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Author: Subject: 5-ATZ(5-Aminotetrazole), the nitrotetrazolate ion and friends
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[*] posted on 22-2-2024 at 11:28


Quote: Originally posted by dettoo456  

AgNTz IS NOT COMPATIBLE WITH ALUMINUM THOUGH!


Quote: Originally posted by B(a)P  

It is interesting that you say this, I have tested this by placing a small sample into an aluminium tube for over 12 months. At the end of the test, there was no obvious mark on the metal or any noticeable change to performance. I note that because the sample was so small I was only able to do limited testing - direct flame test and indirect flame test wrapped in foil.


Quote: Originally posted by Etanol  

I read that nitrotetrazolates are reduced by Mg,Zn,Al into aminotetrazolates. I mix recrystallized AgNTZ, Al and dist water at room temperature but I did not see a sign of the reaction within 2 day. Maybe this reaction is very slow or requires impurities.


The recrystallized AgNT was stored 8 days at room temperature in a mix with distilled water and aluminum foil. During this time, a few gas bubbles formed and the sample became similar in color to the powder of metal silver. However, the dried sample worked as well as freshly prepared AgNT. The Al-foil has not changed.

On the contrary, wet magnesium reacts very quickly, in minutes, into grey-black powder.

[Edited on 22-2-2024 by Etanol]

[Edited on 22-2-2024 by Etanol]
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[*] posted on 22-2-2024 at 17:28


It might indeed be fine to store with Al, I just saw that the old report I linked advised against it, citing quick decomposition.

I haven’t carried out any tests personally, so store it at your own risk.
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[*] posted on 22-2-2024 at 18:42


Quote: Originally posted by Etanol  

The recrystallized AgNT was stored 8 days at room temperature in a mix with distilled water and aluminum foil. During this time, a few gas bubbles formed and the sample became similar in color to the powder of metal silver. However, the dried sample worked as well as freshly prepared AgNT. The Al-foil has not changed.



Thank you for sharing your findings. That you had a reaction when water was involved indicates to me there is an incompatibility. So maybe it is ok to use aluminium as a cavity liner, so long as it is not stored. Seems to me though aluminium is best avoided in this application.
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[*] posted on 2-3-2024 at 00:33


A simple way to extract nitrotetrazole for NH4NT

Add 15-20%-H2SO4 into NaNT*4H2O to pH=2...1
Heat a little to completely dissolving
Add 4-5 volumes of isopropyl alcohol, shake
Wait
Solid sodium sulfate settled. Transparent yellow nitrotetrazole solution should be assembled with a pipette and neutralized by water ammonia, then dried.
What impurities can remain in the product with such an extraction?
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[*] posted on 3-3-2024 at 00:49


Why is it recommended to recrystallize BNCP from 1% HClO4, not water NH3? This is a base complex. Acid should decompose it into NH4ClO4, NH4NT, Co(NT)2OH, Co(ClO4)2OH, Co(OH)3 etc.

[Edited on 3-3-2024 by Etanol]
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[*] posted on 3-3-2024 at 09:18


The nitrotetrazole ligands are not strongly coordinated, and amines will take their place if too much base is applied. HClO4 at such low concentrations likely wouldn’t mess with the already acidic nitrotetrazole ligands.

Just speculation though; I’m not an inorganic chem wiz.
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[*] posted on 4-3-2024 at 02:48


Spontaneous detonation of lead 5-nitrotetrazolate!

It seems I understood why there is no mention of lead nitrotetrazolate Pb(NT)2.
There is only a short message of the salt Pb(OH)NT, which they say it does not have initiating properties.

I tried to make about 0.5 grams of Pb(NT)2 like Pb(N3)2.
2NaNT*4H2O+Pb(NO3)2=>Pb(NT)2+2NaNO3+8H2O
I prepared diluted solutions of NaNT*4H2O and Pb(NO3)2 in distilled water and added 2 drops of acetic acid to NaNT to get Pb(NT)2 rather than Pb(OH)NT.
However, when I mixed the solutions together, the precipitate did not fall out.
Then I put a plastic cup with a solution on a hot pipe of water heating for evaporation.
In the middle of the night, I woke up when I heard strange crackles.
After a few seconds, an explosion occurred, which tore the cup and threw it off the pipe.
However, not all the substance detonated. Most of the substance was smeared in a cup, sprayed with drops and froze with a light yellow crust on the pipe.

