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I have a quick question about counterion exchange. I have this very practical problem at my hands that I have a ethyl sulfate $(\ce{EtSO4-})$ counterion for a $\ce{R4N+}$ moiety ($\ce{R}$ = 3 different substituents).

I need to change the counterion to something like a $\ce{BF4-}$ or a $\ce{NO3-}$. What would be the best approach? What role does the solubility of my $\ce{R4N+}$-moiety play? (good solubility in: $\ce{EtOH},$ $\ce{MeOH},$ $\ce{DMSO};$ medium in: water, $\ce{CH3CN},$ choloroform; insoluble in: $\ce{EtOAc})$

I thought about a classical silver-halide approach where I introduce a silver salt with the fitting counter-ion, but I am afraid that the $``\ce{AgEtSO4}"$ might be too soluble and that I get silver contamination. ($\ce{Ag2SO4},$ for example, has a solubility product of $10^{-5},$ whereas $\ce{AgBr}$ has $10^{-13},$ so there is a big difference.)

Any tips are appreciated!

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    $\begingroup$ Look up ion-exchange resins and papers on ionic liquids. They do a lot of exchange of ions. $\endgroup$
    – M. Farooq
    Nov 22 '19 at 23:53

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