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XX.—Preparation of adipic acid and some of its derivatives

Walter H. Ince
1895 Journal of the Chemical Society Transactions  
IN the course of an investigation of some derivatives of adipic acid and their condensation products, large quantities of the acid were required, but as Wislicenus' method (Annulen, 1867, 144, 2.11) of preparing it, namely, heating P-iodopmpionic acid with silver, was found to be tedious and unsatisfactory, other methods were investigated. According to Laurent (Ann, G'him. Phys., [a], 66, 166), Rromeis (Annalen, 1840, 35, 105), and Malaguti (Ann. Chirn. Phys., 1846, [ 3 ] , 16, 84), adipic acid
more » ... 6, 84), adipic acid is easily prepadred by oxidising fats with nitric acid, sebacic acid being formed as an intermediate product ; in fact, a method of obtaining adipic acid from sebacic acid by oxidising the latter with nitric acid is given in detail by Arppe (Zeit. f. Chem., 1865, 300). The following is an account of my attempts t o prepare adipic acid by these methods. Action of Nit& acid on Sebacic acid.-Fitt's method (Ber., 1874, 7, 220) for prepariug sebacic acid gives very satisfactory results. Castor oil is saponified with sodium hydroxide, and the soap obtained is heated until the evolution of octylic alcohol ceases ; it is then dissolved in water, and the acid precipitated by means of hydrochloric acid. Arppe (Zoc. cit.) states that he oxidised sebacic acid by heding it with nitric acid, expelled the excess of the latter, and crystallised the residue from hot water. The crystals, after being dried and heated until they fused, were powdered when cold and then shaken with ether, which readily dissolves the adipic acid, but not the succinic acid, as the latter is insoluble in ether. O n heating sebacic acid on a water Sath for four hours with a
doi:10.1039/ct8956700155 fatcat:jaxvsazjrnbonciqlglmhqnmnq