CwisGons
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Synthesis of Isopropyl or Ethyl Acetate using Sodium Bisulfate?
Hello everyone. I would like to try a Fischer Esterification using ethanol/isopropyl alcohol and acetic acid. However, I do not plan on distilling
sulfuric acid to use as a catalyst since I want to not die. I know I could probably use the impure sulfuric acid drain cleaner.
However, I wanna try something different, so I could get another reagent out of it as well. I wanna try using sodium bisulfate which I can buy mostly
pure from my local Home Depot or Leslie's. Could I use this as my acid catalyst for the Fischer esterification? I could also get some sodium sulfate
drying agent from it.
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theAngryLittleBunny
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You'd probably have to use a much bigger amount of sodium bisulfate then with sulfuric acid since it's a weaker acid and probably has a very low
solubility in acetic acid and ethanol/ isopropanol. On top of that, sodium bisulfate is almost certainly sold as the monohydrate, so you'd have to dry
it beforehand.
Also, how would that reaction make sodium sulfate? When you use the sodium bisulfate as a catalyst, it will still be sodium bisulfate when you're done
with it. I would just use the sulfuric acid drain cleaner as a catalyst, whatever colouring they put in there won't distill over so it's really not an
issue. The destillation would also go much smoother then if you had a big chunk of sodium bisulfate in the distilling flask at the end which you would
have to heat really long to get out all the ester that is trapped in it.
You seem to be quite new to practical organic chemistry, so I would say making the ester itself would be a huge success, I wouldn't worry about making
some useful side product, especially one that's so cheap, it's not worth the extra hassle.
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BauArf56
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Yes, bisulfate works as well (from The Golden Book of Chemistry Experiments, page 89). I can confirm this, as i tried with concentrated acetic acid
and ethanol.
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theAngryLittleBunny
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Quote: Originally posted by BauArf56  | Yes, bisulfate works as well (from The Golden Book of Chemistry Experiments, page 89). I can confirm this, as i tried with concentrated acetic acid
and ethanol.
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Did you also distill ethyl acetate? I've noticed that mixtures of acetic acid, ethanol and water and an iron salt start to smell of ethyl acetate
after a while, even though only a tiny amount of it has esterified.
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Amos
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You can get a mixture to smell like the ester even by adding 40% phosphoric acid and heating... it doesn't mean you can produce and isolate something
at a preparative scale.
[Edited on 9-12-2021 by Amos]
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CwisGons
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Also, I made a mistake. I wanted to use sodium bisulfate with sodium acetate, to make acetic acid and that would leave me with acetic acid.
How much of the impure sulfuric acid drain cleaner would I use? Would 10% of the reaction mixture be good?
Here is the one I'm thinking of buying:
http://media.lifeandhome.com/media/downloads/2397/40153573_M...
https://shop.cornells.com/p/drain-opener-sulfuric-acid-03790...
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theAngryLittleBunny
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That wouldn't really work well since sodium acetate and sodium bisulfate are both solids so they wouldn't really react well. You could melt them, but
that's way more dangerous then distilling sulfuric acid. And a few % by weight should be enough, like 3 to 5% I think. There are also many videos on
Youtube about esterification reactions where you'll find more details. And yeah, 93% would work perfectly fine, that's what most people use for OTC
esterifications.
Here is a good video: https://www.youtube.com/watch?v=iwcQO9pxAGE&ab_channel=N...
Oh wait, you use sodium acetate? You can still do it with that, but then you'd need an equimolar amound of sulfuric acid to the sodium acetate.
[Edited on 12-9-2021 by theAngryLittleBunny]
[Edited on 12-9-2021 by theAngryLittleBunny]
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