At first, I took polycarbonate glasses, then I took a piece of substance from the cup and tried to break it and burn it. But it did not explode.

Then I tried to remove the yellow crust from the pipe with a wooden stick. There was another strong explosion, from which a ringing in the ears appeared!

Summarizing: Pb(NT)2 is well soluble in water and cannot be obtained in pure form.
It seems, Pb(NT)2 forms a non-explosive (or difficult explosive) hydrate, which loses water at elevated temperature.
However, water-free lead nitrotetrazolate Pb(NT)2 is hypersensitive as NI3 and is able to explode spontaneously when dried.

[Edited on 4-3-2024 by Etanol]
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[*] posted on 4-3-2024 at 08:09


A couple of months ago I tried to prepare the Lead salt of 3-Nitro-1,2,4-triazole and got the same sort of thing you mentioned - although the Lead salt was not very energetic. It was prepared from simple metathesis of sodium 3-nitro-1,2,4-triazolate w/Pb(NO3)2 but the product only crystallized out of the solution after around 2 weeks.

IMG_1600.jpeg - 1.8MB
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[*] posted on 4-3-2024 at 09:23


Quote: Originally posted by dettoo456  
A couple of months ago I tried to prepare the Lead salt of 3-Nitro-1,2,4-triazole and got the same sort of thing you mentioned - although the Lead salt was not very energetic. It was prepared from simple metathesis of sodium 3-nitro-1,2,4-triazolate w/Pb(NO3)2 but the product only crystallized out of the solution after around 2 weeks.


It is interesting. But I have no desire to continue experiments with Pb(NT)2 after the incident.
It is strange that the compounds of lead and tetrazols are so sensitive when azides of lead and silver have almost identical properties. My colleague had a sudden explosion when he tried to assemble a dry lead azotetrazolate from the filter a long time ago.

There is another unpleasant discovery.
It seems, the green primary explosives of a row (NH4)n-2Me(NT)n*(H2O)4-n do not have a constant formula and easily lose NH4NT when washing water.
I tried to prepare the complex (NH4)2Cu(NT)4*2H2O, but I used a more diluted solution than the leadership requires. When I cooled the mixture in the ice, filled, washed with water and dried it, I received only 62% of theoretical mass (NH4)2Cu(NT)4*2H2O.
However, I am sure that I have not lost so much substance because I collected the entire solution and it was almost colorless.
62% of the theoretical mass of (NH4)2Cu(NT)4*2H2O is about 100% of theoretical mass of Cu(NT)2*2...4H2O.
Thus, this is just a crystalline mixture of two salts: Cu(NT)2*nH2O and NH4NT.
Disappointment.

Update. It seems, I realized how to get pure double salt (NH4)n-2Me(NT)n*(H2O)4-n. Need to separately prepare copper salt Cu(NT)2.
CuSO4 or Cu(NO3)2 + NaNT =>Na2SO4 or NaNO3 + Cu(NT)2
wash it from Na salts.
Then mix Cu(NT)2 with an excess of an ammonia salt NH4NT solution, heat, mix for a long time, cool. Should’t wash the product with water!

[Edited on 4-3-2024 by Etanol]
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[*] posted on 4-3-2024 at 20:08


Quote: Originally posted by Etanol  
A simple way to extract nitrotetrazole for NH4NT

Add 15-20%-H2SO4 into NaNT*4H2O to pH=2...1
Heat a little to completely dissolving
Add 4-5 volumes of isopropyl alcohol, shake
Wait
Solid sodium sulfate settled. Transparent yellow nitrotetrazole solution should be assembled with a pipette and neutralized by water ammonia, then dried.
What impurities can remain in the product with such an extraction?


This is a very nice procedure for the synthesis of ammonium nitrotetrazole, thanks for sharing, I will try it for myself soon. I don't see that there would be any significant contamination.

