I wonder if I am the only one who have ever got this idea. It may be possible to make nitramine by removal of one water molecule from AN, but as we
know, further dehydration would give nitrous oxide. This would mean an easy way to nitramine, if this partial dehydration is possible.
Is this just my "brain fart", or a possible reaction?
What catalysts should be used?
Let's discuss. Wanna hear your opinions on this.
[Edited on 15-2-2012 by Adas]Pulverulescent - 15-2-2012 at 16:31
Quote:
Is this just my "brain fart", or a possible reaction?
Nitramide, NH<sub>2</sub>NO<sub>2</sub> is formed by dehydration by
H<sub>2</sub>SO<sub>4</sub> of NH<sub>4</sub>NO<sub>3</sub>!
It is unstable and, AFAIK, has not been isolated . . .
Even "Crystals suitable for an X-ray crystallographic study
were grown by vacuum sublimation at room temperature."
It has zero practical value due to its instability (except maybe for some synthesis).Adas - 16-2-2012 at 00:46
Thanks, guys. I don't really need to isolate it, but I would like to try condensing it with urea. I have both AN and urea, but no sulfuric acid.Pulverulescent - 16-2-2012 at 01:56
Russians published quite easy synthesis of nitramide via hydrolysis of dinitrourea:
Preparation of nitramide from urea. Oleum
(20% of SO3), 35 g, was added to 35 g of nitric acid
(d = 1.5 g/cm3), and 10 g (0.1667 mol) of urea was
added in portions at -5 to 0°C under continuous stirring.
The mixture was stirred for 40 min at 0 to 5°C
and poured while stirring into 300 g of an ice-water
mixture, maintaining the temperature below 10°C. The
mixture was extracted with ethyl acetate (2x100 ml
and 4x50 ml), and the extract was washed with water
(3x40 ml), kept for 2 h at 20°C, and evaporated to
dryness under reduced pressure. Yield 15.5 g (75%).
The product was dissolved in 30 ml of ether, the
solution was poured into 400 ml of hexane, and the
precipitate was filtered off. Additional recrystallization
from dichloroethane-2-propanol (9 : 1) gave 13 g
(63%) of nitramide with mp 78°C. UV spectrum
(H2O): lmax = 206 nm, e = 7600 l mol-1 cm-1.
(from Russian Journal of Organic Chemistry, Vol. 38, No. 1, 2002, pp. 136. which is translated from Zhurnal Organicheskoi Khimii, Vol. 38, No. 1,
2002, pp. 11316.)
The problem for most people will be fuming NA and oleum for dinitrourea synthesis. What do you think you'll prepare from nitramide and urea ?
[Edited on 16-2-2012 by Maniak]Adas - 16-2-2012 at 06:34
