"US patent 5043488: slow addition of nitric acid to acetone produces an unknown explosive", probably ethylnitrolic acid (1-Nitro-1-oximinoethane).
CH3C(NOH)NO2
"was prepared by mixing acetone with nitric acid (of 24% concentration) and a little fuming HNO3 and allowing the mixture to stand for 8 days at room
temperature. An ether extraction gave on evaporation some acetylmethylnitrolic acid"
Beil 3,621 and
R. Behrend & H. Tryller, Ann283,221- 3( 1894)
"... right after the strong oxidation left behind was a clear, thick yellow oil of a pungent odor. According to Jahresbericht über Fortschritte der
Chemie (1902), Behrend and Tryller, p. 1075-77 this oil contained one-third to half acetylmethylnitrolic acid (CH3.CO.C(NOH).NO2) (cryst., mp. 62
deg., very decomposable) and other byproducts, including pyruvic and oxalic acids. They say in the same instance methyethyl ketone affords CH3COOH,
HCOOH, and considerable amounts of ethylnitrolic acid and dinitroethane"
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