104 PROCEEDINGS OF THE AMERICAN ACADEMY. 



is the yield increased by the use of iodine. In the separation by fractional 

 distillation of the products of the ohlorination, our experience is not in 

 accordance with that of Schorlemmer, who stated that neither the chlorides 

 nor the acetates could be separated by distillation. With long continued 

 distillation, as our results will show, the crude product of the clilorination 

 may be separated into its constituents sufficiently to yield constant boiling 

 points and satisfactory analytical data. 



Since Beilstein* found that isobatane boils at — 17°. 5, it seemed rea- 

 sonable that it should be contained in our product — 10°, especially since 

 a considerable portion of this distillate condensed below — 15°. In sub- 

 mitting 200 grams of this distillate in several portions to the action of 

 chlorine with all possible precautions, a considerable portion of the chlo- 

 rine product was lost, probably because it consisted to a large extent of 

 the more volatile chlorine derivatives of propane. Although much of the 

 unchanged hydrocarbon must have escaped with the gaseous hydrochloric 

 acid, 100 grams remained after the chlorination, which was washed, dried, 

 and distilled. Prolonged distillation, however, failed to collect any con- 

 siderable portion within sufficiently close limits to indicate the presence 

 in appreciable quantity of an individual hydrocarbon. A small quantity, 

 perhaps 5 grams, collected between 65° and 70°, doubtless isobutane, 

 which had not been completely removed into the higher fractions at 0°. 

 But the product distributed itself along in degree fractions from 30° to 

 150° at no point in quantities larger than half a gram or one gram. 



Between —10° and —2° much smaller quantities of the hj'drocarbon 

 distillates were obtained, but within the limits —2° and 2°, 300 grams 

 came together, and the distillate — 0°-l° gave, as its specific gravity at 

 0°, 0.6029, and at— 12°, 0.6141. Ronalds found as its specific gravity 

 0.6000. A vapor density determination gave the following value : — 



0.0945 gram of the oil gave 73.6 c.c. of vapor at 5°, and under 

 370.4 mm. of mercury. 



Calculated for C^E^a- Found. 



2.01 2.07 



In quantities of 100 grams each, the fractions —2° to 2° were con- 

 verted into the chlorine derivatives. The chlorinition of such a quantity 

 is of necessit}' somewhat tedious ; it requires continuous operation during 

 ten or twelve days, and it cannot be hastened, since too rapid absorption 

 generates heat, and rapid escape of hydrochloric acid carries off the pro- 



* Ann. Chem. Pliarra., CXLIV. 10. 



