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Author: Subject: Exotic Primaries - Complex Salts
Microtek
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[*] posted on 23-12-2023 at 02:39


I have tried tackling the problem of reliable sensitivity tests myself. I experimented with vertical impacts at first, but in the end I settled on oblique pendulum hammer impacts on a sample placed on a strip of sand paper on a steel plate. Then I experiment with release heights to find where at least 3 out of five attempts give detectable decomposition (by sound, sight or smell).

My reasoning for this test method was that, in ordinary handling, a primary will only rarely be exposed to accidental impacts that are powerful enough to set it off. So, the foremost safety concern is probably when the primary is exposed to grinding or shearing actions, hence the oblique impact on sand paper.
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[*] posted on 23-12-2023 at 23:07


Someone reported an extraordinarily powerful primary. It’s the combination of ammonium dinitramide and decaborane.

Can anyone experiment or replace with ammonium perchlorate? I can’t find a source for decaborane
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[*] posted on 24-12-2023 at 01:29


Decaborane is available on Chemcraft: https://chemcraft.su/product/24824
But I doubt it's practical. Even if dinitramide can be substituted with perchlorate, decaborane is still volatile, highly flammable, toxic and astronomically expensive.
Though, if someone is brave enough, synthesis is not so hard: Decaborane(14)


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sad.gif posted on 20-1-2024 at 08:01
Synthesis failed


Quote: Originally posted by dettoo456  
Anyone had experience with Silver 5-ATz complexes such as [(2Ag)5-ATz] NO3 or ClO4? The perchlorate is mentioned in engager’s tetrazole write up and a patent but there doesn’t seem to be much discussion on it. I tried to make the nitrate the other day according to klapotke’s procedure (https://pubmed.ncbi.nlm.nih.gov/19105192/) but it didn’t seem to yield anything that great. To start, 5-ATZ doesn’t dissolve that great in conc (anything higher than azeo %) Nitric Acid, and if you add too much water, the complexation time with AgNO3 can be ruined by just dumping out the Silver salt of 5-ATz. Too high conc of acid will form the 5-ATz nitrate salt instead which has low solubility as well and hinders complexation as well.

My product crashed out of the sol immediately on addition of AgNO3 to the 5-ATz/HNO3 mix as an off-white precipitate that started to yellow to a pastel yellow on air drying on a filter.

The product is supposed to detonate on flame contact and indirectly at 298C. For me, it does crackle faintly but I can’t seem to get it to dry. I would wager it’s like AgNTz in that it is a pain to detonate when wet but really goes when dry, but I can’t get this complex to dry to see anything amazing.

This salt could be a great alternative to LA, nitrotetrazoles, and such since it’s so seemingly easy to prepare, but I can’t get make it to match klapotke’s results. -My HNO3 and AgNO3 are pure and my 5-ATz is decently pure so idk.



This week I tried the nitrate salt, with similar results. I´ve used 65 % reagent grade nitric acid (I guess close to azeotropic is what they mean with "concentrated", otherwise they state "fuming" which is close to 100 %) and had also problems to dissolve the 5-ATZ. A warm water bath helped me to dissolve it.

Then I added the AgNO3 solution dropwise. Each drop changed immediately into a cheese-like white consistency after contact with the acidic 5-ATZ solution, but redissolved after some swirling. After several drops added, the solution remains turbid and it was no longer possible to redissolve it even with prolonged swirling.

After complete addition of the silver nitrate solution the whole reaction was dense white, like yoghurt. Here is a clear difference to the cited reference (Klapötke et al), they state that after addition of water the reaction mixture becomes turbid and some precipitate was formed.

I´ve also added some water, but it was impossible for me to see if the additional water produced additional precipitate.

After standing over-night I´ve filtered the precipitate, washed three times with distilled H20, then three times with IPA and let it dry over-night.

In contrast to your result, my product remains pure white with a flour-like consistency, but the behaviour against flame seems to be the same. No ddt, just a flash (not really impressive). See attached video.

So I would like to know what was wrong if you, microtek and I were unable to repeat the deceptive easy preparation.

And BTW my yield was much lower than cited (from 2,5 gram silver nitrate more than 4,2 gram was expected, but I got only 2,6 gram - something really went wrong).



