The substitution reaction of benzoyl chloride (PhCOCl) and sodium acetate (CHsCOONa) using pyridine 1-oxide (PNO) as the inverse phase-transfer catalyst (IPTC) in a two-phase system of organic solvent and water was studied. The effects of the polarity of the organic solvent on the conversion of benzoyl chloride, the yield of the main product acetic benzoic anhydride (PhCOO-COCH3), and the reaction rate was investigated. A larger reaction rate was observed for a more polar organic solvent. In order to confirm this deduction, mixtures of inert organic substances of varied polarity were used as organic solvents in a two-phase reaction. The effects of such solvents, pyridine 1-oxide (PNO), and temperature on the conversion of benzoyl chloride, the reaction rate, and the yield of the main product acetic benzoic anhydride (PhCOOCOCH3) were also investigated in detail.

The reaction of benzoyl chloride (PhCOCl) and sodium dicarboxylate (R(COONa)2) catalyzed by an inverse-phase-transfer catalyst (IPTC) in the two-phase medium H2O/CH2Cl2 was investigated. Pyridine 1-oxide (PNO) was used as the inverse-phase-transfer catalyst. Ten dicarboxylates, namely oxalate, malonate, maleate, succinate, adipate, nonanedioate, fumarate, phthalate, isophthalate, and terephthalate, were selected for study. In general, the observed mixed products included mono- and bis(benzoyloxycarbonyl) compounds, benzoic anhydride and benzoic acid, depending on the molecular structure of the dicarboxylate ion. Dicarboxylates of four types were classified according to distribution of products. The reaction rate is strongly affected by PhCOCl and R(COONa)2 due to their influence on the distribution of PNO in the organic phase. A mechanistic interpretation of the experimental data is presented.