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Axt
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[*] posted on 9-8-2005 at 02:54
Ethylenedinitramine


Ethylenedinitramine (EDNA) is a practical and powerful military explosive. Problem is, the routes to EDNA, as published always use either exotic chems or very high or very low pressures to form the precursor - ethyleneurea.

I found the following article that seems to open itself up to OTC synthesis. In this case made by the condensation of urea (fertiliser) with ethylene glycol (antifreeze) at 1atm, though the distillation/extraction of ethyleneurea as described requires very low pressures and high heat.

http://www.sciencemadness.org/scipics/axt/ethyleneurea-from-...

I have attempted this, with mixed results. Firstly this reaction scheme was assumed:



Thus, if the intermediate "resin" as described in the article was assumed to be polyethyleneurea it should be possible to directly nitrate it, then cleave it though hydrolysis to ethylenedinitramine, thus removing the need to isolate the monomer though high temps & low pressures.

In the following urea, was as fertiliser and ethylene glycol was as 95% antifreeze.


Experimental 1:

3mol urea was refluxed with 1mol ethylene glycol in this setup, the wine bottle was filled with hot water to condense the reaction products, but be hot enough to prevent the formation of ammonium carbonate (decomp. ~58°C). The hotplate on "high" initially stabalised at ~140°C which gradually increased throughout the reaction to 210°C where gassing nearly stopped and the product foamed up. This took about 3.5 hours and weight was reduced to 96% of theory of the scheme above. Much ammonia was released and some ammonium carbonate did form on the "condensor" which had to be removed throughout the course of the reaction.

The product set to a brittle solid that was easily powdered in a mortar & pestle, making the assumption that this could be polyethyleneurea, 20g was nitrated in KNO3/H2SO4 @ 5°C for two hours, when dunked into water a large quantity of precipitate formed, and was filtered. Since EDNA is decomposed by dilute, boiling H2SO4 the recrystalisation was attempted in 5% sodium acetate formed by neutralising white vinegar with NaOH. This should buffer the solution and prevent decomposition by H2SO4 which is converted to sodium sulphate. The product dissolved easily in boiling solution but on cooling no product was formed.

A couple possibilities for the failure: The acid solution still decomposed the EDNA, or more likely it wasn't EDNA but a primary nitramide which was hydrolised in boiling water to nitramine, with subsequent decomposition.


Experimental 2:

4mol urea was heated with 1mol ethylene glycol without reflux for 6 hours @ 140-180°C. This was then placed into a toaster oven @ a setting of 280°C for two hours, during this time a lot of white smoke was released and a condensate formed on the glass of the oven which showed no reaction to HCl (thus not (NH4)2CO3), but there wasn't enough to do other tests on it. If this white substance was indeed ethyleneurea it shows that it will volitalise at ~280°C and the low pressures in the article are only needed to keep it gasseous or liquid for long enough to make it to a recieving flask.

Sooo, thus far failure, but its an interesting route to an interesting explosive and being a primary nitramine is capable of undergoing further interesting reactions, futher investigation is in order. Since I as yet have no way of achieving the temperatures needed while effectively condensing any product formed I'm thinking of replacing the door of a toaster oven with a steel plate with a hole in it, to allow the "wine bottle condensor" to protrude from it, so the ethyleneurea can condense onto the bottom. Alternatively a microwave could also work and the turntable could be used to stir the solution :). The hard brittle resin from experimental 1 melts and smokes (stinky) within 3 min in my kitchen microwave on "high" so its definately acted on.
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[*] posted on 22-8-2005 at 20:52


I replaced the door of a toaster oven with Al plate, cut a hole for the "condensor" to protrude from but small enough so that the lip of the beaker would catch on it. After heating 4mol urea with 1mol ethylene glycol for 6 hours @ 140->180°C the brittle resin was placed into the oven for a number of hours @ 280°C. When let cool there was only a single drop of the suspected ethyleneurea solidified on the bottom of the bottle. Obviously condensor too hot thus condensing then dripping back off, I was hoping the water filled bottle would regulate the temp to keep it under the melting point of ethyleneurea. I guess you could substitute the water for a lower boiling point liquid (CH2Cl2 etc.) and attach a length of tube to the neck of the bottle to reflux it, but that goes against the simplicity that was the original aim.



I did the same, but raised the bottom of the bottle out of the oven but only recieved a quantity of ammonium carbonate, by this time the resin was black an had a very carbony smell.

Nitration of the refluxed resin after cooling & powdering, which should contain ethyleneurea only resulted in a sticky resinous mass, obviously a lot of other crap present other then ethyleneurea.

