KINETICS OF THE REACTION OF DIBROMOMETHANE AND TWO MIXED n-ALCOHOLS UNDER PHASE TRANSFER CATALYSIS

A novel method was provided to synthesize unsymmetric formaldehyde acetal by reacting two mixed alcohols (e.g., 1-butanol and 1-octanol) and dibromomethane via phase transfer catalysis. Only three final unique products with two alkoxide substituents (one unsymmetric and two symmetric acetals) were observed during the reaction for using higher reactivities of alcohols as the reactants for using higher reactivities of alcohols as the reactants. This result indicated that the rates of the four second reactions in the organic phase are larger than those of the two first reactions in the organic phase. Mass transfer of the catalyst and the active catalyst are very rapid, compared to the reaction in the organic phase. The reaction in the organic phase is a rate-determining step. Based on the fact that the intermediate products were not observed, a kinetic model was developed and simplified. A pseudo-first-order rate law was sufficient to describe the kinetics of reaction. High yields of the two symmteric acetals and the one unsymmetric acetal were produced by employing tetrabutylammonium bromide (TBAB) as a phase transfer catalyst in a high alkaline concentration of KOH/chlorobenzene two-phase medium.