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The hydrogenation of the oleic acid group was investigated with the objective of determining the effect of solvents on the reaction rate and the formation of positional and geometrical isomers. Methyl oleate, either alone or dissolved in one of several solvents, hexane, ethanol,n‐butyl ether, or acetic acid, was hydrogenated to an iodine value of about 50 under atmospheric pressure and at 30°C, with palladium‐on‐carbon and the W‐5 form of Raney nickel as catalysts.Hydrogenation with palladium catalyst, with or without solvents, produced 76.6 to 79.1%trans bonds, based on the total double bonds. This is significantly greater than the 67% obtained previously. Hydrogenation products obtained with Raney nickel and solvents contained as little as 20.7%trans bonds at an iodine value of about 50. In two cases thetrans bonds were equal to about one‐third the positional isomers.Positional isomers formed extensively when the Raney nickel was used in the absence of solvents and when the palladium catalyst was used. When the Raney nickel and solvents were used large proportions of double bonds were found in the original 9‐position.

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Summary In the alkali‐refining of rice oil by the usual procedure employed for cottonseed and similar oils excessive losses occur. A rice oil containing about 5% of free fatty acids may refine with a loss of over 40% by the cup method. A series of experiments has been performed which shows that the adding of certain organic compounds to the crude oil just before carrying out the regular refining procedure greatly reduces the refining losses. The technique was effective in both batch and continuous processes. Depending on the refining process used, reductions in the refining loss of 32 to 55% have been obtained. The organic compounds used as additives contained NH2 and OH groups. Sucrose or blackstrap molasses appears to be the most practical material to use. However ethanolamines and various glycols and alcohols may also be employed.