The Chemistry of Powder and Explosives - Sciencemadness Dot Org

NITROGUANIDINE 333
mixture, is treated with ice-cold nitrating acid prepared by mixing
20 cc of fuming nitric acid (1 50) with 10 cc. of concentrated sulfuric
acid (184) After the evolution of red fumes has stopped, the mixture
,s heated for 1 hour in the boiling-water bath, cooled, and drowned in
300 cc. of cracked ice and water. The precipitate, collected on a filter,
rinsed with water for the removal of acid, and recrystalhzed from
water, yields about 6 grams of /3-nitroguanidme, about 25% of the
theory.
Saturated solutions of nitroguanidine in sulfuric acid of various
concentrations contain " the amounts indicated below.
CONCENTRATION OF
SOLVENT SULFURIC ACID, %
45
40
35
30
25
20
15
0
NlTBOGUANIDlNE (GRAMS) PER
100
at 0°
58
34
20
13
0 75
0 45
030
012
cc at 25°
10 9
80
52
29
IS
105
055
042
Nitroguanidine on reduction is converted first into nitrosoguanidine
and then into aminoguanidme (or guanylhydrazine).
The latter substance is used in the explosives industry for the
preparation of tetracene, In organic chemical research it finds
use because of the fact that it reacts readily with aldehydes and
ketones to form products which yield crystalline and easily characterized
nitrates.
g-NH-C(NH)-NHs
.
Nitroguanidine i , >^
C—-' £N-NH-C(NH)-NH,
^P H; \ Amlnoguanldine
/~VCH=NH-NH- C(NH) -Nff,
Benzalamlnoguanidlne
Preparation of Benzalaminoguanidine Nitrate (Benzaldehyde Guanylhydrazone
Nitrate). Twenty-six grams of zinc dust and 10 4 grams of
mtroguamdme are introduced into a 300-cc. Erlenmeyer flask, 150 cc
of water is added, then 42 cc. of glacial acetic acid at such a rate that
the temperature of the mixture does not rise above 40°. The liquid at
first turns yellow because of the formation of mtrosoguanidine but
"Davis, J. Am. Chem. Soc, 44, 868 (1922).