I'm running a reaction in where riboflavin is derivatized with a crosslinker in DMSO. The final reaction mixture contains riboflavin (non reacted) and riboflavin-crosslinker compound (slightly less polar). I suspect they have similar solubilities because when I form precipitates by adding water to the reaction mixture, the two compounds are present ( confirmed by TLC). I need to synthetize and to separate large amounts (up to 10 grams or more) of this compound so i think column chromatography is not an option and because of the similar solubilities crystallization is not effective. Could you suggest me some options to separate large amounts of compounds with similar solubilities?
I can see two path to separete this compounds. Using liquid-liquid extraction (LLE) that some solvents with different polarity may be used to split you reaction extract or column chromatography at the same condition (sorbent phase and elution condition) than TLC.
Please look at the following below links which may help you in your analysis:
https://www.researchgate.net/publication/230554112_HPLC_Determination_of_Riboflavin_in_Fortified_Foods
https://www.researchgate.net/publication/12413156_Chromatographic_determination_of_riboflavin_and_its_derivatives_in_food
https://core.ac.uk/download/pdf/191950693.pdf
https://tigerprints.clemson.edu/cgi/viewcontent.cgi?article=2745&context=all_theses
Thanks
If the molecules you want to separate have different molecular weights you may be able to separate them with SEPHADEX, I have read articles where it is used to separate compounds that cannot be separated with another stationary phase with column chromatography.
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