Sciencemadness Discussion Board
Not logged in [Login - Register]
Go To Bottom

Printable Version  
 Pages:  1  ..  29    31
Author: Subject: DDNP & related compounds: The über thread!
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 14-2-2019 at 12:00


Quote: Originally posted by nitro-genes  
Not 100% sure, though I'm not 100% sure the earth isn't flat either :P. The melting point of styphnamic is described as 190 C by Benedikt and Hubl, though as 219 C by the chinese article from 1933 (abstract link attached), which is alot more modern. The abstract (see link below) also mentions boiling in water produces dinitropyrogallol as proof of structure, something Benedikt and Hubl didn't provide. The melting point of the styphnamic from the copper/ascorbic reduction seems around 220 C as well, dilute acid hydrolysis produces quantitative yield of a yellow compound melting at around 210 (commercial mp. 4,6-dinitropyrogallol = 209-211C), the left over filtrate when all of the presumed dinitropyrogallol is removed produces an ammonia smell with NaOH, so likely an amino hydrolysed off. It is very unlikely that p-amino phenol derived diazo derivatives somehow form 2-amino resorcinol derivatives, and the 4-DDNR product from these seems much less soluble as the presumed 2-DDNR, as it precipitates from very dilute acid solutions (Klapotke), while the presumed 2-DDNR has an incredibly high solubility in water. Benedict and Hubl also described the diazo derivative from their reduction product to be only precipitated from concentrate solutions and concentrated acids, which also fits the observations of the compound I obtained. Combined with the likely preference for ortho hydroxy-nitro reduction described by Porter and the presumed quinone-nitronate structure mediated reduction, which fits the huge preference for the 2-nitro, this is the absolute most likely scenario, so without any constructive arguments I'll stick to the 2-DDNR. The only remote possibilities seems that the stannous chloride reduction of styphnic produces somehow the 4-amino reduction product and that the 2-amino of styphnamic may rearrange to take the position of one of the other hydroxy groups, AFAIK, this has never been described though for similar compounds.

The astract can be found here: http://delibra.bg.polsl.pl/Content/16820/P-321_1933_Oct.pdf

[Edited on 14-2-2019 by nitro-genes]


That is 104 pages of abstracts so could you be specific or extract the page of interest. Thanks.

What I was thinking would be Styphnamic Acid on parallel to Picramic acid is what would generally result from a sodium sulfide reduction or other ordinary reduction .....like an ascorbate reduction :D on the Styphnic Acid Salt of a base, like sodium or magnesium styphnate and this would be a parallel to the ordinary reduction schemes for an alkaline base salt of Picric Acid.

So I had supposed the styphnamic acid analogue of picramic acid would be 4-amino (I think when I was looking at this 2 years ago) But then there is also possible the iso-styphnamic acid by working from a different precursor having the amino to be later diazotized in a different ring position, analogous to iso-picramic acid.

Now which one of the isomers you get could be pH dependent and could be reaction sequence dependent which could be co-dependent and also dependent on the ring position of the amino.

Speaking of what is and isn't flat on Valentine's Day

[inappropriate image removed j_sum1]


[Edited on 2/14/2019 by Rosco Bodine]

[Edited on 24-2-2019 by j_sum1]
View user's profile View All Posts By User
nitro-genes
International Hazard
*****




Posts: 968
Registered: 5-4-2005
Member Is Offline

Mood: No Mood

[*] posted on 14-2-2019 at 12:12


Uploaded the relevant abstract, you were clearly busy... :P



[Edited on 14-2-2019 by nitro-genes]
View user's profile View All Posts By User
Laboratory of Liptakov
International Hazard
*****




Posts: 692
Registered: 2-9-2014
Member Is Offline

Mood: cool.gif

[*] posted on 14-2-2019 at 13:23


Finally, good chemistry.......:cool:



Safety explosive Alfred Nobel 1867. Safety ecologic detonator Dr. Liptakov 2015.
View user's profile View All Posts By User
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 14-2-2019 at 14:21


Here is that extract again

Styphnamic -Sah and Hsia, J Chinese chem soc, 1933, 1, p92-95.bmp - 336kB

Okay I see where you are getting the 2-amino for styphnamic acid and then that would provide a 2-diazo for the DDNR, with decomposition of the diazo to a 2-hydroxyl.....which would provide the 1,2,3 trihydroxyl for pyrogallol.

This clears up the matter of the other two possible DDNR isomers derived from nitration product of paracetamol acetate, later diazotized by two different methods, which would both have the 4-diazo structure, with one isomer forming a para 4-1 diazo oxide while the alternative isomer of Klapotke would form an ortho 4-3 diazo oxide preceded by hydrolysis decomposition of the nitro at 3 under the conditions for diazotization used by Klapotke. Applying the different diazotization method of Meldola which does not hydrolyze the 3-nitro results in the para 4-1 diazo oxide.

How this relates back to the compound of Benedikt and Hubl is something I would need to review to see which isomer is likely for that.

It appears there are at least 3 isomers possible by different reaction schemes, similarly as was the case of DDNP.

Quote: Originally posted by nitro-genes  
Uploaded the relevant abstract, you were clearly busy... :P

[Edited on 14-2-2019 by nitro-genes]


Lady was hitch hiking in the rain and just by coincidence the brakes suddenly locked up like a random mechanical failure ....these things just happen sometimes....it's an anomaly for sure. :D

[Edited on 2/14/2019 by Rosco Bodine]
View user's profile View All Posts By User
nitro-genes
International Hazard
*****




Posts: 968
Registered: 5-4-2005
Member Is Offline

Mood: No Mood

[*] posted on 15-2-2019 at 18:11


Judging by the high solubility of the potassium salt they obtained (not much evidence though), it seems Benedikt and Hubl may have obtained something different than 2-diazo 4,6-dinitroresorcinol from their rather forcing diazotization procedure using an excess of nitrite in boiling sulfuric. My guess would be that they obtained a diazo dinitrophloroglucinate instead which would match the solubility of the potassium salt obtained for the product of the nitration of styphnamic. The Patents from Hagel et al. (US4246052) describes reduction and diazotization of styphnamic, but describe the product as 4-diazo 2,6-dinitroresorcinol, and also the patent from Kohler (US6946042B2) only mentions the 4-diazo derivative due to their ease of preparation, even though I can't see the logic of why they would talk about the 4-diazo derivative when the 2-diazo derivative is much more likely to be formed from the reduction/diazotization of styphnamic acid instead, is this a nomenclature issue or is styphnic really that different in reductions? Am I just dumb, or are these patent really wrong? What is strange is that the hydrochloric solubility of the reduction product described in US4246052 seems much higher than that of the product I obtained, and they do not mention the almost insoluble hydrochloric acid salt. If this is really all true, the salts of 2-diazo 4,6-dinitroresorcinol may have never been described, nor patented. :o Though, again... is the reduction of styphnic using stannous chloride really expected to yield 4-amino 2,6-dinitro resorcinol, I just can't believe it...

Starting to feel like Alice tumbling down the rabit hole....damn this is interesting! :o:D

[Edited on 16-2-2019 by nitro-genes]
View user's profile View All Posts By User
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 15-2-2019 at 19:17


After reviewing I see it was recognized back four years ago July 2015, there was uncertainty about the structure of DDNR, and Von Herz thought it was 2-diazo and diagrammed it in his patent as 2-diazo. But it was recognized that the 4-diazo is also possible.

Here linked is the page 20 from July 2015
http://www.sciencemadness.org/talk/viewthread.php?tid=439&am...

You have pretty conclusively shown the 2-diazo is correct for the DDNR normal isomer as would be the analogue of DDNP.

