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Author: Subject: Nitroguanidine
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[*] posted on 14-2-2014 at 09:43


Quote: Originally posted by VladimirLem  

i dont think they put it in cartridges cause it looks so nice :D


xaxaxaxaxa!! realy funny!! :D :D

[Edited on 14-2-2014 by underground]
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[*] posted on 20-12-2015 at 13:13
Explosive performance of nitroguanidine


If you have guanidine nitrate, nitroguanidine could easily be prepared.

Apart from being a useful raw material for a lot of other things and also as a propellant:

How would it perform as a high explosive for shaped charges and other interesting experiments?
I found velocity figures from 6750 to 8200m/s, that sounds useful, even though it's not as energetic as the more common HEs.

I wonder how it behaves in practice concerning the typical problems one encounters, like achieving the right density, critical charge diameter and sensitivity to initiation.


Any practical experience?
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[*] posted on 20-12-2015 at 13:21


One major problem with guanidine nitrate (EDIT: typo, meant nitroguanidine, thanks philou!) is that its morphology (needles) makes it very difficult to get anything approaching a reasonable density for application in shaped charges.

Better to turn it into 5-AT, and make the nitrate salt. That has around 8800 m/s and density 1.8 if I remember correctly.

[Edited on 20-12-15 by The_Davster]
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[*] posted on 20-12-2015 at 14:45


@ The_Davster,
Nitroguanidine, not guanidine nitrate!

From Explosives 4th revised and extended edition, Josef Köhler and Rudolf Meyer

p248 and 249
Nitroguanidine (H2N)2C=N-NO2
MW: 104.1 g/mol
Enthalpy of formation: -213.3 kcal/kg
OB: -30.7%
%N: 53.83%
Volume of detonation gases: 1075 L/kg
Heat of explosion (H2O gas): 687 kcal/kg
specific energy: 98 mt/kg
density: 1.71 g/cm³
melting point: 232°C = 450°F (decomposition without deflagration)
lead block test for 10g: 305 cm³
VOD at max density and confinement: 8200 m/s
impact sensitivity: up to 49 Nm --> no reaction
friction sensitivity: up to 353 N pistil load --> no reaction
critical diameter of steel sleeve test: 1 mm --> no reaction ... Thus very insensitive even if confined!
Soluble in hot water but almost unsoluble in cold water. Sparingly soluble in alcohol and insoluble in ether.
Readily soluble in alkali (formation of salts NQ is a nitramine NH2-C(=NH)-NH-NO2).
Excellent chemical stability and not very sensitive to shock or impact.





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[*] posted on 20-12-2015 at 14:49


thanks! I typed the wrong compound
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[*] posted on 20-12-2015 at 15:10


Does anyone know the properties of aminoguanidine nitrate ? Aminoguanidine can be made by reduction of nitroguanidine. Then just neutralize it with HNO3

Nitroguanidine looks to be an interesting nitramine

[Edited on 20-12-2015 by underground]
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[*] posted on 20-12-2015 at 21:28


Gargamel-

I have merged your new nitroguanidine thread with another nitroguanidine thread.

If you please. If you don't have an actual lab you conducted to report on, or time to give the references /links to show your sources of information leading to questions- and the topic has been repeatedly discussed, with multiple pre existing threads...POST YOUR QUESTION IN AN EXISTING RELATED THREAD.

Thanks-




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The explosion removed the windows, the door and most of the chimney.
It was the sort of thing you expected in the Street of alchemists. The neighbors preferred explosions, which were at least identifiable and soon over. They were better than the smells, which crept up on you.
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It is essential that persons having explosive 
substances under their charge should never 
lose sight of the conviction that, preventive 
measures should always be prescribed 
on the hypothesis of an explosion.

Marcellin Berthelot - 1892 
Explosives and their power - Page 47
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[*] posted on 21-12-2015 at 04:31


Quote: Originally posted by PHILOU Zrealone  
@ The_Davster,
Nitroguanidine, not guanidine nitrate!

