Sciencemadness Discussion Board - FOX-7

FOX-7

rot - 16-2-2006 at 05:28

This relatively new explosive has a massive VoD of 8870m/s. not as high as newer explosives like HMX or HNIW, but it's very easy to make once you have 2-methoxy-2-methyl-4,5-imidazolidinedione.
here is the synthesis from megalomania.
The synthesis of 2-methoxy-2-methyl-4,5-imidazolidinedione is here (scroll down).
To make it, the following compounds are needed:
Sodium Methoxide, Acetamidine Hydrochloride and diethyl oxalate.
to make sodium methoxide you can add sodium metal to methanol. pretty simple.'
2CH3OH + 2Na --> 2CH3NaO + H2
For ethyl oxalate you can react ethanol with oxalic acid.
2C2H6O + H2C2O4 --> C6H10O4 + H2O (I think)
For acetemidine hydrochloride I don't know, maybe add hydrochloric acid to acetemide? does anyone have some ideas?

lacrima97 - 17-2-2006 at 06:07

Man, that sounds like a few expensive/exotic chemicals just to have it decomposed again.

Chris The Great - 17-2-2006 at 15:43

I have posted a potential synthetic route from FOX-7 to the hypothetical DTTO (detonation pressure calculated to be 5 times greater than that of HMX). Do a search on DTTO and you should find the diagram of potential reactions.

It might be worth it if you can make DTTO from it, or just as something different. I think other explosives, such as PETN, are much easier to make for the performance this explosive offers. The only real advantage FOX-7 offers is that it is an insensitive explosive, which the military likes because their shells and rockets get bumped alot and have to survive flying through walls before exploding.

FrankRizzo - 17-2-2006 at 16:28

BUT...you tie up a great deal of energy in the process, which is later utilized for some very neat applications.

Quote:

Originally posted by lacrima97
Man, that sounds like a few expensive/exotic chemicals just to have it decomposed again.

Nitrojet - 25-10-2006 at 01:03

Megalomania's method of synthesis of Fox-7 actually works. But also it has a trick in one step which is not mentioned directly in his recipe! After wasting many hours on the process and spending lots of money on expensive chemicals i came into conclusion than the distillation step cannot be successfully carried out unless, it is done under vaccum. i used a water aspirator for this purpose and it worked! after that my waste of time and money completely stopped!!

Axt - 25-10-2006 at 01:45

Quote:

Originally posted by Nitrojet
Megalomania's method of synthesis of Fox-7 actually works.

Its copied from the attached article, or from where ever these researchers took the process. The article is quite a nice review of FOX-7.

Quote:

i came into conclusion than the distillation step cannot be successfully carried out unless, it is done under vaccum

What distillation step?

[Edited on 25-10-2006 by Axt]

Attachment: FOX-7 a new insensitive explosive.pdf (4.2MB)
This file has been downloaded 4565 times

Nitrojet - 25-10-2006 at 03:02

The synthesis method of Fox-7, refers to an intermediate product which is then nitrated and treated with ammonia to give DADNE. It is 2-methoxy-2-methyl-4,5-imidazolidinedione which was the most challanging step towards preparation of FOX-7. A simple distillation procedure is mentioned for removing the last traces of sodium chloride from our intermediate product:
"At this point a precipitate of sodium chloride should have formed. Pour the contents of the flask over a filter to remove this solid. The salt collected on the filter paper can be discarded. Pour the liquid filtrate back into the flask and set the flask up for a simple distillation. Very gently heat the flask to distill off the methyl alcohol. This alcohol should be fairly pure and can be recycled. In this situation the flask is distilled to dryness to remove all alcohol and leave a solid white powder. When very little alcohol remains reduce the heat to around 30 degrees until dry"
As a matter of fact such a distillation even if carried out with very gentle heat can have a deteriorationg effect on the highly unstable 2-methoxy-2-methyl-4,5-imidazolidinedione. i tried the procedure may times and i received nothing. however when the process was rendered in a relatively weak vaccum, i could successfully separate out my product in enough quantities for the next stage which is Nitration and ultimately it gave afew grams of fox-7.

Axt - 25-10-2006 at 03:16

OK, never clicked the second link. The article I attached just mentions to evaporate at <30°C which makes that step quite trivial, on a small scale theres no need to complicate things by reclaiming the methanol. Bubble air through it via aquarium pump to aid in evaporation.

