1869.] Mr. C. Schorlemmer on the Derivatives of Propane. 29 



found in petroleum. It gives, by the proper reactions, a considerable 

 quantity of a primary alcohol, and a smaller quantity of a secondary one ; 

 the latter is not identical with methyl-hexyl carbinol, but consists most 



CHI 



probably of ethyl-amyl carbinol, q 2 h 5 j CH OH, as, on oxidation, it 



yields valerianic and propionic acids. 



The primary alcohol appears to differ from the primary octyl alcohol, 

 which has been found lately by Zincke in the seeds of Heracleum spon- 

 dylium*. The essential oil of these seeds consists chiefly of an octyl 

 acetate, boiling at 206°-208°, and possessing an orange-like smell, whilst 

 that which I obtained smells strongly of pears, and boils at 198°-202°. 

 By oxydising his alcohol, Zincke obtained a caprylic acid, which solidified 

 at 12°, whilst the acid which I got remained liquid at 0°. Zincke's 

 alcohol is most likely the normal alcohol, and that which I obtained an 

 alcohol containing the group isopropylf. 



(3) On acting upon the hydrocarbons of the series C»H2»+2 with chlo- 

 rine, a mixture of primary and secondary chlorides is formed. This is 

 proved by the fact that the alcohols derived from these chlorides yield, on 

 oxidation, besides an acid containing the same number of atoms of carbon 

 as the alcohol, also acetones, or the characteristic oxidation products of 

 secondary alcohols. Not only the above researches show this, but also 

 my former experiments on the oxidation of amyl-alcohol prepared from 

 the hydride, which gave, besides valerianic acid, also acetic acid and the 

 acetone, C 5 H 10 OJ. 



It is certainly very remarkable that the hydrocarbon from petroleum 

 yields methyl-hexyl carbinol, whilst the hydrocarbon which is obtained 

 from methyl-hexyl carbinol is not reconverted into this alcohol, but gives 

 ethyl-amyl carbinol, and besides a primary alcohol. 



The further investigation of this subject is certainly of the highest theo- 

 retical interest ; but there is great difficulty in pursuing this research, as 

 I have already observed, in consequence of the small yield of pure alcohol 

 from large quantities of the hydrocarbons. 



XVI. " On the Derivatives of Propane." By C. Schorlemmer. 

 Communicated by Prof. Stokes, Sec.R.S. Received June 17, 

 1869. 



The chief product obtained by the action of chlorine upon propane 

 consists, as I have already stated in my last communication §, of propylene 

 dichloride ; besides this compound, we find in smaller quantities the 

 normal propyl chloride and products richer in chlorine, which boil between 



* Zeitschrift fur Cbemie, N. F. vol. v. p. 55. 

 t Proc. Roy. Soc. vol. xvi. p. 379. 



% Ibid. p. 374. § Ibid. No. Ill, 1869. 



