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Author: Subject: Nitroxamide
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[*] posted on 20-5-2002 at 19:39
Nitroxamide


I am thinking that nitroxamide, NH2OCCONHNO2 would make a decent energetic material. I postulate that it would be prepared by the action of concentrated nitric acid on oxamide, forming (CONH2)*HNO3; then treating that with concentrated sulfuric acid, which should dehydrate it to NH2OCCONHNO2. Any comments?



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[*] posted on 20-5-2002 at 19:39


The process exist for urea nitrate to make nitrourea what decompose slowly and continuously in the presence of water (since water is a catalyst here and is renewed at the end)!
NH2-CO-NH3NO3 -H2SO4-> NH2-CO-NHNO2
NH2-CO-NHNO2 + H2O --> NH2-CO-OH + NH2NO2
NH2NO2 --> N2O(g) + H2O
NH2-CO2H --> NH3(g) + CO2(g)

An analogous reaction involve the making of dinitrourea a more powerful explosive, but also more unstable towards moisture, heat and shocks!
NH2-CO-NH2 + 2HNO3 conc --H2SO4--> O2N-NH-CO-NH-NO2 + 2H2O
O2N-NH-CO-NH-NO2 + 2H2O --> 2NH2NO2 + H2CO3
H2CO3 --> CO2(g) + H2O
2NH2NO2 -->2H2O + 2N2O
Here the reaction is autocatalytic since 3 molecules of water are produced by 2 starting ones!

No doubt NH2-CO-CO-NH-NO2 would be similar in reaction and more interesting too as a propellant-if it exists...oxalic link is quite reductive and HNO3 is oxydative so the molecule might be destroyed before being able to react that way with HNO3!

Another more interesting stuff would be:
O2N-NH-CO-CO-NH-NO2 but again nothing is sure about the possible survival of it to experimental conditions!

PH Z
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[*] posted on 7-6-2002 at 16:00


I believe I have stumbled upon a superior method of preparing dinitroxamide. I was attempting to use oxamide to purge HNO3 of NO2 when I made a discovery. When the oxamide was added to the HNO3, there was a small amount of fizzling, and the HNO3 lightened slightly, indicating that some NO2 had been removed by this reaction:

2(CONH2)2 + 2NO2 --> 4CO + 3N2 + 4H2O

However, most of the oxamide clearly was not destroyed in that manner, because the HNO3 mainly became cloudy with an ultrafine white precipitate! When this was dumped into cold water, a respectable quantity of a white precipitate formed; there was about 0.5cm of foaming on the surface of the water / HNO3 solution. The foaming continued until all of the white precipitate at the bottom of the beaker was gone.

(CONHNO2)2 + H2O --> CO + CO2 + 2NH2NO2

After foaming had ceased, l poured this into a solution of ammonia; it turned greenish-yellow!

I believe I successfully prepared dinitroxamide by nitrating oxamide with mixed acid at 5C for an hour. Details are on the way.




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[*] posted on 27-8-2002 at 23:53
A little off topic...


what is the trivial name for oxamide?
and is nitroxamide really unstable? I don't think just the addtition of nitrogen in the form of amines and nitrates would make it unstable. To my knowlege it is N-N bonds that cause instability nicht.
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[*] posted on 9-9-2002 at 14:19


What do you mean by trivial name?
Oxalic diamide --> oxamide
like acetic amide --> acetamide

Nitramides are unstable by nature much more than nitramines...they hydrolyse upon moisture contact to yield nitramines
Nitrate salt won't make it unstable; but nitration will lead to unstable nitramide or dinitrooxamide.AMINES WON'T REACT WITH IT!

N-N bonds are not all unstable!
See R2N-NO, HMX, diazabenzene, triazene 12,4
triaminoguanidine nitrate (NH2-NH-)2C=N-NH3NO3!

Some of the above are stable explosive; some are not explosive at all!

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[*] posted on 30-9-2002 at 17:40
Nitroxamide?


Well, I think nitroxamide is unstable like nitrourea. But what about MNO (dimethyldinitroxamide)? :)
Here is its formula: CH3N(NO2)COCON(NO2)CH3. Its power is similar to tetryl. Also it is thermally stable (not decay when heated to 100 degrees C. for 30 days - if my memory doesn't fail me) and it can form cast eutectic mixtures with other explosives.
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[*] posted on 2-10-2002 at 00:39


Can you post more information and attributes of „...oxamide...“

dinitrodimethyloxamide
C4H6N4O6
or
N,N'-dinitroso-N,N'-dimethyloxamide
C4H6N4O4
or
[C2H3N3O4 ?]

I hope, it`s not toxic than tetryl, what should justify
the usage of it with a vod of only >7000 m/s ?




all you need is C - H - O - N
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[*] posted on 2-10-2002 at 00:52


Or you should looking for the
(X-nitro)-1,2,4-triazole family ?




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[*] posted on 3-10-2002 at 12:01


Oxamides:
Here's some info from Urbanski's book.
Dinitrodimethyloxamide (MNO).
CH3N(NO2)COCON(NO2)CH3
Melting point 124 degrees C. Can be prepared from anhydrous HNO3 and N, N'-dimethyloxamide which can be readily produced from methylamine and ethyloxalate. Nitrated product dissolves in nitric acid and can be separated by adding of this solution to water. Decays in contact with conc. H2SO4 or at boiling in alkaline solutions (in this case salts of methylnitramine are forming).
MNO is rather stable. Heating for 30 days at 100 degrees C. does not lead to NOx elimination. MNO is insensitive to impact, it doesn't explode when 5 kg hammer falls from 90 cm height.
VOD is 7130 m/s (at d=1.33 g/cm3) or 8500 m/s (for cast MNO). Trautzl's test gives 370 ml.
MNO forms eutectic mixtures:
- with 37% of PETN, mp 100.5 degrees C.,
- with 45% of picric acid, mp 78.6 degrees C.

Dinitrodiethyloxamide.
C2H5N(NO2)COCON(NO2)C2H5
mp 34-35 degrees C.
Chemical properties are similar to MNO. Is weaker than MNO: Trautzl's test gives 220 ml. Has less impact sensitivity than TNT.

Dinitroethyleneoxamide (2,3-diketo-1,4-dinitropiperazine). mp 197-198 degrees C. Raw material for EDNA (haleite).

There're no comments about toxicity of this oxamides. It seems to be less than tetryl.

Nitrotriazoles: you can look it in US patent office.

[Edited on 18-10-2003 by Hystrix]
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[*] posted on 23-7-2003 at 09:37


How about nitrosylamide, NH2NO?
NH3+NOCl=>NH2NO+HCl:o
(NH2-NO+?)
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