[Edited on 25-10-2006 by Axt]

Nitrojet - 25-10-2006 at 05:46

Yeah, it is a good idea to remove the Methanol by means of a constant stream of air bubbling through it. Water aspirators also can be successfully used to distill methanol under vaccum. They are simple to set up and are more rapid in removing methanol. at any rate, gentle heating of liquor is not recommended atall as it cause decomposition of the unstable intermediate.

hanky - 25-10-2006 at 18:34

This is the informative Link about the FOX-7 where the procedure of its synthesis is given in detail originally
http://www.dsto.defence.gov.au/publications/2412/DSTO-TR-123...
Hope this will improve your sythetic procedures.
:cool:

Here is the theortical side...or computational side
http://www.dsto.defence.gov.au/publications/2274/DSTO-TR-105...

[Edited on 26-10-2006 by hanky]

Fox-8

Nitrojet - 20-2-2007 at 09:52

Hypothetically, the two amino groups in Fox-7 molecule can be further oxidized to 1,1,2,2-Tetranitroethylene.

does anybody have any idea of this? Is it possible?

halogen - 21-2-2007 at 08:59

Possibly, but in the process you might come out with dinitro-diamino-oxirane (OOH!!) or otherwise mess up your fancy double bond.

dinitro-diamino-oxirane

Nitrojet - 21-2-2007 at 22:47

Yes, The pi bond seems to be the most vulnerable to an oxidative attack, It can be assumaed that any oxidizing agent powerful enough to oxidize Amino groups, can have its 1st attack to double bond.

Comparative Evaluation of FOX-7

franklyn - 5-4-2007 at 18:24

http://www.dtic.mil/ndia/2003insensitive/lochert2.pdf

.

Ritter - 30-7-2008 at 11:38

The attached synthesis starting from commercially available 4,6-dihydroxy-2-methylpyrimidine gives a yield reported to be >90%.

Reference: Org. Process Res. Dev., 11 (1), 56 -59, 2007

[Edited on 30-7-2008 by Ritter]

FOX-7.gif - 20kB

Ritter - 30-7-2008 at 12:49

The byproduct dinitromethane is unstable & decomposes. This patent deals with its synthesis & stable forms for use as a non-Cl-containing oxidizer: [url][http://www.pat2pdf.org/patents/pat6340780.pdf/url]

Engager - 1-8-2008 at 17:32

Dinitrobiurete seems much more easy to make (urea is starting material) and seems identical in power...

Ritter - 2-8-2008 at 14:18

Quote:

Originally posted by Engager
Dinitrobiurete seems much more easy to make (urea is starting material) and seems identical in power...

See the thread New Energetic Materials - Current Research for the structure & synthesis of dinitrobiuret.

The_Davster - 2-8-2008 at 14:26

Quote:

Originally posted by Engager
Dinitrobiurete seems much more easy to make (urea is starting material) and seems identical in power...

Assuming one has 4,6-dihydroxy-2-methylpyrimidine (and 100% nitric acid which the synth is easy on, no huge excess needed) the synthesis of fox-7 is obscenely easy.

Most papers on the synthesis use incomplete reaction times, and longer nitration times and longer crystalization times are necessary.(Can't remember the paper that said this). Yields reach 90% with longer times. They all state 90% yields, but only one paper has long enough reaction times to allow this.

EDIT: There is also stability differences, the Dinitrobiurete explodes at 124, and fox7 is classed as an IHE, I don't remember its decomp temp, but it is high.

[Edited on 2-8-2008 by The_Davster]

Formatik - 2-8-2008 at 14:54

Quote:

Originally posted by Engager
Dinitrobiurete seems much more easy to make (urea is starting material) and seems identical in power...

That's a good one. VOD estimate is 8.66 mm/ms and P = 33.9 GPa according to this PEP article.

Ritter - 3-8-2008 at 08:22

Quote:

Originally posted by The_Davster
Assuming one has 4,6-dihydroxy-2-methylpyrimidine (and 100% nitric acid which the synth is easy on, no huge excess needed) the synthesis of fox-7 is obscenely easy.

