140 GIKBS. 



at once with pure, moisture-free fihenol in the liquid state and more 

 slowly when the phenol is in the form of crystals. The reactions which 

 take place are largely influenced by the temperature. At the room 

 temperature, 30°, the first action is the production of quinone, and 

 possibly quinol, as indicated by the coloration. As the reaction proceeds 

 an ozonide is undoubtedly produced. This is evidenced by the copious 

 evolution of carbon dioxide and the formation of glyoxylic acid, a 

 reaction analogous to the breaking do-mi of the triozonide of benzene, 



>03+3H20=2CHO . CHO+2CO,+4H,0, 



0. 



as demonstrated by Harries and Weiss. ^' 



When ozone acts npon dry phenol, the water which seems to be neces- 

 sary to the breaking down of the ozonide, and which also accelerates the 

 reaction, is produced during the formation of quinone as follows: 



C„H, . 0H+20 = C„H,0,+H,0 



AVhen ozone reacts upon moist phenol, the same reaction products are 

 produced, quinol resulting in larger quantities than quinone. 



Wliether it is the diozonide of quinone or the triozonide of quinol 

 which breaks down according to the reactions — 



= 2H00C . CHO+2CO,+2H,0 



or 



H 









=2H00C . CH0+2C0„+H,0 



HC 



CH 



c --. 



0, 





 H 



"Ber. d. deutschen chem. Ges. (1904), 37, 3431. 



