Acetic Acid → 2-Undecanone

HRID 46011

Reaction equation

[C:1]([OH:12])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:13](O)(=O)C>>[CH3:13][C:1](=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 2

HCID 176Acetic Acid2×

HCID 2969Decanoic Acid

Product 1

HCID 81632-Undecanone

Procedure

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.

Sources & evidence

ORD record: ord-cc5584df6ac14b829492612c14279b8d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541626B2

Linked notes

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