Cerium oxide as a catalyst for the ketonization of aldehydes: mechanistic insights and a convenient way to alkanes without the consumption of external hydrogen

Orozco, Lina M.; Renz, Michael; Corma, Avelino

doi:10.1039/c6gc03511f

Cited by 40 publications

(23 citation statements)

References 45 publications

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“…8 Orozco et al carefully investigated the role of water in the oxidation of aldehyde to carboxylic acid use ZrO 2 and CeO 2 as model catalysts. [31][32][33] Surface hydroxyl group (from water adsorption and decomposition) could combine with adsorbed aldehyde to form aldehyde hydrate, which then is able to transfer a hydride species and further form molecular hydrogen. Meanwhile, with a surface proton derived from the initial water adsorption, carboxylic acid product can be formed.…”

Section: Results Of Characterizationmentioning

confidence: 99%

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Production of acetic acid from ethanol over CuCr catalysts via dehydrogenation-(aldehyde–water shift) reaction

Xiang

Ran

et al. 2017

RSC Adv.

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A series of CuCr catalysts were prepared by co-precipitation method and used to produce acetic acid from ethanol via dehydrogenation-(aldehyde-water shift) reaction. The catalysts were characterized by X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Brunauer-Emmett-Teller analysis (BET), inductively coupled plasma atomic emission spectroscopy (ICP-AES), and temperature programmed reduction (TPR). The effects of copper contents and atmosphere on catalytic performance were investigated. The enhanced catalytic performance can be ascribed to the existence of chromium oxide.

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Section: Results Of Characterizationmentioning

confidence: 99%

“…31 use O 2 as oxidant, whether pure oxygen or air. As Scheme 1 shows, oxidation of ethanol to acetic acid generally proceeds in two steps.…”

mentioning

confidence: 99%

Production of acetic acid from ethanol over CuCr catalysts via dehydrogenation-(aldehyde–water shift) reaction

Xiang

Ran

et al. 2017

RSC Adv.

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“…In the last few years, CeO 2 -based materials have attracted much attention due to their wide use in various catalytic systems [1][2][3][4][5][6]. The success of ceria and ceria-based materials in catalysis is often due to facile Ce 4+ /Ce 3+ redox cycling without disruption of the fluorite lattice structure [6].…”

Section: Introductionmentioning

confidence: 99%

“…The symbol "ν" denotes stretching vibrations, "δ" denotes in-plane deformations, "β" denotes out-of-plane deformations; and the band is marked with "as"-asymmetric vibrations, "s"-symmetric, "ar"-vibrations of the aromatic ring 2. The frequency is given for a sample of CA/CeO 2 (0.6 mmol/g) 3.…”

mentioning

confidence: 99%

Thermal Transformation of Caffeic Acid on the Nanoceria Surface Studied by Temperature Programmed Desorption Mass-Spectrometry, Thermogravimetric Analysis and FT–IR Spectroscopy

Nastasiienko

Palianytsia

Кartel

et al. 2019

Colloids and Interfaces

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The studies of pyrolysis of caffeic acid (CA) and its surface complexes is important for the development of technologies of heterogeneous catalytic pyrolysis of plant- and wood- based renewable biomass components. In this work, the structure and thermal transformations of the surface complexes of CA on the surface of nanoceria were investigated using Fourier transform–infrared (FT–IR) spectroscopy, thermogravimetric analysis (TGA) and temperature-programmed desorption mass spectrometry (TPD MS). It was found that CA on the surface of cerium dioxide forms several types of complexes: bidentate carboxylates, monodentate carboxylates and complexes formed as a result of interaction with phenolic hydroxyl groups. This is due to the ability of nanosized cerium dioxide to generate basic hydroxyl groups that can deprotonate phenolic groups to form phenolates on the surface. The main pyrolysis products were identified. The possible ways of forming 3,4-dihydroxyphenylethylene, acetylene carboxylic acid, pyrocatechol and phenol from surface complexes of CA were suggested. It was established that on the nanoceria surface effectively occur the decarboxylation, decarbonylation, and dehydration reactions of the CA, which are the desirable processes in biomass conversion technologies.

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“…El aldehído en presencia de agua se oxida al correspondiente ácido carboxílicos que termina formado la cetona por descarboxilación cetónica. [90][91] En el caso de los alcoholes, algunos autores abogan también por la formación de un aldehído que se transforma en ácido carboxílico como intermedios de reacción. [92][93] En la bibliografía se pueden encontrar varios ejemplos de la descarboxilación cetónica de aldehídos.…”

Section: Descarboxilación Cetónica De Aldehídos Y Alcoholesunclassified

Transformación de biomasa a productos químicos de interés y carburantes mediante descarboxilación cetónica e hidrodesoxigenación

Tomás¹

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The purpose of the present thesis was the use and valorisation of biomass platform molecules or their derivatives, applying the principles of sustainable chemistry. The reaction of ketonic decarboxylation of carboxylic acids was studied in the presence of metal oxides. ZrO2 was shown to be an excellent catalyst for the reaction, reasonably stable with time on stream and reusable. The reactivity of different substrates over ZrO2 was investigated with respect to the degree of substitution of the carbon in alpha position. 2-methylbutanoic acid, with one methyl replacing one of the alpha H atoms and, thereby, introducing a steric hindrance, showed slower reaction rates than pentanoic acid with two alpha Hα. It was concluded that for 2-methylbutanoic acid reactions occurred preferentially at the edges and the corners of the catalyst.

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Cerium oxide as a catalyst for the ketonization of aldehydes: mechanistic insights and a convenient way to alkanes without the consumption of external hydrogen

Abstract: The atom-efficient transformation of two aldehyde molecules into a linear alkane at the expense of one carbon dioxide molecule.

Cited by 40 publications

References 45 publications

Production of acetic acid from ethanol over CuCr catalysts via dehydrogenation-(aldehyde–water shift) reaction

Production of acetic acid from ethanol over CuCr catalysts via dehydrogenation-(aldehyde–water shift) reaction

Thermal Transformation of Caffeic Acid on the Nanoceria Surface Studied by Temperature Programmed Desorption Mass-Spectrometry, Thermogravimetric Analysis and FT–IR Spectroscopy

Transformación de biomasa a productos químicos de interés y carburantes mediante descarboxilación cetónica e hidrodesoxigenación

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