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Author: Subject: TRIOXANE
quicksilver
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[*] posted on 15-4-2006 at 19:13
TRIOXANE


The providors to the government is selling off surplus Trioxane heating fuel from the military service at an astoundingly low price now as it appears to be replacing this with another heating technique. Current price is 93 cents a pound!

Does Trioxane have any use similar to hexamine or as any precurser to energetic materials in common (or uncommon) use?




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enhzflep
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wink.gif posted on 15-4-2006 at 19:27


Well, i could've sworn that the stuff was useless, Buuuut -
according to
http://www.roguesci.org/theforum/chemistry-related/997-triox...

cutefix reckons that you can use it to make RDX.

Says that you should reffer to patent no 3,937,703
enhzflep.
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quicksilver
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[*] posted on 16-4-2006 at 08:26


Thank you - Very interesting stuff; I apprieciate the tip....
I checked 3,937,703 & it appears to be a method utilizing H2SO4 for a pure RDX product but extremely low yield (what else is new for RDX, right?). However this appears to be of some value as the product is produced with less by-products as well as the use of H2SO4...could that be the thrust of the concept....so one could possibly use a mixed acid concept? The patent is broad in scope, therefore I wonder if that's it. I quote from the patent:
".....conditions for the nitrolysis of the triazine derivative with concentrated nitric acid, are known and are generally suitable for use in the present process with the exception that in the nitration step of the present process the nitric acid is contacted with the triazine intermediate without isolation of the latter from the reaction slurry in which it is formed." The full patent appears to contain trade secrects as it's generalization are similar to those containg same.
I had heard of Trioxane utilized in place of formaldehyde in several instances. And even one comparing it's structure to acetaldehyde (?).
Again we see 5 parts of nitric acid per part of reaction slurry. And I too thought initially it to be useless as what is the value of pure products with such a low yield? The name keeps cropping up and it seems not to make a great deal of sense as a subsitute in those instances. But I may be missing something about this product and it's availablity is great just now.

[Edited on 16-4-2006 by quicksilver]




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Chris The Great
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[*] posted on 16-4-2006 at 22:07


So trioxane is a trimer of formaldehyde? Why not just make hexamine with it using ammonia, then convert that to RDX using the method worked out on this forum that got great yields with small amounts of acid? Or am I missing something?
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quicksilver
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[*] posted on 17-4-2006 at 07:13


indeed: it would be an unending source of hexamine. If one buys about 5Kg for $10, there is a pretty large source of hexamine! It's just that it's already in the trimer form; seems a shame to waste that IF there is some utility there.



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[*] posted on 17-4-2006 at 12:34


When you add an acid to trioxane it releases formaldehyde gas.
This can be used to make Hexamine or Pentaerythritol, for PETN synthesis.
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[*] posted on 5-5-2006 at 08:45
trioxane formaldehyde generator


Would I need an anydrous acid? H2SO4 or would any strong acid work? Like HCl?

I am picturing using a dropping funnel to add acid into a two necked flask with Trioxane in it.
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[*] posted on 5-5-2006 at 09:29


I don't now but I think any mineral acid wil work (hydrochloric, sulfuric, nitric, phosphoric)
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[*] posted on 5-5-2006 at 10:13


It is a strong base and gentle heating which is required for depolymerization of paraformaldehyde , and I
would expect that the same applies to the trimer ,
trioxane . On what basis is it proposed that an
acid should be used for the depolymerization of trioxane ? Because acid is the catalyst for coversion
of formaldehyde to paraformaldeyde , it would seem
counterintuitive that an acid would effect the depolymerization of trioxane , giving formaldehyde
monomer as a product , but rather it would be expected
that if any conversion product occurred it would be
paraformaldehyde . My own guess is that acid will
not depolymerize trioxane , but a base like NaOH will .
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[*] posted on 5-5-2006 at 10:20


From wikipedia:
Quote:

In chemistry, it is used as a stable, easily handled source of anhydrous formaldehyde. In acidic solutions, it decomposes to generate three molecules of formaldehyde.

http://en.wikipedia.org/wiki/1%2C3%2C5-Trioxane
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[*] posted on 5-5-2006 at 11:20


A brief review of some of the references from google
gives the following information .

Trioxane has high thermal and chemical stability ,
showing little reactivity below 250C in the absence
of catalysts for its depolymerization , as some metal salts
one of which is Fe2(SO4) . With regard to solutions
there is no instability above pH 7 according to one reference , which would rule out decomposition by bases . So it would appear that perhaps acidic decomposition may indeed occur , but would need
to be done at elevated temperature where the monomer
produced would escape as gas , rather than residing
in the acidic solution where it would be cycled to
paraformaldehyde , by the same acid acting as a catalyst
for the depolymerization of the trioxane to the monomer , then acting on the monomer and repolymerizing it to paraformaldehyde .

So it looks like heat , acid , and metal salts are your
catalysts desired , and you must obtain your monomer
from the depolymerization as a gaseous product .

[Edited on 5-5-2006 by Rosco Bodine]
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[*] posted on 5-5-2006 at 13:39


Come on people, the ACS monograph on formaldehyde was nicely just provided to us recently. So it would be criminal not to read it.

[self-serving]One can see that my previous comments on formaldehyde are backed up by the book, btw.[/self-serving]
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[*] posted on 5-5-2006 at 19:39


Please Sir Whack, give link to ACS monograph on Formaldehyde, as search turned up no joy...
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[*] posted on 6-5-2006 at 08:47


Is trioxane not a interested solvent for any reactions and
can paraldehyde prepared from trioxane by chlorination or bromination ?

Some suggestion to this is maybe when trinitrotoluene and trinitromethane should synthetisized to 1(trinitromethyl)-2,4,6-trinitrobenzene ;) .

[Edited on 6-5-2006 by Madandcrazy]
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[*] posted on 6-5-2006 at 16:57


In Strikes Total Synthesis (Vol. 2, I believe), he details the depolymerization of trioxane to gaseous formaldehyde by heating the trioxane in a flask immersed in a hot-oil bath, for making Hexamethylenetetramine as a precursor for Methylamine HCl (meth precursor).

No acids or catalysts needed. :)




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[*] posted on 6-5-2006 at 17:03


Quote:
Originally posted by Eclectic
Please Sir Whack, give link to ACS monograph on Formaldehyde, as search turned up no joy...


What little I try to do here is to encourage raising the level of individual and shared knowledge here; to try to make (keep) this the best site for real knowledge (either in content or links) outside of a good library.

That said, I also feel that not holding your hand is in your best interest whether you realize it or not, so search harder in the three most likely places or don't. I'm not going to take 15 seconds to find links for you and paste them here. Others may be happy to do so. If you feel that this makes me a jackass I don't mind if you say so.

TRIOXANE AS A SOURCE OF FORMALDEHYDE

Attachment: iec_39_974_1947.pdf (487kB)
This file has been downloaded 1286 times

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[*] posted on 7-5-2006 at 15:45


Maybe a little peckish, but not a complete jackass ;-)

I had searched FTP#2, but did not think to look in the library, as you can't easily get there from the forum...

Try putting some fuel bars in a large sealed mason jar and sit it on a shelf over a lamp or on top of a water heater. Anything that will make the bottom of the jar just a degree or two warmer than the top... (experiment to be conducted by student)

[Edited on 7-5-2006 by Eclectic]
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