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Author: Subject: Ethylamine Synthesis
ErgoloidMesylate
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[*] posted on 18-8-2022 at 09:08


Will sodium and absolute ethanol reduce acetamide?

https://en.wikipedia.org/wiki/Bouveault%E2%80%93Blanc_reduct...

[Edited on 18-8-2022 by ErgoloidMesylate]
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[*] posted on 19-8-2022 at 17:12


No



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ErgoloidMesylate
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[*] posted on 21-8-2022 at 17:13


Looks like heating acetamide with sodium borohydride makes acetonitrile, which can be reduced with sodium and alcohol to ethylamine

Edit

Heat at 150 c for 6 hours, evolves ammonia, makes alcohol, and acetonitrile in theory.

But that is ridiculous.

I think a better idea is just to reduce nitroethane and be done with it.

[Edited on 22-8-2022 by ErgoloidMesylate]
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[*] posted on 21-8-2022 at 19:27


There are less silly ways to dehydrate acetamide, like simply refluxing over alumina. And acetonitrile is useful enough that it can be worth it to make/buy for its own sake. Polar, aprotic, low boiling. In fact buying acetonitrile is probably the easier option — it's much less of a pain to purchase than nitroethane!

But the reduction is a shitshow. You have to make sodium in an inefficient thermochemical reaction or an elaborate electrochemical setup. Four moles of sodium for one mole of EtNH2 theoretical, more in practice.

However, cobalt-on-nitrogen-doped-carbon catalysts can catalyze the efficient reduction of nitriles with hydrogen:
https://www.sciencedirect.com/science/article/pii/S187853522...
Unfortunately, the paper's interpretation of "mild" conditions refers to 7 bar hydrogen at 110 C. If this were a salsa, it would make children cry.

The Co@CNx catalysts can also be made from sucrose and melamine and can utilize formic acid as a reducing agent:
https://doi.org/10.1002/cssc.201802163

I am not aware of a nitrile reduction using Co@CNx with formic acid, but I also don't know that it doesn't work.

[Edited on 22-8-2022 by clearly_not_atara]




[Edited on 04-20-1969 by clearly_not_atara]
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