ARS | Publication request: Ketonization of Cuphea oil for the production of 2-undecanone

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: August 23, 2012
Publication Date: August 23, 2012
Citation: Jackson, M.A., Cermak, S.C. 2012. Ketonization of Cuphea oil for the production of 2-undecanone [abstract]. American Chemical Society. AGFD 202.

Technical Abstract: The objective of this work was to demonstrate the viability of the cross ketonization reaction with the triacylglycerol from Cuphea sp. and acetic acid in a fixed-bed plug-flow reactor. The seed oil from Cuphea sp. contains up to 71% decanoic acid and the reaction of this fatty acid residue with acetic acid yields the fragrance compound and insect repellent 2-undecanone. To this end, we screened several ketonization catalysts taken from the literature including CeO2, CeO2/Al2O3, CeO2/ZrO2, MnOx/Al2O3. The catalysts were characterized by N2 adsorption/desorption, H2-TPH, CO2-TPD, and XRD. Each of these catalysts affected the conversion but the highest yield was found with a new coprecipitated mixed metal oxide of empirical formula 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. Isolation of the 2-undecanone was accomplished by simple water wash of the organic layer followed by distillation.