Adsorption behaviors of (–)-epigallocatechin gallate and caffeine on macroporous adsorption resins functionalized with carbazole and N-methylimidazole

Abstract

Purpose The purpose of this study is to focus on the preparation of macroporous adsorption resins (MARs) functionalized with carbazole and N-methylimidazole, and adsorption behaviors of (–)-epigallocatechin gallate (EGCG) and caffeine (CAF) on the functionalized MARs. Design/methodology/approach Based on the Friedel–Crafts and amination reactions, novel MARs functionalized with carbazole and N-methylimidazole were synthesized and characterized by the BET method. Accordingly, adsorption behaviors and structure-activity relationships for EGCG and CAF were studied in detail. Findings The results showed that pseudosecond-order kinetic model was provided with a better correlation for the adsorption of EGCG and CAF onto L-1 and L-2, and pseudofirst-order kinetic model was the most suitable model to illustrate the adsorption process for EGCG and CAF on L-3. The result indicated that Langmuir, Freundlich, Temkin–Pyzhev and Dubinin–Radushkevich isotherms all could better illustrate the adsorption processes of EGCG and CAF on L-1, L-2 and L-3. Practical implications This study provides theoretical guidance and technical support for the efficient separation and purification of EGCG and CAF from waste tea leaves by MARs on a large scale. In addition, the results showed that this novel MARs would provide useful help and be used in large-scale production of active ingredients from natural products in the industry and other fields. Originality/value Adsorption kinetic models such as pseudofirst-order, pseudosecond-order and intra-particle diffusion kinetic models, and adsorption isotherm models such as Langmuir, Freundlich, Temkin–Pyzhev and Dubinin–Radushkevich isotherms models were adopted to illustrate the adsorption mechanisms of EGCG and CAF. The main driving forces for MARs with no functional groups were pore sieving effects, p–p conjugation effects and hydrophobic interactions, and the other significant driving forces for MARs functionalized with carbazole and N-methylimidazole were electrostatic interactions, ion-dipole and hydrogen bonding interactions. This study might provide scientific references and useful help for large-scale separating and enriching active ingredients in natural products using the technology of MARs with special functional groups.