Looking at this paten http://www.pat2pdf.org/patents/pat5397781.pdf, this pyrimidine is prepared in Example 1:

Quote:

Preparation of 4,6-dihydroxy-2-methylpyrimidine

To a solution of sodium ethoxide, prepared from
sodium (36.2 g) and ethanol (1000 ml), diethyl malonate
(114 ml) and acetamidine hydrochloride (71 g) were
added at room temperature, and the mixture was stirred
for 5 hours under reflux. After cooling to room temper-
ature, the resulting solid was collected by fltration and
washed with ethanol and then dissolved in water. The
aqueous solution was acidifed to pH Ca.2 with concen-
trated hydrochloric acid (Ca. 170 ml) under ice-cooling.
The formed precipitate was separated by fltration and
washed with water, ethanol and ether to give 153 g
(81%) of the objective compound.

Melting point: > 300° C.

Doesn't sound very difficult, though sourcing or preparing some of the intermediates & reagents might present a challenge.

This compound is available commercially from a number of sources. Finagling a good sized sample might be a possibility.

This company offers it online: http://www.mpbio.com/product_info.php?cPath=491_1_13&pro...

[Edited on 3-8-2008 by Ritter]

Ritter - 3-8-2008 at 09:05

Quote:

Originally posted by rot
For acetemidine hydrochloride I don't know, maybe add hydrochloric acid to acetemide? does anyone have some ideas?

Its preparation is found at Organic Syntheses. It is also used in the synthesis of the alternate starting material 4,6-dihydroxy-2-methylpyrimidine. It is a derivative of acetonitrile: http://www.orgsyn.org/orgsyn/pdfs/CV1P0005.pdf

This company sells it online: http://www.mpbio.com/product_info.php?cPath=491_1_13&pro...

[Edited on 3-8-2008 by Ritter]

Ritter - 3-8-2008 at 09:29

Preparation of FOX-7 via nitration of 2-methylimidazole & other heterocycles is given in this patent http://www.pat2pdf.org/patents/pat6312538.pdf. It also contains a lot of chemical & physical data on this explosive.

Also see the prep from 2-methylimidazole in this patent: http://www.pat2pdf.org/patents/pat6113713.pdf

[Edited on 3-8-2008 by Ritter]

The_Davster - 3-8-2008 at 09:44

Ritter, you make some informative posts, but quit double and triple posting, edit your posts to add more info if they are the most recent ones in the thread.
You may find posts disappearing(read: deleted) if you do not do this

[Edited on 3-8-2008 by The_Davster]

nodoublepost.JPG - 21kB

2-methoxy-2-methyl-4,5-imidazolidinedione

kiko - 3-11-2010 at 03:00

the yield of 2-methoxy-2-methyl-4,5-imidazolidinedione in its preparation is 1 gm !!!!!!!! it must be 37 gm as the paper of FOX-7 A NEW INSENSITIVE EXPLOSIVE by DSTO and i dont know what is the problem???!!!! any one know the problem please????

hissingnoise - 3-11-2010 at 09:02

If the problem is that the synthesis gave you 1g instead of the expected 37, then I suggest you check your procedures and starting materials . . .

kiko - 3-11-2010 at 11:11

Quote: Originally posted by hissingnoise

If the problem is that the synthesis gave you 1g instead of the expected 37, then I suggest you check your procedures and starting materials . . .

the procedure is as in the paper FOX-& A new insensitive high explosive by DSTO??
i dont know if the problem in the dryness step of in the filter paper or in what????

madscientist - 3-11-2010 at 11:45

Right now the way you're describing your problem amounts to gibberish. You haven't shared any details on the procedure and materials and reagents YOU used, no details on any observations during preparation, and nothing on the final product. All you've said is "I looked at this paper and then everything went wrong," with considerably less intelligibility and giant strings of punctuation. You can't seriously expect any answers...

AH-Poster - 6-11-2010 at 11:47

Just a quick thought on a shortcut to Fox-7,
starting with 1,1,1-trinitro ethane

see figure 1.69 in franklyn's post on page 4 of the topic "New Energetic Materials - Current Research".

