[LittleNovice]

Hello all!

I was just wondering why ethyl acetate is such a popular extraction solvent (i.e. when washing with saturated sodium bicarbonate). Are there any good reasons??

I've read that ethyl acetate is slight polar, so why on earth would it be used for aqueous extractions? (Wouldn't it be caught in the aqueous phase?)

Thanks a billion 

[rcmishra]

You are right..it should not be! Few year ago I got allergic to its vapors
Although its lightly polar its almost immiscible with water, has high enough boiling point and less toxic than chlorinated solvents. These properties let it be a popular extracting solvent

[LittleNovice]

You are right..it should not be! Few year ago I got allergic to its vapors
Although its lightly polar its almost immiscible with water, has high enough boiling point and less toxic than chlorinated solvents. These properties let it be a popular extracting solvent

Thanks! That was quite helpful, and I'm sorry to hear that you got allergic to one of the few actually-not-revolting-smelling chemicals in org lab 

[discodermolide]

Hello all!

I was just wondering why ethyl acetate is such a popular extraction solvent (i.e. when washing with saturated sodium bicarbonate). Are there any good reasons??

I've read that ethyl acetate is slight polar, so why on earth would it be used for aqueous extractions? (Wouldn't it be caught in the aqueous phase?)

Thanks a billion 

EtOAc is actually a bad solvent for extractions. It is difficult to remove from the product, it readily undergoes trans-esterification reactions and is toxic.
Better use tert-butyl-methyl ether

[g-bones]

Ethyl acetate is a popular solvent for extraction because water is much less soluble in it than ether (although more soluble than DCM).  In addition it tends to extract much better than ethers, pulling more of your product from the aqueous to the organic layer.  The only downfall is if it pulls too much and impurities come with it (but that is what chromatography is for ).  Unless my product is very volatile I always reach for EtOAc as my extraction solvent.  So it takes a little longer to pull off under vacuum, no big deal, its easy enough to get off.  Its not uncommon to use.

[zeropoint]

I find that many small organic compounds are soluble in it (polarity seems to be just right for the LogP of many compounds most synthetic chemists work with). It's also easy to take off with a wimpy rotovap.

That being said, I use Chloroform for most extractions, this may be better for my chemistry as I deal a lot with nitrogen containing compounds.

[bern2011]

 ;)But Chloroform is more toxic than AcOEt, you can use CH2Cl2 instead