102 PROCEEDINGS OF THE AMERICAN ACADEMY. 



complete the precipitated manganic oxide was filtered and the solution 

 distilled with steam, which carried over any unoxidized sulphur com- 

 pound, leaving behind the oxidation product. When carefully conducted 

 the solution shows no sulphuric acid. From the residue of the steam 

 distillation the oxidation product was extracted with ether and the 

 ether evaporated, leaving a thick heavy oil, which increased in viscosity 

 with increase in molecular weight. In several instances we dissolved 

 the precipitated manganic oxide by saturating with sulphurous oxide and 

 extracted with ether. When the oxidation is complete this is the easier 

 method ; but distillation with steam insures the removal of any decompo- 

 sition products. 



The action of oxidizing agents showed a wide difference in deport- 

 ment between the sulphur compounds from Canadian petroleum and 

 sulphides synthetically prepared. For example, synthetic isoamylsul- 

 phide allowed to stand with concentrated nitric acid showed vigorous 

 reaction only after several minutes with evolutiou of heat. After the 

 reaction ceased heat was applied and water added. The oxidation prod- 

 uct collected above the water and partly dissolved. Only a trace of 

 sulphuric acid was found in the solution. On treating the sulphur com- 

 pounds from Cauadiau petroleum in the same manner, the reaction was 

 much more vigorous, with immediate evolution of heat. The product 

 formed a thick oil heavier than water, and much sulphuric acid was 

 formed. But the oxidized oil contained much sulphur, showing that it 

 consisted in part of an oxidized sulphur compound. This difference in 

 the action of nitric acid is pretty conclusive proof that the sulphur 

 compounds under consideration are not alkyl sulphides, nor, iudeed, 

 members of any other well-known series. It is in accordance with the 

 observation that the hydro-ring compounds, the methylenes, are less 

 stable toward reagents than the aromatic or paraffine compounds. 



Hexyl Thiophane Suephone. 



The presence of hexyl thiophane was indicated in the fraetiou 125°- 

 130° atmospheric pressure, although it was not separated in a pure 

 form. In attempting to prepare the sulphone, the fraction 55 c -57°, 

 50 mm., was treated as described above with potassium permanganate- 

 Oxidation was rapii, even when cooled to 0°. In this instance, after 

 dissolving the manganic oxide in sulphurous acid, the solution was 

 evaporated to dryness and the residue extracted with anhydrous ether. 

 Evaporation of the ether left a thick viscous oil with a sweetish taste 



