Synthesis and characterization of novel soluble multi-site phase transfer catalyst; its efficiency compared with single-site phase transfer catalyst in the alkylation of phenylacetonitrile as a model reaction

The kinetics of C-alkylation of phenylacetonitrile with 1-bromobutane has been studied using a novel alpha,alpha',alpha"-N-hexakis(triethylammoniummethylene chloride)-melamine as a multi-site phase transfer catalyst (MPTC) using a low concentration of aqueous sodium hydroxide as a base. The reaction was carried out at 50degreesC under pseudo-first-order conditions by keeping aqueous base and 1-bromobutane in excess. The formation of the product was monitored by GLC. The effects of various experimental parameters such as [substrate], [NaOH], [catalyst] and temperature on the rate of the reaction have been studied. The results obtained and also the thermodynamic parameters are discussed. The catalytic efficiency of the multi-site catalyst was compared with efficiencies of the commercially available single-site catalysts. (C) 2004 Elsevier B.V. All rights reserved.