264 PROCEEDINGS OF THE AMERICAN ACADEMY. 



the small quantity of distillate collecting here, only 10 grms. after long 

 distillation, excluded this hydrocarbon in any appreciable quantity. 



Under ANAPHTENE, CuH22, 195°. 



Between 188° and 191°, 50 grms. came together at the end of the 

 tenth distillation, which gave the following results on analysis : — 



0.U23 grm. of the oil gave 0.4550 grm. COo and 0.1617 grm. H,0. 



Calculated for C11U22. Found. 



C 85.70 87.20 



H 14.30 12.63 



The specific gravity of this distillate before treatment was 0.8386. 

 After vigorous agitation with fuming sulphuric acid, and washing, the 

 specific gravity was reduced to 0.8044. 



A distillate separated from Russian oil at 197° gave (MarkownikofE 

 and Oglobine) as its specific gravity at 14°, 0.8055, and it was assigned 

 the formula Ci2H24. The quantity of oil remaining after separation of 

 durol, which no doubt was the benzol hydrocarbon in this distillate, was 

 small. That it was a naphtene, as shown by its specific gravity, is con- 

 firmed by analysis : — 



0.1459 grm. of the oil gave 0.4575 grm. CO2 and 0.1886 grm. HjO. 



Calculated for C12II24. Found. 



C 85.70 85.70 



H 14.30 14.40 



Determinations of the molecular weight of this fraction by the Beck- 

 man freezing point method using benzol gave the following value: — . 



0.7901 grm. of the oil and 24.68 grms. benzol gave a depression of 



l.°012. 

 1.1249 grm. of the oil and 25.90 grms. benzol gave a depression of 1°.36. 



Calculated for Found. 



CiiH;,,. I. n. 



154 155 157 



It appears from these results that the hydrocarbon in California petro- 

 leum boiling at 195° is not dodekanaphtene, C12H24, but undekanaphtene, 

 CnHjo. This conclusion is further confirmed, as will appear later, by the 

 composition of the distillate 216°, which appears to be dodekanaphtene, 