Right now I'm prepared to give up on it and start with ethylenediamine which should go to near quantitive yeild without all the resinous intermediates.

All relevant info I possess:

http://scipic.ft100.net/images/ethyleneurea-from-ethylenedia...
http://scipic.ft100.net/images/nitration-of-ethylenediamine....
http://scipic.ft100.net/images/ethylenedinitramine-crystals....
http://scipic.ft100.net/images/EDNA-patents.pdf
http://scipic.ft100.net/images/EDNA-equation-of-state.pdf
http://scipic.ft100.net/images/decomposition-of-haleite.pdf
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[*] posted on 4-10-2005 at 09:48
EDNA from ethylenediamine


Following the article above, a 98% yield of ethyleneurea can be done at 1atm by condensing urea with ethylenediamine with loss of ammonia.

The most important aspect of their method is the moderation of the reaction by water which must be boiled off throughout the reaction. By refluxing the ethylenediamine/water azeotrope (bp ~110°C) but allowing the water once free to be extracted from the reaction. If no water is added, or it not extracted throughout the reaction it notes that the yeilds are very poor.

The "wine bottle condensor" suited this well by allowing the temperature of the bottle to be varied with the quantity of water it holds. Due to the somewhat low surface area of the condensor I filled the bottle ~1/3 full, this stabalised at a temperature of about 75°C throughout the reflux.

Experimental: Into 50g urea and 25ml water was added 50g ethylenediamine in a 600ml beaker. Into the beaker was placed the winebottle proped up with a glass rod to act as the condensor.

With the hotplate on full the temperature of the reactants stabalised at ~110°C rising to 140°C in 1.5 hours, this was then left to reflux for a total of two hours.

After two hours the clear melt become turbid, and then very thick and pasty. This thick solution popped and spluttered as no stiring was (or could be) used. This thick solution lasted about 30 minutes upon which it turned into a clear amber melt. After three hours of reflux no more gassing was seen, and crystals were condensing onto the bottom of the bottle. The molten liquid now over >220°C was poured onto a tray to set, which was then broken up and powdered.

These observations were in agreement with the journal article, although the pasty mass formed about 1 hour quicker, thus the reaction was run 1 hour shorter.

Nitration of the supposed ethyleneurea was carried out by adding 20g ethylene urea to 148g 98% sulphuric acid & 52g 70% nitric acid whilst keeping the temperature around 10°C and leaving the mixture for 30 minutes. After this time the nitration mixture was thick with a white precipitate.

The mixture was poured into 1.5 litres of cold water then filtered, washed with a further 1 litre and filtered again to recieve a decent yeild.

Recrystalisation was done in by dissolving the precipitate into 200ml of dilute sodium acetate solution. Upon boiling much foam was created gas given off as expected from hydrolysis of dinitroethyleneurea to ethylenedinitramine with release of carbon dioxide. Eventually the precipitate went into solution as temperature reached 90°C.

The solution was filtered and placed into a freezer to cool to 5°C. A large crystaline precipitate formed (yay :D ) which was filtered and dried.

The crystals flare off on ignition. No detonation thus far has been attempted. I did attempt to replace the active hydrogens with chlorine by way of NaOCl but thus far nope :( a "chloronitramine", (-NCl-NO2) would have been quite neatly dangerous :cool:

Anyway, this seems like a very simple way to EDNA if ethylenediamine can be had. Pitty it isn't so easy with ethyleneglycol, but the condensor did work as originally planned, with the ethyleneurea condensing onto the bottom surface. So I'm not sure what going wrong with the "antifreeze method".

[Edited on 5-10-2005 by Axt]
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[*] posted on 13-10-2005 at 19:21


The ethylenebis(chloronitramine) (<-- yes, I'm making up names) was again attempted, this time by the action of chlorine gas on the sodium salt:

NaO2N=N-CH2-CH2-N=NO2Na + 2 Cl2 --> O2N-NCl-CH2-CH2-NCl-NO2 + 2 NaCl

Chlorine by way of MnO2 + HCl was bubbled into a solution of sodium-EDNA in a 100ml measuring cylinder. After a few minutes a dangerously large quantity of milky pale yellow oil fell out of the solution. I took a photo then knocked the chlorine generator over filling the cylinder with manganese oxides and HCl, no product could be saved :mad: The liquid product as shown below resembled the tetrachloride but a much paler yellow colour, though it did look like it was in an emulsion with water.



