Acetone

[msimone]

I was playing around with some extractions using different acidified solvents. I tried 0.5% HCl in Acetone. After a few days it turned a deep shade of maroon.

Any idea what I made?? We are mighty curious around here.


Mike

[krickos]

Hi

Have confirmed with one of my collegues and itis usually not a great idea to mix acetone with a strong acid. As you mentioned a red/brown by product is formed.

I am not 100% what you have in the jar by now but as acetone always shifts over a bit to the "enol" form you may have formed a Hemiacetal, those when open chained are typically not so stable to be isolated and reacts further.

Under controlled form you may form hemiacetals with ketones in alcohol and catalyze the reaction with an acid. See for example Solomons Organic Chemistry.

Cheers Chris

[Bruce Hamilton]

You probably made phorone, a yellow solid with a geranium-type smell, and that mixture then reacted further. Fieser and Fieser, or any older organic text probably would discuss some of this.

The characteristic sweetish smell of technical grade acetone, or even old analytical grades, is due to the accumulation of mesityl oxide.

Bruce Hamilton