However, just as there are different isomers possible for DDNP such as the p-DDNP drivative of isopicramic acid, likewise there exists a p-diazo isomer of DDNR. Meldola and Klapotke have identified 2 different 4-diazo isomers obtainable from the nitrated paracetamol acetate derivative, either one obtainable depending on the reaction conditions chosen for the diazotization.

Klapotke identified what would be an ortho diazo-oxy bridge 4-3 anhydride isomer of DDNR.

However by applying the different reaction conditions for diazotization described by Meldola, the nitro at 3 can remain intact, and the p-diazo-oxy 4-1 will result. This p-diazo-oxy isomer of DDNR would be analogous to p-DDNP in regards to having the diazo-oxy bridge completely across the ring. Meldola described the p-diazo-oxy 4-1 DDNR as more hydrolytically stable and identified an orange crystalline sodium salt.

Which one of these 3 isomers corresponds to the Benedikt and Hubl DDNR is unknown. It seems most likely to be the normal o-DDNR having the diazo-oxy 2-1 positions. All of this is very interesting because the 3 different isomers do have slightly different properties and all are highly energetic. It would make sense to be able to identify which of the 3 isomers has the properties that would make it the best candidate for use as an initiator. The most likely candidate would be the p-diazo-oxy 4-1 isomer of DDNR. Acetic anhydride is the reagent needed for the synthetic pathway to p-DDNR via paracetamol acetate.

It could be there is a specific salt or double salt of the more common 2-diazo normal isomer DDNR that would be a practical initiator, or that a specific crystal size and form will have properties that allow practical use. Overly broad generalizations are easily made to reject specific energetic materials because of the misbehavior of a sample that may have an undesirable crystal form, while a different crystalline form of the same material may be entirely practical.

[Edited on 2/16/2019 by Rosco Bodine]
View user's profile View All Posts By User
nitro-genes
International Hazard
*****




Posts: 968
Registered: 5-4-2005
Member Is Offline

Mood: No Mood

[*] posted on 16-2-2019 at 12:44


Yes, been wondering the same. Similarly to lead azide, the potassium salt of 2-DDNR is described by Kohler to be notorious for its tendency to detonate when crystallizing from solution. From >5% concentrations of aqueous solutions of the diazoquinone, the potassium salt tends to instantly crystallize from solution upon introduction of a potassium salt solution, forming a felty network of very fine and long needles (Photo 1) that can turn the whole liquid into a solid gel-like consistency. It is likely that the described auto-detonation tendency during crystallization originates in part from this behavior, as is also the case with lead azide.

The needle crystal morphology can be completely eliminated when a 2% aqueous solution of 2-diazo 4,6-dinitroresorcinol is dripped slowly into a large excess of an ice-cold potassium acetate/acetic buffer at pH 6, that is completely saturated with KCl or KNO3. As such it forms small, compact and cubic crystals (Photo 2) that may exhibit better handling properties and may be less likely to self-detonate during its synthesis.

Then again, I think Kohler and Hagel were were no idiots and these patents originate from a time where the danger of the needle crystal morphology of lead azide was already known and described IIRC. Also pretty sure they read the article of Benedikt and Hubl... so...Would still be interesting to see the difference in friction and impact sensitivity between the two preparation methods of the K-salt described above though. :)

Potassium salt 2-DDNR different crystal morphologies - Copy.jpg - 363kB

Regarding the preference for the 4-DDNR as energetic material, just a random guess (I know next to nothing about theoretical structural chemistry) would be that the 4-DDNR maybe behaves more as a zwitter ion due to the para position and more acidic 1-hydroxy group, while for the 2-DDNR the charge is more delocalized also over the nitrogroups, making that 2-DDNR behaves more readily as an oxidizer? If so, would this still apply to the salts?

[Edited on 17-2-2019 by nitro-genes]
View user's profile View All Posts By User
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 17-2-2019 at 02:32


The benzene ring is a resonant structure always vibrating and the diazo-oxide across the ring like a bowstring dampens the ring vibrations and stiffens the molecule so that effective strength of bonds for the hydrogen substituted groups is also increased and the entire molecule is more stable, less sensitive to decomposition.
When that bowstring breaks, the entire molecule snaps back the opposite direction and flies apart like a suddenly unbalanced gyroscope.

