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

Ultrasonics Sonochemistry, ISSN: 1350-4177, Vol: 16, Issue: 2, Page: 266-272
2009
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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 ® 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 α-dione 9,10-dioxostearic acid.

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