Rigg. — Montan Wax. 279 



The free acid was precipitated by adding alcoholic lead acetate to the 

 boiling solution. The insoluble lead salts were filtered off, and then boiled 

 out repeatedly with alcohol to remove impurities. 



The purified lead salts were then decomposed by glacial acetic acid, 

 and the free acid, after washing with water, was extracted with boiling 

 methyl alcohol in whicb, according to Marie,* melissic acid is insoluble. 

 The solution thus obtained was filtered while hot, and the cerotic acid, 

 which separated on cooling,, was then found to melt at 75-5°. 



The acid was purified by recrystallization from ethyl alcohol, acetic 

 acid, and motor spirit. An acid was thus obtained meltingf at 77'5° 

 Brodie gives 78° for cerotic acid). 



Attempts to improve the process of obtaining cerotic acid by complete 

 saponification of the beeswax with alcoholic potash, followed by the precipi- 

 tation of the acids with alcoholic calcium- chloride, thus retaining the non- 

 acid substances in i olution, were fruitless. It was found that the calcium 

 salts in presence of a saturated solution of high-molecular-weight alcohols 

 were easily soluble, and that the precipitated calcium salts always contained 

 a considerable quantity of organic impurities. Attempts with the lead salts, 

 using the same method, were also unsuccessful. 



Cerotic acid has hitherto been stated to crystallize in microscopic- 

 needles.:]: Although this is the case when prepared by Brodie's method, 

 yet a careful fractionation of the ester of the acid obtained by the above 

 method gives on hydrolysis a pure acid which crystallizes in pearly plates 

 from acetic acid. 



A titration of the cerotic acid purified by fractionation of the ester 

 gave a molecular weight of 392-7, corresponding to the formula§ C 26 H 52 2 , 

 thus confirming the formula of Lewkowitsch|i and Henriques.^ 



Derivatives oj Cerotic Acid. 



Cerotanilide. — This compound has not previously been prepared. It 

 was obtained by heating cerotic acid with twice the theoretical quantity 

 of aniline in a sealed tube to a temperature 150° to 170° for four hours. At 

 the expiration of this period the mixture had formed a homogeneous dark 

 soft solid. This was then washed with dilute acetic acid, in order to 

 remove as much free aniline as possible. The anilide thus obtained was 

 then disso'ved in alcohol, the solution rendered alkaline with ammonia, 

 and the unchanged cerotic acid precipitated by alcoholic calcium chloride. 

 The filtrate from the insoluble calcium salts deposited the anilide on cool- 

 ing. It was purified by crystallization from alcohol, acetic acid, and 

 motor spirit. 



The anilide thus obtained melted at 98-5° C, and the melting-point was 

 unchanged by further crystallization. 



* Journ. Ohem. Soc, 1895, abs. I, 81. 



t The melting-point of the purest cerotic acid obtained by the author was 78°. 

 This was obtained by the conversion <>f the above acid into ester, and then by distillation, 

 under reduced pressure. 



% Beilstein, vol. 1, Supplement, p. 1(31. 



§ 1-5462 grams required 39-37 c.c. * KOH. 



i| Jahrb. f. Chemie, vol. 7, p. 3(59. 



* Zeit, f. Angew. Chem., 1897, p. 36(3. 



