The ultrasound-assisted oxidative scission of monoenic fatty acids by ruthenium tetroxide catalysis: Influence of the mixture of solvents
Résumé
Carboxylic acids and diacids were synthesized from monoenic fatty acids by using RuO 4 catalysis, under ultrasonic irradiation, in various mixtures of solvents. Ultrasound associated with Aliquat Ò 336 have promoted in water, the quantitative oxidative cleavage of the CH@CH bond of oleic acid. A design of experiment (DOE) shows that the optimal mixture of solvents (H 2 O/MeCN, ratio 1/1, 2.2% RuCl 3 /4.1 eq. NaIO 4) gives 81% azelaic acid and 97% pelargonic acid. With the binary heterogeneous mixture H 2 O/AcOEt, the oxidation of the oleic acid leads to a third product, the a-dione 9,10-dioxostearic acid.