Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, ACS Omega called Equilibrium in the Catalytic Condensation of Carboxylic Acids with Methyl Ketones to 1,3-Diketones and the Origin of the Reketonization Effect, Author is Ignatchenko, Alexey V.; DiProspero, Thomas J.; Patel, Heni; LaPenna, Joseph R., which mentions a compound: 18362-64-6, SMILESS is CC(C)C(CC(C(C)C)=O)=O, Molecular C9H16O2, Related Products of 18362-64-6.
Acetone is the expected ketone product of acetic acid decarboxylative ketonization reaction with metal oxide catalysts used in the industrial production of ketones and for biofuels upgrade. Decarboxylative cross-ketonization of a mixture of acetic and isobutyric acids yields highly valued unsym. Me iso-Pr ketone (MIPK) along with two less valuable sym. ketones, acetone and diisopropyl ketone (DIPK). We describe a side reaction of isobutyric acid with acetone yielding the cross-ketone MIPK with monoclinic zirconia and anatase titania catalysts in the absence of acetic acid. We call it re-ketonization reaction because acetone is deconstructed and used for the construction of MIPK. Isotopic labeling of the isobutyric acid’s carboxyl group shows that it is the exclusive supplier of the carbonyl group of MIPK, while acetone provides only Me group for MIPK construction. More branched ketones, MIPK or DIPK, are less reactive in their re-ketonization with carboxylic acids. The proposed mechanism of re-ketonization supported by DFT computations starts with acetone enolization and proceeds via its condensation with surface isobutyrate to a beta-diketone similar to beta-keto acids formation in the decarboxylative ketonization of acids. Decomposition of unsym. beta-diketones with water (or methanol) by the retro-condensation reaction under the same conditions over metal oxides yields two pairs of ketones and acids (or esters in case of methanol) and proceeds much faster compared to their formation. The major direction yields thermodynamically more stable products – more substituted ketones. DFT calculations predict even a larger fraction of the thermodynamically preferred pair of products. The difference is explained by some degree of a kinetic control in the opposite direction. Re-ketonization has lower reaction rates compared to regular ketonization. Still, a high extent of re-ketonization occurs unnoticeably during the decarboxylative ketonization of acetic acid as the result of acetone reaction with acetic acid. This degenerate reaction is the major cause of the inhibition by acetone of its own rate of formation from acetic acid at high conversions.
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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica