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Author: Subject: ethyl acetate
Fery
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[*] posted on 2-5-2022 at 11:34


Antiswat you can buy it everywhere as nail polishing remover - for such usage everyone claims this is "green" solvent. Walking on the street where there are beauty/cosmetic/nails saloons you can scent from faraway that they are using ethyl acetate and not acetone.
The best method of preparation is already described by cheeseandbaloney.
I read similar preparation in one of my scanned copy of org chem book where they also used dropping funnel which extends to the bottom of the reaction flask. It is necessary to made most of ethanol to react and not to distill it off too soon. Hence the necessity to add it to the bottom of reaction flask instead of dropping it to the surface. Second note: ethyl acetate forms an azeotrope with ethanol. So as cheeseandbaloney pointed out, it is necessary to add ethanol slowly so most of it reacts into ethylacetate instead of being distilled off.
there is a ternary azeotrope boiling at 70,3° C with composition 83,2% ethyl acetate + 9,0% ethanol and 7,8% water (but as there is H2SO4 it binds the water so less water distills than in the theoretical ternary mixture without H2SO4)
binary azeotrope ethanol + ethyl acetate boils at 71,8 C and contains 69,2% of ethyl acetate
the difference of b.p. between binary and ternary is so small that without powerful column (I mean e.g. hempel + rashig rings) and variable adjustable reflux ratio distillation head you always distill something between these 2 azeotropes
To get rid of ethanol from the condensate a washing with plenty of water would case loses of ethyl acetate (solubility in water 8,3 g/100 mL at 20 °C) - from water washings you can recover part of ethyl acetate by just simple distillation as the distillate is enriched in ethyl acetate and contains less water as the mixture being distilled.
Using anhydrous CaCl2 to get rid of ethanol (it binds ethanol into complex) you avoid loses by dissolution in water (previous method) but you introduce mechanical loses (adhering ethyl acetate on crystals) from which you can recover some product by heating and distilling off.
As you can see there are a lot of loses which are acceptable at small scale preparation in lab but unacceptable in industry so at industrial scale they use reaction between acetic acid + ethylene instead.

[Edited on 2-5-2022 by Fery]




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