42s
DmEcrIox OF STARCH SUGAR, EL'c.
Similarly the xylene lost not only one of its two methyl groups, forming paratoluic acid, hiit also both of the members of the side chain with the production of phthalic acid. I n the case of cynliiie? however, the propyl group appentwt to break down so much more readily than the methyl group, that thc latter was protected from the oxidizing action, apd the only hy(lroxyIa~c'(1 dwivat,ive was paratoluic acid. B u t the most striking cxeniplitication of this tendency t o forni hydroxyl derivatives v cxhibitecl by naphthalene. S o t only was the carboxyl p i i p 1~roduced,with the generation of phthalic and oxalic acids (both of which chaugcs might be looked upon as evidence of a siniilwity of action b e t w c n hyponitric anhydride and nitric acid), but the new hydroxj-latetl compound, tetroxvnaphthalerit, C,,EI,(OII,), w:ts formed. In this body n o less than four o f tiit. hydrogon atoms iii naphthaletic :ire replaced by hydroxyl. A t the same time, the diyuinoiie, ClcH40k,was formed, in which four atoms of hydrogen are replaced by oxpgeii. I t is not improbable that both dioxynaphthalene, C,,H,(OH),, and naphthoquinow, (',J-I8OI, Irere first formed and afterwards converted into these higher derivatives. 1 5 i i t of these, and of naphthol and of dioxynaphtlioqiiinone, C ~ ~ I 1 4 0 ~ ~ Ono I l )evidenw 2, could be found in t h e final products.
XLVI.--I)ETECTION OF STARCH Sucan MECHANICALLY XIXED WITH COVMEKCIAL Cas>: SUGAH. B Y P.
C'AS.k.\l.\.Jol
