Acetic Acid → 2-Undecanone

Participants

Reaction Steps

The cross ketonization reaction with the triacylglycerol from Cuphea sp. and acetic acid is demonstrated. The seed oil from Cuphea sp. contains up to 71% decanoic acid and the reaction of this with acetic acid yields the fragrance compound 2-undecanone. Several ketonization catalysts from the literature including CeO2, CeO/Al2O3, CeO/ZrO2, MnOx/Al2O3 were screened and compared with a coprecipitated mixed metal oxide of empirical formula Fe0.5Ce0.2Al0.3Ox (also represented as 50Fe20Ce30AlOx). Each of these catalysts effected the conversion but the highest yield was found with Fe0.5Ce0.2Al0.3Ox. In a flow reactor, Fe0.5Ce0.2Al0.3Ox gave 2-undecanone at 91% theoretical yield with reaction conditions of 400° C., weight hourly space velocity of 2, molar ratio of acetic acid to Cuphea oil of 23, and N2 carrier gas flow of 125 ml/min at 2.4 bar. In the absence of acetic acid, coupling of the decanoic acid residues gives 10-ketononadecane.

Provenance & Evidence