Endo
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Ethyl amine from Acetonitrile
I have come across two ways to reduce a nitrile to its corrisponding primary amine. Using Lithium Aluminum Hydride in ether or using Hydrogen at high
pressure over nickle, platinum or palladium catalysts.
Is there any acid catalyzed way to reduce a nitrile to it's corrisponding primary amine?
I noticed in the energetic materials section there was a synth using Acetonitrile with a catalytic amount of conc H2SO4 at refux as an intermediate
step to react with formaldehyde to form hexamine. Would it be possible to setup an acid catalyzed reduction of acetonitrile and somehow isolate
ethylamine from the reaction?
Thanks
Endo
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Nick F
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Acid catalysis will tend to result in acetic acid. After protonation of the nitrogen, you'll still need some source of hydride to attack the nitrile
carbon in order to get ethylamine. If you do it in aqueous solution, the nitrogen will be protonated, water will attack the carbon, --> -->
acetic acid, with loss of ammonia, which will form a salt with the acid. I suspect that this is happening in that hexamine synthesis.
It might be possible with an amalgam reduction, a dissolving metal reduction eg zinc in HCl might still give you problems with acetic acid formation.
Maybe electrolytic reduction could do it?
Must you use acetonitrile? Acetaldehyde with ammonia and Al/Hg probably wouldn't give a terrible yield, and the ethylamine would at least be easy to
seperate. Or ethyl chloride can be made with ethanol, conc. HCl and a lewis acid such as ZnCl2 (~ 70% if done well), then carefully reacting this with
ammonia would also give ethylamine in a useful yield, but seperation from the byproducts might be more tricky.
Are you after ethylamine itself, or using it as an intermediate?
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Endo
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I just happen to have a few liters of ACN laying around...
I was actually interested in making perchlorate salts with ethyl amine. I recently made some imidazole perchlorate and found it interesting.
I thought that if I could use some of this ACN to get to ethyl amine it would be a fun target for a perchoric salt.
Thanks for pointing out a much easier method to get to the ethyl amine!
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