222 PROCEEDINGS OP THE AMERICAN ACADEMY 



VII. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE. 



ON THE ACTION OF PHOSPHOROUS TRICHLORIDE 



ON ANILINE. 



By C. Loring Jackson and A. E. Menke. 

 Presented May 29, 1883. 



The only paper on this subject which we have been able to find 

 was published by Tait in 18(55; * in it he describes the product of tlie 

 action of phosphorous trichloride on aniline as a white salve-like 

 mass easily soluble in water, alcohol, and ether, which, when freed 

 from an excess of aniline, had the composition (C|;H.NII)yP3HCl, 

 gave a chlorplatinate and several double salts, but yielded no satis- 

 factory result when he attempted to set free the base. 



We were induced to take up the study of this reaction by the hope 

 that a further investigation of Tait's substance might lead to interest- 

 ing results ; but in this we were disappointed, as we have not suc- 

 ceeded in obtaining it, and, as far as our experiments go, are inclined 

 to think it must have been a mixture instead of a definite compound. 

 At the same time, we cannot state with absolute certainty that it is not 

 present in the product formed when a decided excess of aniline is 

 used, since the impossibility of continuing our work after the begin- 

 ning of the summer vacation prevented us from making the investiga- 

 tion of this product as thorough as we wished. For the same reason 

 other parts of this research can be published only in a very fragmen- 

 tary and imperfect condition. 



The isolation of the compounds containing phosphorus formed by 

 the action of phosphorous trichloride on aniline, in the proportion of 

 one molecule to three, is surrounded by difficulties which we have 

 found insurmountable; but, in spite of this, our experiments have 

 determined with a fair degree of certainty the nature of these com- 

 poimds, as will appear from the following general statement of our 

 results, and the argument which can be based upon them. 



* Jahresbericht der Cliera. 1865, p. 411. Instit. 1805, p. 264. 



