Benzyl Benzoate from Benzyl Chloride and Sodium Benzoate

Esters from the Reactions of Alkyl Halides and Salts of Carboxylic Acids. Comprehensive Study of Amine Catalysis

“…The heterogeneous reaction mixture does not lend itself to a precise kinetic study. Rueggeberg et al (1946) postulated that in the reaction of sodium benzoate and benzyl chloride, the tertiary amine reacts with benzyl chloride to form the quaternary ammonium chloride. This chloride salt then reacts with sodium benzoate to yield the quaternary ammonium benzoate salt, which then thermally decomposes to benzyl benzoate and regenerated amine.…”

“…and 30 minutes. Rueggeberg et al (1946) and Thorp et al (1947) used amine catalysts to drive the reaction of sodium benzoate and benzyl chloride to yield benzyl benzoate in nearly quantitative yields. Rueggeberg et al conducted some amine catalyst screening and concluded that whereas most tertiary amines gave good results, hexamethylenetetramine and pyridine gave undesirable side reactions.…”

A systematic modelling framework for phase transfer catalyst systems

“…The first known commercial use of a PTC system was reported by Rueggeberg et al (1946), for the production of benzyl benzoate from benzyl chloride and sodium benzoate catalysed with diethyl-and triethylamines as PTC.…”

Esters from Reactions of Alkyl Halides and Salts of Carboxylic Acids. Reactions of Primary Alkyl Chlorides and Sodium Salts of Carboxylic Acids

“…Kester et al (1943) obtained 60 to 90% yields of glycidol esters from the reactions of epichlorohydrin; however, the high yield reactions were restricted to the sodium salts of high molecular weight acids (soaps). Rueggeberg et al (1946) and Thorp et al (1947) also used amine catalysts to drive the reaction of sodium benzoate and benzyl chloride to give benzyl benzoate in nearly quantitative yields in a few hours under mild conditions. This process w'as successfully scaled up to the pilot plant by the same investigators.…”