Abstract
t-Butyl hydroperoxide-initiated cycloterpolymerization of diallylaminoaspartic acid hydrochloride [(CH2[double bond, length as m-dash]CHCH2)2NH+CH(CO2H)CH2CO2H Cl-] (I), maleic acid (HO2CH[double bond, length as m-dash]CHCO2H) (II) and cross-linker tetraallylhexane-1,6-diamine dihydrochloride [(CH2[double bond, length as m-dash]CHCH2)2NH+(CH2)6NH+ (CH2CH[double bond, length as m-dash]CH2)2 2Cl-] (III) afforded a new pH-responsive resin (IV), loaded with four CO2H and a chelating motif of NH+⋯CO2 - in each repeating unit. The removal of cationic methylene blue (MB) (3000 ppm) at pH 7.25 and Pb(ii) (200 ppm) at pH 6 by IV at 298, 313, and 328 K followed second-order kinetics with E a of 33.4 and 40.7 kJ mol-1, respectively. Both MB and Pb(ii) were removed fast, accounting for 97.7% removal of MB within 15 min at 313 K and 94% of Pb(ii) removal within 1 min. The super-adsorbent resin gave respective q max values of 2609 mg g-1 and 873 mg g-1 for MB and Pb(ii). IV was also found to trap anionic dyes; it removed 91% Eriochrome Black T (EBT) from its 50 ppm solutions at pH 2. The resin was found to be effective in reducing priority metal contaminants (like Cr, Hg, Pb) in industrial wastewater to sub-ppb levels. The synthesis of the recyclable resin can be easily scaled up from inexpensive starting materials. The resin has been found to be better than many recently reported sorbents.