MrDoctor
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making sodium ethyl sulfate from spent acid-ether reaction mixture
Since sodium/calcium ethyl sulfate is a moderately useful reagent, and people have such a tough time getting decent yields as it were, i thought it
might be a good idea to neutralize and save the spent reagents after producing diethyl ether from sulfuric acid and ethanol since the reaction
eventually stops or has to be stopped due to a buildup of tar and water, and further attempts to remove the water, cause even more buildup of tar, and
consequently foaming.
Ethyl sulfate is supposedly also lost from the reaction, slowly entrained by the ether/ethanol distillate, as is evident from the sheer amount of CO2
produced during the bicarbonate washing, more than i would think to see from sulfuric acid mist.
I was wondering, what kind of workup or conditions would be needed in order to successfully convert the ethyl sulfate waste product im left with, in
my reaction and receiving flasks, into a salt? I was reading up on peoples attempts to produce it and, yields seem terrible and varied. furthermore
water content seems to be a big issue as well.
My intuition is telling me theres more to this reaction than simply neutralizing the ethyl sulfate with carbonate, unless im misreading and the issue
is, making ethyl sulfate efficiently, not the salt.
The other thing too is, im only really guessing as to what the composition of my tarry acid water is at the end of an ether synthesis. With
considerable effort i have managed to "regenerate" unusable ethyl sulfate solution with aggressive heating, vacuum distillation and/or the addition of
much less acid than the subsequent ether produced could be made with (mostly to dry it out not replace acid), so there must be appreciable amounts of
ethyl sulfate there i would think.
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jackchem2001
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On your last point, I wonder if cautiously adding H2O2 to the spent reaction acid mixture could regenerate its ability to produce ether.
[Edited on 26-9-2024 by jackchem2001]
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MrDoctor
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Quote: Originally posted by jackchem2001  | On your last point, I wonder if cautiously adding H2O2 to the spent reaction acid mixture could regenerate its ability to produce ether.
[Edited on 26-9-2024 by jackchem2001] |
i did consider this, and did try, unfortunately though no reaction occurs at temperatures where foaming is problematic, once foaming becomes an issue.
so if this is tried, youd probably want to end the reaction early, then cook out any tar and water before it can turn problematic. It might also just
be worthwhile to try frying some in a test tube big enough to hold any foam that forms, just to see if eventually clean sulfuric is left behind
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