Effects of Metal Acetylacetonates on the Autoxidation of Methyl Oleate and the Decomposition of Hydroperoxide of Methyl Oleate

Mochida, Yoshiyuki; Yamada, Tomishi

doi:10.5650/jos1956.32.163

Cited by 2 publications

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“…As for the oxygenated compounds (except for carboxyl groups) formed other than KO, HE (R-CH(O)CH-CH(OH)-R'), HO (R-CH=CH-CH(OH)-R'), and EP (R-CH(O)CH-R', cis isomer and trans isomer), which are mixtures of positional isomers, optical isomers, and geometrical isomers, were detected. These isomers were more significantly produced by air oxidation 2) in the presence of various metal salts. These compounds having an equal or similar molecular weight (in particular, geometrical isomers and positional isomers) in the mixture are required to be isolated and then identified.…”

Section: Resultsmentioning

confidence: 96%

“…It is well-known that the first product from oleic acid methyl ester (OM) is methyl hydroperoxyoleate (OMH) 1) , which consists of four kinds of positional isomers. If a metal salt coexists, the second products 2) were produced more remarkably. The second products mean the epoxy hydroxides formed by the intermolecular transfer of OMH itself, the epoxides of the geometrical isomer formed by an intermolecular oxidation between OMH and OM, the hydroxides of positional isomers, and oxo compounds.…”

Section: Introductionmentioning

confidence: 99%

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Effect of the Amount of Liquid Phase in Packed Column GC on Air Oxidation Product of Methyl Oleate

Mochida

Oka

Sugawara³

et al. 2009

J. Oleo Sci.

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The analysis or preparative isolation of a specimen by a packed column gas chromatograph is affected by the kind and amount (concentration) of the liquid phase coated on the stationary phase. In particular, compounds having the same or similar molecular weight and similar functional groups are largely affected. Methyl oleate, which is a typical component of fats and oils, produces hydroperoxide by air oxidation as a first step. After that, various oxygenated compounds with a carbon number of 19 are produced. In this study, the effect of the concentration of ethylene glycol succinate polyester (EGS) as the liquid phase was examined for these compounds. The retention time of the hydroxides increased with an increase in the EGS concentration. The effect of the EGS concentration on the retention time decreased when these compounds were trimethyl silylated (TMS). The retention time of epoxides and oxo compounds increased with an increase in the EGS concentration independently of trimethyl silylation. Correction values were required for all quantitation.

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Effect of the Amount of Liquid Phase in Packed Column GC on Air Oxidation Product of Methyl Oleate

Mochida

Oka

Sugawara³

et al. 2009

J. Oleo Sci.

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Eco-friendly Lubricating Oil: Effects of Functional Groups in Methyl Oleate and Olive Oil on Lubrication.

Mochida¹,

Kudou²,

Ookouchi³

et al. 2003

J. Mass Spectrom. Soc. Jpn.

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The lubrication characteristics of the olive oils, which are used as biodegradable lubricants, on the steel ball were examined on the viewpoint of their growing area and quality of the olive oil. The discoloration of virgin olive oil and the friction face and/or the friction force of the steel ball were found to be dependent on their growing area as well as pure olive oil.Property of the constituent metal constituents of steel ball on the air oxidation of methyl ester of oleic acid, which is major constituent fatty acid of olive oil and the lubrication characteristics of the resulting oxidation products, were investigated. The autoxidation of methyl oleate under the existence of each acetylacetonatos of Cr, Mn, Fe, Ni, Cu, and V was carried out by blowing dry air at 80̮. All the metal salts except V facilitated the oxidation. The metals employed a#ect the yields and the types of the products, i.e., hydroperoxide, hydroxide and epoxide whom the functional group exists for the center location of molecular chain.Friction test for ball bearing was conducted by using each oxidation product and parent methyl oleate. The surface of the steel ball was the abrasive wear condition by hydroperoxide. The hydroxide gave excellent lubrication characteristics by hydroxy group adsorbed on the surface of steel ball. Epoxide increased the coe$cient of friction. Methyl linoleate, having two double bonds, provided the flatted frictional surface at the ball bearing, but it is easy to be oxidized.To sum up the major characteristics of the autoxidation products which a#ect friction surface of steel ball, the function groups of center position in molecular chain of methyl oleate are of most significance. It was found that double bond and hydroxyl function of a-position of double bond are e#ective under the boundary lubrication.

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Effects of Metal Acetylacetonates on the Autoxidation of Methyl Oleate and the Decomposition of Hydroperoxide of Methyl Oleate

Cited by 2 publications

References 0 publications

Effect of the Amount of Liquid Phase in Packed Column GC on Air Oxidation Product of Methyl Oleate

Effect of the Amount of Liquid Phase in Packed Column GC on Air Oxidation Product of Methyl Oleate

Eco-friendly Lubricating Oil: Effects of Functional Groups in Methyl Oleate and Olive Oil on Lubrication.

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