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76 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

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The oxime decomposes giving off hydrogen cyanide:

COOH

C=NOH + 2CO 2 + H 2 O + HCN

COOH

As is well known, hydrogen cyanide hydrolyses to form formic acid and ammonia,

the formic acid being readily decomposed in concentrated acid with the evolution

of CO:

HCN -> HCOOH + NH 3

H 2 SO 4

H 2 O + CO

If the para position on the phenol nucleus is occupied, o- quinone oxime is

formed and the reaction proceeds in a similar way, but with the formation of oxalic

acid and dioxysuccinic acid oxime, which then decomposes, giving off HCN:

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oxidation products of alkyl R

-> 2CO 2 + CO + H 2 O + HCN

Similarly the nitration of dimethylaniline yields p- nitroso derivative, which
undergoes similar reactions, to form HCN.
According to Seyewetz [81] not only phenols can undergo such a reaction in the
nitration process. This opinion is based on Graebe’s observation [82] that nitro-
naphthalenes isomerize to nitrosonaphthols under the influence of fuming sul-
phuric acid :