The Chemistry of Powder and Explosives - Sciencemadness Dot Org

394 NITROAMINES AND RELATED SUBSTANCES
CH2—NH. • CHj—NH—NO2
CH-—NH/ x CH2—N(NO2k / CH2—NH—NO2
Ethyleneurea \ ! /CO / Ethylenedinitramine
\ CH2—N(NO,K /
Dinitroethyleneurea
It is a dibasic acid and forms neutral salts, the silver salt a
pulverulent precipitate, the potassium salt needles from alcohol.
It is sparingly soluble in water, about 1 part in 200 at 25°, and
is not affected by refluxing with this solvent. On refluxing with
dilute sulfuric acid it gives nitrous oxide, acetaldehyde, and
glycol. Hale '" has reported that it explodes spontaneously when
heated to 180°, in which respect it resembles mercury fulminate
and nitroglycerin, but that it corresponds in resistance to shock
more nearly to the relatively insensitive high explosives, like
TNT and picric acid, which are used as the bursting charges of
shells. He found that it is exploded by a 10-inch drop of a 2kilogram
weight, the same as picric acid, and reported that it
withstands the standard 120° stability test as well as tetrvl.
Dinitrodimethyloxamide
This substance was prepared by Franchimont 28 by dissolving
dimethyloxamide in very strong nitric acid (specific gravity
1.523) without cooling, allowing to stand, and pouring into water,
and by Thiele and Meyer 29 by dissolving dimethyloxamide in
crude nitric acid, adding fuming sulfuric acid to the chilled solution,
and pouring onto ice. Dimethyloxamide is prepared readily
by the interaction of methylamine with an ester of oxalic acid.
COOR CO—NH—CH3 CO—N(N02)—CH,
I + 2NH2-CH3 > I > I
COOR CO—NH—CH3 CO—N(N02)—CH3
Dimethyloxamide Dinitrodimethyloxamide
Dinitrodimethyloxamide is very slightly soluble in water, sparingly
in ether and chloroform, and soluble in alcohol from which
it crystallizes in needles which melt at 124° and decompose at a
higher temperature. By reduction with zinc and acetic acid in
alcohol solution it yields dimethyloxamide. It is not destroyed
by refluxing with concentrated hydrochloric acid. Concentrated
sulfuric acid splits off nitric acid, and the substance accordingly
27 U. S. Pat. 2,011,578 (1935).
28 Rec. trav. chirh., 2, 96 (1882); 4, 197 (1884); 13, 311 (1893).
2»Ber., 29, 961 (1896).