The ultrasound-assisted oxidative scission of monoenic fatty acids by ruthenium tetroxide catalysis: Influence of the mixture of solvents

Carboxylic acids and diacids were synthesized from monoenic fatty acids by using RuO4 catalysis, under ultrasonic irradiation, in various mixtures of solvents. Ultrasound associated with Aliquat® 336 have promoted in water, the quantitative oxidative cleavage of the CHCH bond of oleic acid. A design of experiment (DOE) shows that the optimal mixture of solvents (H2O/MeCN, ratio 1/1, 2.2% RuCl3/4.1 eq. NaIO4) gives 81% azelaic acid and 97% pelargonic acid. With the binary heterogeneous mixture H2O/AcOEt, the oxidation of the oleic acid leads to a third product, the α-dione 9,10-dioxostearic acid.