With regard to your questions on lead nitrotetrazole, I am surprised to hear that it is soluble. I will (cautiously) try it for myself and report back. I wonder if nitric acid is better for the acidification.
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[*] posted on 5-3-2024 at 02:33


Quote: Originally posted by Etanol  
A simple way to extract nitrotetrazole for NH4NT

Add 15-20%-H2SO4 into NaNT*4H2O to pH=2...1
Heat a little to completely dissolving
Add 4-5 volumes of isopropyl alcohol, shake
Wait
Solid sodium sulfate settled. Transparent yellow nitrotetrazole solution should be assembled with a pipette and neutralized by water ammonia, then dried.
What impurities can remain in the product with such an extraction?


Quote: Originally posted by B(a)P  

This is a very nice procedure for the synthesis of ammonium nitrotetrazole, thanks for sharing, I will try it for myself soon. I don't see that there would be any significant contamination.


upd
Isopropanol pulls a little water and excess sulfuric acid. Therefore, another stage:
Dry dirty NH4NT should be dissolved in hot isopropanol or acetone, filtered.
NH4NT is soluble in hot isopropanole, (NH4)2SO4 is not.
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[*] posted on 6-3-2024 at 04:09


The article "5-Aminotetrazoles and Silver-based Primary Explosives" provides formulas and names of complexes AgATz*AgClO4 and AgATz*AgNO3, but they describe the syntheses and yields that correspond to the complexes Ag(ATz)ClO4 and Ag(ATz)NO3.
Has anyone tried to add by drops 0.01 mol 5-aminotetrazole hot solution into 0.01mol AgNO3 solution, then cool it? [AgATz*Ag]NO3 or [Ag(ATz)]NO3 will precipitate?
Theoretically, [Ag(ATz)]NO3 is very effective if it exists.

[Edited on 6-3-2024 by Etanol]
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[*] posted on 6-3-2024 at 08:59


See the thread for ‘Exotic Primaries’
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[*] posted on 10-3-2024 at 01:00


Quote: Originally posted by dettoo456  
See the thread for ‘Exotic Primaries’

Thanks. I find.

Sadness
I did not think that the complexes of row (NH4)nMe(NT)n+2(H2O)4-n are so fragile.
I tried to get a (NH4)4Cu(NT)6 complex from approximately 5-10% solutions, but after cooling with ice, filtering and flushing cold water again received, judging by the mass, the copper salt Cu(NT)2*4H2O with about 10% content of NH4NT.
It is more likely that in a solid form, this series of substances exists as an ordinary mixture of independent salts Cu(NT)2 and NH4NT.
Similarly, I tried to get nickel-ammonia salt in a more concentrated solution. The result is the same.
I don't know how to get these comlexes in pure form :(
It seems AgNT is the only more or less stable and applicable tetrazole as a primary explosive.

[Edited on 10-3-2024 by Etanol]

[Edited on 10-3-2024 by Etanol]
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[*] posted on 16-4-2024 at 03:53


How to remove 5-ATz from 5-NTz?
5-NTz, 5-ATZ and its Na/NH4 salts are soluble in water, acetone and hot alcohol.
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[*] posted on 16-4-2024 at 11:22


Excess nitrous acid to convert all 5-ATz is likely the easiest way
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[*] posted on 16-4-2024 at 12:55


Quote: Originally posted by Etanol  
Quote: Originally posted by dettoo456  
See the thread for ‘Exotic Primaries’

Thanks. I find.

Sadness
I did not think that the complexes of row (NH4)nMe(NT)n+2(H2O)4-n are so fragile.
I tried to get a (NH4)4Cu(NT)6 complex from approximately 5-10% solutions, but after cooling with ice, filtering and flushing cold water again received, judging by the mass, the copper salt Cu(NT)2*4H2O with about 10% content of NH4NT.
It is more likely that in a solid form, this series of substances exists as an ordinary mixture of independent salts Cu(NT)2 and NH4NT.
Similarly, I tried to get nickel-ammonia salt in a more concentrated solution. The result is the same.
I don't know how to get these comlexes in pure form :(
It seems AgNT is the only more or less stable and applicable tetrazole as a primary explosive.

