A process for converting a salt of a hydroxycarboxylic acid to an unsaturated
carboxylic acid, or esters thereof. The process involves converting an
ammonium salt of a hydroxycarboxylic acid in
aqueous solution to a corresponding hydroxycarboxylic acid and
ammonium cation in
aqueous solution; and separating the
ammonium cation from the
aqueous solution, leaving the hydroxycarboxylic acid in aqueous solution. The converting and separating steps may be accomplished by employing a hydrophobic acid or an acid
ion exchange resin, each of which must have an
acid dissociation constant, i.e., pKa, at least 0.5 less that that of the salt of the hydroxycarboxylic acid. Where a hydrophobic acid is used, it must be immiscible in water, and its salt must also be immiscible in water, and the resulting multi-phase solution comprises an aqueous phase comprising the corresponding hydroxycarboxylic acid, as well as a non-aqueous phase comprising a neutralized acid. Alternatively, where the
ion exchange resin is used, the aqueous solution of the ammonium salt of a hydroxycarboxylic acid is contacted with the resin, thereby converting the salt to a hydroxycarboxylic acid and capturing the ammonium cations on the resin. In either case, the aqueous solution is treated, such as by heating, to separate and recover the hydroxycarboxylic acid. The non-aqueous phase or resin is treated to separate and recover
ammonia useful for preparing additional ammonium salt of a hydroxycarboxylic acid.