2-Nitrodiphenylamine is an
organic chemical
Some chemical authorities define an organic compound as a chemical compound that contains a Carbon–hydrogen bond, carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. F ...
with the formula . It is a
nitrated derivative of
diphenylamine
Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidiz ...
. It is a red solid, usually found in form of flakes or powder. It is polar but
hydrophobic
In chemistry, hydrophobicity is the chemical property of a molecule (called a hydrophobe) that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water.
Hydrophobic molecules tend to be nonpolar and, thu ...
.
Diphenylamine
Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidiz ...
is used to extend the shelf-life of explosives containing nitrocellulose or nitroglycerin. Such nitrated materials release nitrogen oxides, which deteriorate the device. The diphenylamine traps NO
2, affording the title compound and related species. And the title compound further traps additional nitrogen oxides. One of its major uses is to control the explosion rate of
propylene glycol dinitrate
Propylene glycol dinitrate (PGDN, 1,2-propylene glycol dinitrate, or 1,2-propanediol dinitrate) is an organic chemical, an ester of nitric acid and propylene glycol. It is structurally similar to nitroglycerin, except that it has one fewer nitrat ...
.
As a stabilizer, its major role is to eliminate the acidic nitrates and
nitrogen oxide
Nitrogen oxide may refer to a binary compound of oxygen and nitrogen, or a mixture of such compounds:
Charge-neutral
*Nitric oxide (NO), nitrogen(II) oxide, or nitrogen monoxide
* Nitrogen dioxide (), nitrogen(IV) oxide
* Nitrogen trioxide (), o ...
s produced by gradual decomposition of nitric acid esters, which would otherwise
autocatalyze further decomposition. Its amount is usually 1-2% of the mixture; higher amounts than 2% degrade the propellant's ballistic properties. The amount of the stabilizer depletes with time; remaining content of less than 0.5% (with initial 2% content) requires increased surveillance of the munition, with less than 0.2% warranting immediate disposal, as the depletion of the stabilizer may lead to autoignition of the propellant.
Other stabilizers of a similar nature are
4-nitrodiphenylamine,
N-nitrosodiphenylamine. While
N-methyl-p-nitroaniline (MNA also used in
IMX-101
IMX-101 is a high-performance insensitive high explosive composite mixture developed by BAE Systems and the United States Army to replace TNT in artillery shells. IMX stands for "Insensitive Munitions eXplosives", which refers to the purpose of IM ...
), and
diphenylamine
Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidiz ...
(DPA) are more commonly employed.
References
External links
General information
{{DEFAULTSORT:Nitrodiphenylamine
Anilines
2-Nitrophenyl compounds
Dyes
Pyrotechnic chemicals