Sciencemadness Discussion Board

Ammonium nitrate + amines. Reaction?

Adas - 15-12-2011 at 09:31

Hello SM,

I was thinking about reactions between amines with ammonium nitrate (if there are any).
For example, if HMTA is more basic than ammonia (I am sure it is), in reaction with NH4NO3 it may form HMTA-(di)nitrate.

If it works, it can be a good way of producing amine-nitro salts.
If I had HMTA, I would have tried this. Can anyone try? It is easy to determine reaction, because of NH3 evolution.

[Edited on 15-12-2011 by Adas]

hissingnoise - 15-12-2011 at 09:48

Quote:
For example, if HMTA is more basic than ammonia (I am sure it is), in reaction with NH4NO3 it may form HMTA-(di)nitrate.

Hexamine is a much weaker base than ammonia and it does not react with NH<sub>4</sub>NO<sub>3</sub>.


Adas - 15-12-2011 at 09:49

And what about, for example diethyl amine? Or others?

AndersHoveland - 15-12-2011 at 17:25

Some amines (which are a weaker base than ammonia) that do not have low boiling points, such as urea, can be carefully heated with ammonium salts to drive off the NH3 as a gas. Hydrated silica acts as the catalyst.

Hydrazine is an example of an amine that can displace the ammonia at room temperature. This is probably an endothermic reaction, as hydrazine is a weaker base than NH3.

Possibly also of interest:
Ethylammonium nitrate can be produced by heating ethyl nitrate with an alcoholic solution of ammonia.
Rudolph Fittig (2008). Wohler's Outlines of Organic Chemistry. Read Books. p. 56

[Edited on 16-12-2011 by AndersHoveland]

PHILOU Zrealone - 23-1-2012 at 16:04

If an amine is less volatile or stronger base than amonia; then the process will work...
So one can expect that ethylene diamine will expell NH3 and catch HNO3 to form ethylene diamine dinitrate salt.

The same applies to NH4ClO4!
But then heat must be applied with caution because detonation might occure!

AndersHoveland - 23-1-2012 at 21:57

Quote: Originally posted by PHILOU Zrealone  

The same applies to NH4ClO4!
But then heat must be applied with caution because detonation might occure!


I think this would be very unsafe, with the perchlorates. I certainly would not attempt it.