Attachment: Disilver-5-aminotetrazole nitrate.mp4 (732kB)
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[*] posted on 20-1-2024 at 10:46


I’d attribute the yellow color I got from pure lazy experimental methods - I just had all of the starting materials lying around so I thought I’d prep the complex in <15min. I didn’t even measure yield. Besides that though, the product SHOULD detonate on flame contact, albeit weaker than AgNTz or Pb(N3)2. Mine was only able to detonate after drying fully (sitting out at room temp for a couple of days).

It had trouble combusting in contact with a fuse though, in contrast to the more standard primaries like AgNTz.

If you’re paranoid about temperature stability (or friction and shock at that), I’d recommend the complex for cap designs but besides that, standard AgNTz or DBX-1 seems to be, ironically, easier to handle.

I’ll try to report stability results in the future with samples though.
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[*] posted on 20-1-2024 at 13:44


Well, Klapötke mentioned a possible explanation:

However, it must be noticed that the crystalline state of the sample is of extreme importance when testing the sensitivity of energetic compounds, i.e., crystalline compounds tend to show higher sensitivities to impact and friction.

This could be an explanation for the weak response of my amorphous flour-like sample to flame, but not for immediate precipitation after dropwise addition of the silver nitrate to the acidic 5-ATZ solution.

The experimental parameters are well defined.

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[*] posted on 20-1-2024 at 22:09


Quote: Originally posted by Nemo_Tenetur  

This could be an explanation for the weak response of my amorphous flour-like sample to flame, but not for immediate precipitation after dropwise addition of the silver nitrate to the acidic 5-ATZ solution.

No. The crystalline state affects mechanical sensitivity, but has little effect on DDT.
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[*] posted on 6-3-2024 at 22:03


Quote: Originally posted by MineMan  

Those sensitivities are impressive. The copper version of NAP is 2J impact but 20N friction if I remember. I regard friction as more important. There are primaries that are immune to friction. This does look like a complex snyth tho. Wish the friction was less sensitive

Excuse me, what is NAP? Nickel aminotetrazole perchlorate?

upd
O, I find, Nickel aminoguanidine diperchlorate

[Edited on 7-3-2024 by Etanol]
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[*] posted on 2-4-2024 at 08:02


I wasn't sure where else to put this, so I am asking here.

I made some more NHN yesterday. Using 130ml of 95% (closer to 96%) ethanol, 43.5g of hydrazine sulfate, and 26.6g sodium hydroxide. The only difference is I was using bought nickel nitrate and not made. I dissolved 63g of nickel nitrate in 150ml of water with 0.005% dextrin by weight of the NN. The temperature did rise over 70C a few times which caused me concern.

I put in around 50ml of the solution, or a little less. But it was an excess. Everything appeared to run smoothly. My vacuum pump had issues so it was effectively gravity filtered. As I washed out the excess nickel nitrate with copious amounts of warm water and around 350ml of 95% ethanol.

The color is mostly OK. But there is that little tinge in it that bothers me. It is drying as of now, but I am wondering if it is something I should be concerned about.

I never saw any information on recrystalizing NHN. But I did hear that ammonia (I have 27% ammonia) works as a solvent. Would it dissolve it and simply be able to crash out the impurities? If they are impurities that is.

IMG_20240402_060513328.jpg - 2.8MB
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[*] posted on 2-4-2024 at 23:43


I don't know how labile the hydrazine ligands are, but I would expect at least some of them to be replaced with the rather similar ammonia ligands if you try treating the NHN as a simple salt. Ammonia is more volatile than hydrazine, so maybe you could evaporate it off to reform the hydrazine complex, but I don't think it likely.
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[*] posted on 3-4-2024 at 03:45


Well it probably wasn't something major since the NHN appears to be of good quality.

But there is one major problem: I was expecting at least 12g of yield based on all the previous attempts I made. But I only got 4! I am legit baffled as to what happened.

My estimates that is I did not freebase enough hydrazine from my hydrazine sulfate, and the heating went out of control for a bit. The other thing is that my nickel nitrate solution was too concentrated. I diluted what I had to resemble more of what people showed when they used it (it is still quite dark green).

I am going to try again with similar quantities but I will take more care with heating on my mantle to not allow it to rise above 63 or 65c. My new mantle is very powerful, but a little finicky.
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[*] posted on 5-4-2024 at 13:52


Was the filtrate almost colorless (a very weak blue) or turquoise to green? From my experience, concentrated nickel nitrate solution doesn´t hurt the yield, but I´ve always performed the synthesis with commercially hydrazine hydrate solution.

