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Topic: Change of colour after recrystallization  (Read 4488 times)

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Offline pinke

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Change of colour after recrystallization
« on: December 10, 2015, 08:10:05 AM »
We have synthesized few imidazole derivatives, their purity ranges between 88-93 % and they are in white color . we left them for 2 months ( still in white color ) and decided to recrystallize them to get more purified compound. after re crystallization purity was increased and the color of the compound was changed from white to beige/wheatish color.  please tell me what could be the reason behind this color change. during the 2 months of time there's not any change in color , but after re crystallization only, drastic change in color was observed. please which one should i use for activity analysis ? and what color should i mention in the final report. I've attached an image showing the color of the same compound before and after re crystallization.

please kindly help me.
Thank you

Offline TheUnassuming

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Re: Change of colour after recrystallization
« Reply #1 on: December 10, 2015, 08:12:10 AM »
How are you determining purity?
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Offline pinke

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Re: Change of colour after recrystallization
« Reply #2 on: December 10, 2015, 08:16:26 AM »
How are you determining purity?

By HPLC chromatogram

Offline orgopete

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Re: Change of colour after recrystallization
« Reply #3 on: December 10, 2015, 10:06:49 AM »
Ah, the old "predict the solubility of my unknown compound" question. In general, I'd say an increase in color is due to oxidation. Since you are starting with a mixture, we don't know if this is oxidation of your product or an impurity.

I cannot answer your question about the color and whether it may have occurred on the solid during storage or during crystallization (more likely as contact has increased), but I can make a suggestion on how you might purify your compound. I used to start with TLC. Faster moving impurities are generally less polar and less likely to precipitate in non-polar solvents. Slower are generally more polar and more likely to precipitate from a non-polar solvent and less likely from a polar solvent. One can add the strategy of chromatography/filtration to recrystallization. A non-polar impurity may adhere more to charcoal in a polar solvent and a polar impurity may adhere to silica gel in a non-polar solvent.

A qualitative opinion of the solids is that neither look like the kind of crystalline solid characteristic of a pure compound. A slower crystallization favoring precipitation of like-to-like crystals may be all that is necessary.
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Offline discodermolide

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Re: Change of colour after recrystallization
« Reply #4 on: December 10, 2015, 12:06:21 PM »
What solvent did you use for the re-crystallisation.
What happened when you took a melting point?
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Offline critzz

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Re: Change of colour after recrystallization
« Reply #5 on: December 17, 2015, 03:55:05 PM »
It's funny, because the same has happened to me while recrystallizing a 6 membered lactam.
I started with an off-white >95% pure powder and ended up with neat orange crystals (pentane/EtOAc).
I only determined the purity with NMR though.

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