1868.] 



New Derivatives of Acetone. 



365 



it sufiicieiitly pure for analysis. I therefore subjected it directly (having 

 simply washed it with a dilute solution of carbonate of soda) to the action 

 of the before-mentioned reagents The results were altogether unex- 

 pected. 



I have since ascertained that the. chlorinated oil can be obtained without 

 the intervention of alcohol, I will now give a detailed account of my ex- 

 periments. 



Dry hydrochloric acid gas was passed to saturation into a quantity of 

 pure acetone contained in a glass vessel surrounded with cold water. The 

 product was set aside for ten or twelve days, and then Vvell washed with a 

 dilute solution of carbonate of soda. Equal weights of the oil thus formed 

 and of pure cyanide of potassium were then introduced into a glass balloon 

 together with a large quantity of alcohol. The balloon was attached to a 

 reversed Liebig's condenser, and subjected for about twelve hours to the 

 temperature of a water-bath. At the expiration of this time its contents 

 were, when quite cold, filtered, and the precipitate well washed with cold 

 alcohol, and then with cold distilled water till the wash-water ceased to 

 give a precipitate with nitrate of silver. A white powder was thus obtained 

 which was insoluble in cold water and in cold alcohol. Boiling alcohol, 

 however, dissolved it to a small extent, from which it crystallized on cool- 

 ing in beautiful shining plates like naphthaline. These sublime at a high 

 temperature (about 300° C), apparently without decomposition. It is a 

 neutral body and contains nitrogen. It does not evolve ammonia when 

 heated with an alcoholic solution of caustic potash. It is decomposed by 

 nitrous acid, with the production of a compound having acid properties. 

 The composition of this body I hope to be able to give in a future com- 

 munication. 



I will now turn to the alcoholic solution filtered from the neutral body 

 I have just described. This I introduced into a balloon together with some 

 sticks of caustic potash. The balloon was then attached to a reversed 

 Liebig's condenser, and exposed to the temperature of a water-bath till 

 ammonia had ceased to be evolved. When this v/as observed, the alcohol 

 was distilled off and the residue dissolved in water. The solution was 

 then neutralized with hydrochloric acid, filtered, evaporated considerably, 

 and then treated with a large excess of the same acid. After standing for 

 some time it became a mass of crystals. These were thrown upon a filter 

 and washed with cold distilled water till the filtrate ceased to give a preci- 

 pitate with nitrate of silver. The powder obtained in this way was readily 

 purified by crystallizing from hot alcohol, and then from boiling water. 

 From the latter solvent it separates in brilliant colourless prismatic needles, 

 sometimes upwards of an inch in length. Dried at 100° C, these gave the 

 following numbers on analysis, which accord sufficiently well with the for- 

 mula CJI,3N03:— 



* I had performed these experiments before the appearance of Baeyer's paper " Ueher 

 die Coiidensationsproducte des Acctons," Annalen der Cheinie, vol. cxl. p. 297. 



