Deoxybenzoin Impurity
I've had some deoxybenzoin of approximately 98-ish% purity stored in an amber bottle for many months (but less than a year) and it has also been kept
cool, dry, dark, etc. Nevertheless what started out as nice clean white crystals has now taken on a deep orange color and a rather bad smell.
I decided to recrystallize a sample from boiling water to salvage what I could, if anything, and see what the situation was. The orange impurity was
completely insoluble in the boiling water, melted somewhere in the range of 90-100C, and formed a liquid layer beneath the water with a dark
orange-red color. After separating the deoxybenzoin solution and recrystallizing it I turned my attention back to the impurity, which was now a solid
mass at the bottom of my test tube. I did a quick check to see if it was soluble in toluene, which it was.
Anyone have any ideas what this orange substance might be? I assume it is some kind of decomposition/polymerization/oxidation product of deoxybenzoin.
I'll do some more tests later when I recrystallize the rest of the batch and isolate more to work with.
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