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Author: Subject: Acetonedicarboxylic acid preparation using oxone instead of sulfuric acid.
bmays
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[*] posted on 1-9-2016 at 12:01
Acetonedicarboxylic acid preparation using oxone instead of sulfuric acid.


I've having trouble isolating the product. Any ideas?

The sulfuric acid method did not work out too well for me either, its really hard to isolate because its quite soluble in water. Maybe i should add ethanol and distill in an effort to get the diethyl ester? Then i'm going to end up with diethyl ether. I don't know.


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[Edited on 1-9-2016 by bmays]
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chemrox
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[*] posted on 2-9-2016 at 15:01


Why not start with what you did? It may seem tedious but it's hard to comment without more data.



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bmays
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[*] posted on 3-9-2016 at 11:42


I have made a series of attempts. First was roughly 15g of anhydrous citric acid in 50ml hardware store (dried) sulfuric acid. no evolution of gas overnight at -20c, gas started to evolve at about 0c, i heated to about 40c for 20mins until gas evolution mostly stopped. Quenched with ice and left in the freezer but nothing precipitated. Next attempt i did the same thing except instead of ice i added ethanol and refluxed for a period of time, then quenched with ice/water. No layer of the insoluble diester separated, no ester smell was apparent. Attempt 3 was using pool oxone in a 0.05M ammonium iron(III) sulfate, although i had no real plan on how to separate out the product. I left it in the freezer and filtered the precipitate which turned out not to be the dicarboxilic acid. I assume extraction with ether might be possible if the aqueous layer was saturated with brine.
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[*] posted on 10-10-2016 at 23:25


Good thinking! I was also considering using Oxone as a starting material instead of fuming 20% H2SO4 few months ago. It's working. You can skip a step using Oxone, depending what you're after. Extract Acetonedicarboxylic Acid in Ethyl Acetate.

[Edited on 11-10-2016 by ronstark]
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