Commercially available nickel nitrate is almost always the hexahydate, because it is VERY hard to get the anhydrous salt. Did you respect this within your yield calculation?

And, by the way, the use of dextrin is pretty useless IMHO. I know the patent which claim a higher density, but I can´t confirm this. From my experience - dozens batches - the highest bulk density is obtained with concentrated solutions. I always use a few percent hydrazine excess to ensure complete consumption of the nickel and to avoid an incomplete complexation.

I´ve seen a paper with an NHN accident ("spontaneous explosion of a normally stable complex salt" by Herbert Ellern an Donald E. Olander ) where an incomplete complexation lead to an unstable product with self-deflagration even when moist!

Just for your information that even with such a "safe" primary shit can happen.
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[*] posted on 6-4-2024 at 18:10


Quote: Originally posted by Nemo_Tenetur  
Was the filtrate almost colorless (a very weak blue) or turquoise to green? From my experience, concentrated nickel nitrate solution doesn´t hurt the yield, but I´ve always performed the synthesis with commercially hydrazine hydrate solution.

Commercially available nickel nitrate is almost always the hexahydate, because it is VERY hard to get the anhydrous salt. Did you respect this within your yield calculation?

And, by the way, the use of dextrin is pretty useless IMHO. I know the patent which claim a higher density, but I can´t confirm this. From my experience - dozens batches - the highest bulk density is obtained with concentrated solutions. I always use a few percent hydrazine excess to ensure complete consumption of the nickel and to avoid an incomplete complexation.

I´ve seen a paper with an NHN accident ("spontaneous explosion of a normally stable complex salt" by Herbert Ellern an Donald E. Olander ) where an incomplete complexation lead to an unstable product with self-deflagration even when moist!

Just for your information that even with such a "safe" primary shit can happen.


I am aware that danger can happen. this is why I treat all energetics with the utmost respect.

I've bumped up another thread about this for further discussion. I am not happy with what is going on.
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[*] posted on 7-4-2024 at 01:50


Quote: Originally posted by Nemo_Tenetur  
I always use a few percent hydrazine excess to ensure complete consumption of the nickel and to avoid an incomplete complexation.

I´ve seen a paper with an NHN accident ("spontaneous explosion of a normally stable complex salt" by Herbert Ellern an Donald E. Olander ) where an incomplete complexation lead to an unstable product with self-deflagration even when moist!

Just for your information that even with such a "safe" primary shit can happen.

Mentioned paper (doi: 10.1021/ed032p24) says that in another, more serious accident hydrazine hydrate was used in 5% excess. And that hydrazine occluded in product's crystal, higher complexation, or contamination by combustible organics are possible causes of spontaneous explosion. Meaning that both excess and deficiency of hydrazine can be dangerous.
Conclusion: Hydrazine is generally unpleasant compound.

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[*] posted on 7-4-2024 at 02:35


When I reading last problems about hydrazine, respectively about NHN, maybe will better focusing on SA-DS. Yes, sensitivity is higher and is it full primary, but preparation is very easy and results are constant. I know, this mention is out of thread.....:cool:



Development of primarily - secondary substances CHP (2015) Lithex (2022) Brightelite (2023) Nitrocelite (2024)
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[*] posted on 7-4-2024 at 05:30


Quote: Originally posted by Laboratory of Liptakov  
When I reading last problems about hydrazine, respectively about NHN, maybe will better focusing on SA-DS. Yes, sensitivity is higher and is it full primary, but preparation is very easy and results are constant. I know, this mention is out of thread.....:cool:


I made successful NHN several times before. I think what happened wrong is that I didn't freebase it correctly. It was simply too cold to freebase (all reagents were stored in a fridge for days to cool). I was not aware that it wouldn't freebase or react if it is too cold.

All previous successful times I did it at room temperature but simply kept everything cooler in an ice bath.

Remember LL, this is the first time I ran into issues with NHN synthesis! :p
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[*] posted on 7-4-2024 at 06:13


I had only one failure with NHN. This batch was of very low bulk densitiy, difficult to dry and hard to ignite. The color was more like pale pink, precipitated in high dilution.

