Abstract: The nucleophilic substitution reaction of chloromethylated polystyrene was performed using the sodium salt of p-hydroxybenzaldehyde as the nucleophilic substitution agent via phase-transfer catalysis, and polystyrene with aldehyde groups on its side chains was prepared. The structure of the product was characterized by FT-IR spectroscopy. The effects of various factors, such as the polarity of solvents, the kind and used amount of the catalysts, and the ratio of organic phase to water phase, on the phase-transfer catalysis reaction were studied, and these effects were analysed according to the reaction mechanism and kinetics theory. The results showed that functionalization of polystyrene could be realized by phase-transfer catalysis, the chlorine atoms on the chains of chloromethylated polystyrene could be favorably transformed, and polystyrene with aldehyde groups on its side chains was successfully obtained. For this phase-transfer catalysis system, the suitable catalyst is tetrabutylammonium bromide, the solvent with stronger polarity is favorable, and the fitting volume ratio of organic phase to water phase is equal to 1/2.

Key words: phase-transfer catalysis, chloromethyleted polystyrene, nucleophilic substitution, hydroxybenzaldehyde, functionalization