168 Mr. Scliorlemmer on the Hydrocarbons [April 6, 



I. Heptyl Compounds. 



The ethyl-amyl which is obtained by acting upon a mixture of the 

 iodides of ethyl and amyl with sodium contains generally traces of ethyl- 

 ether and ethyl-amyl-ether, the formation of which is easily explained by 

 the presence of traces of moisture and amyl-alcohol, both of which can be 

 completely excluded only with difficulty. In order to remove these ethers, 

 I treated the crude ethyl-amyl, from which, by fractional distillation, the 

 amyl was as much as possible separated, and which boiled between 70- 

 120 C., with a mixture of concentrated nitric and sulphuric acids, by which 

 not only the ethers, but also traces of iodides, which obstinately adhere, 

 are removed. By washing with water, drying over caustic potash, and 

 rectification over sodium, pure ethyl-amyl was obtained as a light mobile 

 liquid possessing a faint ethereal odour which cannot be distinguished 

 from that of hydride of heptyl. It boils at 90-91 C., and has the spe- 

 cific gravity 0'6819 at 17'5 C. 



The boiling-point of the hydride of heptyl I have formerly stated as 

 98 C., whilst Pelouze and Cahours give it as 92-94 C. I have lately 

 convinced myself that the latter observation is the more correct one. The 

 boiling-point of this hydrocarbon becomes lowered after being repeatedly 

 treated with a mixture of nitric and sulphuric acids, by which traces of 

 nitro-compounds of the benzol series of hydrocarbons are removed, which 

 obstinately adhere*. 



Mr. Ch. R. Wright continued the fractional distillation of the hydride, 

 which was very well purified in the above manner for a long time. In the 

 beginning of these rectifications, the largest quantity of the liquid distilled 

 between 95-100, whilst always a small quantity with a boiling-point above 



* Pelouze and Cahours state that the American petroleum which they used did not 

 contain hydrocarbons of the henzol series, whilst I found a not inconsiderable quantity 

 of these compounds in the rectified petroleum from which I isolated the hydrides. As 

 it was not impossible that this was an accidental or intentional admixture, I endeavoured 

 to procure some genuine crude American petroleum ; but I did not succeed in obtaining 

 crude genuine Penusylvanian, as none of it had reached the Liverpool market for months. 

 I however got some real Canadian rock-oil, as a thick black liquid of a very unpleasant 

 odour. I distilled it, and treated the portion boiling below 150 C. with concentrated 

 nitric acid, which acted violently. The acid liquid was then diluted with water, and 

 heavy liquid nitro-compounds separated, possessing the odour of bitter almonds. These 

 were treated with tin and hydrochloric acid, and the solution thus obtained was distilled 

 with caustic potash. The aqueous distillate, in which some drops of an oily liquid were 

 suspended, had the odour of aniline, and gave with a solution of bleaching-powder the 

 most distinct aniline-reaction. The beautiful rosaniline-reaction could also easily be 

 obtained by heating one of the oily drops with bichloride of mercury. Canadian petro- 

 leum contains therefore the series of benzol hydrocarbons. In the preparation of hydride 

 of decatyl from rectified petroleum, the portion boiling between 150-170 was purified 

 by nitric and sulphuric acids, and thus liquid and solid nitro-compounds obtained. 

 The solid portion was several times recrystallized from alcohol, and the whole of the 

 needle-shaped crystals thus obtained gave on analysis numbers very nearly agreeing 

 with the formula of trinitro-cumol, C 9 H 9 (N0 2 ) 3 . 



