The Autoxidation of Methyl Oleate

Ross, John H.; Gebhart, Arthur I.; Gerecht, J. Fred

doi:10.1021/ja01169a073

Cited by 80 publications

(26 citation statements)

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“…Synthesis of diketostearate dimer. The diketostearate dimer was prepared by oxidation of the dihydroxystearate dimer with the method described by Ross et al (17).…”

Section: Methodsmentioning

confidence: 99%

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Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Christopoulou

Perkins

1989

J Americ Oil Chem Soc

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Dimers, structurally representative of those formed during thermal‐oxidative reactions in fats and oils, including the dihydroxy, tetrahydroxy, and the diketo dimer of methyl stearate, were synthesized to be used as standards and model compounds for the development of various Chromatographic methods needed for further studies. The mass spectra of both the methyl ester and trimethylsiloxy derivative of the synthetic dimeric compounds were investigated in order to facilitate development of methodology for the separation and structural determination of similar polar dimer structures isolated from actual oxidized or “abused” oil samples.

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“…Synthesis of diketostearate dimer. The diketostearate dimer was prepared by oxidation of the dihydroxystearate dimer with the method described by Ross et al (17).…”

Section: Methodsmentioning

confidence: 99%

“…Diketostearate dimers were prepared by Cr0 3 oxidation of the dihydroxystearate dimer as described by Ross et at. (17) (Fig. 5).…”

Section: Examplementioning

confidence: 97%

Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Christopoulou

Perkins

1989

J Americ Oil Chem Soc

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“…When refluxed with ethanolic PPh3, (I) gives nitrosyltris-(tripheny1phosphine)iridium (IO), whose cobalt and rhodium homologues are already known. N O and IrH(CO)(PPh3)3 react to form a mixture of carbonylnitrosylbis(triphenylphosphii1e)iridium ( / / ) and a The molecular weights of the halogenonitrosyl compounds could not be determined, because (2), (3), and (4) are unstable in solution, and (5), (6), and (7) are almost insoluble. The presence of N O bridges can however be excluded for (2), (3), and (4), at least, as two NO bridges would bring the coordination number of the iridium(-I) up to the improbable value of seven.…”

Section: The Reaction Of A@-unsaturated Ketones With Thioureamentioning

confidence: 99%

Sugar Esters of Nitrogenous Fatty Acids

Ismail¹,

Simonis²

1963

Angew. Chem. Int. Ed. Engl.

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Hitherto, activated methyl groups attached to heterocycles other than quaternary bases could not be formylated (see, for example [ 1 I).Arnolil recently reported the reaction of y-picoline with dimethylformamide/acid chloride complexes to give (4pyridyl)malondialdehyde [2]. We have obtained (4-pyrimidy1)malondialdehyde (3) by the reaction o f 4-methylpyrimidine (I) with 2 moles of diniethylformamide/phosgene complex (Z), and subsequent hydrolqsis. I n contrast to the reaction of y-picoline, however, the monoformylation product, vir. 4-($-dimethylaminovinyl)pyrimidine (4), was also successfully obtained in 80 :4 yield from the reaction of ( I ) with (2) in the presence of molar quantities of HCI. Compound (4) is also formed in 70 % yield from ( I ) and dimethylformamide diethylacetal. ----CH3 C1 CKa Br CsH5 C1 GHs C I GHs Br GH5

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“…Found: X, 11.8. Ross, et al (3) reported that the semicarbazone of 10-ketostcaric acid melts a t 101-103". 10-Hydroxystearic acid.…”

Section: ((2)mentioning

confidence: 99%

HYDROXYSTEARIC ACIDS. I. THE CATALYTIC HYDROGENATION OF THE 9, 10-EPOXYSTEARATES²

Mack¹,

Bickford²

1953

J. Org. Chem.

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The lithium salt of 12-hydroxystearic acid is an important ingredient of high quality specialty greases. At present, this salt is derived entirely from hydrogenated castor oil. Because of the increased demand for castor oil fatty acids in the production of other derivatives, such as plasticizers, lubricants, surface coatings, etc., the preparation of supplementary materials from oils of domestic origin is highly desirable. Epoxystearic acids (1) can be readily prepared from oils of domestic origin and therefore, the possibility of reducing these acids to the corresponding monohydroxystearic acids was investigated.Reference to the literature revealed that the catalytic hydrogenation of epoxystearic acid has received very little attention and no information is available regarding the mechanism of this reduction. Pigulevskii and Rubashko (2) reported the hydrogenation of ethyl cis-9,lO-epoxystearate to the 10-hydroxystearate in alcohol solution using palladium-black catalyst. According to Ross, et al.(3) methyl cis-9,lO-epoxystearate can be hydrogenated with Raney nickel in ethanol neutral to phenolphthalein to yield a mixture of 9-and 10-hydroxystearates in which they found 85 % or more of the 10-isomer. Other workers have encountered considerable difficulty in the hydrogenation of long chain epoxy compounds. Thus, Newman, et al. (4) were unsuccessful in hydrogenating 1,2-epoxydecane in absolute ethanol with platinic oxide (Adams' catalyst) or with Raney nickel under ordinary conditions at room temperature, although they did succeed in reducing it to decanol with Raney nickel at a temperature of 150". In no case previously described does the hydrogenation of the oxirane group proceed with the same degree of ease as does the hydrogenation of the ethylenic linkage.In this laboratory repeated attempts to effect the hydrogenation of various samples of the methyl 9 , 10-epoxystearates in alkaline ethanolic solution using either electrolytic nickel or Raney nickel catalyst prepared by the method described in Organic Syntheses (5) were unsuccessful3. Attempts to hydrogenate the epoxy compounds with Raney nickel (5) in the absence of solvent under various conditions of temperature (25-200") and pressure (1-15 atmospheres) were also unsuccessful. Various solvents including acetic acid and petroleum ether also failed to promote the hydrogenation of these compounds when Raney nickel was used as the catalyst. However, it was found that 9'10-epoxystearates ' One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agri-* Presented a t the Southwide Chemical Conference, Auburn, Alabama.a Ross and eo-workers employed a Raney nickel specially prepared a t a low temperature by the method described by Pavlic and Adkins (6), according to s private communication from J . Ross, Julv 31, 1051. 686cultural Research Administration, U. S. Department of Agriculture.

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The Autoxidation of Methyl Oleate

Cited by 80 publications

References 1 publication

Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Sugar Esters of Nitrogenous Fatty Acids

HYDROXYSTEARIC ACIDS. I. THE CATALYTIC HYDROGENATION OF THE 9, 10-EPOXYSTEARATES²

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The Autoxidation of Methyl Oleate

Cited by 80 publications

References 1 publication

Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Sugar Esters of Nitrogenous Fatty Acids

HYDROXYSTEARIC ACIDS. I. THE CATALYTIC HYDROGENATION OF THE 9, 10-EPOXYSTEARATES2

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HYDROXYSTEARIC ACIDS. I. THE CATALYTIC HYDROGENATION OF THE 9, 10-EPOXYSTEARATES²