1,1,1-trinitro ethane reacts with KOH to form
1,1-dinitroethylene and KNO2. This can be inferred from the description of the picture, and this was specifically stated in one of the articles from
Journal Russian Chemical Bulletin
S. S. Novikov1, I. S. Korsakova1 and K. K. Babievskii
N. D. Zelinskii Institute of Organic Chemistry Academy of Sciences USSR, USSR
(they authored several articles about similar compounds)

A similar reaction, except the base pulling out an HCl instead of a HNO2 can be seen on wikipedia,
http://en.wikipedia.org/wiki/1,1-Dichloroethene

Obviously dinitroethylene can be expected to react with chlorine gas, to generate 1,1-dinitro,2,2-dichloro ethylene,
and from here simply condense with anhydrous ammonia.

I cannot find a specific reference for dichloro ethylene reacting with amines or ammonia, likely because (with the nitro groups not present) the product would be a gunky mess. Basically an imine of acetaldehyde that would be unstable because of the acidity of the HCl.

It is probably easer to make 1,1,1-trinitroethane than the
normal imidazolidinedione precursor. For example, from ethyl nitrolic acid CH3C(=NOH)NO2 reacting with more NO2.
A google books "organic chemistry of explosives" claims that
the double nitrolate of ethane can be nitrated to hexanitroethane by being treated with concentrated H2SO4 and HNO3 dissolved in CH2Cl2 (92% yield). Obviously this would be unsuitable for ethyl nitrolic acid, since the methyl group would get oxidized, but perhaps using NO2, which is known to form psuedonitrosoles from oximes. There are references on my site about NO2 oxidizing nitroso groups or nitrites. For specifics about ethyl nitrolic acid there is information already posted on this site for ethyl nitrolic acid, see A. Hantzsch and O. Graul (Ber. 1898, 31, p. 2854),
and post #13 (which is subtitled 1,1,1-trinitroethane)
in the topic "1,2,2 trinitro propane". Ethyl nitrolic acid results from nitric acid nitration of acetone. See the topic "Silver salt of acetylmethylnitrolic acid".

The article at the bottom of this page
https://sites.google.com/site/energeticchemical/5-dinitromet...

discusses an even more energetic compound (which can form salts) which can be made by diazotizing the amines of Fox-7 into a tetrazole ring. This might not be as powerful as DTTO, but at least the route is straightforward.

[Edited on 6-11-2010 by AH-Poster]

hissingnoise - 7-11-2010 at 10:01

Energeticchemical is your site Anders?

Easy synthesis for Fox-7 ?

AndersHoveland - 16-8-2011 at 16:26

This is just an idea for a procedure to make the energetic compound, Fox-7, using readily obtainable precursors.

(1) oxidize ethylene glycol to glycolaldehyde
(the glycolaldehyde does not need to be separated from the unreacted ethylene glycol)
Glycolaldehyde is also common and easily obtainable from chemical supplies, if you find the oxidation procedure to be too messy or inconvenient.

(2) reflux the glycolaldehyde with ammonia solution and acetic acid. This will form 2-methyl imidazole.

A similar condensation cyclisation has already been described in the literature: "Imidazoles from ammoniacal solutions of glycolaldehyde and hydroxypyruvaldehyde" M.R. Grimmett and E.L. Richards

(3) Perform a nitration on the 2-methyl imidazole using mixed acids. This should yield 2-dinitromethyl-4,5-dinitro imidazole.

(4) Dilute with water and separate out the nitrated product.
Then react with concentrated ammonium hydroxide. The 2-dinitromethyl-4,5-dinitro imidazole will hydrolyse into Fox-7, ammonium nitrite, and an aldehyde-ammonia condensation product.

So basically, the only precursors needed would be:
anti-freeze
KMnO4
white vinegar
98%conc H2SO4
KNO3 or 70%conc HNO3
household cleaning ammonia

What do you think? Any comments? Obviously it has not been tested, but it seems relatively straightforward.

(you might also see my other post about using Fox-7 to make an even more powerful explosive)

Quote: Originally posted by AndersHoveland

click here ^ to be directed to the other post

Reacting 1,1-diamino-2,2-dinitroethylene (Fox-7) with NaOCl (bleach) might form 4,4’-Dinitro-3,3’-diazenofuroxan (DDF).

[Edited on 17-8-2011 by AndersHoveland]

watson.fawkes - 17-8-2011 at 06:28

Quote: Originally posted by AndersHoveland

What do you think?

