[welsh_Ajo]

I am performing a liquid liquid separation on two fairly polar molecules; the only appropriate separation system seems to be Brine-AcCN, while the process is very good it leaves my product in the brine layer. Is there any easy way to now separate the salt from my product?   

The compounds I am trying to seseparatere are both Benzopyrans with a c-glucoside, a  phenolic group and a carbonyl substituted on the the benzopyran. The only structural differenc between the two compounds is a p-Coumaryl group on the glucoside in the unwanted compound. Due to the polarity of these molecules I feel very limited in the solvents I can use for the sepseparation. The AcCN will separate but the desired product ends up in the Brine.

 The compound is also not volvolatile so unfunfortunately sublimation and distillation are out. 

I am trying to avoid any column separation as eventually I wish to perform the process on a bulk scale

 

[DrCMS]

It might help if you give us some details of what you are trying to separate from what.  Chemical type and functional groups present rather than specific compounds if you don't want to disclose that info.

[Custos]

If your compound is soluble in brine you have only a few options to separate it from the salt. You can (possibly) change the polarity of the molecule, e.g. if it's an acid or base salt itself you could neutralize it, or change the counter ion - then extract out of the brine with an organic solvent. Alternatively, if your compound is reasonable volatile you could evaporate off the water and then distill (or sublime) your compound out of the remaining salt.

Neither of these methods might work though. Not knowing the structure of your compound makes giving advice difficult.

[marcel44]

try to saturate the brine solution with ammonium chloride, if you have any chance in life, your compound will be less soluble and crash out of solution, this will work well on a solid on small scale or large scale, if you expect an oil, evaporate to dryness and triturate with EtOH or iPrOH to remove your product. Do not use MeOH as some salt will come in solution. When most is removed you can solubilize in iPrOH and pass it through a plug of silica gel (yes, dont worry it will not come with the iPrOH) and that's it...!

[DrCMS]

Try adding toluene and distilling out the water/toluene azeotrope using a Dean & Stark setup.  Once you have all the water out hopefully your product will be soluble in the toluene but the salt will not.  Filter salt out of the toluene solution then distill the mixture down to isolate your product.