November 30, 2021, 07:12:34 PM
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Topic: I wonder if i could get triethyl citrate by mixing ethanol and citric acid  (Read 513 times)

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Offline pity.fx

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anyway, what's the molar and mass ratio?
THX for your answers

Offline Babcock_Hall

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A good place to start is to write the balanced equation.

Offline pity.fx

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the balance site says 1:3, but do i need additional components?

Offline Babcock_Hall

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Almost certainly yes.  If I were doing this reaction, the first thing I would do is to use SciFinder to see how others have done it.  There are several considerations:  How thermodynamically favorable the reaction is, how fast it is, and are side-reactions possible.  To the third point, is there another functional group on citric acid besides the three carboxylic acids that might also react?

Offline Meter

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Babcock_Hall: genuine question, why couldn't this just be made using a classical Fischer esterification and a LARGE excess of EtOH? The equilibrium could probably be shifted using a Dean Stark apparatus and molecular sieves if that's a problem.

Offline pity.fx

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i understand nothing. do i need sulfuric acid (unobtaineable for me) and a destiller (to expensive for me) or is it just "pour liquid on solid and shake well"?

Offline Babcock_Hall

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@OP, We can put the question of a side-reaction on the back burner for now.  Yes, I think you need a catalyst of some kind, and an acid catalyst is the first thing that comes to mind.  What is your intended use of the product?

@Meter, I think that a Fischer esterification would probably work, especially with a large excess of ethanol.  The side reaction might not be a significant problem.  The existence of the product suggests that the side reaction can be avoided or minimized.
 
« Last Edit: June 03, 2021, 11:28:04 AM by Babcock_Hall »

Offline rolnor

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If you look in wikipedia "citric acid" you find some chemistry. There is a tertiary alcohol that gives dehydration essily with strong acid.
Here is a reference to some ester synthesis:
https://www.sciencedirect.com/science/article/abs/pii/S0040402096010617?via%3Dihub

Offline pity.fx

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thank's y'all, i only wanted to make food stuff, but it tends to be impossible with my tiny knowledge.

Offline rolnor

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You can buy this ester, not expensive.

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