Abstract
AbstractThe reaction of dibromomethane and 1‐butanol to synthesize dibutanoxymethane in a very high alkaline concentration of KOH (i.e. large amount of solid KOH/organic solvent) by phase transfer catalysis was studied. Only one unique final product with two butanoxide substituents was observed in the organic phase, thus indicating a very fast rate for the second reaction. The reaction rate was significantly enhanced by adding a small amount of quaternary ammonium salt. Only a pseudo‐first‐order rate law can be applied to describe the reaction at a very high concentration of KOH. This peculiar phenomenon was explained by the limitation of the chemical reaction equilibrium in the aqueous phase as the controlling step at a low KOH concentration, and the reaction in the organic phase as the controlling step at a high KOH concentration. The experimental results indicate that the mass‐transfer resistance of the active catalyst ((C4H9)4N+ ‐OC4H9; QOR) is negligible, compared with the reactions in the two phases. When using TBAB as the catalyst, the only way to increase the product yield is by the use of a solvent with appropriate polarity and a small amount of water at a very high alkaline KOH content.
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