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madscientist
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OC(NN)2CO
I would think that OC(NN)2CO would be an excellent energetic material. It would have the following structure:
O=C(N=N)2C=O
I think the best route to preparing it would be adding liquid bromine to urea, or passing chlorine gas over urea. I tried something else today,
however. I mixed six grams of CO(NH2)2 and seven grams of Ca(OCl)2. I retreated indoors for fear that phosgene (COCl2) might be liberated. I returned
outside ten minutes later to find an off-white mass that had clearly been molten, giving off large volumes of gas, and then had solidified. I added
10mL of water, and it foamed a little. More tales of my pursuit of OC(NN)2CO are surely on the way.
I weep at the sight of flaming acetic anhydride.
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madscientist
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Here's the equations.
2CO(NH2)2 + 2Ca(OCl)2 ----> OC(NN)2CO + 4H2O + 2CaCl2
2CO(NH2)2 + 4Br2 ----> 2CO(NHBr)2 + 4HBr ----> OC(NN)2CO + 8HBr
2CO(NH2)2 + 4Cl2 ----> 2CO(NHCl2 + 4HCl ----> OC(NN)2CO + 8HCl
I weep at the sight of flaming acetic anhydride.
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madscientist
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I am getting very angry about not being able to edit posts!
I just realized that I made a goof when typing up the first equation. It should be:
2CO(NH2)2 + 4Ca(OCl)2 ----> OC(NN)2CO + 4H2O + 4CaCl2
I am now strongly suspecting that phosgene may have been liberated. Noone try this unless you really think you are ready to deal with phosgene, I
don't want anyone killing themselves. I'll try to resolve this myself.  Does
anyone have any particularily brilliant idea for detecting phosgene? This is how it could be formed.
2CO(NH2)2 + 4Ca(OCl)2 ----> 2COCl2 + 2CaOCl2 + 2Ca(OH)2 + 2N2 + 2H2O
That theory was backed up by my heating of some of the white solid with my lighter. It fizzled slowly, and I could smell chlorine.
If I get around to it, I'll put some insects in a flask, mix urea and calcium hypochlorite in another, put a tube in a rubber stopper and jam it in
the mouth of the flask with the chemicals, then put the other end of the tube in the flask containing insects. Then I'll back way the hell off - I
don't want to suffer the fate that the insects will probably face.
I weep at the sight of flaming acetic anhydride.
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madscientist
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Argh! Another brain fart! My correction on the equation that I thought for a moment was unbalanced but actually was balanced was incorrect! The
original equation WAS balanced.
I must figure out what is wrong with the board software.
I weep at the sight of flaming acetic anhydride.
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Ramiel
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Test for phosgene
No, the insect one wouldn't work...
Insects generally have different respiratory systems to mammals, they have pores on thier exosceletons i believe, which allows them to breathe. So if
you wanted to test for phosgene; you would have to use a mammal. Or you could inhale it... if you get red and yellow angry blisters on your trachea,
followed by coughing fits and bleeding lungs, it's probably only chlorine...
I would strongly suggest investing in one of these phosgene dosometers if you are
serious about that experiment.
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madscientist
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Here's the best idea for a phosgene test that I have so far. I'll pass the produced through a metal tube that is being heated by a propane burner. If
a yellowish gas is emitted from the tube, then it'll be clear this is happening.
COCl2 ----> CO + Cl2
I weep at the sight of flaming acetic anhydride.
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Rhadon
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The phosgene test-papers are based on a reaction of phosgene with 4-(dimethylamino)benzaldehyde and either diethyl-, dimethyl- or diphenylamine. If
phosgene is present, the color changes to orange.
Another test would be detecting the characteristic (foul, sweetish) smell in the air. Phosgene can already be smelled in very low concentrations, but
only in concentrations in which it is toxic. Tough, I doubt that you'll be able to do tests with it without even getting a little bit of it into your
nose (unless you wear a mask).
According to "The War Gases Chemistry and Analysis", one single ml of gaseous phosgene placed in a 500 ml flask that it filled with ordinary air can
still be smelled after 15 days (this was to test how fast phosgene's hydrolysis takes place). And if they were able to notice the smelled of phosgene,
they must have smelled it, presumably without taking harm from it. Anyway, I didn't want to try that.
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madscientist
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I'm fairly convinced that the reaction between 6g of urea and 7g of calcium hypochlorite is producing phosgene. I did another experiment with it
today. I mixed 6g of urea with 7g of calcium hypochlorite in a flask, and quickly stoppered it with a rubber stopper that had a thin rubber tube
running through it. I placed the other end of the tube in a flask that was in a salt/ice bath. I then backed way the hell off. After about thirty
seconds the reaction began at a visible rate, and rapidly accelerated. The reaction flask and the condensation flask quickly filled up with a white
gas. The white gas was almost immediately pouring out of the condensation flask and running along the ground - to be expected, considering that the
condensation flask was only 250mL. I waited until all traces of the whitish gas were no longer to be seen before approaching the setup. I took a deep
breath, then marched forward and dropped an ant into the condensation vessel (there was maybe 2mL of liquid in it). The ant flailed around for a short
period of time, then curled up and died.
I weep at the sight of flaming acetic anhydride.
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raistlin
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Is it possible that it did of more less drowning?
\"To ignite, or not to ignite, that is the question.\"
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raistlin
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I had meant to say "Is it possible that it could have died of drowning?"
\"To ignite, or not to ignite, that is the question.\"
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madscientist
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Nope, the ant never came in contact with the liquid while it was alive. In a 250mL flask, 2mL of a liquid is not going to appear to be that much. I
tilted the flask, and tossed the ant in, which seemed to be flailing wildly trying to avoid sliding into the liquid immediately before it died.
I weep at the sight of flaming acetic anhydride.
