Triphase catalysis. II. Alkylation of phenylacetone with 1‐bromobutane catalyzed by aqueous NaOH and polystyrene‐supported benzyltriethyl ammonium chloride
- 1 February 1993
- journal article
- research article
- Published by Wiley in Journal of Polymer Science Part A: Polymer Chemistry
- Vol. 31 (2) , 317-323
- https://doi.org/10.1002/pola.1993.080310203
Abstract
Insoluble microporous polystyrene‐bound benzyltriethyl ammonium chloride has been used as a catalyst in the alkylation of phenylacetone with 1‐bromobutane, and the kinetics of this reaction was investigated under phase‐transfer catalytic conditions. The observed reaction rates depend on many experimental parameters, viz., stirring speed, substrate amount, basicity of aqueous NaOH, amount of 1‐bromobutane, temperature, order of addition of the reactants and particle size, percent active site, and percent crosslinking of the polymer. The rates are nearly 12 times higher at lower concentrations of base than at higher concentrations and do not vary appreciably with a variation in stirring speed from 200 to 700 rpm. The rate of alkylation increases with a decrease in the particle size of the catalyst and crosslinking of the polymer. Based on the results obtained, a suitable mechanism in which a combination of intraparticle diffusion and intrinsic reactivity limit the reaction rates has been proposed. © 1993 John Wiley & Sons, Inc.Keywords
This publication has 18 references indexed in Scilit:
- Triphase catalysis. I. Kinetics and mechanism of alkylation of phenylacetonitrile with alkyl halides catalyzed by aqueous naoh and polymer‐supported benzyltriethylammonium chlorideJournal of Polymer Science Part A: Polymer Chemistry, 1990
- Mechanisms of polymer-supported catalysis. 4. Alkylation of phenylacetonitrile with 1-bromobutane catalyzed by aqueous sodium hydroxide and polystyrene-bound benzyltrimethylammonium ionsThe Journal of Organic Chemistry, 1983
- Mechanisms of polymer-supported catalysis. 1. Reaction of 1-bromooctane with aqueous sodium cyanide catalyzed by polystyrene-bound benzyltri-n-butylphosphonium ionJournal of the American Chemical Society, 1981
- Triphase catalysis. Influence of percent ring substitution on active-site mobility, macroenvironment, microenvironment, and efficiencyMacromolecules, 1981
- Polymeric onium salts as catalysts in preparative organic chemistryDie Makromolekulare Chemie, 1981
- Importance of mass transfer and intraparticle diffusion in polymer-supported phase-transfer catalysisJournal of the American Chemical Society, 1980
- Polymer-supported phase-transfer catalysts. High catalytic activity of ammonium and phosphonium quaternary salts bonded to a polystyrene matrixJournal of the American Chemical Society, 1979
- Triphase Catalysis [New synthetic methods (27)]Angewandte Chemie International Edition in English, 1979
- Triphase catalysis. C-Alkylation of nitrilesThe Journal of Organic Chemistry, 1978
- Triphase catalysis. Kinetics of cyanide displacement on 1-bromooctaneJournal of the American Chemical Society, 1976