Nitro propanol dinitramine??

[BrendanK]

Has anyone tried nitrating 1,3-diamino-2-propanol before? I am now searching for chemical suppliers who supply such chemical compounds, well, hopefully it's cheap enough for me to do some research. I am still having some doubt in its sensitivity, since it has two primary amino groups and an ether group.
Well, I might be wrong. The nitrated chemical compound may have:

O2N-NH-CH2-CHONO2-CH2-NH-NO2


Hey, if I'm wrong ... Plz don't ban me.

[vulture]

I am still having some doubt in its sensitivity, since it has two primary amino groups and an ether group.

I'm not following you here. There is no ether group in 1,3-diamino-2-propanol. Only 2 amine functions and a hydroxy (alcohol) function.

As for the nitration, I don't know, haven't tried. Predicting how such amines will react to nitrations is dangerous, so I won't make any wild guesses.

[simply RED]

Before doing something ask yourself : Why?
There si no sense in nitrating this, you will get unstable product and the "nitration" will be extremely difficult. Such chemicals are not synthesed by direct nitration.
(Exception O2N-O-CH2-CH2-NNO2-CH2-CH2-O-NO2 but it is also synthesed by catalytical nitration - ZnCl2 cat.)
See MEDINA.

CH3-CO-NH-CH2-NH-CO-CH3 + HNO3 (Acetic ANH) = NO2NH-CH2-NHNO2 + 2CH3-COOH

See also EDNA...

[Hystrix]

BrendanK:
I've looked for this stuff. Its mp 164-165 deg. C. (dec), ignites at 230 deg. C. There are two links - look US patents 2,065,113 and 2,485,855 (sorry but I can't try them now, I have to go).

[BrendanK]

Well, has anyone tried nitrating acetone? It forms yellow to brown precipitate which is plastic and sticks like glue. I think it probably undergoes this reaction:


CH3-CO-CH3 + H+ + H2O --> CH3-C(OH)2-CH3
CH3-C(OH)2-CH3 + HNO3 --> CH3-C(ONO2)2-CH3

Because it's plastic, I have problem in drying it... Probably hygroscopic.
I placed it into a small metal tube (obtained from a radio antenna) , sealed both end and heated the whole tube... Kaboom...

[blindreeper]

http://www.sciencemadness.org/talk/viewthread.php?tid=28

That may help but not sure if its what your after...

[BrendanK]

Thanks blindreeper. But why didn't anyone try (I mean discuss about dinitroacetone) it in this forum(from my search using keyword "Dinitroacetone"). I think it's quite " an explosive" to be made, though, it almost detonated while nitration, years ago when the temperature of the mix got as high as <110ºC ... Puffs.... I should have removed the layer of explosive produced on the top as it gets thicker...

[Jacks Complete]

Originally posted by BrendanK
I think it's quite " an explosive" to be made, though, it almost detonated while nitration, years ago when the temperature of the mix got as high as <110ºC ... Puffs.... I should have removed the layer of explosive produced on the top as it gets thicker...

Can you post up the procedure you used? Give it some detail - what concentrations of chemicals did you use, glassware used, etc. so we can have a look and see if we can follow your work? Also, if you have photos and results from your dinitroacetone synthesis, include them. What sort of sensitivity was the DiNitroAcetone (DNA? :D )? Include any lessons learned, like removing some of the products as they formed.

Ta.

[Hystrix]

Originally posted by BrendanK
Well, has anyone tried nitrating acetone? It forms yellow to brown precipitate which is plastic and sticks like glue. I think it probably undergoes this reaction:


CH3-CO-CH3 + H+ + H2O --> CH3-C(OH)2-CH3
CH3-C(OH)2-CH3 + HNO3 --> CH3-C(ONO2)2-CH3
--------
...But why didn't anyone try (I mean discuss about dinitroacetone) it in this forum(from my search using keyword "Dinitroacetone").

You won't obtain 1.3-dinitroacetone via direct nitration of acetone. As for nitroacetone, it's an intermediate product in nitration process but the methylene group in its molecule (ch3-co-CH2-no2) will be activated (by NO2 and CO). Thus it'll be immediately nitrated to 1,1,1-trinitroacetone and then hydrolysed to acetic acid and nitroform (but that's correct only for nitration with pure NA).
CH3-C(ONO2)2-CH3 - not a chance.
Mononitroacetone can be produced according to this scheme:
CH3CHO + CH3NO2 -----> CH3-CH(OH)-CH2-NO2 ----(oxidation)---> CH3-CO-CH2-NO2.
That orange stuff... What nitrating agent was used?

[BrendanK]

I used sulphuric acid (98%) 100ml with nitric acid (95%) 75ml in a 500ml beaker. Just as the acid mix reaches 60ºC-70ºC (heat given out while mixing the acid), start adding acetone (50ml) from a dropper, slowly. If the mixture gets too hot, use an ice bath, maintain the temp between 60ºC-70ºC... not below 40ºC because.... the reaction will stop or slow down (not very sure about the reaction). As the thing reacts, brown gas (NO2) was released ( not sure about my procedure... maybe some wrong way or something went wrong). A layer of brown to yellow foam formed and should be collected as the addition of acetone continues (with a glass rod)... Because I had an experience.... A 5 mm of this foam blew up while nitration... The foam will then solidify and turned into a sticky brown-yellow plastic... I brought a few mg of that to a flame... It burned with bright, blinding flame (pop)... What is that, Hystrix ??