Catalytic Air Oxidation of Methyl Oleate and Characterization of the Polymers Formed<sup>2</sup>

Swern, Daniel; Knight, H. B.; Scanlan, J.; Ault, W. C.

doi:10.1021/ja01223a027

Cited by 44 publications

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“…Furthermore, oxygen was also applied as oxidant in the presence of V 5þ containing catalysts [78], metal porphyrines [79], Co naphthenate [80], and Co oleate [81]. However, the yields of AA and selectivities were rather poor probably due to predominant radical reaction pathways and side reactions.…”

Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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“…under an atmosphere of nitrogen and that, under these conditions, oleic acid is intermolecularly oxidized to form 9,10-epoxy-oleic acid and 9,10-dihydroxystearic acids. The low-melting form of 9,10-dihydroxystearic acid has been isolated from oxidized oleic acid or its derived esters by Ellis (7), Swern etal., (8), and Banks and Hilditch (9). The highmelting isomeric 9,10-dihydroxystearic acid, m.p.…”

Section: Discussionmentioning

confidence: 99%

The oxidation of methyl oleate. II. A reaction between methyl hydroperoxido oleate and oleic acid

Swift

Dollear

1948

J Americ Oil Chem Soc

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Oleic acid is intermolecularly oxidized by methyl hydroperoxido oleate at 90~ through the addition of oxygen at the olefinie bond with the formation of epoxy and dihydroxy compounds. Only the lowmelting isomeric form of dihydroxystearic acid could be isolated from tile reaction mixture. The oxidation of olefinic linkages by hydroperoxides appears to account, at least in part, for the observed reduction of unsaturation in autoxidizing fats.

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“…The cleavage with oxygen as oxidant was investigated in the presence of V(V) catalysts [4], metal porphyrines [5], Co naphthenate [6] and Co oleate [7]. However, the yields of azelaic acid were rather poor.…”

Section: Introductionmentioning

confidence: 99%

Catalytic cleavage of methyl oleate or oleic acid

Köckritz

Blumenstein²,

Martin

2010

Euro J Lipid Sci & Tech

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Different reaction pathways are discussed for the Os-catalyzed oxidation of methyl oleate and oleic acid using O 2 /aldehyde as oxidation system. Monomethyl azelate and pelargonic acid were the main products obtained in yields of approximately 50-70% starting from methyl oleate. Besides, varying amounts of methyl 9,10-epoxystearate and methyl 9,10-dihydroxystearate were found as by-products. Azelaic acid and pelargonic acid were obtained exclusively from oleic acid used as reactant. Some mechanistic considerations led to the conclusion that the observed products are formed in parallel reaction paths. The effective oxidant for the scission of the C=C double bond seems to be very likely an in situ formed peracid generated by Os-catalysis from O 2 /aldehyde. Additional investigations concerning the cleavage of oleic acid and methyl oleate with in situ formed performic acid from H 2 O 2 /formic acid corroborate this assumption.

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Catalytic Air Oxidation of Methyl Oleate and Characterization of the Polymers Formed²

Cited by 44 publications

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Synthesis of azelaic acid from vegetable oil‐based feedstocks

Synthesis of azelaic acid from vegetable oil‐based feedstocks

The oxidation of methyl oleate. II. A reaction between methyl hydroperoxido oleate and oleic acid

Catalytic cleavage of methyl oleate or oleic acid

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Catalytic Air Oxidation of Methyl Oleate and Characterization of the Polymers Formed2

Cited by 44 publications

References 0 publications

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Synthesis of azelaic acid from vegetable oil‐based feedstocks

The oxidation of methyl oleate. II. A reaction between methyl hydroperoxido oleate and oleic acid

Catalytic cleavage of methyl oleate or oleic acid

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Catalytic Air Oxidation of Methyl Oleate and Characterization of the Polymers Formed²