The lead salt was also made by precipitating a solution of Na-EDNA (5g EDNA, 2.6g NaOH) with 10.8g lead acetate. The fine white amorphous precipitate was filtered and dried. On ignition it is quite feeble and certainly no initiating explosive.


movie


The remainder of the EDNA (4.5g) was detonated with 0.5g PETN, it went ... bang.
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[*] posted on 14-10-2005 at 23:29


I still had some EDNA in the form of its potassium salt in water solution (by taking up EDNA with K2CO3). So I had another shot at ethylenebis(chloronitramine) henceforth known as "EBCN".

Interestingly, when chlorine was bubbled through this solution the oil formed as before but quite quickly turned into a white crystalline mass. These were filtered and dried.

Now that this has happened, when I poured out the other attempt contaminated with Mn oxides/HCl there was a hard black lump, but I payed no attention to it at the time. This was probably the same crystalline substance.

These burn much more readily then EDNA (which tends to melt and put itself out) has a much lower melting point, and ignition point then EDNA or its lead salt and can no longer be taken into solution with K2CO3.

It doesn't seem to explode with the vehemence needed for a primary explosive but if we assume it actually is EBCN, it is probably a powerful castable explosive (being very careful of low ignition point!) having better oxygen balance and likely higher density then EDNA. Of course I'm saying nothing of stability or toxicity!.

EDNA
VOD = 7850 @ 1.6g/cm3
%OB = -31.97
Impact sensitivity = 48cm (TNT=100cm)
MP = 174°C
Ignition point = ~210°C

EBCN
%OB = -7.31

EDIT: Just ignited some inside and was met with biting HCl fumes. I'm yet to determine if its a dichloride or monochloride-monopotassium salt, its hard to tell it such small quantities but the flame looked like it had a violet tint.

[Edited on 15-10-2005 by Axt]
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[*] posted on 15-10-2005 at 05:18


That's absolutely fascinating!

Have you seen the O2-NCl-R system elsewhere in the literature before?

Otherwise is it possible the the C-H's are attacked instead? Although the fact that the putative EBCN does not dissolve in K2CO3 argues against it.

Also, did you bother to determine the mp (i.e. melt in water)? Density should be also trivial to figure out....




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[*] posted on 15-10-2005 at 14:39


I havn't seen it mentioned before, and I am makng up the "chloronitramine" group. Its correct name N,N'-dichloro-N,N'-dinitroethylenediamine gives nothing.

Google doesn't recognise "chloronitramine", pubs.acs.org gives one hit for chloronitramine but the chloride isnt on the nitrogen.

Google doesn't recognise "N-chloro-N-nitro" but pubs.acs.org gives 79 hits though I cant open the articles from here. (Im not sure if its searching for the string or individual words).

I'm yet to get figures on MP/density.

EDIT: OK, today google does give a hit for chloronitramine, directing to US patent 6,603,018. It doesnt really make sense (They say chlorination of diethylenetriamine results in solution of nitramine?) They must mean the chloramine. Then its nitrated to the chloronitramine. Treating the chloronitramine with NaOH resulted in the diethylenetrinitramine.

EDIT 2: Yes, looking at the full text it does have the same structure -NCl-NO2 here on page 8 of pdf, http://64.132.7.41/pcgi-bin/patents/us/pdfcache/6603018.pdf

The patent goes on to mention US5243075 which gives synthesis for "N-chloromethyl nitramines" which arent N-chloro's at all rather C-chloro structures, bloody idiots. The Cl-CH2-N(NO2)- structure is said to be unstable.

[Edited on 16-10-2005 by Axt]
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[*] posted on 15-10-2005 at 21:57


Hmmm.

Now that you made a putative N-chloro nitramine, do you think that might be worth reacting with NaNO2, or AgNO2? Do you have DMF, or similar solvents?

This would potentially result in (O2N)2N-CH2CH2-N(NO2)2.

What are the acs links you can't open? Maybe it's worth posting a request in 'References and wanted translations'.




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[*] posted on 16-10-2005 at 00:03


Yes. I think it definately worth trying. I dont have DMF, whats the reason for choosing that solvent?

The documented synth of N,N-dinitramines being by reacting a primary nitramine in acetonitrile with a nitronium salt [patent attached]. If an analogous reaction was possible with nitrosyl salts it would produce a N-nitro-N-nitroso of O% OB. As far as I know there is no solvent for the easily made nitrosyl perchlorate/sulphate. I believe direct nitrosation of EDNA only results in ethyleneglycol.

Pitty no properties are reported for anything containing the -N(NO2)2 structure, its very interesting.

