Question

The solubility of aniline in water is 35 g/L; it is miscible in both ether and carbon tetrachloride. explain how you could seperate an equimolar mixture of toluene and aniline from ether?

Answer 1

Liquid-liquid extraction by using solvent like ethyl acetate, carbon tetrachloride and ether:

The reaction mixture is treated with aqueous HCL solution by shaking in separating funnel for some time form anilinium chloride C₆H₇NH⁺Cl^-, which is water soluble. The anilinium chloride salt will go to the aqueous phase and the toluene is ether soluble.

Due to polarity of basic aniline easily soluble in aqueous acidic HCl solution, where as non polar toluene easily soluble in ether.