MABERY AND QUAYLE. — CANADIAN PETROLEUM. 113 



we have never noticed the evolution of hydrobromic acid in any con- 

 siderable quantity. Perhaps it is more reasonable to assume that our 

 distillates contained no higher homologues of this series than those that 

 were identified. 



With reference to the solvent power of sulphuric acid for the hydro- 

 carbons described above it is doubtless true that compounds with this 

 acid of the hydrocarbons with high molecular weights are less stable 

 and partake more of the nature of mechanical solutions. It is doubtless 

 true also that the mechanical solvent power of the acid is increased by 

 the other oils that the acid dissolves. If the acid solution separated 

 from the oil be neutralized with calcium hydrate, certain lime salts are 

 formed crystallizing in long needles, and consisting at least in part of 

 nitrogen bases. But sulphonates of the ethylene hydrocarbons and 

 of allied series have not been observed. That unsaturated hydrocarbons 

 may be extracted by sulphuric acid and precipitated by dilution, has 

 been shown in several experiments. We diluted a carboy of sludge acid 

 by pouring slowly into water, and found the precipitated oils to contain 

 these hydrocarbons. As to their relative proportion in the crude oil we 

 have no precise data, but in comparison with the principal constituents 

 it is extremely small. 



Since the sulphur compounds described in this paper, as well as the 

 alkyl sulphides, are also readily soluble in sulphuric acid, they should be 

 removed as a part of sludge in refining burning oil distillates. 



The results described in this paper may be summarized as follows : 

 The separation from Canadian petroleum of the following series of sul- 

 phur compounds : hexyl, heptyl, octyl, nonyl, decyl, undecyl, quart- 

 decyl, sexdecyl, octodecyl thiophanes ; the formation of corresponding 

 sulphones by oxidation. 



Canadian petroleum contains in minute proportions unsaturated hydro- 

 carbons C n H 2n apparently of the ethylene series. Canadian petroleum 

 contains certain sulphur-free oils soluble in alcohol and different in odor 

 and in other respects from the series hitherto identified in petroleum, 

 possibly terpenes. 



We desire to acknowledge our obligations to Messrs. C. A. Lattimer 

 and R. C. McBride, for assistance in the purification and analysis of the 

 sulphur compounds. 



vol. xli. — 8 



