MABERY. — CONSTITUENTS OF PETROLEUM. 159 



separated, more remaining in solution. After several crystallizations from 

 alcohol, in which it is quite insoluble, the nitro derivative melted at 225°, 

 near the melting point of trinitromesitylene. The hydrocarbon oil was 

 separated from the acid and boiled several hours with tin and hydrochloric 

 acid, which caused the yellow color to be absorbed by the acid solution, 

 and a small amount of a heavy oil separated, insoluble in the acid, evi- 

 dently a product of the vigorous reduction. The crude distillate lost 20 

 per cent in weight by this purification. The oil remaining after the re- 

 duction, when shaken with fuming sulphuric acid, washed, and dried, gave 

 only the characteristic odor of the petroleum hydrocarbons. Upon ana- 

 lysis it gave the following results : — 



0.1455 gram of the oil gave 0.4517 gram CO2, and 0.1980 gram HgO. 



While these results point clearly to the composition C„Ho„^2 ^or the 

 principal hydrocarbon with this boiling point, they also suggest, as has 

 already been mentioned, a constituent of Canadian oil so inert toward re- 

 agents that it cannot be removed by ordinary means. No doubt the diffi- 

 cultv is increased by the great dilution of this impurity in the larger body 

 of the decane. In its behavior toward reagents, dekanaphtene is sug- 

 gested. Whatever may be the composition of this body, it is doubtless 

 present in largest quantity in Canadian petroleum, a smaller amount in 

 Ohio oil, and a still smaller proportion in Pennsylvania oil. But even in 

 the Canadian oil, the proportion is evidently very small. 



The formula of the principal constituent at 1 63° found still further 

 support in a determination of its molecular weight by the method of 

 Beckmann, in which Mr. Hudson obtained 142; the formula C10H22 

 requires 142. 



The purified distillate 160°-161°, Canadian petroleum, behaved toward 

 chlorine precisely like the corresponding distillates from Ohio and Penn- 

 sylvania oils. 17 grams absorbed 4 grams chlorine, and was then frac- 

 tioned in vacuo. About 1 c.c. was obtained after five distillations at 200°- 

 204° atmospheric pressure, without decomposition, and it gave by analysis 

 the composition required for C10H21CI : — 



I. 0.1922 gram of the substance gave 0.1536 gram AgCL 

 II. 0.1873 gram of the substance gave 0.4710 gram CO2. and 0.207' 

 gram HjO. 



