1. I am trying to separate quarternery ammonium salt which is forming during the workup of my product, the product has high solubility in water. Tried extraction with different solvents & water combinations but does not help much, the product along with the salt is coming to the water part.
2. The salt formation could have been avoided in the first place if extra triethylamine (TEA) had been removed from the reaction mixture without the addition of acid, which resulted in salt formation.
Already tried alternatives such as
a. Kept under high vacuum at 60 deg C as the boiling point of TEA is 89 deg C
b. formed different azeotropes but TEA remains.
Could you add a ion pairing reagent like a carboxylate (acetate) in water and then extract the cation into an slightly polar solvent which is not water mixible?
I would attempt to neutralize the liquid to slightly >7.0 pH followed by a solvent extraction. Choice of solvent would depend on the organic species. If successful, step "a" from your previous work.
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