[Edited on 10-3-2024 by Etanol]

[Edited on 10-3-2024 by Etanol]


I am not sure I understand you. Are you saying that AgNT is the only useful primary of all the tetrazoles? Or are you saying AgNT is the only useful nitrotetrazole? Either way I tend to disagree with this statement. Here are just a few examples:
Tetrazoles
5,5' - azoterazolates
bis tetrazoles
hydrazotetrazoles
There are many others less accessible to the amateur, but not out of reach, for example azidotetrazoles

Nitrotetrazoles
A raft of transition metal, ammonium nitrotetrazole complexes

I don't understand the copper complex that you were trying to synthesise. Firstly, wouldn't it have water in it, I don't see how it would be excluded from the complex when you are using it as a solvent? Also wouldn't it be (NH4)2?
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[*] posted on 16-4-2024 at 16:19


Quote: Originally posted by B(a)P  

Are you saying that AgNT is the only useful primary of all the tetrazoles?

Right

Quote: Originally posted by B(a)P  

Tetrazoles
5,5' - azoterazolates
bis tetrazoles
hydrazotetrazoles
There are many others less accessible to the amateur, but not out of reach, for example azidotetrazoles

5,5' - azoterazolates - small explosive energy
bis tetrazoles - small explosive energy and slow DDT
hydrazotetrazoles - small explosive energy and slow DDT.

May be nitraminotetrazoles and more difficult compounds...I don't know.
BNCP? There is a small hope. I read that not everyone gets good DDT.
May be double salts aminotetrazoles or azoterazolates or bis tetrazoles or hydrazotetrazoles with HNO3 or HClO4. They seem corrosion active and unstable to moisture.

Quote: Originally posted by B(a)P  

Nitrotetrazoles
A raft of transition metal, ammonium nitrotetrazole complexes

Hg(NT)2 is very toxic
Cd(NT)2 is very toxic
Ni(NT)2,Fe(NT)2,Co(NT)2,Cu(NT)2 form strong hydrates in normal conditions, which causes many failures.
Pb(NT)2 - strong hydrates and high sensitive
DBX-1 quickly decomposes in oxygen
Double complex salts NH4NT or NaNT with Cu(NT)2 or Fe(NT)2 or Ni(NT)2 or Co(NT)2 easily hydrolyzed with water into very soluble NH4NT or NaNT and poorly soluble transition metal nitrotetrazolate.

Quote: Originally posted by B(a)P  

I don't understand the copper complex that you were trying to synthesise. Firstly, wouldn't it have water in it, I don't see how it would be excluded from the complex when you are using it as a solvent? Also wouldn't it be (NH4)2?

According to articles (NH4)2[Cu[NTZ]4(H2O)2] is one of the members of the series:
[Cu[NTZ]2(H2O)4]
NH4[Cu[NTZ]3(H2O)3]
(NH4)2[Cu[NTZ]4(H2O)2]
(NH4)3[Cu[NTZ]5(H2O)]
(NH4)4[Cu[NTZ]6]
With a decrease in the number of water, the sensitivity to the flame grows, the percentage of ignition failures becomes less.
Does it make sense to carry out a reaction in ethyl or methyl alcohol without water and rinse the product only with alcohol?

Sometimes I think NH4CuNT etc are not chemical compounds but mechanical mix of NH4NT and Cu(NT)*nH2O

[Edited on 17-4-2024 by Etanol]
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[*] posted on 17-4-2024 at 02:03


Quote: Originally posted by Etanol  



5,5' - azoterazolates - small explosive energy
bis tetrazoles - small explosive energy and slow DDT
hydrazotetrazoles - small explosive energy and slow DDT.



What is this based on? I have not done much testing on anything other than azotetrazolates and what I have done has been limited, but it did not seem to be that azotetrazolates lacked explosive energy. I would be curious to read any references you have on these compounds.

Quote: Originally posted by Etanol  


According to articles (NH4)2[Cu[NTZ]4(H2O)2] is one of the members of the series:
[Cu[NTZ]2(H2O)4]
NH4[Cu[NTZ]3(H2O)3]
(NH4)2[Cu[NTZ]4(H2O)2]
(NH4)3[Cu[NTZ]5(H2O)]
(NH4)4[Cu[NTZ]6]
With a decrease in the number of water, the sensitivity to the flame grows, the percentage of ignition failures becomes less.
Does it make sense to carry out a reaction in ethyl or methyl alcohol without water and rinse the product only with alcohol?



