Organic Polymeric Resins Embedded with Pd NPs: Newly Designed, Efficient and Chemoselective Catalyst for Reduction of Nitrobenzenes

Basu, Basudeb; Paul, Soumen; Kundu, Samir; Byström, Emil; Irgum, Knut; Almqvist, Fredrik

doi:10.2174/2213337203666160524143615

Cited by 5 publications

(4 citation statements)

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“…The same ion-exchange resin, Amberlite IRA 900 Cl − , did not control Pd NP formation when the Pd precursor was reduced with formic acid (the reducing agent was not immobilized). 252 This resulted in an exceptionally broad Pd NP size distribution. The catalyst has been studied in the transfer hydrogenation of nitrobenzenes in the presence of different hydrogen donors including H 2 and allowed for good to excellent yields of target molecules.…”

Section: Ion Exchange Resins and Polymers With Anionic Moietiesmentioning

confidence: 99%

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Role of Polymer Structures in Catalysis by Transition Metal and Metal Oxide Nanoparticle Composites

2019

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Nanoparticle (NP)/polymer nanocomposites received considerable attention because of their important applications including catalysis. Metal and metal oxide NPs may impart catalytic properties to polymer nanocomposites, while polymers with a different structure, functionality, and architecture control the NP formation (size, shape, location, composition, etc.) and in this way, govern catalytic properties of nanocomposites. In this review we will discuss the influence of the polymer nanostructure (thin or grafted layers, polymer ordering, polymer nanopores), architecture (branched vs linear), functional groups (coordinating or ionic), specific properties (reducing, stimuli responsive, conductive), etc. on the formation of metal or metal oxide NPs and the catalytic behavior of the nanocomposites. The development of novel and efficient catalysts is crucial for progress in chemical sciences, and this explains a huge number of publications in this area in recent years. Taking into consideration previous review articles on NP/polymer catalysts, we limited this review to a discussion of a narrow temporal scope (2017–April 2019), while embracing a broad subject scope, i.e., considering any polymers and NPs which form catalytic nanocomposites. This gives us a unique view of the field of catalytic polymer nanocomposites and allows understanding of where the field is going.

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Section: Ion Exchange Resins and Polymers With Anionic Moietiesmentioning

confidence: 99%

“…The same ion-exchange resin, Amberlite IRA 900 Cl – , did not control Pd NP formation when the Pd precursor was reduced with formic acid (the reducing agent was not immobilized) . This resulted in an exceptionally broad Pd NP size distribution.…”

Section: Ionic Polymersmentioning

confidence: 99%

Role of Polymer Structures in Catalysis by Transition Metal and Metal Oxide Nanoparticle Composites

2019

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“…Heterogeneous catalysis allows for catalyst separation and reuse but often suffers from lower selectivity and activity. The heterogeneous catalysts for the transfer hydrogenation of nitroarenes include Co-and Ni-containing molecular sieves, , perovskites, , Pd/C, , free or polymer stabilized Pd nanoparticles (NPs), , Ag NPs stabilized in a mesoporous polymer, graphene derivative (GD) based catalysts, , etc. In consideration of the importance of anilines for chemical and pharmaceutical industries, the quest for the development of efficient, selective, and reusable catalysts for this process is continuing.…”

Section: Introductionmentioning

confidence: 99%

Graphene Derivative in Magnetically Recoverable Catalyst Determines Catalytic Properties in Transfer Hydrogenation of Nitroarenes to Anilines with 2-Propanol

Das¹,

Mazhar²,

Gregor³

et al. 2018

ACS Appl. Mater. Interfaces

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Here, we report transfer hydrogenation of nitroarenes to aminoarenes using 2-propanol as a hydrogen source and Ag-containing magnetically recoverable catalysts based on partially reduced graphene oxide (pRGO) sheets. X-ray diffraction and X-ray photoelectron spectroscopy data demonstrated that, during the one-pot catalyst synthesis, formation of magnetite nanoparticles (NPs) is accompanied by the reduction of graphene oxide (GO) to pRGO. The formation of Ag NPs on top of magnetite nanoparticles does not change the pRGO structure. At the same time, the catalyst structure is further modified during the transfer hydrogenation, leading to a noticeable increase of sp carbons. These carbons are responsible for the adsorption of substrate and intermediates, facilitating a hydrogen transfer from Ag NPs and creating synergy between the components of the catalyst. The nitroarenes with electron withdrawing and electron donating substituents allow for excellent yields of aniline derivatives with high regio and chemoselectivity, indicating that the reaction is not disfavored by these functionalities. The versatility of the catalyst synthetic protocol was demonstrated by a synthesis of an Ru-containing graphene derivative based catalyst, also allowing for efficient transfer hydrogenation. Easy magnetic separation and stable catalyst performance in the transfer hydrogenation make this catalyst promising for future applications.

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“…These polymerizations showed a relatively slow polymerization rate due to the low activity of activated metals. Palladium nanoparticle (Pd NP) is an effective catalyst for a lot of organic reactions [ 42 , 43 , 44 , 45 , 46 , 47 ]. In this work, we found that the monodispersed Pd NPs were highly active for the polymerization of vinyl monomers such as MMA, methyl acrylate (MA), vinyl acetate (VAc) and butyl acrylate (BA) in the presence of organic halides and developed a facile and versatile approach for the synthesis of ultrahigh molecular weight PMMA.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Ultrahigh Molecular Weight Poly(Methyl Methacrylate) by Organic Halides in the Presence of Palladium Nanoparticles

Yuan

Cui

et al. 2020

Polymers

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A facile and versatile approach for the synthesis of ultrahigh molecular weight poly(methyl methacrylate) (PMMA) at mild conditions was developed. Certain organic halides combined with a catalytical amount of palladium nanoparticles (Pd NPs) were found to be very effective in initiating polymerizations of methyl methacrylate (MMA), methyl acrylate, vinyl acetate and other vinyl monomers. An ultrahigh molecular weight PMMA with a number-average molecular weight of 4.65 × 106 Da and a weight-average molecular weight of 8.08 × 106 Da was synthesized at 70 °C using 2-bromoisobutyric acid ethyl ester (EBiB) as an initiator in the presence of catalytical amount (10.1 ppm) of Pd NPs. A kinetic investigation found that the orders of polymerization with respect to EBiB, Pd NP and MMA were 0.23, 0.50, and 0.58, respectively. Proton nuclear magnetic resonance (1H NMR) combined with matrix-assisted laser desorption ionization time of flight mass spectroscopy (MALDI-TOF) and gel permeation chromatography (GPC) were used to prove that the macromolecular chain had an end-group of EBiB residue. The electron spin resonance (ESR), transmission electron microscope (TEM), and X-ray photoelectron spectroscopy (XPS) results reveal that the reaction of EBiB with Pd NPs caused a bromo atom (Br) transfer from EBiB to Pd NPs and resulted in the generation of EBiB residue radical to initiate the polymerization of MMA and the formation of PdIIBr2 on the surface of Pd nanoparticles.

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Organic Polymeric Resins Embedded with Pd NPs: Newly Designed, Efficient and Chemoselective Catalyst for Reduction of Nitrobenzenes

Cited by 5 publications

References 0 publications

Role of Polymer Structures in Catalysis by Transition Metal and Metal Oxide Nanoparticle Composites

Role of Polymer Structures in Catalysis by Transition Metal and Metal Oxide Nanoparticle Composites

Graphene Derivative in Magnetically Recoverable Catalyst Determines Catalytic Properties in Transfer Hydrogenation of Nitroarenes to Anilines with 2-Propanol

Facile Synthesis of Ultrahigh Molecular Weight Poly(Methyl Methacrylate) by Organic Halides in the Presence of Palladium Nanoparticles

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