Easterfield and Taylor. — Higher Fatty Acids. 303 



4. Isolation of Oleone from Commercial Olein. — P. W. Robertson* showed 

 that stearone is present in the last runnings from the iron stearine stills, 

 and it appeared probable that oleone would also be present in the olein 

 pressed from commercial stearine. This was found to be the case. Com- 

 mercial olein was freed from solid matter by filtering at 10-12° and 

 then submitted to fractional distillation at 40 mm. pressure, an efficient 

 dephlegmating column being employed. From that portion which did 

 not distil below a temperature of 300° solid matter was separated by 

 dissolving in alcohol and adding a faint excess of alkali. The solid matter 

 was proved by its melting-point (59°) and microscopic appearance to be 

 oleone, which, though easily soluble in an alcoholic solution of oleic acid, 

 is very sparingly soluble in an alcoholic solution of sodium oleate. 



5. Oleone Oxime. — This compound is easily soluble in alcohol, and 



melts at 31°. 



Found. Calculated. 



N = 2-73 2-70 



6. Reduction of Oleone by Hydriodic Acid. — When oleone is treated 

 with phosphorus pentachloride and subsequently reduced by hydriodic 

 acid and phosphorus at 240° n.-pentatriacontane (C 35 H 72 ) results. The 

 substance melted at 72-73° (KrafTt gives 74°). 



Found. Calculated. 



C = 85-8 85-3 



H = 14-8 14-6 



7. Preparation of Elaidone and Brassidone. — These ketones were pre- 

 pared from elaidic and brassidic acids, under conditions similar to those 

 described for the preparation of oleone from oleic acid, with the aid of 

 metallic iron. The yield of elaidone was 15 per cent., that of brassidone 

 50 per cent., of the theoretical quantity. 



Elaidone melts at 70°, its oxime at 32°. 

 Analysis of elaidone : — 



Found. Calculated. 



C = 83-33 83-62 



H = 13-27 13-14 



Analysis of elaidone oxime : — 



Found. Calculated. 



N = 2-9 2-7 



Brassidone melts at 80°, its oxime at 51°. 

 Brassidone : — 



Found. Calculated. 



C = 83-49 84-03 



H = 13-32 13-35 



Brassidone oxime : — 



Found. Calculated. 



N = 2-1 N = 2-2 



* Trans. N.Z. Inst., vol. 37 (1905), p. 577. 



