Nanocellulose 3, 5‐Dimethylphenylcarbamate Derivative Coated Chiral Stationary Phase: Preparation and Enantioseparation Performance

Abstract

Nanocrystalline cellulose (NCC) with high surface area and high ordered crystalline structure was prepared from microcrystalline cellulose (MCC) under the hydrolysis of sodium hypochlorite. NCC was further reacted with 3,5-dimethylphenyl isocyanate to obtain the nanocellulose derivative, and then coated successfully on the surface of silica gel to a prepared NCC-coated chiral stationary phase (CSP) as a new kind of chiral separation material. Similarly, MCC derivative-coated CSP was also prepared as contrast. The chiral separation performance of NCC-based CSP was evaluated and compared with MCC-based CSP by high-performance liquid chromatography. Moreover, the effects of the alcohol modifiers, mobile phase additives, and flow rates on chiral separations were investigated in detail. The results showed that 10 chiral compounds were separated on NCC-based CSP with better peak shape and higher column efficiency than MCC-based CSP, which confirmed that NCC-based CSP was a promising packing material for the resolution of chiral compounds.Chirality 28:376-381, 2016. © 2016 Wiley Periodicals, Inc.

HPLC with cellulose Tris (3,5‐DimethylPhenylcarbamate) chiral stationary phase: Influence of coating times and coating amount on chiral discrimination

“…[6][7][8] The CDMPC-CSP was typically prepared by coating CDMPC onto large pore silica gel with the coating amount of 20 wt%. 13 Okamoto 14 and Zhang 15 have reported the influence of the properties of CDMPC, for instance, the degree of polymerization or the molecular weight of the cellulose used for preparing CDMPC and the substitution degree of the prepared CDMPC. Much work so far has focused on the effect of the physical and chemical property of silica, including particle size, 9 pore size, 5,[10][11][12] and functional groups on the silica gel surface.…”

“…Much work so far has focused on the effect of the physical and chemical property of silica, including particle size, 9 pore size, 5,[10][11][12] and functional groups on the silica gel surface. 13 Okamoto 14 and Zhang 15 have reported the influence of the properties of CDMPC, for instance, the degree of polymerization or the molecular weight of the cellulose used for preparing CDMPC and the substitution degree of the prepared CDMPC. Considerable research efforts have also been devoted to the influence of the parameters of coating process, such as the type of coating solvent, 5,16 coating amount, 5,11 and the method of removing solvent.…”

A Review of the Surface Modification of Cellulose and Nanocellulose Using Aliphatic and Aromatic Mono- and Di-Isocyanates

“…Aliphatic and aromatic mono-isocyanates such as phenyl isocyanate (PI) and n-octadecyl isocyanate (OI), and di-isocyanates such as toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), hexamethylene diisocyanate (HMDI), and their polymeric forms have all been used for the modification of cellulose and nanocellulose (Figure 3) [25,26,27,28]. PI and OI were mainly used to decrease the hydrophilicity of cellulose and nanocellulose as they do not have the necessary second isocyanate to function as a linker, while TDI, PPDI, MDI, and HMDI have been used both as surface modifiers and chemical linkers [29,30]. TDI, MDI, and HMDI differ mainly in their molecular rigidity, which is mainly dependent on the benzene rings.…”

Eluent Tolerance and Enantioseparation Recovery of Chiral Packing Materials Based on Chitosan Bis(Phenylcarbamate)-(n-Octyl Urea)s for High Performance Liquid Chromatography

“…Among commercialized CSPs, those made from the derivatives of cellulose and amylose have attracted much more attention, due to their strong chiral recognition capability and wide applicability [6,7,8,9]. To date, lots of works on the preparation, chiral recognition mechanism and application of the CSPs derived from cellulose and amylose have been reported [10,11,12,13], and on those of the CSPs made with cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and amylose tris(3,5-dimethylphenylcarbamate) (ADMPC) in particular [14,15,16,17]. To overcome the drawback of dissolution or high swelling of chiral selectors in chromatographic mobile phases, cellulose/amylose derivatives are covalently immobilized on a support [18,19,20].…”