Sciencemadness Discussion Board

Weird compound

guy - 24-6-2006 at 12:43

About a week ago I made some ethyl acetate by sodium hypochlorite and ethanol. Then I added some ammonia (for some random reason) and left it there (uncovered in the sun) for a week. When I came back, it smelled so bad, like feet (and it still had a sweetish smell). Does anyone know what could have been formed?

garage chemist - 24-6-2006 at 14:00

Originally posted by guy
About a week ago I made some ethyl acetate by sodium hypochlorite and ethanol.

WTF? There's no way that ethyl acetate could be formed here. Ethyl acetate needs strong acid catalyst to be formed, and NaClO is basic.

The bad smell is chloramine, formed from NaClO and ammonia.

guy - 24-6-2006 at 14:07

No you can make ethyl acetate from hypochlorite. See here

It oxidizes alcohol to aldehyde then acid, then somehow it combines with remaining alcohol to form an ester. I can conform by its sweet fruity smell too. I think the Cl+ helps the reaction move along.

So chloramine smells like feet? I have mixed ammonia and hypochlorite together before but I swear it didnt smell like this. This is smells like bad feet stepped in feces. :)

Could this be Acetamide? CH3COOCH2CH3 + NH3 <---> CH3CONH2 + CH3CH2OH

Chemical dictionary says has strong odor of mice. I have never smelled a mouse before but I'm thinking it smells bad.

[Edited on 6/24/2006 by guy]

[Edited on 6/24/2006 by guy]

frogfot - 25-6-2006 at 01:01

That's a quite useful method and they seem to get pretty big yields.

You're right about acetamide, it's formed quite easy at room temperature from ethyl acetate and ammonia. It actually does smell like mice poo.. that smell comes from an impurity and can be easily removed (text based on Vogel):

virgil - 25-6-2006 at 03:31

I take it that no one has access to a GC/MS. The "sweetish odor of feet" is reminiscent of valerianic acid or one of its derivatives. Valerian root is said to smell like old gym socks, and, having analyzed my share of valerian and its derivatives, I can attest to that statement. The reaction sequence and mechanism escape me, but putting it in the sun seems to allow for the possibility of free radical processes to occur.

unionised - 26-6-2006 at 10:47

I wondered about ethanol oxidised to the aldehyde reacting to give the aldol. Dehydration and oxidation would give butenoic acid and I bet that stinks.