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Author: Subject: Sodium methylenenitronate isolation
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[*] posted on 23-2-2016 at 09:59
Sodium methylenenitronate isolation


Hi, I'm wondering if there's any way to dry and store sodium methylenenitronate.
It's easy to obtain it in anhydrous conditions (I used NaOH in MeOH because I don't have at the moment soidum methoxide or ethoxide), but it turns dark brown even sealed in an Eppendorf wet with nitromethane.
It's possible to dry it completely without oxidation? Any ideas apart from vacuum?

Thank you.
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PHILOU Zrealone
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[*] posted on 25-2-2016 at 08:14


It is methyl-nitronate and not methylene-nitronate!

How do you know for sure your NaOH, MeOH and NM are anhydrous?
To me seems very difficult to get an anhydrous media...since both involved reactions induces water formation:
NaOH + CH3-OH <==--> Na-O-CH3 + H2O
NaOH + CH3-NO2 <==> Na-O-N(O)=CH2 + H2O

If you use the search engine of the forum with as keyword "nitronate" you should find the answer to your question...
The best is to use plain Na or basic materials NaOMe, NaOEt, NaCH3 (or other light MW alcanic derivatives)...the last is probably the best since the product of acido-basic reaction leads to a gaseous product leaving the reaction media...
CH3-NO2 + Na-CH3 --> Na-O-N(O)=CH2 + CH4(g)
Beware for explosion from the sensitive salt and gaseous flamable methane.

In the same spirit, you may succeed by using Na-C#C-Na...
2 CH3-NO2 + Na-C#C-Na --> 2 Na-O-N(O)=CH2 + H-C#C-H (g)
Beware for explosion from the sensitive salt and gaseous flamable ethyne (acetylen).

[Edited on 25-2-2016 by PHILOU Zrealone]




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[*] posted on 27-2-2016 at 12:59


Thank you for your answer PHILOU! I'll give it another try when I get NaOMe.
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[*] posted on 27-2-2016 at 14:28


Quote: Originally posted by PHILOU Zrealone  

The best is to use plain Na or basic materials NaOMe, NaOEt, NaCH3 (or other light MW alcanic derivatives)...the last is probably the best since the product of acido-basic reaction leads to a gaseous product leaving the reaction media...
CH3-NO2 + Na-CH3 --> Na-O-N(O)=CH2 + CH4(g)
Beware for explosion from the sensitive salt and gaseous flamable methane.


I would beware the explosion from the pyrophoric methylsodium, myself. Sodium alkoxides would work just fine.




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[*] posted on 6-3-2016 at 12:06


If you are searching the older literature, which has lots of really interesting chemistry for this compound, try searching for methazonic acid.

There are also several detailed preparation under this name too for both the salt and the free acid, neither is stable but the free acid has some amazing chemistry. It is, along with fulminic acid, one of the organic alchemists, that is a compound capable of "transmuting" simple molecules into a breathtaking array of new and fascinating compounds as they introduce similtaneously C, N and O.
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[*] posted on 6-3-2016 at 19:00


Hello, I have made sodium nitro-methanate in my video on nitromethane by reaction of sodium ethoxide in ethanol with nitromethane. I've also made it with sodium hydroxide in ethanol. Both times the solid turned brown after a few days open to the air however I did not really try to stop this (I had no intention of storage) but I believe that ethoxide produced nitromethanate will take a while to turn brown if washed well with an anhydrous solvent and stored in a desiccator.
How long is a while? I don't quite know, but a few weeks seems obtainable, to me given how slowly it turned while open to the air (a day or two, so we're not talking rapid water instability here). Some explosives just don't have a great shelf life.

And yes, I do prefer sodium nitromethanate than sodium methyl nitronate, but only just. It really was a 50/50 decision which term to use in the video and now i've used one I might as well stick to it until someone gives me a reason why it's wrong.
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[*] posted on 7-3-2016 at 08:11


Quote: Originally posted by Tdep  
Hello, I have made sodium nitro-methanate in my video on nitromethane by reaction of sodium ethoxide in ethanol with nitromethane. I've also made it with sodium hydroxide in ethanol. Both times the solid turned brown after a few days open to the air however I did not really try to stop this (I had no intention of storage) but I believe that ethoxide produced nitromethanate will take a while to turn brown if washed well with an anhydrous solvent and stored in a desiccator.
How long is a while? I don't quite know, but a few weeks seems obtainable, to me given how slowly it turned while open to the air (a day or two, so we're not talking rapid water instability here). Some explosives just don't have a great shelf life.

And yes, I do prefer sodium nitromethanate than sodium methyl nitronate, but only just. It really was a 50/50 decision which term to use in the video and now i've used one I might as well stick to it until someone gives me a reason why it's wrong.

Nice video and experiments!
And yes your face-shield is hot ;)




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