Then I switched back to concentrated solutions and everything was fine again. In general, I think it´s good primary. But you require several hundred milligram and some containment for reliable DDT. Such a quantity produce alot of nickel dust, this isn´t the healthiest thing.
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[*] posted on 7-4-2024 at 07:58


Quote: Originally posted by Nemo_Tenetur  
I had only one failure with NHN. This batch was of very low bulk densitiy, difficult to dry and hard to ignite. The color was more like pale pink, precipitated in high dilution.

Then I switched back to concentrated solutions and everything was fine again. In general, I think it´s good primary. But you require several hundred milligram and some containment for reliable DDT. Such a quantity produce alot of nickel dust, this isn´t the healthiest thing.


That is true. But with an ETN mixed in at a 1:1 ratio or with other mixtures it can be an extremely powerful initiating agent. NHN has been in use in commercial detonators for decades now. It isn't an unproven new thing.

I've made a lot of progress with using NHN detonators and I plan on continuing with them.

For LL. I wish to inform him that CHP and LL8 are on the table. :)
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[*] posted on 8-4-2024 at 04:34


Quote: Originally posted by EF2000  
(doi: 10.1021/ed032p24)

Electrostatic discharge?
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[*] posted on 13-4-2024 at 12:29


Quote: Originally posted by Nemo_Tenetur  
Quote: Originally posted by dettoo456  
Anyone had experience with Silver 5-ATz complexes such as [(2Ag)5-ATz] NO3 or ClO4? The perchlorate is mentioned in engager’s tetrazole write up and a patent but there doesn’t seem to be much discussion on it. I tried to make the nitrate the other day according to klapotke’s procedure (https://pubmed.ncbi.nlm.nih.gov/19105192/) but it didn’t seem to yield anything that great. To start, 5-ATZ doesn’t dissolve that great in conc (anything higher than azeo %) Nitric Acid, and if you add too much water, the complexation time with AgNO3 can be ruined by just dumping out the Silver salt of 5-ATz. Too high conc of acid will form the 5-ATz nitrate salt instead which has low solubility as well and hinders complexation as well.

My product crashed out of the sol immediately on addition of AgNO3 to the 5-ATz/HNO3 mix as an off-white precipitate that started to yellow to a pastel yellow on air drying on a filter.

The product is supposed to detonate on flame contact and indirectly at 298C. For me, it does crackle faintly but I can’t seem to get it to dry. I would wager it’s like AgNTz in that it is a pain to detonate when wet but really goes when dry, but I can’t get this complex to dry to see anything amazing.

This salt could be a great alternative to LA, nitrotetrazoles, and such since it’s so seemingly easy to prepare, but I can’t get make it to match klapotke’s results. -My HNO3 and AgNO3 are pure and my 5-ATz is decently pure so idk.



This week I tried the nitrate salt, with similar results. I´ve used 65 % reagent grade nitric acid (I guess close to azeotropic is what they mean with "concentrated", otherwise they state "fuming" which is close to 100 %) and had also problems to dissolve the 5-ATZ. A warm water bath helped me to dissolve it.

Then I added the AgNO3 solution dropwise. Each drop changed immediately into a cheese-like white consistency after contact with the acidic 5-ATZ solution, but redissolved after some swirling. After several drops added, the solution remains turbid and it was no longer possible to redissolve it even with prolonged swirling.

After complete addition of the silver nitrate solution the whole reaction was dense white, like yoghurt. Here is a clear difference to the cited reference (Klapötke et al), they state that after addition of water the reaction mixture becomes turbid and some precipitate was formed.

I´ve also added some water, but it was impossible for me to see if the additional water produced additional precipitate.

After standing over-night I´ve filtered the precipitate, washed three times with distilled H20, then three times with IPA and let it dry over-night.

In contrast to your result, my product remains pure white with a flour-like consistency, but the behaviour against flame seems to be the same. No ddt, just a flash (not really impressive). See attached video.

So I would like to know what was wrong if you, microtek and I were unable to repeat the deceptive easy preparation.

And BTW my yield was much lower than cited (from 2,5 gram silver nitrate more than 4,2 gram was expected, but I got only 2,6 gram - something really went wrong).

Try to change mixing method ATz and AgNO3:
add ATz to AgNO3, not AgNO3 to ATz.
Try don't add HNO3.
Add 5mmol hot ATZ solution into 10mmol solution of AgNO3, cold it.

