Sciencemadness Discussion Board

glycerol triazide

halogen - 16-5-2004 at 04:02

Well? If glycerol trinitrate can be made, cant the azide?
(CH2NO2)2CHNO2
(CH2N3)2CHN3
Due to the products of decomposition, id say thered be a fireball if it blew but the (predicted by me) instability would make it impractical.
What would you say-- And how can you make it?

vulture - 16-5-2004 at 07:46

Glyceroltrinitrate is an ester of nitric acid, the O that binds the NO2 to the carbon skeleton is from glycerine itself and not nitric acid.

Therefore one would get a O-N3 bond which is extremely unstable IMHO.

Furthermore, start taking more care of your posts! They're a pain to read!

Pyrovus - 21-5-2004 at 22:33

Perhaps the azide could be made by some kind of dispacement reaction, like something along these lines:
CH2(Cl)CH(Cl)CH2(Cl) + 3AgN3 -> CH2(N3)CH(N3)CH2(N3) + 3AgCl?

Theoretic - 26-5-2004 at 04:02

You wouldn't get a O-N3 bond, as a hydroxide group would be taken off the glycerine, a hydrogen atom off the HN3 (if that's what you use) and the azide would be directly linked to the carbon skeleton.

halogen - 8-7-2004 at 14:56

Thank you.
But I still have no idea if it even exists.
Or its properties for that matter.

If it were to explode in an environment with no O2, there would be a lot of organic resdue, right?
So oil might possibly be created.
(mmm!)

Nick F - 8-7-2004 at 15:22

I can think of easier ways to get oil...

Theoretic - 9-7-2004 at 06:29

I think that if glycerol triazide was slowly decomposed, you would get the propynyl C3H5 radical, which would dimerise into C6H10, hexyne. The triazide itself could be made from hydrazoic acid (nice) - aqueous solution of course - and glycerol. Or, alternatively, from glycerol trihydrogensulfate (from glycerol and sulfur trioxide) or trichloride (from glycerol and hydrogen chloride) and an azide salt.
Why wouldn't it exist? I don't see a reason.

halogen - 24-7-2004 at 06:50

too unstable, maybe?
It's just that I'd never heard of it.

Dany - 4-11-2013 at 14:07

1,2,3-Triazidopropane can be prepared from glycerol. First glycerol is phenylsulfonated (so to form a good leaving group) than the sulfonated product is subjected to an S2N reaction with NaN3.

The azide, is very sensitive to external stimuli as stated in [1], however, 1,2,3-Triazidopropane is a useful starting materials for the synthesis of more interesting energetic materials such as the 1,2,3-Trinitraminopropane, for more information, see my post:

http://www.sciencemadness.org/talk/viewthread.php?tid=26459

in the attached [1] file you will find the procedure for the synthesis of 1,2,3-Triazidopropane published in 1998 (A. Zimmer, I. Müller, G. J. Reiß, A. Caneschi, D. Gatteschi and K. Hegetschweiler, Eur. J. Inong. Chem., 1998, 2079). However the oldest reference for the synthesis of 1,2,3-Triazidopropane date back to 1985 (Owston, Philip G.; Peters, Roger; Tasker, Peter A. Journal of Chemical Research, Miniprint, 1985, 11, 3686-3694).

Dany.

Attachment: [1].pdf (169kB)
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[Edited on 4-11-2013 by Dany]

halogen - 5-11-2013 at 14:26

I started this thread long ago, but thank you Dany! I hope you've had fun searching through the depths of the forum.

Fantasma4500 - 6-11-2013 at 10:09

TCCA (TriChloroisoCyanuric Acid) i have been told can be made into an azide of some sort, if this has any interest i could attempt to get some references on it..

on glycerol i recall reading a thread on SM about perchlorate salts where glycerol perchlorate was synthesised, it was about hexamine di perchlorate..
the glycerol compound had similar properties as in chemistry as picric acid, a potassium salt was made by neutralizing it with potassium carbonate

before this will be taken as being too far off topic: relation i see is energetic glycerol compound, and energetic atypical azide (: