Catalyzed Hydration of Nitriles to Amides

Haefele, L. R.; Young, H. J.

doi:10.1021/i360043a022

Cited by 15 publications

(2 citation statements)

References 2 publications

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“…Traditional methods involve the use of strong acid or base catalysts, which has as drawbacks the over hydrolysis of amides into carboxylic acids and the formation of salts after neutralization of the catalysts. Different types of catalysts have been tested, including both homogeneous (e.g., Pt(II), Ru(II), Co(III), and Mo(IV) complexes) and heterogeneous (e.g., Ru(OH) 3 supported on alumina and MnO 2 ). CeO 2 has also been shown to act as a selective heterogeneous catalyst for the hydration of nitriles that have a heteroatom (N or O) adjacent to the α carbon of the CN group …”

Section: Introductionmentioning

confidence: 99%

Ceria/Polymer Hybrid Nanoparticles as Efficient Catalysts for the Hydration of Nitriles to Amides

Mari

Müller

Landfester

et al. 2015

ACS Appl. Mater. Interfaces

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We report the synthesis of ceria/polymer hybrid nanoparticles and their use as effective supported catalysts for the hydration of nitriles to amide, exemplified with the conversion of 2-cyanopiridine to 2-picolinamide. The polymeric cores, made of either polystyrene (PS) or poly(methyl methacrylate) (PMMA), are prepared by miniemulsion copolymerization in the presence of different functional comonomers that provide carboxylic or phosphate groups: acrylic acid, maleic acid, and ethylene glycol methacrylate phosphate. The functional groups of the comonomers generate a corona around the main polymer particle and serve as nucleating agents for the in situ crystallization of cerium(IV) oxide. The obtained hybrid nanoparticles can be easily redispersed in water or ethanol. The conversion of amides to nitriles was quantitative for most of the catalytic samples, with yields close to 100%. According to our experimental observations by high-performance liquid chromatography (HPLC), no work up is needed to separate the product from unreacted substrate. The substrate remains absorbed on the catalyst surface, whereas the product can be easily separated. The catalysts are shown to be recyclable and can be reused for a large number of cycles without loss in efficiency.

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Section: Introductionmentioning

confidence: 99%

Ceria/Polymer Hybrid Nanoparticles as Efficient Catalysts for the Hydration of Nitriles to Amides

Mari

Müller

Landfester

et al. 2015

ACS Appl. Mater. Interfaces

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“…Commonly, the applied strategies face difficulties related to the recovery of the catalyst, purity of the product, high prizes, use of organic solvents, or low conversions due to the strong coordination of heteroaromatic nitriles to the metal centers [7]. The selective hydration of nitriles in water under mild conditions has also been reached by using heterogeneous catalysts, such as Ru(OH) 3 supported on alumina [8], MnO 2 [9], or CeO 2 [10].…”

Section: Introductionmentioning

confidence: 99%

Magnetically enhanced polymer-supported ceria nanocatalysts for the hydration of nitriles

Álvarez-Bermúdez¹,

Torres-Suay²,

Pérez-Plá³

et al. 2020

Nanotechnology

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The heterogeneous catalysis of the hydration of nitriles to amides is a process of great industrial relevance in which cerium(IV) oxide (also referred to as ceria) has shown an outstanding catalytic performance. The use of non-supported ceria nanoparticles is related to difficulties in the purification of the product and the recovery and recyclability of the catalyst. Therefore, in this work, ceria nanoparticles are supported on a polymer matrix either by synthesizing polymer particles by so-called Pickering miniemulsions while using ceria nanoparticles as emulsion stabilizers or, as a comparison, by in-situ crystallization on preformed polymer particles. The former strategy presents significant advantages over the latter in terms of time and consumption of resources, and it facilitates an easier scale-up of the process. In both strategies, the incorporation of a magnetoresponsive core within the polymer matrix allows the recovery and the recycling of the catalyst by simple application of a magnetic field and offers an enhancement of the catalytic efficiency.

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Continuous Flow Hydration of Pyrazine‐2‐carbonitrile in a Manganese Dioxide Column Reactor

et al. 2018

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A procedure that yields pyrazinamide as a fine white powder is presented. A glass column reactor is used containing Celite and manganese dioxide and is mounted vertically in a heating jacket. Following the procedure are notes on the instruments and chemicals used and required. The chapter concludes with a discussion on the general concepts regarding preparation of pyrazinamide.

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Catalyzed Hydration of Nitriles to Amides

Cited by 15 publications

References 2 publications

Ceria/Polymer Hybrid Nanoparticles as Efficient Catalysts for the Hydration of Nitriles to Amides

Ceria/Polymer Hybrid Nanoparticles as Efficient Catalysts for the Hydration of Nitriles to Amides

Magnetically enhanced polymer-supported ceria nanocatalysts for the hydration of nitriles

Continuous Flow Hydration of Pyrazine‐2‐carbonitrile in a Manganese Dioxide Column Reactor

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