[Edited on 13-4-2024 by Etanol]
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[*] posted on 30-4-2024 at 18:46


Are exists base complexes of 5-aminotetrazole and Ni or Cu or Co and NO3 or ClO4 anions?

[Ni(ATZ)n](ClO4)2
[Ni(ATZ)n](NO3)2
[Co(ATZ)n](ClO4)2
[Co(ATZ)n](NO3)2
[Cu(ATZ)m](ClO4)2
[Cu(ATZ)m](NO3)2

m=? n=?

Complexes of Co(III)?
[Co(ATZ)n](ClO4)3
[Co(ATZ)n](NO3)3

upd
from wiki: "The N-4 is basic as indicated by its binding to metal halides, such as the coordination complex [CoCl2(aminotetrazole)4"
Then only [Cu(ATZ)4](ClO4)2 has acceptable oxygen ballance:

[Cu(CH3N5)4](ClO4)2=>CuCl2+10N2+6H2O+2CO+2C

[Edited on 1-5-2024 by Etanol]
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[*] posted on 1-5-2024 at 12:33


As I commented in another thread, there definitely is a Ni complex with aminoTRIazole, so I find it very likely that it forms one with 5-ATz as well. I do have some 5-ATz and some Ni(NO3)2 so I could test if something precipitates either on mixing or when adding a perchlorate (or chlorate) solution.
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[*] posted on 1-5-2024 at 14:37


Quote: Originally posted by Microtek  
As I commented in another thread, there definitely is a Ni complex with aminoTRIazole, so I find it very likely that it forms one with 5-ATz as well. I do have some 5-ATz and some Ni(NO3)2 so I could test if something precipitates either on mixing or when adding a perchlorate (or chlorate) solution.


Thanks. But I do not think that Ni complex will be effective. It contains very little oxygen:
[Ni(CH3N5)6](ClO4)2=>NiCl2+15N2+8H2O+H2+6C

According to the article
"SPIN TRANSITION IN HETEROANION COMPLEXES IN THE Fe2+-4-AMINO-1,2,4-TRIAZOLE–NO3−SO4−SYSTEM" (10.1134/s0022476620090048) from sci-hub

,there is a complex Fe(ATrz)3(NO3)2⋅nH2O (ATrz = 4-amino-1,2,4-triazole),
which means that the 4-amino-1,2,4-triazole is bivalent as ligand.
Then ATrz complexes are more effective, especially copper:

[Ni(C2H4N4)3](ClO4)2=>NiCl2+6N2+6H2O+2CO+4C

[Cu(C2H4N4)2](ClO4)2=>CuCl2+4N2+4H2O+4CO or 2CO2+2C at high density
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[*] posted on 2-5-2024 at 22:54


I tried copper, cobalt, zink, iron(III), nickel, aluminum and magnesium as the central ion in 4-amino-1,2,4-triazole complexes with perchlorate anions some weeks ago. Al and Mg does not seem to give anything. I didn't really expect them to, but it rarely hurts to try.
The copper complex seems fairly soluble, but does give an energetic precipitate that explodes on heating wrapped in Al foil, though nothing spectacular.
The cobalt complex seems to be very insoluble, and gave a high yield of very fine cream precipitate. I did a second run with slow addition of the cobalt ions to a hot, stirred solution of ATrz and NaClO4, and cooled slowly with continued stirring, and this gave a slightly more coarse powder that could more easily be filtered. I ran it through the plate dent test after discovering that I could not set it off by mechanical stimulus, either by manual hammer blows on my anvil, or by the oblique abrasive pendulum impact test at 5.5 J (the highest setting of my apparatus). In the plate dent test, it performed disappointingly - somewhere in the vicinity of TNT, possibly due to a surprisingly low density of 1.58 g/cc. The nickel complex seemed most promising as it is non-hygroscopic, insensitive and undergoes DDT in 20 mg amounts when lightly confined. I haven't tested the actual initiating ability yet, nor the power in the plate dent test.
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[*] posted on 25-5-2024 at 09:35


Has anyone done any work on metal-ligand complexes between a metal perchlorate and melamine?

Melamine could conceivably act as a bridging ligand between two (or maybe even three) metal centers and increase the density of the product compared to aminoguanidine perchlorate complexes, while not being much more challenging to prepare.

[Edited on 26-5-2024 by Yorty2040]
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