Preparation of Poly-(GMA-EDA-β-CD-co-TMPTMA) Monolith as High Performance Liquid Chromatography Chiral Stationary Phase Column

Abstract

An enantiomer molecule consisted of the chiral atom has different structure conformations, which exhibit different activities as well. Yet, its separation considerably difficult since ordinary separation could not separate both molecules. One of the popular enantioseparations which are often used was using organic polymer monolithic column modified by ethylenediamine-β-cyclodextrin (EDA-β-CD) as the enantioseparations site. The aim of this research was to produce chiral stationary phase column for enantioseparations of (±)-citronellal. It was conducted by preparing monolithic column using monomer glycidyl methacrylate (GMA), trimethylolpropane trimethacrylate (TMPTMA) as crosslinker, 1-propanol, 1,4-butanediol, and water as pore-forming agents (porogens) in the presence of α,α'-azoisobutyronitrile (AIBN) as radical initiator inside polyetheretherketone (PEEK) tubing. It was then modified with EDA-β-CD synthesized from β-CD. Finally, it was installed as a high-performance liquid chromatography column. The result shows the produced chiral stationary phase column could separate (±)-citronellal at a retention time of 44.76 and 45.71 min.

Immobilization of trypsin onto porous methacrylate-based monolith for flow-through protein digestion and its potential application to chiral separation using liquid chromatography

“…The presence of the sulfonate group provides advantages for further modification through the introduction of the methacryloyl group, allowing the chemical bonding of monolith with the inner wall of PEEK tubing. Additionally, the methacryloyl group is also used to terminate the sulfonation process, preventing degradation of PEEK tubing [ 28 , 29 ].…”

“…However, incomplete separation results of R/S-citronellal in this work were not caused by the use of a larger diameter of column (1.0 mm i.d). In our previous work [ 29 ], we could separate R/S-citronellal (Rs > 1.5) using Poly-(GMA-co-TRIM) modified with ethylenediamine-β-cyclodextrin (EDA-β-CD) inside 1.0 mm i.d x 100 mm tubing. Although this monolith exhibited its potential for enantioseparation of R/S citronellal, its chemical stability still needs improvement due to loss of EDA-β-CD after 250 h usage.…”

“…Additionally, the synthesis procedure of EDA-β-CD was also complicated. To the best of our knowledge, reports on R/S-citronellal enantioseparation using a monolithic liquid chromatography are scarce [ 29 , 39 ].…”

“…Before use, the polyetheretherketone (PEEK) tubing as a column housing was treated according to our previous work [ 28 , 29 ]. This tubing is filled with sulfuric acid/water (1:1) and left to stand at room temperature for 6 h with both ends of the tubing closed.…”

Characterization of Organic Polymer Monolith Columns Containing Ammonium Quarternary As Initial Study For Capillary Chromatography

“…The Cr (VI) ion could be adsorbed using a magnetic polymer containing an amine group , Zhao et al, 2010, removal of Pb 2+ , Cu 2+, and Zn 2+ (Mokadem et al, 2020), trace Cd (II) in biological samples (Chen et al, 2020), and removal of Pb(II) from water medium (Naushad et al, 2020). Methacrylate-based polymers with the epoxy ring-opening method have been successfully prepared and applied for separation of organic compounds such as Bisphenol A (BPA) , Bovine Serum Albumin (BSA) (Shamim et al, 2007), alkylbenzene (Wang et al, 2014), pentachlorophenol (Pan et al, 2014), and enantioseparation (Angga et al, 2019). Furthermore, it is also applied for the adsorption of some ions, such as Cu (II) (Shen et al, 2012) and Hg (II) ions (Pan et al, 2014.…”