Preparation of reversed-phase/hydrophilic chromatographic stationary phase based on dialdehyde microcrystalline cellulose-functionalized C18

doi:10.3724/SP.J.1123.2019.03009

Abstract

Abstract:

A novel reversed/hydrophilic chromatographic stationary phase based on dialdehyde microcrystalline cellulose (DMCC)-functionalized C₁₈ was prepared by covalent bonding between the amino groups of octadecylamine with the aldehyde groups of DMCC, which was used in reversed-phase liquid chromatography (RPLC) and hydrophilic interaction liquid chromatography (HILIC) modes. The prepared DMCC-functionalized C₁₈ modified silica (C₁₈-DMCC/SiO₂) stationary phase exhibited good hydrophobic selectivity and aromatic selectivity by separating alkylbenzenes and polycyclic aromatic hydrocarbons (PAHs) in the RPLC mode. Polar compounds, including anilines, phenols, and glycosides were chosen as analytes to evaluate the polar selectivity of this column in the RPLC mode, and the evaluation results were satisfactory compared with the commercial C₁₈ column. Nucleobases were used for evaluating the hydrophilic interaction liquid chromatography performance of the C₁₈-DMCC/SiO₂ column. By investigating the impact of organic solvent content on the retention, it could be found that this new stationary phase had the typical characteristics of reversed-phase/hydrophilic chromatography.

Key words: reversed-phase liquid chromatography (RPLC), hydrophilic interaction liquid chromatography (HILIC), high performance liquid chromatography (HPLC), stationary phase, preparation, dialdehyde microcrystalline cellulose (DMCC), C₁₈

CLC Number:

O658

GAO Jie, WU Qi, CHEN Lixiao, LI Hui, DONG Shuqing, LUO Guoying, ZHANG Shusheng, QIU Hongdeng, ZHAO Liang. Preparation of reversed-phase/hydrophilic chromatographic stationary phase based on dialdehyde microcrystalline cellulose-functionalized C₁₈[J]. Chinese Journal of Chromatography, 2020, 38(4): 414-423.

Figures/Tables 13

Fig. 1 Synthesis of C18-DMCC/SiO2 composite

Fig. 2 SEM images of (a) MCC, and DMCC under (b) low and (c) high magnifications

Fig. 3 FT-IR spectra of MCC and DMCC

Fig. 4 PXRD patterns of MCC and DMCC

Fig. 5 SEM images of (a) NH2/SiO2 and (b) C18-DMCC/SiO2

Fig. 6 FT-IR spectra of NH2/SiO2, DMCC/SiO2, and C18-DMCC/SiO2

Table 1 Elemental analysis datas of NH2/SiO2, DMCC/SiO2, and C18-DMCC/SiO2

Sample	Element contents/%
Sample	N	C	H
NH₂/SiO₂	1.33	3.97	0.80
DMCC/SiO₂	1.28	6.77	0.87
C₁₈-DMCC/SiO₂	1.38	8.54	1.19

Fig. 7 Chromatograms for the separation of (a) alkylbenzenes and (b) PAHs on the C18-DMCC/SiO2 and commercial C18 columns a. 1. benzene; 2. methylbenzene; 3. ethylbenzene; 4. n-propylbenzene; 5. isobutylbenzene; 6. phenylpentane. b. 1. benzene; 2. diphenyl; 3. p-distyrene; 4. o-terophenyl; 5. pyrene; 6. chrysene. Mobile phases: C18-DMCC/SiO2 column, ACN-water (60∶40, v/v) in (a) and ACN-water (50∶50, v/v) in (b); commercial C18 column, ACN-water (80∶20, v/v) in (a) and ACN-water (70∶30, v/v) in (b).

Fig. 8 Plots of lg k versus the number of methylene groups for different mobile phase compositions ACN-H2O were used as the mobile phases, and the volume fractions of acetonitrile were labeled.

Fig. 9 Plots of lg k of alkylbenzenes versus volume fractions of acetonitrile in the mobile phases

Fig. 10 Chromatograms for the separation of (a) anilines, (b) phenols and (c) glycosides on the C18-DMCC/SiO2 and commercial C18 columns a. 1. aniline; 2. N-methylaniline; 3. 3,4-dimethylaniline; 4. methylnaphthylamine; 5. diphenylamine. b. 1. catechol; 2. phenol; 3. p-xylenol; 4. 2-aminophenol; 5. tert-butyl phenol. c. 1. loganin; 2. scopolin; 3. scopoletin; 4. aurantiamarin; 5. naringin. Mobile phases: C18-DMCC/SiO2 column, ACN-water (50∶50, v/v) in (a), ACN-water (25∶75, v/v) in (b), and ACN-water (15∶85, v/v) in (c); commercial C18 column: ACN-water (30∶70, v/v) in (a), ACN-water (40∶60, v/v) in (b), and ACN-water (20∶80, v/v) in (c).

Fig. 11 Chromatograms for the separation of nucleobases on the C18-DMCC/SiO2 and commercial HILIC columns 1. thymine; 2. adenine; 3. cytosine; 4. guanine. Mobile phases: C18-DMCC/SiO2 column, ACN-water (92∶8, v/v) containing 10 mmol/L ammonium acetate; commercial HILIC column, ACN-water (90∶10 v/v) containing 10 mmol/L ammonium acetate.

Fig. 12 Plots of lg k versus (a) the volume fractions of water and (b) logarithmic mole fractions of water in mobile phases Mobile phase: ACN-water, contained 10 mmol/L ammonium acetate.

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Preparation of reversed-phase/hydrophilic chromatographic stationary phase based on dialdehyde microcrystalline cellulose-functionalized C₁₈

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