OF ARTS AND SCIENCES. 223 



"When aniline is added to phosphorous trichloride in the proportion 

 of three molecules of the former to one of the latter, the product, a 

 variable mixture of aniline chloride and a substance containing phos- 

 phorus, gives a clear solution with water or alcohol. If, however, this 

 product is heated, a waxy mass is obtained, which is soluble in alco- 

 hol ; but water throws down from this solution a white precipitate 

 having the formula (C^H.NH).,PHO. Of the three most probable 

 products of the reaction of phosphorous trichloride and aniline, 



(1) QH^NIIPCl,, 



(2) (C„H,NII), PCI, 



(3) (C,II,NII)3P, 



only (2) could yield (CyH.Nn)2PH0 by the action of water or 

 alcohol, and we therefore infer that (CgH.NH)2PCl exists in the 

 product after it has been heated. On the other hand, this substance 

 cannot exist in the original product, as this dissolves in water with- 

 out residue, whereas (C^H.NH)2PC1 is converted by water into the 

 insoluble (CgH.NH)2PH0 ; but it must be formed from one of the 

 constituents of the crude substance during the heating. Of the two 

 probable products of the reaction, (I) and (3), mentioned above, it is 

 hard to see how (3), (CeH.NH)gP, by heating with aniline chloride, 

 could be converted into (C,H,NH)2PC1, while (1), C,H5NHPCl2, 

 could easily undergo this change under these conditions ; from which 

 we conclude that CjjHgNHPClj and aniline chloride are the products 

 of the action of aniline on phosphorous trichloride under the condi- 

 tions mentioned. This conclusion is supported by the fact that alco- 

 hol or water acts violently on the original product forming aniline 

 phosphite, and it is highly improbable that (CgHj.NII)3P would give 

 such a violent reaction. 



The remainder of this paper contains a detailed account of the 

 experiments on which the above conclusions are based, a description 

 of the properties and behavior of the new substance (CJl5NH).,PHO, 

 and a somewhat fragmentary account of two crystalline substances 

 formed by boiling the crude product with an excess of aniline, one of 

 which may he a derivative of (CeH.NH)3P, although this point needs 

 confirmation by further experiments. 



Action of Phosphorous Trichloride on Aniline. 



When aniline is added to phosphorous trichloride, the reaction is 

 attended with so much heat, that each drop of the aniline hisses like 



