Sciencemadness Discussion Board

Informations about nitrosoguanidine?

Mephisto - 8-12-2002 at 02:51

Does anybody now, where I can find some detailed informations about nitrosoguanidine (except Megalomania's page)? I searched already in Urbanski's, but there are only some general informations.

disappeared "k"

Mephisto - 8-12-2002 at 02:59

Oh, I see the "k" in "know" disappeared. :D

Nick F - 8-12-2002 at 03:34

I don't have any information on it, although there is a little bit in COPAE I believe, but having made it myself a few times I might be able to tell you how it behaves.
As far as I'm concerned it's only useful as something to play with, it has little power and when pressed into a plastic straw it does detonate but the inside of the chamber I was doing it in was dusted with a thin layer of yellow nitrosoguanidine, indicating that it wasn't a complete detonation.
It is definitely fun though, just lighting off 5g or 10g piles of the stuff. It instantly turns into a big cloud of smoke with little noise, and if the air's still it forms perfect smoke rings. After I found this out I didn't do anything serious with it, I enjoyed burning it too much!

Mephisto - 8-12-2002 at 04:19

Nick F: Thank you for your help! Actually I haven't heard antyhing about COPAE.

I also search for informations like sensitivity, explosive velocity, ...

Reference - 18-7-2010 at 02:18

I looked at the synthesis and it seems to basically make Nitrosoguanidine
by reducing nitroguanidine. Not much of a stretch to understand, until you realize that what is called "Nitroguanidine" is actually really N-methyl-N'-nitro-N-nitrosoguanidine.

"Prepare a mixture of 21 g of nitroguanidine, 11 g of ammonium chloride, 18 g of zinc dust, and 250 mL of water in an 800-mL beaker. Cool this mixture in a salt-ice bath and keep the temperature between 20-25 °C while stirring with a magnetic stirrer. After 2 hours of stirring the gray color of the zinc should have disappeared and the mixture should now be yellowish, cool the mixture to 0 °C or lower with the salt-ice bath. Filter the mixture to collect the nitrosoguanidine."

Could someone please tell me how this reaction works? Where does the methyl group come from? How does a guanidine with one nitro, end up with both a nitro and another nitroso?

I found this too:
"I made N-methyl-N-nitroso urea but I've no idea about the mechanism!
I've attached the first step (I hope the pic is attached!), which involves urea reacting with methylamine in aqueous acidic solution. I know methylamine is a pretty good nucleophile, but does it attack urea?
I reacted the product of that step with sodium nitrite in H2SO4 at -5 degrees Celcius." at
Maybe methylamine is also involved in making "nitrosoguanidine" but the author forgot to include it?
Maybe I could make monomethylhydrazine by further reducing the I made N-methyl-N-nitroso urea, and breaking off the urea (by adding a NaOH).

Taoiseach - 18-7-2010 at 21:58

I tried this procedure some time ago and almost no nitrosoguanidine precipated.

mnick12 - 19-7-2010 at 12:01

Here is one from the library

"Preparation of Nitrosoguanidine.25 Twenty-one grams of nitroguanidine,
11 grams of ammonium chloride, 18 grams of zinc dust, and
250 cc. of water in an 800-cc. beaker are stirred together mechanically
while external cooling is applied to prevent the temperature from rising
above 20-25°. After 2 hours or so the gray color of the zinc disappears,
the mixture is yellow, and on settling shows no crystals of nitroguanidine.
The mixture is then cooled to 0° or below by surrounding the
beaker with a mixture of cracked ice and salt; it is filtered, and the
nitrate is discarded. The yellow residue, consisting of nitrosoguanidine
mixed with zinc oxide or hydroxide and basic zinc chloride, is extracted
with 4 successive portions of 250 oc. each of water at 65°. The combined
extracts, allowed to stand over night at 0°, deposit nitrosoguanidine
which is collected, rinsed with water, and dried at 40°. Yield
8.0-9.2 grams, 45-52% of the theory.
The flashlessness of nitrosoguanidine may be demonstrated safely by
igniting about 0.5 gram of it on the back of the hand. The experiment
is most striking if carried out in a darkened room. The sample being
poured out in a conical heap on the back of the left hand, a match
held in the right hand is scratched and allowed to burn until the mateas
Davis and Rosenquist, /. Am. Chem. Soc, 59, 2114 (1937).
rial which composes the burnt head of the match has become thoroughly
heated, it is extinguished by shaking, and the burnt head is
then touched to the heap of nitrosoguanidme. The nitrosoguanidine
explodes with a zishmg sound and with a cloud of gray smoke, but
with no visible flash whatsoever. The place on the hand where the
nitrosoguanidme was fired will perhaps itch slightly, and the next day
will perhaps show a slight rash and peeling of the skin There is no
sensation of being burned, and the explosion is so rapid that the hand
remains steady and makes no reflex movement."

there you go

Hoveland - 30-7-2010 at 13:43

Could someone please help me. What is the formula for "nitroguanidine"? I have seen it in various places as either
NH2C(NH)NHNO or as NO2NHC(NH)N(NO)CH3. I am very confused. The first of these structures does not appear like it would be stable, as I do not think any primary nitrosamines exist. Possibly the "nitrosamine" might really be a
If the second structure is the correct one, I do not see where that extra methyl group could have come from, as the synthesis I read seemed like it would only reduce the nitro. Also, if a nitramine group remains, where did the nitrosamine come from? Another molecule that go hydrolyzed apart?

Are there two different "types" of nitroguanidine that have gotten confused together?

[Edited on 30-7-2010 by Hoveland]

hissingnoise - 30-7-2010 at 15:11

Are there two different "types" of nitroguanidine that have gotten confused together?

These compounds differ, as might be expected, by one oxygen - NH2-C(NH)-NH-NO2 and NH2-C(NH)-NH-NO