Methylnitrolic acid

Evaporation by heating a filtrate from precipitation of potassium cobaltinitrite caused it to turn purple and explode violently [1]. This was attributed to interaction of nitrite, nitrate, acetic acid and residual cobalt with formation of fulminic or methylnitrolic acids or their cobalt salts, all of which are explosive [2], Mixtures containing nitrates, nitrites and organic materials are potentially dangerous, especially in presence of acidic materials and heavy metals. A later publication confirms the suggestion of formation of nitro- or nitrito-cobaltate(III) [3],... 

Experiment.—Methylnitrolic acid.1—Nitromethane (3-2 g.) is dissolved in 30 c.c. of ice-cold 2 N-sodium hydroxide solution and a... 

When methylnitrolic acid is heated in nitric acid solution it decomposes into nitrous and fulminic acids. The latter can be isolated as silver fulminate if silver nitrate is present. 

The production of fulminates (silver and mercury fulminates) from ethyl alcohol and nitric acid takes place by way of methylnitrolic acid. This question was discussed on p. 149. 

According to Tscherniak methylnitrolic acid decomposes in water to give formic acid and N2O, while Wieland found that when methylnitrolic acid 02NCH=NOH is boiled in aqueous solution, with or without the addition of a mineral acid it yields formic acid, nitrous oxide and fuhninic acid, which is precipitated as the silver or mercuric salt if silver or mercuric nitrate is added to the above mixture (equation 9). The yield of fulminate is increased by the presence of mineral acid and by boiling, but it is also formed at ambient temperatures. 

Decomposition of methylnitrolic acid into fulminic acid and nitrous acid... 

Fulminic acid can be regarded as the simplest oxime. A number of compounds with an oxime group C=NOH can form salts which possess initiating properties, for example salts of nitroformoxime (methylnitrolic acid) (I) which can be obtained in a known way by the action of nitrous acid on nitromethane. Salts of form-hydroxamic acid (II), particularly the mercuric salt, also possess initiating properties [66]. Formhydroxamic acid can be obtained by the action of hydroxylamine on formic acid esters or by oxidation of methylamine. 

Methylnitrolic Acid (Nitromefhane oxime, nitroformaldoxime, nitro-oosimino-methane, niiro-isonltroso-rnethane)... 

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