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Ricinelaidic acid and methyl ricinelaidate. Their preparation and determination by infrared spectroscopy

1959; Wiley; Volume: 36; Issue: 3 Linguagem: Inglês

10.1007/bf02639983

1558-9331

Marian A. McCutchon, R. T. O’Connor, Elsie F. DuPré, L. A. Goldblatt, W. G. Bickford,

Crystallization and Solubility Studies

Summary Improved methods for the preparation of ricinelaidic acid and methyl ricinelaidate are described. The methods depend upon the elaidinization of methyl ricinoleate with a relatively small quantity of a nitrite‐nitric acid solution, fractional crystallization of the methyl ricinelaidate, and its subsequent hydrolysis to ricinelaidic acid. The infrared spectra of these two compounds are presented, and bands arising from a deformation of the C−H about the trans C=C group are discussed. Absorptivity values for this band in chlorform and in carbon disulfide solutions are given as additional criteria of purity of ricinelaidic acid and its methyl ester. The infrared absorption procedure for the quantitative determination of isolated trans ethylenic bond was applied to the determination of both ricinelaidic acid and methyl ricinelaidate. Details of specific procedures for the determination of each compound are given with the equations necessary for their calculation. Use of these methods is illustrated with the analysis of elaidinization mixtures. The repeatability and accuracy obtaineble are given. A value is reported for the methyl ricinoleate—methyl ricinelaidate equilibrium and the mechanism of the reaction is discussed briefly.