2-Nitrodiphenylamine
Encyclopedia
2-Nitrodiphenylamine, also called NDPA, 2-NDPA, 2NO2DPA, Sudan Yellow 1339, C.I. 10335, CI 10335, phenyl 2-nitrophenylamine, 2-nitro-N-phenylaniline, or N-phenyl-o-nitroaniline, is an organic chemical, a nitrated
aromatic amine
, a derivate of diphenylamine
. Its chemical formula is C12H10N2O2, or C6H5NHC6H4NO2. It is a red crystalline solid, usually in form of flakes or powder, with melting point of 74-76 °C and boiling point of 346 °C. It is polar but hydrophobic.
2-Nitrodiphenylamine is used as a stabilizer
for synthetic rubber
s, explosives, propellant
s (e.g. in Otto fuel II
, smokeless powder
s, in some US Army double-base propellants in solid rocket
s, and in other applications involving nitric acid esters), plastic
s, and lubricant
s. It is also an intermediate for organic synthesis, and a civilian solvent dye
.
In some explosives, it is used to control the explosion. One of its major uses is to control the explosion rate of propylene glycol dinitrate
.
As a stabilizer, its major role is to eliminate the acidic nitrates and nitrogen oxides 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, N-methyl-p-nitroaniline, and diphenylamine
.
Nitration
Nitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...
aromatic amine
Aromatic amine
An aromatic amine is an amine with an aromatic substituent - that is -NH2, -NH- or nitrogen group attached to an aromatic hydrocarbon, whose structure usually contains one or more benzene rings. Aniline is the simplest example....
, a derivate of diphenylamine
Diphenylamine
Diphenylamine is the organic compound with the formula 2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities.-Preparation and reactivity:...
. Its chemical formula is C12H10N2O2, or C6H5NHC6H4NO2. It is a red crystalline solid, usually in form of flakes or powder, with melting point of 74-76 °C and boiling point of 346 °C. It is polar but hydrophobic.
2-Nitrodiphenylamine is used as a stabilizer
Stabilizer (chemistry)
In chemistry a stabilizer is a chemical which tends to inhibit the reaction between two or more other chemicals. It can be thought of as the antonym to a catalyst...
for synthetic rubber
Synthetic rubber
Synthetic rubber is is any type of artificial elastomer, invariably a polymer. An elastomer is a material with the mechanical property that it can undergo much more elastic deformation under stress than most materials and still return to its previous size without permanent deformation...
s, explosives, propellant
Propellant
A propellant is a material that produces pressurized gas that:* can be directed through a nozzle, thereby producing thrust ;...
s (e.g. in Otto fuel II
Otto fuel II
Otto fuel II is a monopropellant used to drive torpedoes and other weapon systems. It is not related to the Otto cycle.-Properties:This distinct-smelling, reddish-orange, oily liquid is a mixture of three synthetic substances: propylene glycol dinitrate , 2-nitrodiphenylamine, and dibutyl...
, smokeless powder
Smokeless powder
Smokeless powder is the name given to a number of propellants used in firearms and artillery which produce negligible smoke when fired, unlike the older gunpowder which they replaced...
s, in some US Army double-base propellants in solid rocket
Solid rocket
A solid rocket or a solid-fuel rocket is a rocket engine that uses solid propellants . The earliest rockets were solid-fuel rockets powered by gunpowder; they were used by the Chinese in warfare as early as the 13th century and later by the Mongols, Arabs, and Indians.All rockets used some form of...
s, and in other applications involving nitric acid esters), plastic
Plastic
A plastic material is any of a wide range of synthetic or semi-synthetic organic solids used in the manufacture of industrial products. Plastics are typically polymers of high molecular mass, and may contain other substances to improve performance and/or reduce production costs...
s, and lubricant
Lubricant
A lubricant is a substance introduced to reduce friction between moving surfaces. It may also have the function of transporting foreign particles and of distributing heat...
s. It is also an intermediate for organic synthesis, and a civilian solvent dye
Solvent dye
A solvent dye is a dye soluble in organic solvents. It is usually used as a solution in an organic solvent. Solvent dyes are used to color organic solvents, hydrocarbon fuels, waxes, lubricants, plastics, and other hydrocarbon-based nonpolar materials. Fuel dyes are one use of solvent dyes. Their...
.
In some explosives, it is used to control the explosion. One of its major uses is to control the explosion rate of propylene glycol dinitrate
Propylene glycol dinitrate
Propylene glycol 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 -O-NO2 group...
.
As a stabilizer, its major role is to eliminate the acidic nitrates and nitrogen oxides produced by gradual decomposition of nitric acid esters, which would otherwise autocatalyze
Autocatalysis
A single chemical reaction is said to have undergone autocatalysis, or be autocatalytic, if the reaction product itself is the catalyst for that reaction....
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, N-methyl-p-nitroaniline, and diphenylamine
Diphenylamine
Diphenylamine is the organic compound with the formula 2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities.-Preparation and reactivity:...
.