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filingDate 1939-01-23-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1940-07-31-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-524163-A
titleOfInvention Improvements in or relating to the oxidation of unsaturated fatty acids
abstract 524,163. Carboxylic acids. DU PONT DE NEMOURS & CO., E. I., and ELLINGBOE, E. K. Jan. 23, 1939, No. 2322. [Class 2 (iii)] The oxidation of unsaturated aliphatic longchain carboxylic acids to produce saturated mono- and di-carboxylic acids is effected with strong nitric acid and a vanadium catalyst at ordinary or slightly elevated temperature, such as 0-40‹C. The nitric acid should be of 80 per cent. or higher strength and should be used in the molecular ratio of 5-15 per molecule of unsaturated acid. In an example for the oxidation of oleic acid, the product is diluted with water, yielding two layers. The aqueous' layer after decolorizing is cooled to 10-0‹C. to crystallize dibasic acids (largely azelaic acid) and the mother-liquor after concentration and cooling yields more dibasic acids ; the oily layer is steam-distilled, to recover monobasic acids (principally pelargonic acid); the residue of the distillation in further treatment with nitric acid and vanadium catalyst yields some further dibasic acids and a nitrogen-containing residue. Alternatively, the original oxidation product may be neutralized with potassium carbonate, the organic acid salts being then separated by crystallization from the potassium nitrate. In another example, erucic acid is oxidized yielding brassylic acid which is insoluble in water ; the products may be separated by esterifying the mixture and fractionating the esters. For this purpose the reaction product is treated with water and the waxy material is separated and dissolved in sodium hydroxide, zinc dust being added to reduce the nitrated products and acidified with hydrochloric acid ; the insoluble material thus freed from the nitrogen compounds is washed and dried and then esterified with methanol in the presence of hydrochloric acid. The mixed esters on fractionation yield methyl pelargonate and brassylate.
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