94 PROCEEDINGS OF THE AMERICAN ACADEMY. 



ISOOCTTL ThIOPHANE. 



Fraction 183°-185° (At. Pres.), C 8 H 16 S. 



A large amount of distillate collected at 97°-99°, 50mm., at the end 

 of the seventh distillation, that gave by analysis the same empirical 

 formula as the sulphur compound previously described. The terra iso- 

 octyl is applied to this compound to distinguish it from its isomer. Upon 

 treatment with mercuric chloride and second precipitation, a large amount 

 of sulphur-free oil collected on dilution of the alcohol, and analysis 

 showed that this constituent was completely removed by the second 

 treatment. After fractioning in vacuo this product collected to the extent 

 of 15 c.c. at 94° -9 6°, 50 mm., and distilled with some decomposition at 

 183°-185°, atmospheric pressure. Specific gravity at 20°, 0.8937. 



This oil gave the required percentages of carbon, hydrogen, and sul- 

 phur for the formula C 8 H 1G S. 



I. 0.1458 gram of the oil gave 0.3592 gram C0 2 . and 0.1470 gram H 2 0- 

 II. 0.1561 gram of the oil gave 0.3814 gram C0 2 , and 0.1575 gram H 2 0. 

 III. 0.2670 gram of the oil gave 0.4183 gram BaSG 4 . 



Calculated for Found 



C 8 H„,S I. II. Ill 



C 66.67 67.19 66.16 



H 11.11 11.27 11.29 



S 22.22 21.52 



It will be observed that the last two compounds have the same 

 empirical composition, but differ by 16° or more in boiling points, and 

 differ also in specific gravity. It will also be observed that they agree 

 closely in boiling points with butyl and isobutyl sulphides ; but they 

 differ widely from the latter in specific gravity : butyl sulphide, 0.8523 

 at 0° : isobutyl sulphide, 0.8363 at 10°, and in other properties. 



Nonyl Thiophane. 



Fraction 139° -195° (At. Pres.), C U H 18 S. 



A portion of the distillate that collected in considerable quantity at 

 106°-108°, 50 mm., was treated in the same manner as previously de- 

 scribed with two precipitations for the separation of the sulphur com- 

 pound. The product was fractioned in vacuo until it collected for the 

 most part at 106°-108°, 50 mm. Under atmospheric pressure it boiled 

 at 193°-195°, and gave as its specific gravity at 20°, 0.8997. On 