Another hare brained idea, cyclisation of EBCN with sodium peroxide, by using my nomenclature skillz that would give "cycloethyleneperoxydinitramine" OB also O% :D

BTW, "EBCN" MP is <60°C, melts into a clear oil when dropped into hot water out of the tap.

[Edited on 16-10-2005 by Axt]

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[*] posted on 16-10-2005 at 18:03


I've changed the movie to show the deflagration of EDNA compared to EBCN. EBCN's impact sensitivity is quite high, seemingly more sensitive then PETN. EBCN is readily exploded with a hammer on steel, while I couldn't initiate EDNA like this.


movie
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[*] posted on 29-10-2005 at 23:46


A word on yeilds, for EDNA I'm only getting about a gram of EDNA per gram of ethyleneurea after filtering, washing and bottling. This is about 50% of theory. Losses are probably from unreacted urea and ethylenediurea in the ethyleneurea which are destroyed in the hydrolysis. Also I'm unsure how soluble dinitroethyleneurea (its hygroscopic) so some is likely lost when flushing the H2SO4 out. Then the expected losses from that left on filter paper etc.

The chlorination of Na-EDNA goes to quantitive yield, ~14g EBCN from 10g EDNA the precipitate after chlorination is shown below.



Both EDNA and EBCN will react with copper, I dripped some molten EBCN over copper powder on a pourous disk and left it a couple days before taking the photo below. I also dropped some on a copper sheet. The areas where Cu was in contact with EBCN and the atmosphere turned green but not under the EBCN on the Cu plate, so it is probably stable if dry and not exposed to moisture in the air (same as EDNA).


enlarge


To confirm the presence of chlorine the copper/EBCN was ignited, copper burns blue in the presence of chlorine.



[Edited on 30-10-2005 by Axt]
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[*] posted on 30-10-2005 at 01:16


The silver salt of EDNA flashes violently on ignition, though still not an initiating explosive.


MOVIE
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[*] posted on 30-10-2005 at 12:14


Thats a beautiful picture (the blue one)



F. de Lalande and M. Prud'homme showed that a mixture of boric oxide and sodium chloride is decomposed in a stream of dry air or oxygen at a red heat with the evolution of chlorine.
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[*] posted on 30-10-2005 at 18:49


Axt: this is what makes this discussion board a fine one.
Although, since my expertise in this area is profoundly limited I connot contribute anything useful to this experiment, I can simply add a "Bravo!". The issues discussed are not only facinating but the direct approach to utilizing an OTC methodology is apprieciated. That is where another whole element of creativity is in play. And that creativity is not wasted on the readers.....Well done.
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[*] posted on 4-11-2005 at 03:19


Thanks, I was a bit worried that I was talking to myself :P

I found the reason we don't hear much of the -N(NO2) group in explosive literature.

"All covalently bound alkyldinitramines suffer instability problems that presumably originate from a combination of the steric hindrance between the two nitro groups and the high electonegativity of the N,N-dinitro group. A N,N-dinitro group leaves the alkyldinitramine electron deficient, especially at the central nitrogen. These effects destabilize alkyldinitramines and the instability can be observed in their thermal properties; all known alkyldinitramines thermally decompose at temperatures less than 70 °C and are highly shock and impact sensitive." JACS, 1997, 119, 9405-9410

The rest of the article relates to the dinitramide anion, which is significantly more stable.
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[*] posted on 6-11-2005 at 06:37


^ N(NO2) should of course be N(NO2)2.

Anyway....bingo!

"Little work has been reported on the synthesis and reactions of N-halo-N-nitro amine derivatives. N,N'-Dichloro-N,N'-dinitro-l,2-ethylenediamine, isolated by Smart and Wright in 1948, remained the sole example of this class of compounds until the recently reported synthesis of simple N-chloro-N-nitroalkylamines by the chlorination of aqueous salts of alkylnitramine. The synthesis of N-chloro-N-nitrocarbamates by this method was reported by Thomas in 1955. N-Bromo-N-nitro amine derivatives have not been reported. N-Chloro-N-nitramines and N-chloro-N-nitrocarbamates are explosive compounds and decompose rapidly on storage." Vytautas Grakauskas, Kurt Baum; J. Org. Chem.; 1972; 37(2); 334-335.

Confirms the synthesis but also mentions its instability. I've stored some 8g cast for ~2 weeks now with seemingly no change, better get rid of it soon.

The article itself focuses on N-fluoronitramines, I'll attach the full article when I get it. It mentions N-fluoro-N-nitrobutylamine that it was stored @ room temp for months without apparent decomposition.

hmmm.. fluorine gas :) The ethylenediamine derivative would HAVE to be powerful.

