150 PROCEEDINGS OF THE AMERICAN ACADEMY. 



takes place, in this experiment the stream of chlorine happened to be 

 exceptionally vigorous, but it was completely absorbed from the beginning 

 to the extent of 5 grams during the first ten minutes. Hydrochloric 

 acid escaped from the oil with brisk effervescence, although the chlorine 

 was delivered at some distance above the surface of the oil. This rapid 

 substitution at low tem[)eratures is quite unlike the substitution of 

 chlorine in dekanaphtene observed by Markownikoff and Oglobine, as 

 shown by ihe following statement:* " Lorsqu'on fait agir du chlore sec 

 sur les vapeurs du decanaplitene en ebullition et sous I'influence de 

 I'insolation directe, la reaction se fait lentement avec decragement d'acide 

 chlorhydrique et demande un tres grand exces de chlore en comparaison 

 de ce qu'il en faut d'apres le calcul theorique." Yet in the residue of 

 the hydrocarbon not acted on by chlorine, Markownikoff and Oglobine 

 found a somewhat lower percentage of carbon and a higher percentage 

 of hydrogen, from which, together with a slightly lower specific gravity, 

 0.792, than decanaphtene, 0.795, they infer that " ces chiffres semblent 

 indiquer la presence d'une quantite notable d'un hjdrocarbure sature." 

 In accordance with my observations on all the hydrocarbons from Penn- 

 sylvania, Ohio, and Canadian oil which I have chlorinated, these bodies 

 should be saturated long before the naphtenes, especially if the latter 

 substitute chlorine slowly at a boiling temperature. 



In fractiouing in vacuo under 80 mm. the chlorinated oil, after several 

 distillations about 8 cc. collected at 134°-136°, with a small propor- 

 tion of unaffected hydrocarbon which came over at a lower temperature. 

 Analyses of this product gave numbers corresponding to the composition 

 of chlordecane : — 



I. 0.2773 gram of the oil gave 0.6977 gram COo, and 0.2886 gram 



HoO. 

 II. 0.1623 gram of the oil gave 0.4085 gram CO2, and 0.1679 gram 

 HoO. 

 III. 0.2117 gram of the oil gave 0.1707 gram AgCl. 



III. 



19.93 



A determination of the specific gravity of this chlordecane at 20° gave 

 0.8895. Under atmospheric pressure, it distilled with some decomposi- 



* Ann. Chim. Phys., (6.), II. 453. 