For a possible double salt it would be good to look at Barium Styphnate / Barium DDNR. Mixed solutions of very soluble, probably the Magnesium salts of Styphnic Acid and DDNR would be added to a stirred solution of Barium Nitrate.

For other possible double salts, instead of Barium Nitrate other metal nitrates could be used, or a mixture of 2 different nitrates could be used for possible compound salts, such as Potassium Nitrate and Nickel Nitrate. Nitric Acid could be used to adjust the pH of the solution of Nitrate/s and different temperatures for the reaction could be observed to determine what is useful.

[Edited on 2/17/2019 by Rosco Bodine]
View user's profile View All Posts By User
Laboratory of Liptakov
International Hazard
*****




Posts: 692
Registered: 2-9-2014
Member Is Offline

Mood: cool.gif

[*] posted on 19-2-2019 at 12:52


When I go through this whole thread about DDNP, it seems that DDNP is worse in all parameters than CHP. (TeACP-hexamine clathrate) In production and explosive parameters. And even in next parameters. Or did I overlook something? Thank you for explaining from anyone.....:cool:....LL



Safety explosive Alfred Nobel 1867. Safety ecologic detonator Dr. Liptakov 2015.
View user's profile View All Posts By User
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 20-2-2019 at 14:37


Yeah you overlooked a design criteria for "green" initiators that is they do not contain perchlorate as would cause corrosive residues if used in firearms.
View user's profile View All Posts By User
Laboratory of Liptakov
International Hazard
*****




Posts: 692
Registered: 2-9-2014
Member Is Offline

Mood: cool.gif

[*] posted on 21-2-2019 at 00:44


Well, for firearms use is DDNP sure better. Thanks for explanation.....:cool:...LL



Safety explosive Alfred Nobel 1867. Safety ecologic detonator Dr. Liptakov 2015.
View user's profile View All Posts By User
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 21-2-2019 at 08:56


Quote: Originally posted by nitro-genes  
Yes, been wondering the same. Similarly to lead azide, the potassium salt of 2-DDNR is described by Kohler to be notorious for its tendency to detonate when crystallizing from solution. From >5% concentrations of aqueous solutions of the diazoquinone, the potassium salt tends to instantly crystallize from solution upon introduction of a potassium salt solution, forming a felty network of very fine and long needles (Photo 1) that can turn the whole liquid into a solid gel-like consistency. It is likely that the described auto-detonation tendency during crystallization originates in part from this behavior, as is also the case with lead azide.


A "diazoquinone" huh? How about a resorcinoquinone? :D

A massive precipitation of low density fibrous crystals is something that can also occur for picrates and styphnates as an intermediate product that requires further processing with very specific conditions of dilution and temperature and pH and stirring, to produce a more desirable and compact crystalline form that is a drastic difference required to provide a useful material. Under certain specific conditions the initial low density precipitate can form and can then be transformed to the high density material simply by manipulation of the conditions that redissolve the initial precipitate which may be a higher hydrate, and then recrystallize as a lower hydrate or anhydrous form at a higher temperature and different, usually lower pH. Sometimes the formation of a double salt will accomplish the dehydration if the double salt forms preferentially to a single salt hydrate.
Quote:

The needle crystal morphology can be completely eliminated when a 2% aqueous solution of 2-diazo 4,6-dinitroresorcinol is dripped slowly into a large excess of an ice-cold potassium acetate/acetic buffer at pH 6, that is completely saturated with KCl or KNO3. As such it forms small, compact and cubic crystals (Photo 2) that may exhibit better handling properties and may be less likely to self-detonate during its synthesis.
[Edited on 17-2-2019 by nitro-genes]

And it may be possible also to regulate the mesh size of the crystals and their hydration by changing the temperature and pH and rate of addition and speed of stirring along with the concentration of the solutions being reacted. Process details can be worked out that produce a constant condition reaction zone for the solubles that exist in the supernatant solution in which the crystals are suspended to an extent governed by their density and by the strength of the current in the turbulent liquid. When crystals have grown to a specific size, the crystals settle as heavy sediment in the stirred liquid. These aspects of "process chemistry" have great bearing on the precise physical properties of a material like a sensitive initiator.


