterogeneous catalysis and biocatalysis. A monolith is composed of a solitary mass filled with interconnected pores, which include both large flow‐through pores and smaller meso‐ or micropores. These porous monolithic materials have several advantages over conventional packed beds of porous polymeric beads, owing to their macroporosity and lack of interstitial spacing. Their large pores contribute to mass transfer, which allows the structure to withstand higher back pressures than conventional packed beds, whereas their small pores still operate by diffusion. The effect of multiple parameters, such as the temperature, the cross‐link density, and the type and content of porogenic solvent on the pore formation and pore size distribution is outlined for monoliths prepared through free radical polymerization and ring‐opening metathesis polymerization (ROMP). Post‐functionalization of these monoliths to control the surface chemistry of the supports and/or affix functional catalysts is elucidated, as well as employment of these supports in continuous catalytic reactions. Significant advances in supported catalysis for metathesis, Heck, Suzuki, Sonogashira–Hagihara, and biocatalytic reactions are described.

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Palladium-mediated organic synthesis using porous polymer monolith formed in situ as a continuous catalyst support structure for application in microfluidic devices

Cited by 78 publications

References 45 publications

Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

Development of Batch and Flow Immobilized Catalytic Systems with High Catalytic Activity and Reusability

Catalysts Immobilized on Organic Polymeric Monolithic Supports: From Molecular Heterogeneous Catalysis to Biocatalysis

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