Cyclic process for activation, use and recovery of phase-transfer catalysts

A process for making an organic product using phase transfer catalysis and via nucleophilic displacement reaction by reacting a nucleophile with an organic reactant having the following general formula:

• R(X).sub.a (I)
• where:
• R is a mono- or polyvalent organic group containing 1 to 720 carbon atoms that is selected from the group consisting of aliphatic radicals, aromatic radicals and combinations of such radicals, can contain or be substituted with moieties that are unreactive with the nucleophile or the organic product and do not adversely affect the desired product;
• X is a leaving group selected from the group consisting of Cl, Br, NO.sub.2, NO.sub.3, and OSO.sub.2 R', where R' is an organic group selected from the group consisting of alkyl groups, aryl groups, fluoro-substituted alkyl groups and combinations thereof;
• and a is a number of 1 to 60;
• said process comprising the steps of:
• (a) reacting said organic reactant with a nucleophile in a liquid organic phase in which no water is added thereto, said nucleophile being derived by:
• (1) metathesis of a water-miscible, thermally stable, cationic phase transfer catalyst selected from the group consisting of quaternary ammonium salts and pyridinium salts with an amount of nucleophilic precursor, said phase transfer catalyst having less than 16 carbon atoms per nitrogen atom, and a cationic portion with at least 10 carbon atoms per nitrogen atom, and said amount of nucleophilic precursor being in excess of the stoichiometric amount required to displace the leaving groups of the organic reactant;
• (2) followed by activation of the product of step (a)(1) by separating water from the product;
• (b) extracting the organic product from the product of step (a) with extracting agent comprising water, thereby forming;
• (1) an aqueous phase comprising the phase transfer catalyst and a by-product salt, and
• (2) an organic phase comprising the organic product;
• (c) separating phases (b)(1) and (b)(2) to recover the organic phase comprising the organic product;
• (d) treating the separated aqueous phase resulting from step (c) with a partially water-miscible alcohol having 4 to 6 carbon atoms and salting agent, the phase transfer catalyst being more soluble in said alcohol and salting agent than it is in an aqueous solution of the salting agent, thereby forming:
• (1) an alcohol phase comprising the phase transfer catalyst and water, and
• (2) an aqueous phase comprising the by-product salt and salting agent;
• (e) separating phases (d)(1) and (d)(2);
• (f) mixing the separated alcohol phase from step (e) with a replenishing amount of said nucleophilic precursor in order to metathesize the phase transfer catalyst with said nucleophilic precursor;
• (g) separating the water and alcohol from the mixture of step (f) thereby forming said nucleophile;
• (h) recycling the so-formed nucleophile of step (g) to step (a), and, if necessary in order to obtain an effective amount of said nucleophile to promote the conversion of the organic reactant to the organic product, adding nucleophile derived by the process of steps (a)(1) and (a)(2);
• (i) recycling the separated alcohol from step (g) to step (d);
• and
• (j) repeating steps (a) through (i) to make a desired amount of the organic product.