View user's profile View All Posts By User
Tsjerk
International Hazard
*****




Posts: 1376
Registered: 20-4-2005
Location: Netherlands
Member Is Offline

Mood: Mood

[*] posted on 21-2-2019 at 09:27


Quote: Originally posted by Rosco Bodine  


Speaking of what is and isn't flat on Valentine's Day

[inappropriate image removed j_sum1]

[Edited on 2/14/2019 by Rosco Bodine]


Keep your eyes on the road man, keep your eyes on the road.

Offering to anyone who can communicate a solid plan for the use of Na2S (to my judgement) in order to make DDNP; I'm willing to ship it to you when you pay me for the shipping costs. I have quite a lot of it and I don't see any probable need for it in the future.

I don't remember if I have this stuff or the anhydrous stuff which is not listed anymore, but it is clean Na2S.

Edit: I think I have the anhydrous, the only condition is that you report your findings here. When I send you the goods I will of course let you know whether or not it is the nona or the anhydrous.

Edit2: I will note your name here when I send you the goods.


[Edited on 21-2-2019 by Tsjerk]

[Edited on 23-2-2019 by j_sum1]
View user's profile View All Posts By User
nitro-genes
International Hazard
*****




Posts: 968
Registered: 5-4-2005
Member Is Offline

Mood: No Mood

[*] posted on 22-2-2019 at 11:57


@ Rosco....Yeah, I get the feeling there may be some hydrates involved here and there after all. I wont be continuing with the salt of 2-DDNR though, think it is time to quit with eyes, ears and fingers still working and attached.

"A "diazoquinone" huh? How about a resorcinoquinone? :D" I don't get it, What do you mean by that?

Recrystallized some of the last completely dry 2-DDNR from acetone solubility in boiling acetone is about 1 g 2-DDNR /33.5 ml acetone....seems to work fine.




[Edited on 22-2-2019 by nitro-genes]

Attachment: 2-diazo 4,6-dinitroresorcinol recrystallized acetone.avi (769kB)
This file has been downloaded 36 times

2-diazo 4,6-dinitroresorcinol recrystallized acetone-2.jpg - 217kB
View user's profile View All Posts By User
nitro-genes
International Hazard
*****




Posts: 968
Registered: 5-4-2005
Member Is Offline

Mood: No Mood

[*] posted on 23-2-2019 at 06:41


Curiosity won again... Ok, one final experiment with the potassium salt! :D

The brown compact crystals of the potassium salt of 2-diazo 4,6-dinitroresorcinol as obtained from 2% aqueous solutions of the 2-DDNR (as in my writeup in prebub) present somewhat of a mystery it seems. I performed the exact same precipitation reaction again, the only difference only being that instead of the crude 2-DDNR, the acetone recyrstallized product was used. The KNO3 saturated potassium acetate/acetic buffer was exactly the same, as I made a large batch to make some comparisons and had quite some left. From a 2% aqueous solution of the acetone recrystallized 2-DDNR, there was still a lot of the the fibrous needle morphology material present. Only when the 2-DDNR solution was diluted further to about a 0.2% aqueous solution, the potassium salt precipitated as the small more compact crystals, only the colour was not a brownish, though a light yellow. Even from the 0.2% solution, some sporadic needles were present when looked under the binoc. With very high stirring rates (probably very dangerous) and very slow addition, the compact crystals can be also formed from a 2% aqueous solution of the pure 2-DDNR.

