lOW.A ACADEMY OF SCIENCES. 117 



AMOUNTS OF SUBSTANCES EMPLOYED. 



Aniline 100 grams. 



Concentrated hydrochloric acid . . 325 grams. 



Water 900 grams . 



Sodium nitrate, a '•ufficient quant ty to diazo'ize the aniline. 

 Phenol containing 10 per cent of water 550 grams. 



When a portion of the diazo solution was added to the 

 phenol, warmed to 65° C, nitrogen was evolved quite rap- 

 idly, and very rapidly at 85°. Most of the diazo solution 

 was added at the higher temperature. When 100 c. c. of 

 the diazo solution was added to the phenol solution it took 

 only a few minutes to evolve its nitrogen. 



On distilling, the phenol with one or two other sub- 

 stances came over below 210°, when the temperature rose 

 rapidly to 260°, where the higher boiling substances began 

 to come over. As a final result there were obtained a few 

 grams of a substance having the odor of geraniums and 

 boiling at 250°. This was undoubtedly phenyl ether. 

 There was also obtained 40 grams of a crystalline solid, 

 boiling between 275° and 280°. This substance was 

 obtained by neither Hirsch nor Hoffmeister. No attempt 

 was made to purify or analyze this substance or the one 

 mentioned further on, as the chief object of this research 

 was to obtain a considerable quantity of phenyl ether. 

 The neutral oil mentioned by Hirsch, boiling between 

 820° and 350° C, and which he suggested to be diphenyl 

 phenyl ether, was not obtained. A very small quantity of 

 tar remained at the end of the first distillation. 



On fractionating the portion boiling below 210°, there 

 was obtained a liquid not soluble in caustic soda, which 

 boiled a few degrees higher and melted a few degrees 

 lower than phenol. It crystallized in long needles 

 on standing at room temperature. This substance was 

 not mentioned by Hirsch. It would be easily over- 

 looked, since it distills over with the phenol, but 

 mostly with the last portion. However, it may not have 

 been formed in his experiments since he kept the tempera- 

 ture considerably lower than in this experiment during 

 the addition of the diazo solution to the phenol. While I 



