Surface molecular imprinting on polystyrene resin for selective adsorption of 4-hydroxybenzoic acid

Abstract

Using chloromethylated polystyrene resin, N,N-diethylaminoethyl methacrylate, and ethylene glycol dimethacrylate as support, functional monomer and cross-linker, respectively, the molecularly imprinted resin (MIR) and non-imprinted resin (NIR) were fabricated by the combination of atom transfer radical polymerization and surface imprinting technique for the selective adsorption of 4-hydroxybenzoic acid (4-HB) from aqueous solutions. The prepared adsorbents were characterized by N₂ adsorption/desorption isotherms, Fourier-transform infrared spectroscopy, and X-ray photoelectron spectroscopy. The adsorption processes of the 4-HB with MIR and NIR followed pseudo-second-order kinetics, and the adsorption isotherms were appreciably described by the Langmuir model. Furthermore, the adsorption efficiencies of MIR and NIR for different compounds in single and binary solutions proved that MIR exhibited high adsorption capacity and favorable selectivity toward 4-HB over other structurally related organic compounds (i.e., benzoic acid, 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, phenol, and 2-hydroxynaphthalene). In addition, MIR could effectively remove 4-HB from a simulated effluent in a dynamic adsorption experiment. This study illustrates in-depth perspectives on the adsorption mechanisms of 4-HB onto MIR; interactions between the adsorbate and adsorbent were proposed based on the adsorption behaviours and instrumental analyses. The resulting MIR is a promising material for the interference-free adsorbent in the selective adsorption of 4-HB from mixed solutions.

Keywords: 4-Hydroxybenzoic acid; ATRP; Polystyrene resin; Selective adsorption; Surface-imprinting.