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Precipitates
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[*] posted on 24-5-2024 at 20:43


Quote: Originally posted by Yorty2040  
Does anyone have any information on melamine diperchlorate? Solubility, handling, decomposition temp, sensitivity, shelf life, etc?


I could only really find this article on Melamine Diperchlorate Hydrate.

I assume reasonable solubility, not ridiculously sensitive and relatively stable.

[Edited on 25-5-2024 by Precipitates]
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dettoo456
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[*] posted on 28-5-2024 at 08:08


Has anyone carried out a destructive nitration procedure on a ketone before? I couldn’t find much information on them; it seems Russian chemists were messing around with the principles and kinetics in the mid 90s, but those journal entries are very hard to find, let alone translate.

As far as I can tell, it’s basically the same conditions as for the preparation of Nitroform from Acetone (or from the dehydration of IPA and subsequent nitration). Carbonyls, mainly ketones but apparently carboxylic acids as well, undergo decarboxylative nitration to yield the trinitromethyl or dinitromethyl derivative at the alpha position relative to the carbonyl.

This polynitromethyl product though, can be generated by the action of WFNA/H2SO4 with the ketone at 0C, and Hexanitroethane can even be prepared like this in up to a 75% yield from the terminal-trinitro ketone (authors reported using trinitropentanone, though I believe this was a mistake, and trinitrobutanone might have been used instead).

https://www.researchgate.net/publication/250556009_ChemInfor...

This abstract does not provide much insight as to the conditions (molar equivalent, addition rate, extraction), and I couldn’t find the article in the Russian Org Chem journal.

In short, is it plausible that this reaction could be applied to something like MEK, to yield 1,1,1-trinitroethane?
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Yorty2040
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[*] posted on 14-6-2024 at 17:44


So methazonic acid (2-nitroacetaldoxime) can be produced by the base-catalyzed self-condensation of nitromethane, followed by acid workup.

Is there any info on using sodium perborate + glacial AcOH to convert it to 1,2-dinitroethane? The procedure should work, but the devil (and yield) is in the details of the procedure and subsequent workup.
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dettoo456
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[*] posted on 14-6-2024 at 20:14


I’m assuming you’re referencing this paper (linked below) for the oxidation with perborate. As you mentioned though, the preparation will suffer in yields with the scope being so wide (small chain aldoxime already with a nitro substitutient compared to mainly aryl ketoximes reported being used).

A more sketchy method to yield 1,1,2-TRInitroethane could be the ponzio reaction; NO2 or N2O4 in ether or a suitable polar nonprotic at low temperature).

Or, some other, cleaner oxidizer like oxone or H2O2. Though, in any case, including the Perborate/GAA method, oxidation of the aldehyde to carboxylic acid and oxime to carbonyl is probably the reason for such low reported yields.

[Edited on 15-6-2024 by dettoo456]

Attachment: Oxime Oxidation to NO2.pdf (159kB)
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Yorty2040
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[*] posted on 17-6-2024 at 16:22


What's the technical, physicochemical explanation for why complexing the oxoacid salt of a nitrogenous base with a transition metal typically increases sensitivity compared to the uncomplexated salt?

[Edited on 18-6-2024 by Yorty2040]
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