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Ramiel
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New Venture?
You could very well start up a new buisiness venture by the sounds of things...
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Rhadon
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| Quote: | | Is it possible that it could have died of drowning? |
As far is I know, all animals are able to swim, except for monkeys (and humans). At least in water. And even if it sinks beneath the surface of the
liquid, it should take a significant time for the animal to die from mere lack of oxygen.
Madscientist, perhaps this reaction will serve you as a test for phosgene:
in acetone solution
COCl2 + 2 NaI --> CO + I2 + 2 NaCl
Thus, leading that gas through a solution of sodium iodide in acetone should tell you whether it is phosgene or not.
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raistlin
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No, it would only take a few seconds for an ant to die of drowning, because of the fact that they breath constantly throught small, pore-like openings
on the sides of their body. I would think that if it was submerged for only a matter of a few seconds, the ants respiration would cease... The way
Madscientist worded it made me think that it had actually been placed into the liquid.
Raistlin
\"To ignite, or not to ignite, that is the question.\"
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Rhadon
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Ants have no lungs, but they do have blood. So if there is no access to oxygen from the atmosphere, there will still be some dissolved in the blood.
When ants are in their "homes" down in the earth, they aren't supplied with oxygen as well as above the surface. I suppose that they are adapted to
this and have low needs of oxygen.
| Quote: | | No, it would only take a few seconds for an ant to die of drowning (...) |
This is not the case, perhaps because their brains are less easily affected by lack of oxygen than that of mammals. Here
is what someone found out when experimenting with drowning them.
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madscientist
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Another possibility:
2CO(NH2)2 + Ca(OCl)2 ----> CaCl2 + 2N2H4 + 2CO2
I weep at the sight of flaming acetic anhydride.
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Madog
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today i gassed an ant with Chlorine. it took under a second and it was on its back curled up.
Most people outgrow their pyro tendencies, we are the ones who\'s tendencies outgrew us.
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Rhadon
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Perhaps the experiments should be carried out on more resistant animals - such as spiders (they're nasty anyway, it doesn't matter if there are some
less...). They may be harder to find than ants, but it might be worth the effort.
I once caught a relatively large one, placed it in a marmalade jar that had two holes in the lid. In one, there was introduced a pipe that served for
inducing different substances.
I started with NH3 gas. The spider took notice of it, but wasn't too affected. Next was (liquid) acrolein, which didn't seem to harm it at all
(perhaps it was already too pampered with NH3  ). This surprised me somewhat, since
the affect of acrolein on humans is significantly higher than that of NH3. Anyway, I continued my experiments with chlorine. The spider got quite
agile in contact with it, but this state didn't last long - after some seconds it died, bot not instantly.
Does anyone know what kind of respiration spiders have? Perhaps they are suitable for tests on phosgene, but I'm afraid they're not.
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Madog
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the Cl made it high?!!?!
that is crazy. i cant believe the damn thing lived. well, im not realy into cruely killing animals so im not gona do any tests.
Most people outgrow their pyro tendencies, we are the ones who\'s tendencies outgrew us.
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Rhadon
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Perhaps what I said wasn't clear. I wanted to say:
The Cl2 made it run in its glass for a short time, until it died.
Well, usually I'm also not the guy for cruel tests on animals, with the exception of spiders.
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Ramiel
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...Nothing wrong with spiders
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Madog
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i probaly wouldnt do it on anything other than a worm, ant, or small insects. i think spiders are cool. i would never do it on a mamal, thats just
sick
Most people outgrow their pyro tendencies, we are the ones who\'s tendencies outgrew us.
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PHILOU Zrealone
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Indeed MadScientist, there is a patented process to make hydrazine from urea and hypochlorite!
The reaction is something like:
NH2-CO-NH2 + NaOCl --> NaCl + NH2-CO2-NH2 --> NaCl + NH2-NH2 + CO2
But things are not so simple and another reaction happens immediately between the hydrazine and the NaOCl
NH2-NH2 + 2NaOCl --> 2NaCl + N2 + 2H2O.
There is some ways to get to tetraazacyclohexane but they are very much more difficult than what you propose...as you had the impression the compound
is quite unstable and goes fast into decomposition products...reactants are critical and may catalyse decomposition!
2NH2-NH2 + 2Cl2C=O --> O=C(NH-NH)2C=O + 4HCl + linear polymers
O=C(NH-NH)2C=O mild oxydation --> O=C(N=N)2C=O + 2H2O
Cl2C=O may form carbonic esters with alcohols!
It will free I2 from NaI; but Cl2 will aswel do such reaction.
Cl-CO2H may be a good way too with hydrazine; CI2Cl2 may be also good!
PH Z
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Boob Raider
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Well
Madscientst ..... if urea is treated with a hypochlorite ...... N2H4, CO2 and NaCl are the major products like Philou said. Although if you want to
use this as a method of N2H4 prep. .... you need to add a viscolizer (gelling agent) like starch, agar, gelatine or even glycerol to protect the N2H4
from the free OCl-. Agar and gelatine seem to be most effictive.
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Marvin
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Rather wanting to avoid phosgene, Ive found an alternative to PH Z's method.
The cyclic compound O=C(NH-NH)2C=O is called p-urazine, which might help anyone searching for information.
It can be obtained in good yeild by semicarbazide + hypobromite (and presumably hypochlorite, but it doesnt say). Unfortunatly I dont know the
conditions it works well at, I do know the conditions it doesnt work at becuase it produces hydrazodicarbonamide instead.
The references for making p-urazine are, I think,
Linch, F. W. Proc. Chem. Soc. 28,144
J. Chem. Soc. 101, 1755-8 (1912)
C. A. 7, 591 (9)
With some luck someone will have access to these. Making semicarbazide can probably be done directly from chloramine and urea.
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