THE OXIDATION OF PHENOL. 139 



iodide-starch solution, no coloration was produced, allowing that the ozone 

 was entirely removed by reaction with the phenol. Carbon dioxide is 

 given off in considerable quantities during the reaction. 



The tube J was finally opened and a study of the reaction products 

 made. The reddish-brown licjuid was shaken with water, the insoluble 

 portion separated and the aqueous solution extracted repeatedly with 

 chloroform and ether. These extracts were found to contain considerable 

 quantities of unchanged phenol, small amounts of cpiinone and catechol, 

 and considerable amounts of quinol. 



The aqueous solution contained an acid which was volatile with steam, 

 reduced ammoniacal silver solution and mercuric chloride, was precip- 

 itated by calcium hydroxide, and on boiling precipitated calcium oxalate. 

 It gave an orange-yellow precipitate with phenylh)'drazine '■^ in the cold. 

 This precipitate on purification and recrystallization formed yellow 

 crystals. Even though an insufficient quantitj^ of the phenylhydrazine 

 compound was obtained for an analysis, it is reasonably safe to assert 

 that the acid in acjueous solution was glyoxjdic acid. 



Several experiments were completed in the same manner with the 



N 

 difference that the issuing gases were passed through ^ solutions of 



barium hydroxide. The following was the result : 



Grams. 

 Carbon dioxide evolved 0.11 



Weight of the mixture in the tube ./ when the evolution of 



carbon dioxide had practicall3' ceased 3.00 



Acidity of aqueous extract was equivalent to 18 cubic centi- 

 meters .^=glyoxylic acid (CHO.COOH) equivalent to 4.4 



per cent of the residue. 0.13 



Chloroform extract 0.64 



Ether extract 0.23 



The chloroform and ether extracts were dried in a vacuum desiccator with the 

 loss of considerable of the products. The principal loss in weight was due to 

 phenol vaporized. 



Two grams of another residue, on distillation with steam gave an 



N 

 acid distillate equivalent to 16 cubic centimeters - alkali which, cal- 

 culated as glyoxylic acid, equals 5.9 per cent. 



THE ACTIOS" OF OZONE UPON PHENOL. 



Otto^° observed that ozone reacts with phenol producing a red color. 

 He studied the reaction at 16° and 50° and isolated no reaction products. 



Dry ozone is, in general, not reactive. It is more reactive when 

 traces of moisture are present.^'' Pure, dry, ozonized oxygen will react 



'= Fischer, E., Ber. d. deutschen chein. Ges. (1884), 17, 577. 

 ^'Ann. chim. et phys., Paris (1898), III, 13, 136. 

 "Uhrig, Eicharz, Phijs. Ztschr. (1905), 6, 1. 



