376 



Ml'. Schorlemmer on the Constitution of [May 14, 



How this compound, which without cloubt was an aceton, has been formed 

 I am at a loss to understand. The very small quantity of liquid boiling 

 above 120° consisted chiefly of amy] valerate ; at least it had the odour of 

 this ether. 



I should have wished to be able to give more definite results, but the 

 preparation of amyl alcohol from petroleum is difficult and requires a very 

 long time. But as the oxidation-products of the different amyl alcohols 

 are being at present investigated by different chemists, I thought it would 

 not be without interest to publish these incomplete results. 



V. ^' On the Constitution of Capryl Alcohol from Castor-oil/^ 

 By C. Schorlemmer. Communicated by Prof. Gr. G. Stokes, 

 Sec, R.S. Eeceived May 7, 1868. 



There is perhaps no other compound known which has been so often 

 and so fully investigated by different chemists, and yet whose constitution 

 is clouded in so much obscurity, as the alcohol v/hich is obtained by dis- 

 tilling castor-oil soap with caustic alkalies. From the time of its discovery 

 until recently, this compound has been alternately considered by one in- 

 vestigator to be capryl or octyl alcohol, and by another to consist of 

 cenanthyl or heptyl alcohol. As a proof that it is capryl alcohol. Bonis, 

 states that, by the moderate action of nitric acid, a small quantity of caprylic 

 acid is produced, the greater part of the alcohol, however, being oxidized 

 to lower members of the fatty acid series*; and Kolbe concludes, from the 

 formation of these acids, that it is a secondary or isoalcohol, probably 



fCH, 



C H 



methyl-hexyl carbinol, C s |j f. As I shall show in this paper, Kolbe's 



[oh 



view is correct ; by moderate oxidation, the alcohol loses two atoms of 

 hydrogen, and is converted into the corresponding acetone, methyl oenanthol, 

 the same compound which is generally obtained as a byeproduct in the 

 preparation of the alcohol. The alcohol which I used was prepared by 

 distilling a mixture of castor-oil soap and caustic soda in a flask of thin 

 copper-sheeting as quickly as possible. The distillate was repeatedly 

 rectified over fused caustic potash, the portion boiling below 200° C. only 

 being collected. The alcohol was isolated from this liquid by fractional 

 distillation ; its corrected boiling-point was 181° C. The portions having a 

 lower boiling-point consist of hydrocarbons, which combine with bi-omine, 

 probably members of the define series, amongst which octylene, boiling at 

 125° C, preponderates. A considerable quantity of liquid distilled above 

 160°, the boiling-point remaining somewhat constant at 1/0° C. Neither 



-°- Ann. de Chim. et de Phys. 3^ Ser. vol. xliv. p. 123. 

 t Ann. dev Chem. und Pharm. vol. cxxxii. p. 116. 



