Aliphatic nitramines - the next generation of explosives?

[CodeMason]

Hey everybody, I'm sure this has been said before, but I didn't find anything of great use (besides some nifty info on MEDNA and similar compounds), so I decided to post this, which has been bugging me for quite some time. Anyway, I'd really like some input from the more well-versed forum members.
Amines have the general formula R₃N, or, in order to bond to hydrocarbon chains, R-NH₂ (one of the H's being replaced by NO₂ to form an aliphatic nitramine). So I was thinking about nitramine analogs of nitric esters. Take for example glycerol, which is nitrated to give everyone's favourite explosive, and which would have the theoretical amine analog of propane-1,2,3-triamine (??):<font face="fixedsys">
*H
HC-NH2
*|
HC-NH2
*|
HC-NH2
*H</font>

Which would form the nitramine:<font face="fixedsys">
*H
HC-NHNO2
*|
HC-NHNO2
*|
HC-NHNO2
*H</font>

That of course, is speculatory, I have no idea how one would synthesize or even if such a compound is possible. On the other hand, a substance of much more interest, would be a nitramine of pentaerythritol! Forming an incredibly powerful explosive with (I imagine) acceptable stability. Its amine (sp?) might be formed by the condensation of formaldehyde, acetaldehyde and a Ca(NH₂)₂:
8CH₂O + 2CH₃CHO + Ca(NH₂)₂ -> 2C(CH₂NH2)4 + Ca(COOH)₂
Or, in an even more enthralling possibility, the direct formation of the nitramine from the aldehydes and nitramide (probably in the form of its sodium salt)!
The prospects on the home manufacture of these incredible aliphatic nitramines seems very promising. Any comments?

[Edited due to the above crappy text diagrams not coming out right.]

[Oh yeah, I just noticed my condensation reaction was waaaaaaay off, but nevermind, you get the idea. http://theforum.virtualave.net/ubb/smilies/wink.gif]

[This message has been edited by CodeMason (edited September 19, 2001).]

[Hex]

I've never seen 1,2,3-trinitrazapropane, but ethylene dinitramine, EDNA, has been used as an explosive, usually mixed with TNT. See the posts on DINGU, SORGYL, TNGU etc. for details of "ethylene tetranitramine" (even dodgier nomenclature than EDNA there). They are powerful explosives, but are a bit chemically reactive for practical use. Sitting next to me I have 2g of the disodium salt of 1,3,5-trinitro-1,3,5-triazapentane. Which is proving to be a bitch to acidify to the parent nitramine, I can tell you.
I can't see primary nitramines as the next generation of explosives - but they are probably going to be precursors of the next generation.


<font face="Verdana, Arial" size="2">Originally posted by CodeMason:
Hey everybody, I'm sure this has been said before, but I didn't find anything of great use (besides some nifty info on MEDNA and similar compounds), so I decided to post this, which has been bugging me for quite some time. Anyway, I'd really like some input from the more well-versed forum members.
Amines have the general formula R₃N, or, in order to bond to hydrocarbon chains, R-NH₂ (one of the H's being replaced by NO₂ to form an aliphatic nitramine). So I was thinking about nitramine analogs of nitric esters. Take for example glycerol, which is nitrated to give everyone's favourite explosive, and which would have the theoretical amine analog of propane-1,2,3-triamine (??):<font face="fixedsys">
*H
HC-NH2
*|
HC-NH2
*|
HC-NH2
*H</font>

Which would form the nitramine:<font face="fixedsys">
*H
HC-NHNO2
*|
HC-NHNO2
*|
HC-NHNO2
*H</font>
(I hope these badly done text diagrams work first time!)

That of course, is speculatory, I have no idea how one would synthesize or even if such a compound is possible. On the other hand, a substance of much more interest, would be a nitramine of pentaerythritol! Forming an incredibly powerful explosive with (I imagine) acceptable stability. Its amine (sp?) might be formed by the condensation of formaldehyde, acetaldehyde and a Ca(NH₂)₂:
8CH₂O + 2CH₃CHO + Ca(NH₂)₂ -> 2C(CH₂NH2)4 + Ca(COOH)₂
Or, in an even more enthralling possibility, the direct formation of the nitramine from the aldehydes and nitramide (probably in the form of its sodium salt)!
The prospects on the home manufacture of these incredible aliphatic nitramines seems very promising. Any comments?

[Edited due to the above crappy text diagrams not coming out right.]

[This message has been edited by CodeMason (edited September 19, 2001).]</font>