I think you should try it yourself. I also think that if you do so, you should write it up for others to examine.

quicksilver - 17-8-2011 at 06:35

+1
Work on a gram(s) level & document the temps and idiosyncrasies.

497 - 17-8-2011 at 10:17

I don't think you can nitrate that methyl group to a dinitromethyl. There seems to be solid references to back that up. There are other ways to go about it though. Have a look at this:
http://docs.google.com/viewer?a=v&q=cache:z_lnmS1fAe8J:j...

Edit
Yes, you're right, I misread that.

[Edited on 17-8-2011 by 497]

AndersHoveland - 17-8-2011 at 11:03

Quote: Originally posted by 497

I don't think you can nitrate that methyl group to a dinitromethyl. There seems to be solid references to back that up. There are other ways to go about it though. Have a look at this:

That information actually mentions that Fox-7 has been prepared from 2-methylimidazole.

This would seem to contradict the information in your link:
http://books.google.com/books?id=xF5yUHI0m4QC&pg=PA50&am...

That article that you cited essentially says that 2-methyl-4-nitro-imidazole cannot have its methyl group nitrated. The nitration of the methyl group proceeds through an unsaturated tautomer, which is favorable under acidic conditions. Apparently, this tautomer cannot form if there are nitro groups already on the ring. Indeed, both 4-nitro-, and 4,5-dinitro-, 2-methylimidazole also form as byproducts during the nitration of 2-methylimidazole, as their methyl group has apparently become "deactivated".

2-methylimidazole was simultaneously nitrated and oxidized to 2-[dinitromethylene]-4,5-imidazolidinedione, which was then hydrolysed to Fox-7.

[Edited on 17-8-2011 by AndersHoveland]

497 - 17-8-2011 at 14:42

I don't know if this has been mentioned or not but I did notice another very OTC route the 2-methylimidazole that has literature to back it up every step of the way. If Anders' above route works, it would surely be easier, but I was unable to find anything solid to confirm that it works. So here it is:

Alanine + TCCA --H2O/NH3--> acetonitrile 90% yield (or buy it if you can)
Acetonitrile + EtOH + HCl --> iminoether (not isolated)
Iminoether + NH3 --EtOH--> acetamidine 90% yield
Acetamidine + glycolaldehyde/chloroacetaldehyde --> 2-methylimidazole 80-90% yield?

Not too tough... If you have easy access to acetonitrile and glycolaldehyde it would be downright simple.
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1...

Edit
Does anyone know if a 4 alkyl substituent would screw up the nitration? If it didn't, things think chloroacetone could be used instead of glycolaldehyde. Either way the yields on the ring closure reaction should be good according to
http://www.orgsyn.org/orgsyn/prep.asp?prep=v81p0105

[Edited on 17-8-2011 by 497]

AndersHoveland - 18-8-2011 at 15:43

Quote: Originally posted by 497

I was unable to find anything solid to confirm that it works.

Does anyone know if a 4 alkyl substituent would screw up the nitration? If it didn't, things think chloroacetone could be used instead of glycolaldehyde. Either way the yields on the ring closure reaction should be good according to
http://www.orgsyn.org/orgsyn/prep.asp?prep=v81p0105

"A solution of glycolaldehyde in concentrated ammonia solution became straw- coloured after 8 weeks at room temperature. From the resulting mixture imidazole and 2-hydroxyrnethylimidazole have been isolated."
M. R. Grimmett and E. L. Richards, Australian Journal of Chemistry

There is a biref mention to it in this article:
"The formation of imidazole from glycolaldehyde and concentrated ammonia..."
http://www.springerlink.com/content/x9512th9wuu54125/

It seems to be a variation of the Radziszewski reaction.
Apparently amidines (such as acetamidine) readily reacts with α-haloketones (such as chloroacetone) to yield imidazoles.

