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Author: Subject: 5-nitro-3H-1,2,4-triazol-3-one (NTO)
Ritter
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[*] posted on 26-7-2008 at 05:15
5-nitro-3H-1,2,4-triazol-3-one (NTO)


This secondary explosive is disclosed in patent US5034072 to the French explosives & munitions company SNPE. Its performance is described as follows:

detonation velocity = 7700 m/s p= 171 gm/cm^3
(8950 m/s @ p = 1.91 gm/cm^3)
impact sensitivity = 22 J
friction sensitivity 7% @ 353 N

It is further described as having explosive power nearly that of hexogen without having the sensitivity of either hexogen or octogen.

See http://www.pat2pdf.org/patents/pat5034072.pdf.

[Edited on 26-7-2008 by Ritter]

NTO.gif - 13kB




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[*] posted on 26-7-2008 at 12:35


I've prepared NTO via hydrazine + urea -> semicarbazide, glycerine + oxalic acid -> formic acid, semicarbazide + formic acid -> triazolone, triazolone + 70% HNO3 -> NTO.

Its an interesting explosive to play around with crystalisation, the attached picture shows my crystals on left and those from literature on right using different crystalisation methods.

NTO-crys-montage.jpg - 77kB
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[*] posted on 26-7-2008 at 12:43


Quote:
Originally posted by Axt
Its an interesting explosive to play around with crystalisation, the attached picture shows my crystals on left and those from literature on right using different crystalisation methods.


Very nice! Are these polymorphs? Many materials are capable of existing in a large number of discrete crystalline states, especially when you start adding in molecules of the solvents used in the crystallization.

[Edited on 26-7-2008 by Ritter]




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[*] posted on 26-7-2008 at 13:06


Just different crystal forms, I really dont know if different polymorphs are being formed and which is which. NTO does have a number of polymorphs.

The first formed a part of the initial product of nitration, which could be separated by "gold panning" them out as they are quite large and roll easily.

Second was simple crystallisation from water.

Third is the most dense form, small cubes. I used a vibrator attached to the outside of a glass beaker, recrystallised from water. In the literature they used rapid stirring, ultrasound or both.

The spheres in last picture used alcohol, though cant remember the exact method. It was quite hard to get them though. Investigated in the literature as easily flowing form and for casting with TNT.

[Edited on 27-7-2008 by Axt]

vibrator-crystalisation.jpg - 26kB
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[*] posted on 26-7-2008 at 21:05


NTO also forms salts: e.g. hydrazine (HNTO), methylamine, aminoguanidines, etc. (US 5256792). And estimated VOD of 3-nitro-1,2,4-triazol-5-one (NTO) is 8590 m/s at d= 1.91. Using this patent's thermodynamic data, I got with HNTO an estimate of about 7340 m/s at 1.65, and where NTO was 8240 m/s at 1.91.
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[*] posted on 22-8-2009 at 16:20


Axt, I notice that you produced Semicarbazide from Hydrazine and Urea. I was searching for the synthesis of Aminoguanidine from the previously mentioned reagents, thinking they would produce a 'Hydrazone'.

So am I right in thinking that the amino groups are nucleophilic enough to render the oxo group resistant to further nucleophilic attack? Would different conditions favour the production of a Hydrazone?
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[*] posted on 23-8-2009 at 10:49


Well, semicarbazide looks just like an aminated urea. Hydrazine is a good nucleophile, so maybe the amino group kicked out a hydrogen?

@Axt: Did you use anhydrous hydrazine and urea?

Anyone done a test on it yet?
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