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Axt
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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:
<img src="http://www.sciencemadness.org/scipics/axt/ednascheme-2.jpg">
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 <a
href="http://www.sciencemadness.org/scipics/axt/ethyleneurea-condensor.jpg">setup</a>, 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 <a
href="http://www.sciencemadness.org/scipics/axt/ethyleneurea-foam.jpg">product</a> 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 <a
href="http://www.sciencemadness.org/scipics/axt/edna-precip.jpg">precipitate</a> 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 <a
href="http://www.sciencemadness.org/scipics/axt/door-condensate.jpg">condensate</a> 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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Axt
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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.
<center><img src="http://www.sciencemadness.org/scipics/axt/toaster-condensor.jpg"></center>
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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Axt
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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 "<a href="http://www.sciencemadness.org/scipics/axt/ethyleneurea-condensor.jpg">wine bottle condensor</a>" 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.
<i>Experimental</i>: 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 <a href="http://www.sciencemadness.org/scipics/axt/ethyleneurea1.jpg">crystals were condensing onto the bottom of the
bottle</a>. The molten liquid now over >220°C was poured onto a <a
href="http://www.sciencemadness.org/scipics/axt/ethyleneurea2.jpg">tray to set</a>, 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 <a
href="http://www.sciencemadness.org/scipics/axt/edna1.jpg">decent yeild</a>.
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 <a
href="http://www.sciencemadness.org/scipics/axt/edna-recrystalised.jpg">crystaline precipitate</a> formed (yay  ) 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 
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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Axt
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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  The liquid product as shown
below resembled the <a href="http://www.sciencemadness.org/scipics/axt/NTCED.jpg">tetrachloride</a> but a much paler yellow
colour, though it did look like it was in an emulsion with water.
<center><img src="http://www.sciencemadness.org/scipics/axt/chloronitramine.jpg"></center>
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.
<center><img src="http://www.sciencemadness.org/scipics/axt/pb-edna.jpg">
<a href="http://ww1.webtop100.net/~62552/xmovies.webtop100.net/banners/xmovies.html">movie</a></center>
The remainder of the EDNA (4.5g) was detonated with 0.5g PETN, it went ... bang.
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Axt
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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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chemoleo
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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....
Never Stop to Begin, and Never Begin to Stop...
Tolerance is good. But not with the intolerant! (Wilhelm Busch)
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Axt
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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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chemoleo
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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'.
Never Stop to Begin, and Never Begin to Stop...
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Axt
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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%
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]
Attachment: nn-dinitramines.pdf (455kB)
This file has been downloaded 1382 times
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Axt
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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.
<center><img src="http://www.sciencemadness.org/scipics/axt/edna-ebcn.jpg">
<a href="http://ww1.webtop100.net/~62552/xmovies.webtop100.net/banners/edna-derivatives.mpg">movie</a></center>
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Axt
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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.
<center><img src="http://www.sciencemadness.org/scipics/axt/ebcn-chlorination.jpg"></center>
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).
<center><img src="http://www.sciencemadness.org/scipics/axt/ebcn-copper-sm.jpg">
<a href="http://www.sciencemadness.org/scipics/axt/ebcn-copper.jpg">enlarge</a></center>
To confirm the presence of chlorine the copper/EBCN was ignited, copper burns blue in the presence of chlorine.
<center><img src="http://www.sciencemadness.org/scipics/axt/blueflame.jpg"></center>
[Edited on 30-10-2005 by Axt]
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Axt
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The silver salt of EDNA flashes violently on ignition, though still not an initiating explosive.
<center><img src="http://www.sciencemadness.org/scipics/axt/ag-edna.jpg">
<a href="http://xmovies.webtop100.net/banners/ag-edna.mpg">MOVIE</a></center>
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halogen
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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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quicksilver
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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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Axt
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Thanks, I was a bit worried that I was talking to myself 
I found the reason we don't hear much of the -N(NO2) group in explosive literature.
"<i>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.</i>" JACS, 1997, 119, 9405-9410
The rest of the article relates to the dinitramide anion, which is significantly more stable.
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Axt
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^ N(NO2) should of course be N(NO2)2.
Anyway....bingo!
"<i>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 <b>recently reported synthesis of simple N-chloro-N-nitroalkylamines by the chlorination of aqueous salts of alkylnitramine</b>.
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.</i>" 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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Chris The Great
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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
C2H4N4O4F2 --> 2HF + 2N2 + CO2 + CO + H2O
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Axt
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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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Chris The Great
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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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Axt
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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]
Attachment: Synthesis of N-Fluoronitramines.pdf (304kB)
This file has been downloaded 1535 times
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simply RED
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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?
When logic and proportion have fallen sloppy dead...
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Axt
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| Quote: | Originally posted by simply RED
Simple electrolysis of aqueous HF can not give F2.
2F2 + 2H2O = 4HF + O2 |
But since F2 <i>is</i> 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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chemoleo
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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
Never Stop to Begin, and Never Begin to Stop...
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Axt
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| 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.
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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".
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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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Axt
National Hazard
Posts: 778
Registered: 28-1-2003
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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 <a
href="http://xmovies.webtop100.net/banners/N-tetrachloroethylenediamine.mpg">tetrachloride</a>, it really <i>should</i>
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.
<center><img src="http://www.sciencemadness.org/scipics/axt/ebcn-8g.jpg">
<a href="http://xmovies.webtop100.net/banners/cast-ebcn.mpg">movie</a></center>
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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