Do you mind sharing the references you are referring to?
Ethanol might be worth a try, it will dissolve the copper nitrate, I don't know what ammonium nitrotetrazole is soluble in other than water. Or perform the reaction at -40C with liquid ammonia as the solvent :D
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[*] posted on 17-4-2024 at 08:06


The 5,5’-Azobis(tetrazolates) are hygroscopic (at least the Na, K, & Ag salt) and the dry salts (of Na, K, Ag, or transition metals) are too sensitive to be practically useful.

I’d tend to agree with Etanol; IMO AgNTz is the only really practical tetrazole. BNCP is alright in terms of performance and sensitivity but requires a mildly complex synthesis, CuNTz is too sensitive to oxidation back to Cu(ii), and the secondaries like TKX-50 are waaaay to expensive to produce on a reasonable scale.

The (Ag2)5-ATz NO3 could be useful but has a wonky preparative method that hasn’t really been replicated well and it could be too labile to degrade to Ag metal over time.
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[*] posted on 17-4-2024 at 10:27


Quote: Originally posted by B(a)P  
Quote: Originally posted by Etanol  

5,5' - azoterazolates - small explosive energy
bis tetrazoles - small explosive energy and slow DDT
hydrazotetrazoles - small explosive energy and slow DDT.


What is this based on? I have not done much testing on anything other than azotetrazolates and what I have done has been limited, but it did not seem to be that azotetrazolates lacked explosive energy. I would be curious to read any references you have on these compounds.


I tested copper 5,5’-azotetrazolate and 5,5’-Bis-tetrazolyl-hydrazine.

According to the literature, сopper azotetrazolate is the only non-hydrated metal azotetrazolate and therefore the strongest. However, despite the fact that it is able to detonation in the smallest quantity, it seemed to me less brisant than PVA Lead Azide.
Perhaps I am mistaken and the difference is caused by the low bulk density of сopper azotetrazolate compared to PVA LA. I did not measure the mass, but measured it by volume.
In addition, I was afraid to press dry сopper azotetrazolate because it is more sensitive than silver fulminate. It is impossible to work with this in dry form. Maybe I can compress it with alcohol and conduct a correct comparison.

5,5’-Bis-tetrazolyl-hydrazine, Dihydrazinium 5,5’- azotetrazolate and similar substances saturated with hydrogen without oxygen, despite the high enthalpy, do not detonate from fire, but only flare up. Thus, it is not primary explosive.

Energy is my assumption based on their formulas and bonds energies. I could be wrong.

Are you prepare iron 5,5’-azotetrazolate?

Quote: Originally posted by B(a)P  

Quote: Originally posted by Etanol  


According to articles (NH4)2[Cu[NTZ]4(H2O)2] is one of the members of the series:
[Cu[NTZ]2(H2O)4]
NH4[Cu[NTZ]3(H2O)3]
(NH4)2[Cu[NTZ]4(H2O)2]
(NH4)3[Cu[NTZ]5(H2O)]
(NH4)4[Cu[NTZ]6]
With a decrease in the number of water, the sensitivity to the flame grows, the percentage of ignition failures becomes less.
Does it make sense to carry out a reaction in ethyl or methyl alcohol without water and rinse the product only with alcohol?


Do you mind sharing the references you are referring to?
Ethanol might be worth a try, it will dissolve the copper nitrate, I don't know what ammonium nitrotetrazole is soluble in other than water. Or perform the reaction at -40C with liquid ammonia as the solvent :D


For example

Tetrazole Ring-Containing Complexes (R. Matyáš and J. Pachman, Primary Explosives,
DOI 10.1007/978-3-642-28436-6_9, # Springer-Verlag Berlin Heidelberg 2013

Green primary explosives: 5-Nitrotetrazolato-N 2 -ferrate hierarchies
My Hang V. Huynh*, Michael D. Coburn*, Thomas J. Meyer †‡ , and Modi Wetzler

US2006030715 Complex Nitrotetrazole Primary Explosives

and Engager's articles

I prepared NH4NT, Cu(NT)2(hydrate), Ni(NT)2(hydrate) and tried to prepare double salts NH4-Cu and NH4-Ni several times. I noticed the positive effect of NH4NT, but could not bring its content to theoretical.

