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Author: Subject: a-nitro nitrofurfural aNNF
cumbustion
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[*] posted on 8-8-2005 at 05:58
a-nitro nitrofurfural aNNF


I have recently discovered an interesting new energetic material. Dinitro Furfural is a colourless liquid with a very irritating odour. It is rather sensitive and has a VoD of ~4300 m/s. I need help confirming these results and would also fancy any things to increase the yield etc.
Synthesis:
97 grams of furfural were put into a large beaker. In an warm water bath, ammonia gas (anhydride - got it from a friend working in a cheese plant) was passed through it until it was totally clear and a bit longer to be sure. This is now a mixture of alpha furfuryl amine and water.
I added 34.5 grams of caro's acid under gentle heating to serve 3 purpi:
1. to dehydrate it
2. get rid of free ammonia
3. oxidise it to a-nitro furfural
To this was added 63 g. of fuming nitric acid (NO2 from a sugar nitration runaway)
There were two layers. The crude a-nitro nitrofurfural was extracted first it was added to bicarb solution and then the aNNF was added to water and extracted.
Yield: ~65%
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cumbustion
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[*] posted on 8-8-2005 at 07:29


aNNF explodes by the following reaction:
C4H2O(CH2NO2)(NO2) --> 3CO + 2H2O + N2 + 2C
The oxygen balance isn't perfect, so I was wondering if AN could be added to it?
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Axt
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[*] posted on 8-8-2005 at 10:34


Quote:
Originally posted by cumbustion
To this was added 63 g. of fuming nitric acid (NO2 from a sugar nitration runaway)

...so I was wondering if AN could be added to it?


Would that be HNO3 or N2O4.. If its a liquid nitro then you best ditch the AN and try adding it to liquid N2O4, if its stable and miscible I'm sure it would be quite powerful, VOD could even approach 8000m/s.

Did you make furfural? supposedly its not difficult but I've never seen it described in detail. Treating with hydroxylamine hydrochloride (seemingly available at photography supply), then oxidation with hypochlorite to an N-peroxide would be interesting, if only to have an =N-O-O-N= group :P. (PATR V6.F243) Crystals, explodes @ 130°C.

BTW, where did you get the 4300m/s VOD figure?
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cumbustion
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[*] posted on 9-8-2005 at 10:35


At least I think it is. It's very similar in power to PETN which I recall is around that VoD.

I simply distilled sugar with H2SO4 to obtain furfural.

I came up with this idea sort of accidentaly: I was researching furfural as an alternative energy source, and as I was flipping through Hawley's Condensed chemical dictionary I saw the entry for a-furfuryl amine. My mind recalled the old Hexanitrobenzene thread and how -NH2 can be oxidised to -NO2 by Caro's acid. Realising the leftover H2SO4 could be used in further nitration, I thought to use HNO3.

A question: Where would the -NO2 be on the furan-type ring? Would it be opposite the CH2NO2 or below it, or diagonal from it? And would it affect the properties any? If so, is there any way of increasing the percentage of one isomer so as to increase the qualities of the aNNF?
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[*] posted on 22-8-2005 at 05:59


PETN has a MUCH higher vod than that! How would a liquid achieve such a high speed?



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 22-8-2005 at 17:27


TeNM/toluene & N2O4/nitrobenzene are liquids that can >8000m/s. VOD figures are somewhat variable with a lot of liquids even with consistant density some values for TeNM mixtures even pass 9000m/s dependant on initiation, diametre & confinement. So nothing to do with its liquid state.

PETN = 8400 @ 1.7g/cm3 (ref. Meyer "explosives";)

I was letting this one ride, far too many guesses on combustions part. If he was capable of oxidising the amine to nitro it would be acidic thus neutralisation wasn't the best course of action. I really dought the product was as claimed.

Distillation of H2SO4/sugar (sucrose?) I cant see why that would produce furfural, any references to that reaction?

[Edited on 23-8-2005 by Axt]
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[*] posted on 23-8-2005 at 04:25


In Kitzingers chemical dictionary (very old book) It says that furfural can be produced by distilling corncobs or other such mterials with sulfuruic acid... perhaps cumbustion saw a similar procedure and took it a bit further...



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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