Enantioselective separation of (±)‐epinephrine by chiral acidic molecularly imprinted polymer

Abstract

AbstractIn this study, we look into how poly[(4‐styrenesulfonic acid)‐co‐(4‐vinylpyridine)] crosslinked with divinylbenzene can be used as a copolymeric material to effectively recognize l‐epinephrine (L‐EP) and chirally separate (±)‐EP. It was first possible to synthesize and analyze L‐EP‐styrene‐4‐sulfonamide (L‐EP‐SSA). The resulting chiral sulfonamide was used to copolymerize with a 4‐vinylpyridine–divinylbenzene mixture. The integrated L‐EP species were removed by heating the polymer materials under strong alkaline conditions to degrade the sulfonamide links, followed by acidification in HCl solution. The imprinted L‐EP‐IP materials were analyzed using Fourier transform infrared spectroscopy and scanning electron microscopy. The produced L‐EP‐IP displayed selectivity characteristics indicative of an affinity for L‐EP almost eleven times higher than that for d‐epinephrine (D‐EP). At a pH of 7, Langmuir adsorption experiments demonstrated a maximal capacity of 165 mg g−1. Following optical separation by means of a column method, enantiomeric excess levels of L‐ and D‐EP in the initial feeding and subsequent recovering solutions were calculated to be 93% and 80%, respectively. © 2024 Society of Industrial Chemistry.