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 CH=CH 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 alpha-dione 9,10-dioxostearic acid.
Rup
Sandrine
S
Laboratoire de Chimie et de Méthodologies pour l'Environnement, EA 4164, Université Paul Verlaine - Metz, 1 Bd Arago, Metz Technopôle, F-57078 Metz, Cedex 3, France.
Zimmermann
François
F
Meux
Eric
E
Schneider
Michel
M
Sindt
Michele
M
Oget
Nicolas
N
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D003998:Dicarboxylic Acids / Q000737:chemistry; D004655:Emulsions / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry* / Q000528:radiation effects*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D019301:Oleic Acid / Q000737:chemistry; D010084:Oxidation-Reduction; D017975:Ruthenium Compounds / Q000737:chemistry* / Q000528:radiation effects*; D012997:Solvents; D013055:Spectrophotometry, Infrared; D014465:Ultrasonics
D000475:Alkenes; D003998:Dicarboxylic Acids; D004655:Emulsions; D005227:Fatty Acids; D017975:Ruthenium Compounds; D012997:Solvents; D019301:Oleic Acid; C027646:ruthenium tetraoxide; C010038:azelaic acid