MABERY. — CONSTITUENTS OF PETROLEUM. 155 



A determination of its specitic gravity at 20° gave 0.7867, with scarcely 

 any cliange by the action of the fuming acid. Another portion of the 

 crude distillate was shaken with a mixture of nitric and sulphuric acids. 

 The great heat of the reaction was controlled by cooling, and the heavy 

 nitro product allowed to separate by standing. The principal reaction 

 was soon over, the nitro cora[)ound separating in needles on standing. 



In hot alcohol the nitro derivative was readily soluble, but quite in- 

 soluble in cold alcohol. It melted at 165°, and was probably a deriva- 

 tive, or perhaps a mixture of derivatives, of the aromatic hydrocarbons 

 with boiling points in this vicinity, such as isohexylbenzol, or isoamyl- 

 benzol, boiling points 212°-214°, and quite probably contained in petro- 

 leum. After treatment with the acid mixture, the oil was boiled with 

 tin and hydrochloric acid, washed, and boiled with sodium, then distilled. 

 Its boiling point was not appreciably changed, but the specific gravity 

 was reduced to 0.7727, a value practically the same as that of the Penn- 

 sylvania dodecane. A determination of its molecular weight by the 

 Beckmann method gave 172; required for CioHoe, 170. 



In forming the chlorine derivates of this hydrocarbon, 35 grams ab- 

 sorbed 8.5 grams of chlorine, and the product was fractioned under 

 80 mm. After the tenth distillation, about 15 c.c. collected at 150°-160°. 

 In this instance, as in one or two others, the distillate taken for chlorina- 

 tion was not purified, and in the distillation the vapors affected the eyes 

 seriously, doubtless on account of substitution in the side chain in the 

 aromatic hydrocarbons contained in the crude distillate. Either on 

 account of decomposition, or want of sufficient material for complete 

 separation, it was not possible to purify this product sufficiently to give 

 satisfactoi'Y numbers on analysis, although the results show the formation 

 of a mono- and a dichlor dodecane. The percentage of chlorine in the 

 distillate 150°-160° came two per cent too low for monochlor dodecane, 

 and no combustion was made. In a higher distillate collected at 190°- 

 200° the following numbers were obtained : — 



I. 0.2224 gram of the oil gave 0.2607 gram AgCl. 

 II. 0.1952 gram of the oil gave 0.4411 gram CO.2, and 0.1816 gram 

 H2O. 



Found 

 I. II. 



61.63 

 10.33 

 28.99 



