Microtek - 16-8-2023 at 12:58
So, as the title indicates, I recently stumbled on a patent by prof. Klapötke about bis(nitratoethyl)dinitroxamide which is produced by nitrating
bis(hydroxyethyl)oxamide. This compound can be synthesized by reacting diethyloxalate with ethanolamine, and diethyloxalate is produced from ethanol
and oxalic acid.
I made the diethyloxalate a few weeks ago, but did not have ethanolamine until recently. I have just tried the aminolysis of the ester, and it seems
to proceed without issue. I did it in toluene as they write about in the patent, but I don't think that is necessary. Next step is nitration and
purification.
Attachment: Bis(nitratoethyl)dinitroxamide.pdf (3MB)
This file has been downloaded 231 times
Microtek - 21-8-2023 at 22:31
From another Klapötke paper, it seems that nitration with pure nitric acid leads to only O-nitration, ie. formation of nitric esters at the two OH
groups. This produces another, significantly less dense and energetic material. It seems that nitration of the secondary amine moeities requires
something more. In the patent they use oleum which could be prepared through one of the processes discussed here on SM. I think I will try N2O5 (via
P2O5 and 100% HNO3) first, though. When I prepare oleum I get a lot of carbonization of stray organics, and it tends to make a mess unless I distill
the oleum before use.
I think I will also do it as a two step nitration, first isolating the intermediate O-nitrated compound and then nitrating this further with N2O5 in
nitric acid.
[Edited on 22-8-2023 by Microtek]
Raid - 26-8-2023 at 13:14
Thanks