So:

It seems very unlikely the brown material is a hydrate, as Benedikt an Hubl suggest. To see if this is a double salt with some impurity instead (maybe dinitropyrogallol or some quinone/product derived from it?) one would have to do some large scale yield measurements on the crude 2-DDNR or qualitative tests on the brown material, so out of my reach. I must say, I don't think there is enough of any impurity present to form a double salt or explain the difference in crystal morphology by the lower true concentration of 2-DDNR in the crude product. The most likely explanation seems that some impurity is present in the crude 2-DDNR isolated directly from the diazotization that acts as a powerful crystal modifier and allows the compact crystal shape for the potassium salt to form from aqueous solutions of the 2-DDNR at a >10 fold higher concentration and minimal stirring as compared to the (presumably) more pure compound from acetone.
I've been wondering if some of these crystal modifiers act purely as by retarding the onset of first crystallization. Maybe dextrin would be effective for the pure compound...

[Edited on 23-2-2019 by nitro-genes]
View user's profile View All Posts By User
Laboratory of Liptakov
International Hazard
*****




Posts: 692
Registered: 2-9-2014
Member Is Offline

Mood: cool.gif

[*] posted on 23-2-2019 at 08:59


In this thread, I feel like a student who listens to the debate of several university professors of chemistry.....:D...LL



Safety explosive Alfred Nobel 1867. Safety ecologic detonator Dr. Liptakov 2015.
View user's profile View All Posts By User
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 23-2-2019 at 21:40


Quote: Originally posted by nitro-genes  
@ Rosco....Yeah, I get the feeling there may be some hydrates involved here and there after all. I wont be continuing with the salt of 2-DDNR though, think it is time to quit with eyes, ears and fingers still working and attached.


Silver fulminate can be a sensitive beast too but there have been procedures worked out for risk management regarding that material.

Quote:

"A "diazoquinone" huh? How about a resorcinoquinone? :D" I don't get it, What do you mean by that?


Standard nomenclature generally names a quinone with the prefix for the parent aromatic, like anthraquinone for anthracine, benzoquinone for benzene, therefore resorcinoquinone for resorcinol. See?

Quote:

Recrystallized some of the last completely dry 2-DDNR from acetone solubility in boiling acetone is about 1 g 2-DDNR /33.5 ml acetone....seems to work fine.
[Edited on 22-2-2019 by nitro-genes]


It is unknown what the copper salt of DDNR might have as properties, but if it is low solubility it could form as less sensitive colloidal size particles. Maybe prepare a solution of a soluble copper salt and run into it a soluble salt of DDNR and see what you get as a product.
View user's profile View All Posts By User
nitro-genes
International Hazard
*****




Posts: 968
Registered: 5-4-2005
Member Is Offline

Mood: No Mood

[*] posted on 28-2-2019 at 06:59


Final report on styphnamic and its diazoderivative...there, I'm all done! :)
View user's profile View All Posts By User
nitro-genes
International Hazard
*****




Posts: 968
Registered: 5-4-2005
Member Is Offline

Mood: No Mood

[*] posted on 28-2-2019 at 07:06


There, I'm all done! :)


Attachment: Synthesis and some properties of 2-amino 4,6-dinitroresorcinol and 2-diazo 4,6-dinitroresorcinol.pdf (4.1MB)
This file has been downloaded 31 times

[Edited on 28-2-2019 by nitro-genes]
View user's profile View All Posts By User
Rosco Bodine
International Hazard
*****




Posts: 6300
Registered: 29-9-2004
Member Is Offline

Mood: analytical

[*] posted on 28-2-2019 at 12:41


Done huh? Hope springs eternal :D You aren't getting off that easy. :P

Page numbering ? Anyway on what would be numbered as page 5 if you beat me into submission proofreading and editing ;) just above the pictures you wrote:

"Either 2-diazo 4,6-dinitroresorcinol itself or its salts have been tested for use in detonators and priming compositions, though were claimed to be incompatible with certain base charges [20,21]."

