Design and preparation of functional azo linked polymers for the adsorptive removal of bisphenol A from water: Performance and analysis of the mechanism

Abstract

In order to effectively remove refractory bisphenol A (BPA) from water, a novel nitrogen doped organic porous functional azo linked polymer (ALP-p) was designed and prepared according to the physicochemical characteristics of propane linked to two phenol hydroxyl groups. This ALP-p was synthesized with 98.5% yield, from pararosaniline and phloroglucinol, via the diazo coupling reaction to produce multiple adsorption functional groups of benzene ring, hydroxyl group and azo group. This functional material showed high adsorption capacity of 357.8 mg/g for 50 mg/L BPA, at 20 °C. The adsorption kinetics and isotherms were described by the pseudo-second-order and Langmuir model, respectively. The major adsorption mechanisms were attributed to the high specific surface area (259.8 m2/g) and pore volume (0.56 cm3/g) related surface adsorption and pore diffusion through porous stereoscopic stacking cavity anchorage. The functional group from the three-dimensional skeleton structures of ALP-p for BPA anchoring endowed chemisorption via π-π interaction between benzene rings and hydrogen-bonding (O–H⋯O, C–H⋯N, C–H⋯O and C–H⋯C) with the hydrogen atom of benzene ring, –OH from BPA and –OH, NN from ALP-p, respectively. The coexisting organic pollutants and alkali environment posed a negative effect on adsorption, while salinity had no significant effect on the process. The adsorption capacity and recovery of ALP-p were >93.5% and 81.6% after five cycles of operation.