Fairly certain that one would not need to go to the trouble of preparing acetamidine. For the sythesis of the explosive NTO, for example, formic acid is refluxed with semicarbazide to yield 1,2,4-triazole-3-one. Here is the specifics of the procedure if you are interested:
"47 g of semicarbazide and 115 g of 98% formic acid and 200 mL of ethanol is refluxed (heated to 100 degC and stirred) for 1 hour and then the excess of formic acid and the ethanol are distilled off. 58 g of white solid formilsemicarbazide crystallized, with a melting point of 129 degC. This is then dissolved in 150 mL of formic acid and refluxed for 1 hour. The excess of formic acid is distilled off. 25 g of a white solid are obtained which is mostly 1,2,4 triazole-3-oxide." (it can then be nitrated with boiling 70%conc HNO3 to the NTO)

Unfortunately, it is quite probable that a 4-methyl substituent would mess up the reaction. The same thing that is supposed to happen to the methyl group in the 2-position will also/or instead happen to the new alkyl group. The yields would likely be reduced by half, and it could become much more complicated to separate out the final Fox-7 from structurally similar byproducts.

Some people have previously speculated about the reaction between 1,1-dinitro,2,2-dichloro ethylene and anhydrous ammonia. Fox-7 is not formed from this reaction. Unfortunately, the condensation only yields the ammonium salt of dinitroacetonitrile:
NH4(+) NΞC–C(NO2)=NO2(-)

sorry, unable to find the reference now

[Edited on 19-8-2011 by AndersHoveland]

PHILOU Zrealone - 19-8-2011 at 12:43

But 1,1-dinitro-2,2-dichloroethylene reacts with urea or amides to yield related to FOX-7 derivatives...

Also trichlorethylene reacts with HNO3 69% to yield, upon standing (or boiling), 1-nitro-1,2,2-trichlorethylene...the yellow-orange liquid is very pungent and is to my feeling as poisonous as chloropicrin (trichloronitromethane)... It displays the same kind of reactivity towards proteins as the previously mentionned dinitrodichloroethylene

bbartlog - 21-8-2011 at 05:02

Quote: Originally posted by AndersHoveland

(1) oxidize ethylene glycol to glycolaldehyde
(the glycolaldehyde does not need to be separated from the unreacted ethylene glycol)

But can you selectively oxidize just to the glycolaldehyde using KMnO4, as you suggest? Seems like under basic conditions you end up going all the way to the acid (oxalic or maybe glycolic), whereas under acid conditions you just cleave the diol. The German wikipedia page on glycolaldehyde (http://de.wikipedia.org/wiki/Glycolaldehyd) suggests that careful oxidation using Fe(II)SO4 and hydrogen peroxide will do the trick, but the provided reference is a book I don't have access to, so it's hard to say just how finicky the conditions implied by 'careful' are...

[Edited on 21-8-2011 by bbartlog]

AndersHoveland - 22-8-2011 at 10:58

It is not selective oxidation, just limited oxidation. For best yields use a large excess of ethylene glycol.
http://www.erowid.org/archive/rhodium/chemistry/acetaldehyde...

Unfortunately, preparing glyoxal is not quite as easy.

FOX-7 an expensive explosive!

The WiZard is In - 22-8-2011 at 15:15

"The estimated material cost for producing unpurified FOX-7
on a laboratory scale at DSTO vie the preferred FOI Method 2
was calculated at ca. AU$300/100g."

Attachment: Fox 7 page 6.pdf (107kB)
This file has been downloaded 695 times

AndersHoveland - 22-8-2011 at 16:11

Not really. The cost of Fox-7 is estimated to only be around 0.50 USD per gram (or 500/kg) when the production is scaled up. In any case, even TNAZ is not really so expensive in comparison to the cost of typical weapon delivery systems.
If the missile costs 1 million USD, even 10,000 dollars should not be considered overly expensive for the explosive filling, if weight can be reduced or performance increased by a small margin. A 10% reduction in weight of the explosive, for example, could lead to savings of tens of thousands of dollars for a smaller delivery system.

The WiZard is In - 22-8-2011 at 18:42

Quote: Originally posted by AndersHoveland

Not really. The cost of Fox-7 is estimated to only be around 0.50 USD per gram (or 500/kg) when the production is scaled up. In any case, even TNAZ is not really so expensive in comparison to the cost of typical weapon delivery systems.
If the missile costs 1 million USD, even 10,000 dollars should not be considered overly expensive for the explosive filling, if weight can be reduced or performance increased by a small margin. A 10% reduction in weight of the explosive, for example, could lead to savings of tens of thousands of dollars for a smaller delivery system.