[Edited on 17-4-2024 by Etanol]
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[*] posted on 17-4-2024 at 10:38


Here’s another reference to the Cu 5-NTz Amine complex:

[Edited on 17-4-2024 by dettoo456]

Attachment: Less Sensitive 5-NTz Salts.pdf (551kB)
This file has been downloaded 42 times

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[*] posted on 17-4-2024 at 12:18


Quote: Originally posted by Etanol  


According to the literature, сopper azotetrazolate is the only non-hydrated metal azotetrazolate and therefore the strongest. However, despite the fact that it is able to detonation in the smallest quantity, it seemed to me less brisant than PVA Lead Azide.
Perhaps I am mistaken and the difference is caused by the low bulk density of сopper azotetrazolate compared to PVA LA. I did not measure the mass, but measured it by volume.
In addition, I was afraid to press dry сopper azotetrazolate because it is more sensitive than silver fulminate. It is impossible to work with this in dry form. Maybe I can compress it with alcohol and conduct a correct comparison.

5,5’-Bis-tetrazolyl-hydrazine, Dihydrazinium 5,5’- azotetrazolate and similar substances saturated with hydrogen without oxygen, despite the high enthalpy, do not detonate from fire, but only flare up. Thus, it is not primary explosive.

Energy is my assumption based on their formulas and bonds energies. I could be wrong.

Are you prepare iron 5,5’-azotetrazolate?

[Edited on 17-4-2024 by Etanol]


I didn't realise the silver azotetrazolate salt was a hydrate. I agree that they are generally very sensitive.
I have not tried the iron salt.

Thanks very much for the references Etanol and dettoo456.
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[*] posted on 17-4-2024 at 12:21


Quote: Originally posted by dettoo456  
Here’s another reference to the Cu 5-NTz Amine complex:
[Edited on 17-4-2024 by dettoo456]

Thanks for the idea, but it seems to be a bad prymary with long DDT.
I dissolved Cu(NT)2*nH2O in hot water-ammonia mix. The result was a beautiful transparent blue solution. Then I cooled it, I collected blue shiny crystals and dried it.
However, from the fire, the substance only burns with small flashes and stop without detonation.
It looks like wet NH4NT or hexaaammine nickel perchlorate properties.
Crystals muddy. It seems that they consist of two phases.

Quote: Originally posted by B(a)P  

I didn't realise the silver azotetrazolate salt was a hydrate. I agree that they are generally very sensitive.

I forgot it. And Hg. Legends go about it's high sensitivity.

I also tried adding a hot ATZ*H2O solution to hot x2 AgNO3 solution without additional HNO3. A white precipitate formed. The pH of the solution decreased to 1.5! The dried substance only burns, but does not explode.

Quote: Originally posted by dettoo456  
If you are really concerned with yield, just dry out the solids from a 5-ATz synthesis and reflux in anhydrous EtOH for an hour or two to completely extract any available 5-ATz. In my experience though, the crystallization of 5-ATz is consistent enough to disregard a different extraction method.

5-ATz is soluble in hot dry acetone and EtOH bad: c.a. 6g/100g of hot acetone and 3.5g/100g of hot EtOH.
But it soluble in hot water-acetone and water-EtOH mixes.
Na2SO4 is soluble in water-acetone and water-EtOH very bad.

[Edited on 18-4-2024 by Etanol]
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[*] posted on 19-4-2024 at 09:00


Quote: Originally posted by B(a)P  
Quote: Originally posted by Etanol  

5,5' - azoterazolates - small explosive energy

What is this based on? I have not done much testing on anything other than azotetrazolates and what I have done has been limited, but it did not seem to be that azotetrazolates lacked explosive energy.

I was wrong. The calc explosive heat of copper azotetrazolate is sufficient. Due to the high enthalpy of formation.
I think Ni azotetrazolate is perpective if it does not form hydrates, because it should have similar power but less sensitivity. In addition, Ni does not oxidize in the air unlike Fe(2+)=>Fe(3+).

[Edited on 19-4-2024 by Etanol]
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