guy
International Hazard
Posts: 982
Registered: 14-4-2004
Location: California, USA
Member Is Offline
Mood: Catalytic!
|
|
Weird compound
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
chemical wizard
Posts: 1803
Registered: 16-8-2004
Location: Germany
Member Is Offline
Mood: No Mood
|
|
| Quote: | 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
International Hazard
Posts: 982
Registered: 14-4-2004
Location: California, USA
Member Is Offline
Mood: Catalytic!
|
|
No you can make ethyl acetate from hypochlorite. See here http://www.erowid.org/archive/rhodium/chemistry/ether2ester....
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
Hazard to Others
Posts: 212
Registered: 30-11-2002
Location: Sweden
Member Is Offline
Mood: happy
|
|
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):
http://www.frogfot.com/synthesis/acetamide2.html
|
|
|
virgil
Harmless
Posts: 5
Registered: 24-6-2006
Member Is Offline
Mood: No Mood
|
|
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
International Hazard
Posts: 5075
Registered: 1-11-2003
Location: UK
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
