Kigg. — Montan Wax. 



275 



78-78-5°, and were absolutely identical with the cerotic acid of beeswax. 

 This identity was proved as follows : — 



(a.) Both acids had the same melting-point, and a mixture of the two 

 acids melted within 0-5° of the original acid. 



(b.) The ketone prepared from each, by means of the catalytic action 

 of metallic iron, melted at 92-5-93°. 



(c.) The ethyl esters of each acid had the same boiling-point, 285°, 

 at 14 mm. 



(d.) Both acids crystallized in pearly scales. 



Preparation of Pure Montanic Acid. 



Although the method of fractional precipitation did not yield montanic 

 acid in a state of purity, yet by fractional distillation of the ethyl ester 

 of the crude acid under diminished pressure purity was at last attained. 

 100 grams of crude montanic acid were dissolved in 2,300 c.c. of 95-per- 

 cent, alcohol, to which had been added 60 c.c. strong sulphuric acid. The 

 whole was kept hot on the water bath for forty-four hours. It was found 

 that equilibrium was attained within thirty hours, but if 95-per-cent. alcohol 

 is used there still remains 6 per cent, of acid unconverted to ester. The 

 crude ester was therefore reheated with absolute alcohol and a little 

 sulphuric acid in order to complete the esterification, and now gave, after 

 removal of mineral acid, only the slightest trace of free organic acid. 



The ester obtained by the above process was carefully washed free 

 from sulphuric acid, then dried in a vacuum over sulphuric acid, and 

 distilled under reduced pressure. The apparatus employed for this purpose 

 was novel, in that the neck of the distilling-flask was electrically heated, 

 and in that a special type of fractionator was used. Three fractions 

 were always collected from each distillation. The following diagram 

 shows at a glance the method of procedure and the number of distillations 

 performed : — 



Crude Ethyl Montanatc ( Melting -"point, 66°). All distillations done under a pressure 



of 14-16 mm. 



A 

 280°-295 3 



i 



«2 

 Mixed (6'^) 



as 



-289" 



a* 

 -300 : 



Mixed C&5.I 



I I 



-292° Mixed(re<) 



a* 



-290 



Mixed (nG) 



<i9 a l0 



-302° Mixed (6«) 



AG 

 11* 



Melting-point, 

 60-5 61-5 

 Ethyl, cerotate 



A9 



27°/« 



Melting-point, 61 -62° 



B 

 295 3 -310° 



I 



61 



-295° 



Mixed (ai) 



-297° 



Mixed (al) 



! 



67 



-300° 



Mixed («<>) 



I 



610 



-300° 



Mixed (a'-', 



62 &» 



-310° Mixed (c) 



65 6G 



-310° Mixed (c) 



I 

 fcs 



-310° 



69 

 Mixed (c2) 



I I 



fell 612 



-312° Mixed (c5) 



BH 



32 % 



Melting-point, 66'5°-67 5° 



Ethyl montanate 



I 



el 



-310° 



Mixed («5) 



I 



ci 



-310° 



Mixed (6«) 



C 

 310° 



-330° 



-330 



I 



-310 



Mixed (611) 



I 

 C8 



-3-23 1 



Residue 



I 



CG 



Residue 



I 

 eS 



Residue 



C8 



16% 



Ethyl 



melissatk 



C9 



Residues 



12 %. 



