The Chemistry of Powder and Explosives - Sciencemadness Dot Org

448 PRIMARY EXPLOSIVES, DETONATORS, AND PRIMERS
In the presence of mineral acids, sodium nitrite reacts in a
different manner with aminoguanidine, and guanyl azide is
formed.
NH2—C(NH)—NH—NH2 + HONO > N3—C< + 2H2O
\NH2
Guanyl azide
This substance forms salts with acids, and was first isolated in
the form of its nitrate. The nitrate is not detonated by shock but
undergoes a rapid decomposition with the production of light
when it is heated. The picrate and the pcrchlorate explode violently
from heat and from shock. Guanyl azide is not decomposed
by boiling water. On hydrolysis with strong alkali, it yields
the alkali metal salt of hydrazoic acid. It is hydrolyzed by ammoniacal
silver nitrate in the cold with the formation of silver
azide which remains in solution and of silver cyanamide which
appears as a yellow precipitate. By treatment with acids or weak
bases it is converted into 5-aminotetrazole.
/NH ^N N
N3-C< > NH2—Cf ||
X
NH2 5-Aminotetrazole
X NH—N
When the reaction between aminoguanidine and sodium nitrite
occurs in the presence of an excess of acetic acid, still another
product is formed, namely, 1,3-ditetrazolyltriazine, the genesis
of which is easily understood from a consideration of the reactions
already mentioned. 5-Aminotetrazole is evidently formed
first; the amino group of one molecule of this substance is diazotized
by the action of the nitrous acid, and the resulting diazonium
salt in the acetic acid solution couples with a second
molecule of the aminotetrazole,
N — Nv
|| >C—NH2 + HONO + CHr-COOH >
N—NH/
N — N-x
tj >C—N2-O—CO—CH3 + H2O
N—NH/
N — NC—Nr-0—CO—CH3 + NH2—C< || >
N—NH/ \NH—N
N — N.s ^N /N — N
|| >N=N—NH—C< N—NH—CfXNH— l[ + eft—COOH
N—NH/
l^-Ditetrazolyltriazine
X NH—N