[Edited on 6-11-2005 by Axt]
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[*] posted on 6-11-2005 at 13:55


Maybe electrolysis with an excess of hydrofluroic acid (sodium hydroxide created from NaF electrolysis might decompose the wanted products) would serve to produce the -NFNO2 derivative without having to handle fluorine gas.

It would no doubt be powerful, not only would it have a very good O balance, it would produce HF for added energy, and compounds that have had F substituted onto them tend to have increased density over the parent compound :D

C2H4N4O4F2 --> 2HF + 2N2 + CO2 + CO + H2O
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[*] posted on 6-11-2005 at 14:53


I'm not sure what you mean by electrolysis of (aqueous?) HF without generating fluorine gas. Na-EDNA(aq) + HF(aq) -> EDNA precipitate.

Theres quite a good section in Urbanski 4 about fluoramines as explosives, generally NF2's performance mirrors NO2.

[Edited on 6-11-2005 by Axt]
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[*] posted on 6-11-2005 at 20:32


Ahh, good point! I guess NaF would work then.

What I mean by electrolysis is that the fluorine reacts to precipitate the fluorinated EDNA without having to be isolated and handled as a gas.
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[*] posted on 7-11-2005 at 06:46


Not that I know what the hell I'm talking about when it comes to electrolysis, but I at least can't fault the logic, neat idea. NaOH & Fluorine-water reactions may be problematic but it looks good enough to at least try.

[Edited on 7-11-2005 by Axt]

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[*] posted on 12-11-2005 at 04:54


Simple electrolysis of aqueous HF can not give F2.
2F2 + 2H2O = 4HF + O2

F2 is obtained by electrolysis of KHF2/liqid HF. Copper electrodes are used as well as copper crucible. This is the reason F2 has been synthesed much time after its hydride (HF).

What is the sensitivity of R-NF(NO2) derivates?




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[*] posted on 12-11-2005 at 06:14


Quote:
Originally posted by simply RED
Simple electrolysis of aqueous HF can not give F2.
2F2 + 2H2O = 4HF + O2

But since F2 is formed albeit briefly, isn't in within the realm of possiblility that you will get F2-aciEDNA addition, I think thats what Chris's main aim was. HF formed would be neutralised by the formed NaOH, with a slow accumulation of NaOH from precipitated difluoro-EDNA.
Quote:
What is the sensitivity of R-NF(NO2) derivates?

The above reference is the only time I've seen it mentioned, and for that reason I guess it has issues with sensitivity or stability (probably both) at least for commercial/military use.

[Edited on 12-11-2005 by Axt]
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[*] posted on 12-11-2005 at 09:35


This is all fascinating stuff.
I am most impressed that the chlorination works so quantitatively, and that you actually got this to work!

I was wondering whether one could expand that to other nitramines. Nitrourea is one that springs to mind, plus it's probably easier to make than EDNA.

On the note of fluoronitramines - I also doubt it would work, at least with H2O as a solvent. The H2O is at a huge molar excess, and, and reactivity of hydrogen bound to the N would have to be significantly higher to outcompete H2O.

Also, if you make the iodonitramine, you could potentially chlorinate that... similar to what you did in the iodoso/iodoxy thread! If that'd work, you should get a medal :P




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[*] posted on 12-11-2005 at 14:02


Quote:
The H2O is at a huge molar excess, and, and reactivity of hydrogen bound to the N would have to be significantly higher to outcompete H2O.

Im not sure how soluble Na/K-EDNA is, though NaF isnt very soluble, much less then KF. The most concentrated solution may be the potassium salts or a mixture of K & Na. Its adding to the double bond of aci-EDNA, and considering the quick and quantitive yield from chlorination.......! I dont think anyones saying its "likely" to work, only that it is "within the realm of possibility".
Quote:

Also, if you make the iodonitramine, ....

N-I bonds aren't known for their niceties :). I guess one could try precipitating a solution of KI/I2 with Na-EDNA.
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[*] posted on 14-11-2005 at 22:04


8g cast EBCN was detonated against a 3mm plate. The expected performace of EBCN wasnt realised with the explosive effect simular to that of the tetrachloride, it really should have been better then that and is probably the result of low velocity detonation which isnt a surprise, straight cast ETN fails to fire at high velocity in small quantities as well, as does NG even though these are sensitive explosives.


movie


EBCN is sensitive, it fires at 15-20cm in the drop test, where PETN is 40-45cm, ETN is 30-35cm and AP & MEKP is 0-5cm.

[Edited on 15-11-2005 by Axt]
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