Tromethane

[achmed]

Hey there,

I`ve thought about a nitration of a substance called "tromethane" or tris(hydroxymethyl)aminomethane.(C4H11NO3)
The molecule is similar to PE but with an NH2 group instead of an OH-group.
If one would treat this with concentrated nitric acid(like the nitration of PE) it would give a molecule with 3 nitrate-groups and one nitramine-group.
This would surely have similar properties like PETN and a high Vdet.
What do you think?

[markgollum]

Well, There are several problems with this.
1) The nitroamine portion would be acidic, since the parent amine is primary, this would cause stability problems with the nitric ester portions. (evolution of NOx, hydrolysis etc)

2) Primary nitramines tend to be rather difficult to make/form in poor yields.
(think about why EDNA is not made by nitrating ethylenediamine).

However, I still think that something useful could be done with the tris(hydroxymethyl)aminomethane.(tris)

Some ideas, reflux the tris with dimethyl oxalate in a suitable solvent to get (HOCH2)3CNHO(CO)2OHNC(CH2OH)3
Then nitrate this to make
(O2NOCH2)3CNHO(CO)2OHNC(CH2ONO2)3 (C10H14N8O22)
OR
(O2NOCH2)3CN(NO2)O(CO)2O(NO2)NC(CH2ONO2)3 (If 100% nitric is used)
(C10H12N10O26) perfect oxygen balance!.
Anyhow, both should be fairly stable, reasonably sensitive, and very powerful.

[CD-ROM-LAUFWERK]

the ''U.S. Army Research and Development Command Encyclopedia of Explosives and Related Items CD-ROM.''
CD1, ''VOLUME01'' (1. PDF), page A132 left mid, says that both Bis(hydroxymethyl)methylaminomethan-dinitrat and Tris(hydroxymethyl)aminomethan-trinitrat are unstable even at room temp, ref: H. A. Aaronson, P ATR 1412(1942)