Ketonization of carboxylic acids over CeO2-based composite oxides

Nagashima, Osamu; Sato, Satoshi; Takahashi, Ryōji; Sodesawa, Toshiaki

doi:10.1016/j.molcata.2004.10.042

Cited by 156 publications

(153 citation statements)

References 42 publications

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“…[62][63][64][65][66][67][68][69][70] Symmetrical ketones such as 3-pentanone, 6-undecanone, and 7-tridecanone have been obtained from ketonization of the appropriate acids. [62,65] This method was applied to the synthesis of nonsymmetrical ketones used as raw materials for pesticides and pharmaceutical products.…”

Section: Acid Condensationmentioning

confidence: 99%

“…[62,65] This method was applied to the synthesis of nonsymmetrical ketones used as raw materials for pesticides and pharmaceutical products. [66][67][68] For example, methylcyclopropylketone and methylnonylketone were produced by the condensation of acetic acid with cyclopropanecarboxilic acid and decanoic acid, respectively. [66] In the reaction of propanoic acid, the reactivity of the carboxylic acid slightly decreased as its chain length was increased, and branched acids were less reactive than linear ones.…”

Section: Acid Condensationmentioning

confidence: 99%

“…[66] In the reaction of propanoic acid, the reactivity of the carboxylic acid slightly decreased as its chain length was increased, and branched acids were less reactive than linear ones. [68] Aromatic ketones were obtained from aromatic carboxylic acids and acetic acid over CeO 2 /Al 2 O 3 , chosen as an industrial catalyst for the preparation of the 2-methylacetophenone because of its higher productivity, longer catalyst life, and the lifting of legal restrictions on catalyst handling. The catalyst system can also be applied to the preparation of acetophenone, nitroacetophenone, and chloroacetophenone.…”

Section: Acid Condensationmentioning

confidence: 99%

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Ceria‐Based Solid Catalysts for Organic Chemistry

Vivier¹,

Duprez²

2010

ChemSusChem

362

244

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Ceria has been the subject of thorough investigations, mainly because of its use as an active component of catalytic converters for the treatment of exhaust gases. However, ceria‐based catalysts have also been developed for different applications in organic chemistry. The redox and acid–base properties of ceria, either alone or in the presence of transition metals, are important parameters that allow to activate complex organic molecules and to selectively orient their transformation. Pure ceria is used in several organic reactions, such as the dehydration of alcohols, the alkylation of aromatic compounds, ketone formation, and aldolization, and in redox reactions. Ceria‐supported metal catalysts allow the hydrogenation of many unsaturated compounds. They can also be used for coupling or ring‐opening reactions. Cerium atoms can be added as dopants to catalytic system or impregnated onto zeolites and mesoporous catalyst materials to improve their performances. This Review demonstrates that the exceptional surface (and sometimes bulk) properties of ceria make cerium‐based catalysts very effective for a broad range of organic reactions.

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Section: Acid Condensationmentioning

confidence: 99%

Section: Acid Condensationmentioning

confidence: 99%

Section: Acid Condensationmentioning

confidence: 99%

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Ceria‐Based Solid Catalysts for Organic Chemistry

Vivier¹,

Duprez²

2010

ChemSusChem

362

244

View full text Add to dashboard Cite

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“…The mechanism starts with the abstraction of this hydrogen by a basic site of the catalyst surface, which leads to the formation of a nucleophile that can attack another carboxylic acid to form a ketone. This mechanism was corroborated in the ketonization of different acids (acetic acid, propanoic acid, valeric acid, and their derivatives), by using isotopic compounds and with DFT approaches [144,149,150]. Discrepancies arise between the types of adsorption of AcOH on these catalysts, with two main alternatives: (a) non-dissociative adsorption in the form of hydrogen-bonded AcOH molecule, as is detailed in Eq.…”

Section: Acetic Acid Ketonization Catalysts and Reaction Mechanismmentioning

confidence: 88%

“…The β-keto acid is formed by coupling an enolate (enolized carboxylate) and a carboxylate. In the case of acetic acid ketonization, this reaction is between two molecules, but the ketonization of more complex compounds can be intramolecular [149]. The β-keto acid suffers decarboxylation by a mechanism that involves redistribution of six electrons, giving an enol that can be rapidly tautomerized to form the corresponding ketene [153].…”

Section: Acetic Acid Ketonization Catalysts and Reaction Mechanismmentioning

confidence: 99%

Base-Catalyzed Reactions in Biomass Conversion: Reaction Mechanisms and Catalyst Deactivation

Faba

Dı́az

Ordóñez

2016

Green Chemistry and Sustainable Technology

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Although less studied than acid-catalyzed reactions, mainly because of their marginal interest in petrochemical processes, base-catalyzed reactions (either homogeneous or heterogeneous) play a key role in the upgrading of biomass-derived platform molecules. As in most of the chemical processes, the replacement of homogeneous catalysts by heterogeneous catalysts is of key interest. This article reviews the state of the art in the most important base-catalyzed reactions in the biofuel manufacture (biodiesel from triglycerides) and the upgrading of biomass-derived platform molecules (such as acetone, ethanol, furfural, 5-hydroxymethylfurfural, or acetic acid). Transesterification reactions, aldol condensation (alone or in combination with other reactions), and ketonization are the main reactions involved in these biorefinery processes. Reviewed are the most common catalysts proposed for these reactions (mainly heterogeneous), as well as the proposed mechanisms for these reactions, and the main factors governing catalyst deactivation when used in each of these reactions.

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