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IV. 



MONTANIC ACID AND ITS DERIVATIVES. 



By Professor HUGH EYAN and JOSEPH ALGAE, 

 University College, Dublin. 



Read Janxiaky 13. Published Fejjruauy 12, 1913. 



MoNTAN wax, which is prepared by distilling lignite in a current of super- 

 heated steam, contains about fifty per cent, of montanic acid. To extract 

 the latter, the wax is dissolved in hot alcohol, excess of alcoholic potash is 

 added, and the mixture is boiled under a reflux condenser for several hours. 

 The alcohol is then evaporated off, and the dry residue is extracted with 

 petroleum ether in a Soxhlet apparatus until all the unsaponifiahle matter 

 has been dissolved out. Free montanic acid is obtained by warming the 

 potassium montanate with hydrochloric acid. The crude acid is decolorised 

 with animal charcoal and recrystallised several times from hot alcohol. The 

 pure substance melts at 83° C, and its composition as determined by Eyan 

 and Dillon' agrees sharply with the formula G2gH5o02. Eeceutly Easterfield 

 and Taylor,^ when preparing montanone, found the titration value of montanic 

 acid to be exactly that required by the above formula. 



On the other hand, the formula for montanic acid given by Hell,^ by 

 von Boyen,* and by Eisenreich* is C09H53O2. It seemed unlikely that this 

 formula could be correct, owing to the fact that all the higher saturated 

 fatty acids, which occur naturally, and whose empirical formulae have been 

 satisfactorily determined, contain an even number of carbon atoms in their 

 molecules. Various theories have been put forward to explain the manner 

 in which the formation of these higher natural fatty acids takes place. 

 Pfeffer" has shown that the fatty acids are formed from the carbohydrates 

 present in the plant. Emil Fischer' suggests that a kind of aldol condensation, 

 taking place between a number of simple carbohydrates, forms higher sugars. 



' Proc. R. D. Soc, xii, 1909, p. 202. "■ Jour. Chem. Soc, 1911, p. 2302. 



3 Zeitsch. f. Angew. Chem., xiv., 1900, p. 556. 



^ Zeitsch. f. An:;e\v. Chem. xiv, 1901, p. 1110. 



» Chem. Rev. Fett- u. Harz-ind., xvi, 1909, p. 211, <^ Jahrb. wiss. Bot., 8. 



' Oiganische Synthese und Biologie. 



R.T.A. PKOC, VOL. XXX., SECT. B. [O] 



