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Author: Subject: Hydroxylamine or Methylamine?

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[*] posted on 8-2-2017 at 05:04
Hydroxylamine or Methylamine?

If Nitroethane is condensed with Acetic Acid & HCl this would yield what? I know that a good starting product for the preparation of Hydroxylamine is Nitromethane, but I don't know exactly if Nitroethane is used. Methylamine might be favored?

[Edited on 8-2-2017 by ronstark]
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[*] posted on 8-2-2017 at 06:05

I'm pretty sure you'd still get hydroxylamine. I know for certain that methylamine would not be formed.

As below, so above.
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[*] posted on 8-2-2017 at 06:28

With the nitroalkane + HCl method you will always get hydroxylamine and the corresponding carboxylic acid.

Nitromethane and HCl yield hydroxylamine and formic acid
Nitroethane and HCl yield hydroxylamine and acetic acid

I don't think adding acetic acid to the mix is going to do anything. In fact, here is a patent that shows that you can do the same reaction and substitute a carboxylic acid for the HCl:

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[*] posted on 8-2-2017 at 13:59

Definitely don't waste your nitroethane on this. It's getting harder and harder to find.

If you want methylamine, do reformation of sulfamic acid.

Chemplayer did a couple videos on this.

[Edited on 2/8/17 by PirateDocBrown]
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PHILOU Zrealone
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[*] posted on 9-2-2017 at 19:46

If you use Zn/HCl, Fe/HCl or Sn/HCl (or SnCl2/HCl) you will end up with methylamonium or ethylamonium hydrochloride starting from nitrometane or nitroethane respectively.

PH Z (PHILOU Zrealone)

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[*] posted on 11-2-2017 at 14:59

Easiest way by far is aluminum reduction of nitromethane. If you're a fan of the classic Al/Hg reduction, where you add mercury salt to a stirring flask of water with aluminum pieces in it, I've developed a variant of that preparation that uses gallium and indium salts, but for reducing nitromethane, alloying them beforehand (96% Al, 3% Ga, 1% In) is definitely an easier way to go about it.

[Edited on 2/11/17 by Melgar]
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