58 GIBBS. 
Hartley and Leonard,‘ in connection with their work on the 
absorption spectrum of p-quinone, call attention to the powerful 
oxidizing properties of this compound upon polyhydric alcohols 
when submitted to the action of light. Since the quinol band 
shortly made its appearance, the use of ethyl alcohol as a solvent 
was precluded. 
In this connection it is interesting to note that quinone in the presence 
of oxygen is more rapidly colored brown in the light than in the dark,’ 
and that the shorter wave lengths are responsible for the effect. One 
gram of quinone in 20 cubic centimeters of ether showed no change in red 
light, and in blue-violet light formed long needles of quinhydrone in six 
hours." 
Since methyl alcohol is generally oxidized with greater dif- 
ficulty than ethyl alcohol, it seemed of interest to study this 
solvent in connection with quinone, and I have found that methyl 
alcohol will produce the same result on exposure to sunlight in 
presence of p-quinone, the principal ‘products formed being 
formaldehyde and quinol. 
EXPERIMENTAL. 
Quinone, purified by distillation in steam, was dissolved in 
methyl alcohol, 4 grams to 100 cubic centimeters. The following 
mixtures, in sealed tubes, were exposed to the sunlight: ; 
TABLE I.—Sealed tubes containing p-quinone and methyl alcohol exposed 
to sunlight in Manila, January 11 to January 13, 1910. 
|Tube|Duration) Composition of 
No. axpasivel mixture. | Analysis. 
| = = | ent ii 
| 
Days. | 
1 2 | Bec. solution --____- | Formaldehyde. 
2 2 | 5 cc. solution, 5 ce. | Formaldehyde and quinol. 
water. | 
3} 2/5 cc. solution, 10cc. | Formaldehyde 8 parts in 1,000. Neutral to 
water. rosolic acid and to litmus paper. 
4) 2 | 10 ce. solution -____- | Formaldehyde. 
— 
The formaldehyde was quantitatively determined by the ammonia method. 
Qualitative tests were obtained by three methods, Leach’s, Hehner’s, and 
Rimini’s, upon the distillates obtained by volatilization with steam. Quinol 
was identified by the formation of quinhydrone and by oxidation to 
p-quinone. All of the tubes were not analyzed for all of the reaction 
products, and in the above table the results of tests which were made are 
recorded. 
‘ Journ. Chem. Soc. London (1909), 95, 35. 
"Eder, Photochemie. Halle a. S. (1906), 357. 
°Tbid., 3638. 