From Explosives 4th revised and extended edition, Josef Köhler and Rudolf Meyer

p248 and 249
Nitroguanidine (H2N)2C=N-NO2
MW: 104.1 g/mol
Enthalpy of formation: -213.3 kcal/kg
OB: -30.7%
%N: 53.83%
Volume of detonation gases: 1075 L/kg
Heat of explosion (H2O gas): 687 kcal/kg
specific energy: 98 mt/kg
density: 1.71 g/cm³
melting point: 232°C = 450°F (decomposition without deflagration)
lead block test for 10g: 305 cm³
VOD at max density and confinement: 8200 m/s
impact sensitivity: up to 49 Nm --> no reaction
friction sensitivity: up to 353 N pistil load --> no reaction
critical diameter of steel sleeve test: 1 mm --> no reaction ...

Thus very insensitive even if confined!
Soluble in hot water but almost unsoluble in cold water. Sparingly soluble in alcohol and insoluble in ether.
Readily soluble in alkali (formation of salts NQ is a nitramine NH2-C(=NH)-NH-NO2).
Excellent chemical stability and not very sensitive to shock or impact.


From same book p 166:
Guanidine nitrate (H2N)2C=NH.HNO3
MW: 122.1 g/mol
Enthalpy of formation: -767 kcal/kg
OB: -26.2%
%N: 45.89%
Volume of detonation gases: 1098 L/kg
Heat of explosion (H2O gas): 482 kcal/kg
specific energy: 77 mt/kg
density: ??? g/cm³ (1.436 from Wikipedia)
melting point: 215°C = 419°F (deflagrate at 270°C = 518°F)
lead block test for 10g: 240 cm³
VOD at max density and confinement: ??? m/s
impact sensitivity: up to 50 Nm --> no reaction
friction sensitivity: up to 353 N pistil load --> no reaction
critical diameter of steel sleeve test: 2.5 mm

Thus very insensitive but more than NQ because it will blow a 25mm diameter pipe recipient with a 2.5 mm hole heated by Bunzen burners while NQ doesn't with 1mm (Nitroglycerin does it at 24 mm)!

Soluble in alcohol and/or water.

--------------------------------------------------------------
Not asked but related to amino-guanidine nitrate...

From same book p379
Triaminoguanidine nitrate (H2N-NH-)2C=N-NH2.HNO3
MW: 167.1 g/mol
Enthalpy of formation: -67.07 kcal/kg
OB: -33.5%
%N: 58.68%
Volume of detonation gases: 1206 L/kg
Heat of explosion (H2O gas): 876 kcal/kg
specific energy: ?? mt/kg (must be >98 since VODG is bigger just as heat of explosion while energy of formation is less exothermic)
density: 1.5 g/cm³
melting point: 216°C = 420°F (decomposition-dflagrate at 227°C = 440°F)
lead block test for 10g: 350 cm³
VOD at 0.95 density and confinement: 5300 m/s
impact sensitivity: 4 Nm
friction sensitivity: over to 120 N pistil load --> crackling
critical diameter of steel sleeve test: ??? mm

Thus much more sensitive!

Prepared by reacting 1 mole of guanidine nitrate with 3 moles of hydrazine hydrate at 100°C for 4 hours.The reaction is accompanied by the liberation of ammonia.

--------------------------------------------------------------
From Donald Haarmann (The Wizzards is In) VOD tables updated by Formatik in 2008
> Triaminoguanidine nitrate (TAGN)
VOD 5300 at 0.95
and 7930 at 1.46
LBT 350/117% vs TNT
Ref K&M and 2700 T28

> Guanidine nitrate (GN)
VOD 3700 at ??
LBT 10% vs TNT
LBT 110-140 thus vs TNT 36-46%
Ref 2700 G151 and Urbanski (2)

> Guanidine perchlorate
VOD 6000 at 1.15
VOD 7150 at 1.67
LBT 400 vs TNT 133%
Ref Urbanski (2) and Davis and 2700 G152

K&M= Köhler and Meyer
2700 = PATR 2700 Encyclopedia of Explosives and Explosive Items Vol.
Davis = Tenney L. Davis; The Chemistry and powder of Explosives (1943)
-----------------------------------------------------
Conclusions?
1°)Aminoguanidine nitrate must display properties between GN and TAGN.
2°)One can see that the enthalpy of formation of nitrate salt of amine is large, this comes mainly from the neutralization heat of the base by the acid...most amine salts display such effect.
3°)The enthalpy of formation and heat of explosion goes up (less negative) by passing from GN to NQ (a kind of dehydratation)...this fact comes from less water into the molecule...water in exhaust gases reduces the heat of explosion.
4°)The enthalpy of formation and heat of explosion goes up (less negative) by introducing hydrazine into the molecule see GN and TAGN; this fact comes from endothermicity of hydrazine and that the N-N bond will form very stable N#N (dinitrogen) after burning releasing a lot of energy
5°)Perchlorates are better than nitrates, more dense salts results, better OB and energy output --> more sensitive and higher VOD or lead block tests.
6°)Triaminoguanidine perchlorate must be a killer but also quite sensitive :D :cool:


