MABERY AND QUAYLE. CANADIAN PETROLEUM. 101 



QlJATDECYL ThI0PHANE,C 14 H 2 sS. 



The fraction 168°-170° gave quatdecyl thiophane. Its index of 

 refraction, 1.4892, corresponded to the molecular refraction : 



Calci-lated for C U H, 8 S. Found. 



72.33 71.61 



Sexdecyl Thiophane. 



This sulphur hody was found in the fraction 184°-186°, 50mm. Its 

 index of refraction proved to be 1.4903, from which its molecular refrac- 

 tion was calculated : 



Calculated for C l6 H 3 ,S. Found. 



81.52 80.44 



The index of refraction ofoctodecyl thiophane was found to be 1.4977, 

 but the molecular refraction calculated from this value and its specific 

 gravity 0.9625 at 20° gave a value different by four units from the 

 calculated molecular refraction. 



Oxidation Products of the Thiophanes. 



Appreciating the importance of oxidation products in ascertaining the 

 composition of the thiophanes, we have tried very thoroughly the action 

 of oxidation agents, nitric acid, chromic acid, and potassium permanganate. 

 These sulphur bodies absorb oxygen with great readiness, and the re- 

 action must be carefully controlled to prevent ultimate oxidation to 

 sulphuric acid. It was not found possible to limit the oxidation to the 

 formation of the sulphoxide, since the sulphone seems to be the more 

 stable condition. Nitric acid readily oxidizes the sulphur with an ex- 

 tremely violent reaction, but apparently also forms nitro-derivatives, since 

 the products contain nitrogen. 



Chromic acid oxidizes the sulphur readily, with some danger that the 

 reaction proceeds to ultimate oxidation. Potassium permanganate in 

 either alkaline or acid solution readily effects the change with little 

 danger of the formation of sulphuric acid. After careful study of the 

 conditions, it was found that the largest yield of oxidation product was 

 obtained by adding slowly to the oil one and a half times the calculated 

 weight of permanganate dissolved in thirty times its weight of water 

 and keeping the solution cold. With efficient cooling, the permanganate 

 can be added as rapidly as it is decolorized. After the reaction was 



