226 PROCEEDINGS OP THE AMERICAN ACADEMY 



percentage of sulphur. The fraction 135—140° (P = 150 mm., 

 B. P. = 185-190°, P normal) gave 15.40% S. After treatment 

 with mercuric chloride as described above, analysis showed 20.37% S. 

 The higher sulphides were all obtained from fractions of the oil 

 that was extracted from sludge acid. Those of medium boiling points 

 may be separated in smaller quantities from naphtha distillates by 

 mercuric chloride, which has the advantage that the sulphides are 

 uncontaminated by other products. But this method is exceedingly 

 laborious, and the yields are small. We have in miud a modification 

 that works successfully with small quantities of the mercury addition 

 product. It includes recovery of the mercury by conversion of the 

 sulphide into the sulphoxide. 



Ethylpentyl Sulphide. 



After the twenty -second distillation (page 221), a sulphide was ob- 

 tained from fraction 95—100° (P = 100 mm.) through the mercury 

 compound that distilled without decomposition at 156 — 160°. It 

 gave, upon analysis, a percentage of sulphur required for ethylpentyl 

 sulphide (B. P. 158-159°). 



I. 0.2629 gr. of the oil gave 0.4516 gr. BaSO,. 



11. 0.1169 gr. of the oil gave 0.2056 gr. BaSO^. 



Calculated for \ p-xj' [ S 



CH. 1 Q Found. 



c;h„ ^- I. II. 



S 24.24 23.59 24.15 



Isohutyl Sulphide. 



The mercury addition product from fraction 110—115° (P = 

 100 mm.) was decomposed with hydric sulphide and the alcoholic 

 solution diluted with water. After drying over calcic chloride, the 

 oil thus obtained distilled at 170— 176°, which corresponded to the 

 boiling point of isobutyl sulphide (172°) and its composition was 

 further shown by a determination of sulphur. 



0.1750 gr. of the oil gave 0.2760 gr. BaSO,. 



Calculated for (CiHa)„S. Found. 



S 21.92 21.66 



Normal Butyl Sulphide. 



The fraction 117—125° (P = 100 mm.) gave an addition product 

 with mercuric chloride from which an oil was obtained that distilled 

 at 180-185° (B. P. of normal butyl sulphide = 182°), and the 

 percentage of sulphur indicated butyl sulphide. 