[Edited on 21-12-2015 by PHILOU Zrealone]




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[*] posted on 21-12-2015 at 05:11


Biguanide diperchlorate has VoD of 8490 m/s according to US4340755 A


vod.JPG - 82kB

[Edited on 21-12-2015 by ecos]
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[*] posted on 21-12-2015 at 06:03


Good Ecos!

Biguanide diperchlorate (BGDP) H2N-C(=NH)-NH-C(=NH)-NH2.2HClO4 is a kind of dimer of guanidine perchlorate (H2N-C(=NH)-NH2.HClO4)
H2N-(C(=NH)-NH)1-H .HClO4 (VOD 7150m/s at 1.67 g/cm³)
H2N-(C(=NH)-NH)2-H .2HClO4 (VOD 8490m/s at 1.91 g/cm³)

Now we need to find datas for:
-dinitro biguanide O2N-NH-C(=NH)-NH-C(=NH)-NH-NO2
-biguanide dinitrate H2N-C(=NH)-NH-C(=NH)-NH2 .2HNO3
-biguanide dinitroformiate H2N-C(=NH)-NH-C(=NH)-NH2 .2HC(NO2)3

-bisguanidine dinitrate H2N-C(=NH)-NH-NH-C(=NH)-NH2 . 2HNO3
-bisguanidine diperchlorate H2N-C(=NH)-NH-NH-C(=NH)-NH2 . 2HClO4 (probably stronger than BGDP)
-bisguanidine dinitroformiate H2N-C(=NH)-NH-NH-C(=NH)-NH2 . 2HC(NO2)3
-dinitro bisguanidine O2N-NH-C(=NH)-NH-NH-C(=NH)-NH-NO2
And azo dérivatives
H2N-C(=NH)-N=N-C(=NH)-NH2 . 2HNO3
H2N-C(=NH)-N=N-C(=NH)-NH2 . 2HClO4 (probably even stronger)
H2N-C(=NH)-N=N-C(=NH)-NH2 . 2HC(NO2)3
O2N-NH-C(=NH)-N=N-C(=NH)-NH-NO2

Formamidine dérivatives:
-formamidine nitrate H2N-CH=NH . HNO3
-formamidine perchlorate H2N-CH=NH . HClO4
-formamidine nitroformiate H2N-CH=NH . HC(NO2)3
-nitroformamidine O2N-NH-CH=NH
-aminoformamidine nitrate H2N-CH=N-NH2 . HNO3
-aminoformamidine perchlorate H2N-CH=N-NH2 . HClO4
-aminoformamidine nitroformiate H2N-CH=N-NH2 . HC(NO2)3
-nitroaminoformamidine O2N-NH-CH=N-NH2
-O2N-NH-CH=N-N=CH-NH-NO2
-diaminoformamidine dinitrate H2N-NH-CH=N-NH2 . 2 HNO3
-diaminoformamidine diperchlorate H2N-NH-CH=N-NH2. 2 HClO4
-diaminoformamidine dinitroformiate H2N-NH-CH=N-NH2 . 2 HC(NO2)3

Oxaladiamidine dérivatives:
-bisformamidine dinitrate H2N-C(=NH)-C(=NH)-NH2 . 2HNO3
-bisformamidine diperchlorate H2N-C(=NH)-C(=NH)-NH2 . 2 HClO4
-bisformamidine dinitroformiate H2N-C(=NH)-C(=NH)-NH2 . 2 HC(NO2)3
-bisnitroformamidine O2N-NH-C(=NH)-C(=NH)-NH-NO2
And
Diamino dérivatives of oxaladiamidine...
Tetramino dérivatives of oxaladiamidine...

