Ramiel
Vicious like a ferret
Posts: 484
Registered: 19-8-2002
Location: Room at the Back, Australia
Member Is Offline
Mood: Semi-demented
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Ethanol oxidation
I may as well hang my head and ask what's bothering me.
I've been trying to make ethanoic acid from ethanol... pretty simple compared to the other stuff a mad-for-science-scientist [thank you orgie
 ] does, right?
NO! and it's hurting my brain. 
first I tried the acidic permanganate oxidation at ~~10*C. I am greeted with an exceptionally 'estery' smell... and I think to myself - the
acid catalysed esterfication? surely not in these quantities? So I leave it to react at near freezing and after about a week, the solution is the dark
brown sludge of MnO<sub>2</sub>. The smell of baileys became more and more apparent as I was decanting the liquid from the white insoluble
salt. Strange, but I had to stop myself drinking this beautiful smelling nectar.
So I'll distill that later for the ester and forget about the EtOOH.
Next stop is hypochlorite. I added stoichiometric amounts of 96% EtOH to 99% CaOCl.
No reaction.
I walk away and in my absence the reaction runs away, and I'm standing there scratching my head at a dry crater of hypochlorite in my beaker.
I try it again with more ethanol - just as a proof of concept. Nothing happens.
Why won't the hypochlorite give up it's oxygen... my sparse reading suggests it's a straightforward reaction.
Any help is much appreciated
Sincerely
- Ramiel
Caveat Orator
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The_Davster
A pnictogen
Posts: 2861
Registered: 18-11-2003
Member Is Offline
Mood: .
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From ethanol_reactions on the FTP.
"The action of bleaching powder on alcohol was reported by Schmitt and Goldberg in 1879. These compounds reacted spontaneously after a lapse of
7-10 minutes; acetaldehyde and acetal distilled off, together with a greenish yellow oil which was believed to be ethyl hypochlorite. Goldberg
studied the effects of diluting the alcohol with water. In equialent ammounts of water and alcohol there was no dilutent effect in evidence, but
above this ratio water acted as an inhibitor. The presence of chloroform among the products was noted with these diluted reactants."
The PDF mentioned above is really informative, I hope to have a go at oxidizing ethanol to acetaldehyde via an ammoniacal solution of CuO in the near
future.
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