If [Insert quote about the Queen here --> ]

Seems to be that its primary advantage is that it is insensitive.

Ref attached PDF.

Actually its too large try these —

http://www.dtic.mil/ndia/2009insensitive/5AOEstmark.pdf

And —

Accession Number : ADA399359
Title : FOX-7 - A New Insensitive Explosive
Descriptive Note : Technical rept.
Corporate Author : DEFENCE SCIENCE AND TECHNOLOGY ORGANISATION VICTORIA (AUSTRALIA) AERONAUTICAL AND MARITIME RESEARCH LAB
Personal Author(s) : Lochert, Ian J.
Handle / proxy Url : http://handle.dtic.mil/100.2/ADA399359
Report Date : NOV 2001
Pagination or Media Count : 36

Abstract : 1,1-Diamino-2,2-dinitroethene (FOX-7) is an
energetic material developed by FOI Sweden in the late 1990s.
Theoretical studies have predicted that the performance of FOX
-7 should exceed that of RDX. FOX-7 is also significantly less
sensitive than RDX, particularly to impact and frictions stimuli.
Consequently, FOX-7 is an attractive ingredient for application
in high performance, IM-compliant explosive compositions.
AMRL evaluation of FOX-7 has focused on the synthesis,
hazards characteristion and performance studies. Aspects of
these research areas, including preliminary experimental data
that validates the theoretical performance values, are detailed.

By da there is a European and World Patent on Fox-7 e.g.,
WO 9903818. If I really cared how it is made I would look them
up.

Francis0126 - 29-8-2011 at 01:44

Can you image the chemical behavior about Fox-7？

AndersHoveland - 21-2-2012 at 12:10

Also found this in an online search:

Quote:

4-Methylimidazole can be manufactured through the reaction of hydroxy-acetone with formamide and liquid ammonia.

To make Fox-7, of course, one would need to 2-methylimidazole, not 4-Methylimidazole. But this does help show how easy simply precursors can condense to form imidazoles.

Quote: Originally posted by Francis0126

Can you image the chemical behavior about Fox-7？

You might see "The Structure and Chemical Bond of FOX-7: The AIM Analysis and Vibrational Normal Modes", Jamshid Najafpour, Iranian Journal Chemical Engineering, p118

The Fox-7 molecule is aromatic, the amino groups are electron-donating to the nitro groups. The carbon-carbon bond is not a true double bond in character.

(NH2)2C=C(NO2)2

[Edited on 22-2-2012 by AndersHoveland]

Francis0126 - 16-3-2012 at 03:18

thank you for supporting，i want to do more reasearch about the fox-7 while its simple structure. it just like TATB ,hydrogen bonding plays the key role for its insenstive. it is very interesting to combine two fox-7 together.what we can do for improving the insenstive or its detonation velocity? just from the main structure of fox-7,may be some other derivatives?

Quote: Originally posted by AndersHoveland

Also found this in an online search:

Quote:

4-Methylimidazole can be manufactured through the reaction of hydroxy-acetone with formamide and liquid ammonia.

To make Fox-7, of course, one would need to 2-methylimidazole, not 4-Methylimidazole. But this does help show how easy simply precursors can condense to form imidazoles.

Quote: Originally posted by Francis0126

Can you image the chemical behavior about Fox-7？

AndersHoveland - 17-3-2012 at 15:21

There is another derivitive of Fox-7, a very powerful one.
Some researchers have referred to it as "N2FOX-7". It is discussed on page 12 of the thread "5-ATZ(5-Aminotetrazole), the nitrotetrazolate ion and friends" in this forum, the thirteenth post down. (or you can just click the link in the quote box below)

Quote: Originally posted by AndersHoveland

I think the most promising energetic compound may be dinitromethyl tetrazole.
“Syntheis of 5-Dinitromethyltetrazole”, A. V. Shastin, B. L. Korsunskii, T. I. Godovikova, V. P. Lodygina. (2009) Russia

N2Fox7.GIF - 2kB

I made five posts about this compound in that thread, about the research, expected properties, and possible synthesis routes.

