Yin Chai, Xu Chao, Yu Wenhao, Jia Yuxiang, Sun Weizhi, Zhou Guizhong, Xian Mo
Qingdao University of Science & Technology Qingdao 266042 China
Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences Qingdao 266101 China
RSC Adv. 2019 Jan 8;9(2):801-809. doi: 10.1039/c8ra07253a. eCollection 2019 Jan 2.
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) towards Orange G, which is 1.99 times and 3.49 times as much as that of 135-I (56.94 mg g) and commercial resin H-103 (32.51 mg g) 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.
在本研究中，以氯甲基化苯乙烯-二乙烯基苯共聚物为底物，通过两步连续功能化步骤合成了一种新型的由异吲哚酮和乙二胺改性的交联树脂135-I-EDA。第一步，在异吲哚酮存在下利用傅克反应，通过创新的一锅法反应实现交联反应并引入异吲哚酮，得到树脂135-I；第二步，将乙二胺成功引入改性异吲哚酮的羰基上，进一步增加化学相互作用位点。双改性树脂135-I-EDA对橙黄G显示出最佳吸附性能（113.38 mg/g），分别是135-I（56.94 mg/g）和商业树脂H-103（32.51 mg/g）的1.99倍和3.49倍。这归因于其在傅克反应中形成的优异多孔结构以及异吲哚酮和乙二胺中的多个改性基团。π-π共轭和氢键是吸附的主要驱动力。准二级速率方程能很好地表征吸附动力学曲线，且135-I-EDA显示出最快的吸附速率。该研究还证明135-I-EDA在更酸性的溶液、更高温度和更高盐度下对橙黄G具有更好的吸附能力，这为工业染料废水处理提供了依据。
