Synthesis of glucaminium-based ionic liquids and their application in the removal of boron from water

Abstract

A novel class of ionic liquids (ILs), exhibiting high selectivity towards boron species as well as the ability to phase separate from water, were synthesized from N-methyl-D-glucamine. The complexation of boric acid/borate with the ILs was confirmed using (11)B NMR.

A novel surface-confined glucaminium-based ionic liquid stationary phase for hydrophilic interaction/anion-exchange mixed-mode chromatography

“…[25,26] with some modification. 2.5 g of N-methyl-d-glucamine was dissolved in 50 mL of methanol, and then 0.8 g of sodium carbonate was added to the solution under stirring at 45 • C. After being stirred for 30 min, 9.7 g of allyl bromide dissolved in 10 mL of methanol was slowly added dropwise to the reaction solution within one hour, and the reaction was conducted at 45 • C for 98 h. The reaction mixture was evaporated under reduced pressure at 50 • C and then cooled when about 10 mL of mixture remained.…”

“…However, currently only imidazolium and pyridinium ILs are used as bonded selectors for HPLC stationary phases. Glucaminium-based ILs were a new kind of ILs recently developed to remove or extract boron-species, improve the separation of hydrophilic boron compounds under RPLC by using the complexion behavior with borate [25][26][27]. Moreover, glucaminium-based ILs presented good extraction performances to alkyl halides and aromatics [28], deoxyribonucleic acid (DNA) [29], indicating they could provide the ability to function with solutes by multiple interactions.…”

Versatile ligands for high-performance liquid chromatography: An overview of ionic liquid-functionalized stationary phases

“…From the sense of chemical structure, this new class of ILs belonged to ammonium salts functionalized by glucosyl unit. Glucaminium salts were initially used as good media for selective extraction and high-sensitivity detection of boron-species from aqueous samples, due to their excellent complexation ability [110][111][112]. In view of the highly hydrophilic carbohydrate moiety and the ability to undergo multiple interactions, the precursor of glucaminium cation, Nmethylglucamine (also called meglumine), seemed very attractive for construction of hydrophilic silica surface.…”

Glucaminium ionic liquid-functionalized stationary phase for the separation of nucleosides in hydrophilic interaction chromatography

“…Glucaminium-based ILs are a new class of ILs, which are initially designed to bind boron species [20][21][22]. Meanwhile, they show satisfactory extraction performances toward hydrocarbon halides [23] and deoxyribonucleic acid (DNA) [24], indicating the multiple interactions between glucaminium and solutes.…”