[Edited on 17-3-2012 by AndersHoveland]

Francis0126 - 18-3-2012 at 04:56

Quote: Originally posted by AndersHoveland

There is another derivitive of Fox-7, a very powerful one.
Some researchers have referred to it as "N2FOX-7". It is discussed on page 12 of the thread "5-ATZ(5-Aminotetrazole), the nitrotetrazolate ion and friends" in this forum, the thirteenth post down. (or you can just click the link in the quote box below)

Quote: Originally posted by AndersHoveland

I made five posts about this compound in that thread, about the research, expected properties, and possible synthesis routes.

[Edited on 17-3-2012 by AndersHoveland]

I have done some reasearch about the substance 5-Dinitromethyltetrazole , the outstanding work is the synthesis of the Dinitromethyltetrazole salts"Energetic mono and dibasic 5-dinitromethyltetrazolates: synthesis,properties, and particle processing"published in 2007. How about the nitration of dinitromethyltetrazole? Is it possible for the -NH to be -N-NO2?

AndersHoveland - 18-3-2012 at 15:47

Quote: Originally posted by Francis0126

How about the nitration of dinitromethyltetrazole? Is it possible for the -NH to be -N-NO2?

I am not sure, but I think this would just form trinitronitromethyltetrazole, with the 3 nitro groups on the same carbon atom. Further nitration of Fox-7, for example, is certainly possible, but much more difficult. Dinitromethyltetrazole would be even more resistant to nitration. It would probably require N2O5 in HNO3. But I do not understand why one would nitrate it. Dinitromethyltetrazole probably already has a good sensititivity to power ratio. A trinitromethyl group would make it much more sensitive (and lead to thermal stability problems), because the NH group would no longer be able to be electron-donating to the nitro groups.

Synthesis of 5-(Trinitromethyl) tetrazole from trinitroacetonitrile (II) and trimethylsilyl azide. The 5-(Trinitromethyl) tetrazole was isolated in the form of its tetrabutylammonium salt.
"New Synthesis of 5-(Trinitromethyl)tetrazole", A. Shastin, T. Godovikova, B. Korsunskii

[Edited on 18-3-2012 by AndersHoveland]

Francis0126 - 18-3-2012 at 16:37

Quote: Originally posted by AndersHoveland

Quote: Originally posted by Francis0126

How about the nitration of dinitromethyltetrazole? Is it possible for the -NH to be -N-NO2?

Yeah ,I agree with you, the senstivity and thermal behavor are the questions for the -N-NO2 on the tetrazole ring.

AndersHoveland - 31-3-2012 at 22:54

Many people in this forum have thought about making Fox-7 by reacting (NO2)C=CCl2 with ammonia.

The reaction of 1,1-diiodo-2,2-dinitroethylene with NH3 would not make Fox-7, but rather would form dinitro-acetonitrile.
NΞC—CH(NO2)2

This is because the NH3 molecule will immediately condense with both halogen atoms before another NH3 molecule can react.

But it is interesting to think about how hydrazine would react with it.

Here is what happens when (NO2)C=CCl2 reacts with NH3:

Quote:

Dissolve 1,1-dichloro-2,2-dinitroethylene (around 96 g) from the previous step in 800 mL of toluene in a large round-bottomed flask. Place the flask to a weighing machine and bubble dry ammonia gas through the solution. Pour the content of the flask over a filter to collect the crystals, wash them several times with small portions of water and dry them under vacuum. Yield is 73 g or 97% of the ammonium salt of dinitromethylcyanide.

Boffis - 28-7-2012 at 21:07

Hi Anders, where did this quote re 1,1 dichloro 2,2 dinitroethene come from? I've done a search on the SM site and I see you have posted the same quote twice but I can't see the source.

Ah, I've found it! A dud thread from roguesci site that even there had be withdrawn as improbably crap. So I think I'm back to nitration of tetra-iodoethylene to the diiodo-dinitro ethylene.

Has anyone ever tried to prepare tetraiodoethylene? It does sound too difficult; check out Von Richter Vol 1 p96

[Edited on 29-7-2012 by Boffis]

Boffis - 30-7-2012 at 02:47

Just for interest I have found this preperation information for tetraiodoethylene while rumaging around the internet. I don't think this will get you any closer to Fox 7 but 1,1-diiodo-2,2-dinitroethylene sound like an interesting compound in its own right; maybe you can oxidize the iodine as suggested in other threads on this site..