On the Implications of Hemiketal Formation during Ethyl Pyruvate Hydrogenation in Alcohol Solvents

Hemiketal formation between alcohol solvents and α-keto esters is shown to be catalyzed not only by the basic cinchonidine modifier but also by the acidic Pt/Al2O3catalyst. Theoretical considerations and experimental results demonstrate that reaction calorimetry is a valid and accurate measure of th...

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Bibliographic Details
Published inJournal of catalysis Vol. 179; no. 2; pp. 335 - 338
Main Authors Bohnen, Frank M., Gamez, Agnes, Blackmond, Donna G.
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier Inc 25.10.1998
Elsevier
Subjects
Catalysis
Catalytic reactions
Chemistry
Exact sciences and technology
General and physical chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Catalytic reaction
Heat flow
Transition metal
Acid catalysis
Hemiacetal
Experimental study
Reaction rate
Hydrogenation
Supported catalyst
Primary alcohol
Heterogeneous catalysis
Platinum
Asymmetric reaction
Calorimetry
Ketoester
Alumina
Platinoid
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Summary:Hemiketal formation between alcohol solvents and α-keto esters is shown to be catalyzed not only by the basic cinchonidine modifier but also by the acidic Pt/Al2O3catalyst. Theoretical considerations and experimental results demonstrate that reaction calorimetry is a valid and accurate measure of the hydrogenation reaction, provided that the substrate and its hemiketal remain in equilibrium over the course of the reaction. The rate of hemiketal formation and, thus, the probability that the preequilibrium step will remain unperturbed during the hydrogenation reaction, is sensitive to the acidic properties of the support.
ISSN:0021-9517
1090-2694
DOI:10.1006/jcat.1998.2247