Synthesis of a novel isatin and ethylenediamine modified resin and effective adsorption behavior towards Orange G

Abstract

In this study, a novel crosslinked resin 135-I-EDA modified by isatin and ethylenediamine was synthesized through two continuous functionalization steps using chloromethylated styrene-divinylbenzene copolymer as the substrate. In the first step, the cross-linking reaction and isatin incorporation were realized in a creative one-pot reaction using Friedel-crafts reaction in the presence of isatin to give resin 135-I; in the second step, ethylenediamine was successfully introduced on the carbonyl of the modified isatin to further increase the chemically interacting sites. The double-modified resin 135-I-EDA displayed the best adsorption performance (113.38 mg g −1 ) towards Orange G, which is 1.99 times and 3.49 times as much as that of 135-I (56.94 mg g −1 ) and commercial resin H-103 (32.51 mg g −1 ) respectively. This is attributed to its superior porous structure formed in the Friedel-crafts reaction and multiple modified groups in isatin and ethylenediamine. π-π conjugation and hydrogen bonding are the main driving forces for the adsorption. The pseudo-second-order rate equation characterizes the adsorption kinetic curves well and 135-I-EDA displayed the fastest adsorption rate. The study also proved that the 135-I-EDA has a better adsorption capacity for OG in more acidic solution, at higher temperature and higher salinity, which provides a basis for the treatment of industrial dye wastewater.