MABERY AND QUAYLE. CANADIAN PETROLEUM. 105 



Found. 

 I. II. 



59.84 

 9.53 



14.75 



DODECTL TlIIOPIIANE SuLPHONE, C 12 H 24 S0 2 . 



After treating 7 grams of the distillate 142°-144°, 50 mm., with 9 

 grams potassium permanganate, the proportions found most suitable, 

 there still remained a slight odor of the thiophane which was completely- 

 removed by distillation with steam. The residual oil that remained after 

 extraction of the steam residue with ether gave as its specific gravity at 

 20°, 1.1372. Its composition was established by analysis. 



I. 0.1533 gram of the substance gave 0.3483 gram C0 2 , and 0.1402 

 gram H 2 0. 

 II. 0.1645 gram of che substance gave 0.1554 gram BaS0 4 . 



Found. 

 I. II. 



61.98 

 10.23 



12.91 



The sulphur compounds in Canadian petroleum have been shown to 

 belong to a series C n H 2n . Their structure must be explained either as 

 unsaturated, like the ethylene sulphides, or by a ring arrangement. That 

 these bodies are not of the ethylene series is shown by the facts that the 

 ethylene sulphides are solids, and that they absorb bromine without 

 evolution of hydrobromic acid. The petroleum sulphur compounds have 

 a very high specific gravity, and they evolve hydrobromic acid copiously 

 when treated with bromine. They resemble the well-known series of 

 sulphur compounds in forming addition products with mercuric chloride, 

 in the formation of sul phones, the formation of addition products with 

 alkyl iodides and alkaline hydrates. 



In a former paper by Mabery and Smith it was shown that the sul- 

 phur compounds in petroleum are not mercaptans nor thiophenes. The 

 series separated by Mabery and Smith from Ohio petroleum formed 

 crystalline addition products with alcoholic mercuric chloride, and the 

 sulphur oils themselves resembled the alkyl sulphides. But the series 

 contained in the portions of Canadian petroleum with higher boiling 



