SummaryThe relation between fatty acid compositions, tocopherol contents, and autoxidative stabilities of a series of 16 crude oils from different varieties of peanuts has been investigated. It was found that the relative linoleic acid content of the oils is one of the major factors affecting the variations in the stabilities of the oils tested. With the exception of the oils from Runner peanuts the tocopherol compositions of the oils were not found to vary significantly, either in the nature and distribution of individual tocopherols, or in total tocopherol contents. The enhanced stability of the oils from the Runner peanuts may be due in part to the higher tocopherol contents of these oils. There is some evidence that crude peanut oils contain some non‐tocopherol antioxidant and/or synergist.

It has been found that addition of diborme to the ethylenic bond of methyl oleate proceeds smoothly without significant reduction of the carbomethoxy group. Alkaline hydrogen peroxide oxidation of the tris(carbomethoxyalky1)borane resulted in the formation of an equimolar mixture of 9-and 10-hydroxyoctadecanoic acids, establishing that the hydroboration reaction proceeded nonselectively. Little or no isomerization occurred on heat treatment of these substituted trialkyl boranes.

Summary It has been shown that certain alkylbenzenes having a hydrogen atom on the alpha carbon atom react with maleic anhydride to form compounds analogous to the hydroperoxides produced by autoxidation of the alkylbenzenes. The structure of these products has been determined by oxidation with aqueous permanganate and the results have been applied, together with other data, to demonstrate that the reaction proceeds by a free radical chain mechanism involving the abstraction of a hydrogen atom from the alpha carbon atom. In view of the analogy between the products obtained in this investigation and in autoxidation, it is suggested that autoxidation is propagated in a similar manner.

Summary 1. The non‐conjugated unsaturated fatty acid esters react with maleic anhydride at 200° C. or above. 2. At 200° C., methyl oleate reacts with almost 1 mole, methyl linoleate with 2 moles, and methyl linolenate with 2.5 moles of maleic anhydride, when an excess of anhydride is present. Methyl stearate reacts negligibly. 3. Methyl oleate reacts without affecting unsaturation. 4. The first molecule of anhydride reacting with methyl linoleate reacts mostly to saturate one double bond, while the second one adds on without affecting unsaturation. 5. The first two molecules of anhydride reacting with methyl linolenate react mostly to saturate one double bond each, while the third molecule adds on without affecting unsaturation. 6. The possible structures of the reaction products have been discussed.

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.