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Author: Subject: Ethanol to ethyl acetate
International Hazard

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[*] posted on 3-1-2017 at 00:14
Ethanol to ethyl acetate

So I have tried adding oxone to ethanol no reaction occurs
Im trying to find a one pot synthysis
I know of sulfuric acid catalysis but im attempting to form ethyl acetate without it.

Electrolysis with nickel elctrodes might form it
Or some oxidizing agent
Fentons reagent
Or hypochlorite oxidation

[Edited on 3-1-2017 by symboom]
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International Hazard

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[*] posted on 3-1-2017 at 04:31

So, If I understand correctly, you are trying to oxidize a portion of the ethanol to acetic acid whilst distilling off ethyl acetate?

In this case, the esterification would be autocatalyzed by the acetic acid. Because the acid is weak, the rate of forward reaction will be small. It might work better with a small amount of sulfuric acid (e.g. a drop) or strong acid ion exchange resin (which can be filtered out and reused) added to the pot.

"...sulfuric acid catalysis but im attempting to form ethyl acetate without it." Why?


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[*] posted on 6-12-2017 at 14:47

I became interested in this recently. If you consider an oxidation of ethanol to acetaldehyde, in the presence of an alkali ethoxide (Na dissolved in EtOH), the Tischenko reaction occurs converting acetaldehyde to EtOAc. This has been performed using K2CO3 as the base (generates some KOEt in situ) and I2 as the oxidant:

Another method uses TCCA as the oxidant with catalytic TEMPO:

Since TCCA apparently does not react very quickly with sodium ethoxide -- K2CO3 inhibited the second reaction, probably by interfering with TEMPO -- but it will react with I-, I think you could use TCCA as the terminal oxidant with catalytic potassium iodide to perform the first reaction:

2EtOH + Cl3C3N3O3 + cat KI + 2K2CO3 >> EtOAc + K2ClC3N3O3 + 2 KCl + 2 CO2 + 2 H2O

Similar reactions have been reported, such as this variant with N,N-dibromotosylamide:

[Edited on 6-12-2017 by clearly_not_atara]

[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 6-12-2017 at 14:59

Abusing Ethanol in this way is simply unacceptable.

It is a Crime and should be stopped, immediately.

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