Triguanide dérivatives H2N-(C(=NH)-NH)3-H
H2N-C(=NH)-NH-C(=NH)-NH-C(=NH)-NH2
--> dinitrate, diperchlorate, dinitroformiate, dinitro-

Thus stil a lot of simple compounds to discover/study with very potent explosive abilities probably over RDX, PETN...and maybe over HMX or CL-20

[Edited on 21-12-2015 by PHILOU Zrealone]




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[*] posted on 21-12-2015 at 07:00


Do anyone know any info for aminoguanidine nitrate ?
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[*] posted on 21-12-2015 at 09:17


Also related to aminoguanidine...diamino-tetrazine H2N-C(NN)2C-NH2
--> mononitrate, monoperchlorate, mononitroformiate and maybe dinitrate, diperchlorate, dinitroformiate.

Also dihydrazino-tetrazine H2N-NH-C(NN)2C-NH-NH2
--> mononitrate, monoperchlorate, mononitroformiate and maybe dinitrate, diperchlorate, dinitroformiate.




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[*] posted on 21-12-2015 at 09:24


Quote: Originally posted by underground  
Do anyone know any info for aminoguanidine nitrate ?

-It has the formula H2N-C(=NH)-NH-NH2. HNO3
-It must display properties between those of guanidine nitrate and triamino guanidine nitrate...probably closer to TAGN.
--> d close to 1.5, VOD > 7500 m/s, Impact sensitivity in the range 3 < x < 10 Nm

Other infos
-Aminoguanidine can be made from equimolar cyanamide and hydrazine mix; and from guanidine with one hydrazine equivalent.
-Free aminoguanidine easily turns into diamino-tetrazine by air oxydation...

[Edited on 21-12-2015 by PHILOU Zrealone]




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[*] posted on 21-12-2015 at 09:39


Quote: Originally posted by PHILOU Zrealone  
Quote: Originally posted by underground  
Do anyone know any info for aminoguanidine nitrate ?

-It has the formula H2N-C(=NH)-NH-NH2. HNO3
-It must display properties between those of guanidine nitrate and triamino guanidine nitrate...probably closer to TAGN.
--> d close to 1.5, VOD > 7500 m/s, Impact sensitivity in the range 3 < x < 10 Nm

Other infos
-Aminoguanidine can be made from equimolar cyanamide and hydrazine mix; and from guanidine with one hydrazine equivalent.
-Free aminoguanidine easily turns into diamino-tetrazine by air oxydation...

[Edited on 21-12-2015 by PHILOU Zrealone]


I was thinking of making Aminoguanidine from nitroguanidine by reduction of nitroguanidine with zinc in acetic acid

http://www.sciencemadness.org/scipics/Engager/TzOTC/Syntheti...

Not the use of toxic hydrazine at all

diamino-tetrazine looks very interesting, what about diamino-tetrazine dinitrate ?
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[*] posted on 21-12-2015 at 11:16


Here's a thread I made a few years back which contains a ton of info on these guanidine compounds:

http://www.sciencemadness.org/talk/viewthread.php?tid=17908




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[*] posted on 23-12-2015 at 09:50


Sorry Bert, I must have overlooked this thread.

I'm specifically after the practical usefulness of nitroguanidine.


The whole zoo of related compound that can be made with it is interesting, but of rather academical interest, because I cannot get the other precursor materials in quantity.
Guanidine nitrate and sulphuric acid - OK, but not the rest.


By "Quantity" I mean amounts an amateur experimentor would work with, like 10g - 20g SCs.

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[*] posted on 23-12-2015 at 12:41


Quote: Originally posted by Praxichys  
Here's a thread I made a few years back which contains a ton of info on these guanidine compounds:

http://www.sciencemadness.org/talk/viewthread.php?tid=17908

Interesting, thank you for pointing this out!

So DougTheMapper and Praxichys are two faces of the same coin :o, a kind of schizophreny :P or simply loggin lost or the will to change?




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[*] posted on 24-6-2017 at 04:15


So my vacuum pump has failed, and I'm having to do gravity filtration of the nitroguanidine in a Buchner funnel. This is an extremely slow process due to the fine particle size.

I want to preserve the liquid, so I can boil it down to recover the sulfuric acid, but I'm concerned about the stability of nitroguanidine in acid. I know that the concentrated solution from the addition of guanidine nitrate to sulfuric acid, if left to stand, eventually fails to produce nitroguanidine upon dilution (CoPaE). But is NQ degraded in 25-20% sulfuric acid?

[Edited on 6-24-2017 by Chisholm]
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