Ral123
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Trinitroanisole properties
A TNT-like tri nitro aromatic compound. It's the same but with one more oxygen atom between the ring and the CH3. Does it have any interesting
qualities for the amateur enthusiast? Obviously it's storage stable, medium energy, good brisanse. What I really would like you to share is your
opinion about is why it's been produced so much during the war? It's not like they'd need 20 years+ storage stability. The Japanese have used it in
their suicide planes. Why would you go trough the pain of converting aromatics, nitrating them and lift them in the air, when there are so many cheap,
much more powerful options-most of the nitric esters are easy to make and way more powerful. For airplane load, the unsurpassed mass/energy of nitric
esters seems logical. Even methyl nitrate has some advantages over these dense but underpowered nitro aromatics. If I was engineer, I'd put AN/TNT/Al
in torpedoes instead of TNT/Al. For air bombs if not anything else, I'd put large nitric ester booster in the middle of the nitro aromatic charge. For
submarine hunting I'd use super cheap mixtures-HNO3/fuel(NM, TNT, DNB or similar)-more powerful and much cheaper then the hexanitro diphenylamine.
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AndersHoveland
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There were shortages of toluene. And picric acid can be hazardous in storage, because often brass shell casings were used, hence the use of anisole.
[Edited on 4-3-2013 by AndersHoveland]
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Ral123
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Then what about the nitric esters? They used the TNA for a liquid fuel rocket powered suicide plane. So on one side they struggle for high impulse, on
other they use such a low grade explosive. TNA has less then 4kj/g and EGDN more then 7.2kj/g
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AndersHoveland
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Just to clarify, the TNA was used in the bomb, not the liquid rocket fuel.
And just to clarify, the "TNA" used in those Japanese kamakaze planes were trinitroaniline, not trinitroanisole.
EGDN is also more sensitive. No competent military would use EGDN as the main charge in their bombs, even for a suicide plane.
The problem with trinitroaniline (TNA), however, was that is was chemically unstable in storage. Those 3 nitro groups on the aromatic ring
make the compound somewhat oxidizing, enough to gradually oxidize the amino group. The degredation of TNA is not well understood, but the
decomposition can gradually accelerate, the by-products catalyzing further decomposition. In bulk quantities, heat can build up, accelerating the
reaction to the point of detonation in some cases. Did I mention people getting poisoned from handeling it? Aniline itself is rather poisonous, adding
nitro groups just makes it more so.
Other than that worrisome problem, TNA was a great explosive - cheap, easy to make, low sensitivity to impact, more powerful than TNT.
I believe there was some experimental research into reacting TNA with hypochlorite bleach (at 0°C) to tranform it into a new compound,
3,5-dinitro-benzofuroxan, which was both more powerful, and did not have any of the storage stability problems.
[Edited on 4-3-2013 by AndersHoveland]
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Ral123
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Nitroaromatic without storage stability seems worthless. In the movie I watched they said trinitro anisole. Could't they use less of the "stable
explosive" and place high power blast jelly booster "core". It'll be protected from enemy fire and will highly increase power to weight.
I don't see advantage of trinitro aniline compared to tetryl, TNP and the nitric esters.
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Trotsky
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"I believe there was some experimental research into reacting TNA with hypochlorite bleach (at 0°C) to tranform it into a new compound,
3,5-dinitro-benzofuroxan, which was both more powerful, and did not have any of the storage stability problems."
I was aware of this patent: http://www.google.com/patents/US5039812
However, that's 5,7-diamino-4,6-dinitro-benzofuroxan. I don't think I've seen anything about 3,5-dinitro-benzofuroxan.
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AndersHoveland
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Quote: Originally posted by Trotsky  | | However, that's 5,7-diamino-4,6-dinitro-benzofuroxan. I don't think I've seen anything about 3,5-dinitro-benzofuroxan. |
I am sure the reaction is more complicated than that, likely producing some by-products that need to be separated out also. Likely the reason it was
never used industrially. Reaction of hypochlorite with 2,4-dinitroaniline, for example, simply chlorinates it to 6-chloro-dinitroaniline.
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Motherload
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I am a little unsure here.
Tri Nitro Anisole looks just the same to me as Methyl Picrate.
So could one make a solution of Picric acid in methanol and dehydrate/esterify using H2SO4 ?
According to wiki Methyl Picrate has a VOD of 6800m/s
http://en.wikipedia.org/wiki/Table_of_explosive_detonation_v...
"Chance favours the prepared mind"
"Fuck It !! We'll do it live !!"
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