Journal of the American Chemical Society p. 3828 - 3832 (1981)
Update date:2022-08-29
Topics:
Tomoi, M.
Ford, Warren T.
Rates of reaction of benzyl bromide in toluene with aqueous sodium cyanide in triphase mixtures with polystyrene-supported benzyltrimethylammonium and benzyltri-n-butylphosphonium ions as phase-transfer catalysts depend upon mechanical stirring speed, catalyst particle size, and percent of cross-linking of the polymer support.Increases in stirring speed increase reaction rates up to a maximum at about 600 rpm.Decreases in particle size increase reaction rates.Increases in polymer cross-linking decrease reaction rates.Apparent activation energies with benzyltrimethylammoniumion catalyst are 12 - 15 kcal/mol at 70 - 90 deg C.Rates of reaction of benzyl bromide, benzyl chloride, 1-bromooctane, and 1-bromohexadecane all are affected differently by variations in catalyst structure, particle size, and cross-linking.The results are discussed in terms of mass transfer, intraparticle diffusion, and intrinsic reactivity limitations on reaction rates.Slow intraparticle diffusion reduces the reactivity differences between benzyl bromide and 1-bromooctane and between benzyl bromide and benzyl chloride and causes 1-bromohexadecane to react much slower than 1-bromooctane.
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