Who claimed? Federoff ???? Ha! Federoff even fell prey to the classic nitrite-nitrate alternate universe error ! :D Take the Federoff
summary blurb with a HUGE grain of NaCl !! Caveat emptor

The Federoff article is IIRC incorrect and references the Von Herz British patent along with a Chemical Abstract summary I don't recall ever having seen......So this is possibly not correct but is another Federoff typo. The structure of DDNR is also incorrectly identified by Federoff. These compounds were generally called
"quinone diazides" (incorrect) or "diazo-anhydrides" after the cyclic nature was identified for the diazo-oxy linkage displacing a phenolic hydrogen.

In my understanding what I would call this general class of compounds is:

diazo-nitrophenol-anhydrides or probably better
nitrophenol-diazo-anhydrides

Anyway it seems clearly an editing oversight in Federoff referencing a patent and "claims" that do not reconcile with what Federoff shows as "unstable" should read instead as "usable" or "useful" as *is* what the patent claims clearly state along with the measured weights of initiator found "useful" with several commonly used base charges.

Obviously it would be silly for a reputable chemist Von Herz to patent and make "claims" to publish at great expense the discovery of useless and unstable compounds in order to attest to their lack of value. :P More likely Federoff transcribers and editors simply screwed the pooch and left the pooch screwed for posterity.

Who was Von Herz anyway ??? Obscure chemist hardly ...IIRC
Von Herz invented cyclonite or RDX ....but somebody should probably check me on that since I am getting old and confused, probably the senility creeping up on me ;) IIRC it was also Von Herz first filed for patent on the use of DDNP as an initiator.

A reference needed is the Chemical Abstracts (1924) Volume 18, page 1574 which may reference a journal article by Von Herz that a general search may find also, unless the abstract simply announces the British patent which is very likely.

Is there anything in the patent that is specific to instability or other issue related to "certain base charges"?

Federoff DDNR.bmp - 300kB

Here is an interesting compound where hexamethylene tetramine is shown to bridge complex 2 copper compounds, and such a scheme might work for copper DDNR similarly as it does for copper azide and may be useful as a desensitizer integrated on a molecular level. Other metal salts might also be susceptible.

For the complex if it would form with copper DDNR, there would be 4 of the mono-acid DDNR molecules in a compound having 2 copper atoms bridged by hexamethylene tetramine. If the hypothetical compound forms, it may be possible to use the benign ammonium DDNR as a precursor. Whether the speculated compound will form at all or whether any troublesome hydrate may be an issue is completely unknown, since the hypothetical compound is unreported and may be novel.

Glycine should similarly bridge complex 2 copper molecules, and may work better for the same purpose.

hexamethylenetetramine complexed cupric azide.bmp - 221kB

Edmund von Herz (from Vienna Austria) also invented Lead Styphnate primers

von Herz.bmp - 518kB

[Edited on 3/1/2019 by Rosco Bodine]
View user's profile View All Posts By User
Laboratory of Liptakov
International Hazard
*****




Posts: 692
Registered: 2-9-2014
Member Is Offline

Mood: cool.gif

[*] posted on 13-3-2019 at 13:34


Hexamethylenetetramine (hexamine) and CuO and NH3 gas, I consider for the best substances for synthesis most powerful energy salts. After adding some suitable salt, in suitable solvent, always arises some, what has energetic properties. Is it an Holy triad....:cool:...LL



Safety explosive Alfred Nobel 1867. Safety ecologic detonator Dr. Liptakov 2015.
View user's profile View All Posts By User
MineMan
National Hazard
****




Posts: 341
Registered: 29-3-2015
Member Is Offline

Mood: No Mood

[*] posted on 14-3-2019 at 18:06


Tell us more LL. Are these dissolved in ammonia then more gas is bubbles through.

What kind of EM, primary, secondary?
View user's profile View All Posts By User
 Pages:  1  ..  29    31

  Go To Top