基于二醛微晶纤维素功能化C18的反相/亲水色谱固定相的制备

doi:10.3724/SP.J.1123.2019.03009

摘要/Abstract

摘要：

通过十八烷基胺的氨基与二醛微晶纤维素的醛基共价键合,制备了基于二醛微晶纤维素(DMCC)官能化C₁₈的新型反相/亲水色谱固定相(C₁₈-DMCC/SiO₂),该色谱固定相被用于反相色谱(RPLC)和亲水相互作用色谱(HILIC)模式。C₁₈-DMCC/SiO₂色谱柱展现了良好的疏水选择性和芳香选择性,在反相色谱模式下可分离烷基苯和多环芳烃(PAHs)。苯胺类、酚类和糖苷类等极性化合物被用于评估该色谱柱在反相色谱模式下的极性选择性,商品C₁₈柱作对照柱,色谱评价结果令人满意。核酸碱基被用于评估C₁₈-DMCC/SiO₂色谱柱的亲水色谱性能。通过考察有机溶剂含量对分析物保留的影响,发现该新型色谱固定相具有反相/亲水色谱的典型特征。

关键词: 反相色谱, 亲水相互作用色谱, 高效液相色谱, 固定相, 制备, 二醛微晶纤维素, C₁₈

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

中图分类号:

O658

高洁, 武琪, 陈立骁, 李辉, 董树清, 罗国英, 张书胜, 邱洪灯, 赵亮. 基于二醛微晶纤维素功能化C₁₈的反相/亲水色谱固定相的制备[J]. 色谱, 2020, 38(4): 414-423.

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.

图/表 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.

参考文献

[1]	Wang Q, Long Y, Yao L, et al. Talanta, 2016, 146: 442
[2]	Mallik A K, Qiu H D, Oishi T, et al. Anal Chem, 2015, 87(13): 6614
[3]	Zhang Y J, Li Q Q, Dai B L, et al. J Chromatogr A, 2018, 1553: 81
[4]	Wu Q, Chen L X, Gao J, et al. Talanta, 2019, 194: 105
[5]	Ruan C Q, Stromme M, Lindh J. Cellulose, 2016, 23(4): 2627
[6]	Sulaeva I, Klinger K, Amer H, et al. Cellulose, 2015, 22(6): 3569
[7]	He H, Hou X A, Ma B B, et al. Cellulose, 2016, 23(4): 2539
[8]	Wu Q, Sun Y M, Zhang X L, et al. J Chromatogr A, 2017, 1492: 61
[9]	Wu Q, Sun Y M, Gao J, et al. New J Chem, 2018, 42(11), 8672
[10]	Jiang Q, Zhao W J, Qiu H D, et al. Chromatographia, 2016, 79(21/22): 1437
[11]	Qiu H D, Mallik A K, Takafuji M, et al. Anal Chim Acta, 2012, 738: 95
[12]	Ren X J, Zhang K L, Gao D, et al. J Chromatogr A, 2018, 1564: 137
[13]	Wei J, Guo Z M, Zhang P J, et al. J Chromatogr A, 2012, 1246: 129
[14]	Zhang M L, Chen J, Gu T N, et al. Talanta, 2014, 126: 177
[15]	Zhang M L, Chen J, Mallik A K, et al. Anal Chim Acta, 2014, 833: 48
[16]	Mallik A K, Qiu H D, Oishi T, et al. Anal Chem, 2015, 87(13): 6614
[17]	Zhang M L, Mai W P, Zhao L, et al. J Chromatogr A, 2015, 1388: 133
[18]	Wang Q, Long Y, Yao L, et al. Talanta, 2016, 146: 442
[19]	Wang Q, Ye M, Xu L, et al. Anal Chim Acta, 2015, 888: 182
[20]	Calvini P, Conio G, Princi E, et al. Cellulose, 2006, 13(5): 571
[21]	Li H L, Wu B, Mu C D, et al. Carbohyd Polym, 2011, 84(3): 881
[22]	Sirvio J, Hyvakko U, Liimatainen U, et al. Carbohyd Polym, 2011, 83(3): 1293
[23]	Wu M, Kuga S. J Appl Polym Sci, 2006, 100(2): 1668
[24]	Ruan C Q, Stromme M, Lindh J. Carbohyd Polym, 2018, 181: 200
[25]	Mou K W, Li J J, Wang Y Y. J Mater Chem B, 2017, 5(38): 7876
[26]	Zhang X Y, Shen G Y, Sun S Y. Sensors Actuat B-Chem, 2014, 200: 304
[27]	Zheng X J, Zhang Q N, Liu J, et al. RSC Adv, 2016, 6(76): 71999
[28]	Lu T H, Li Q, Chen W S, et al. Compos Sci Technol, 2014, 94: 132
[29]	Czok M, Engelhardt H. Chromatographia, 1989, 27(1/2): 5
[30]	Zhou D, Zeng J, Fu Q F, et al. J Chromatogr A, 2018, 1571: 165
[31]	Hemstrom P, Irgum K. J Sep Sci, 2006, 29(12): 1784.

基于二醛微晶纤维素功能化C₁₈的反相/亲水色谱固定相的制备

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

RichHTML

PDF

可视化

摘要/Abstract

引用本文

使用本文

扫码分享

图/表 13

参考文献

相关文章 15

编辑推荐

Metrics

[1]	史洪飞, 徐伯芃, 徐成鑫, 周修齐, 许宏福. 溶剂萃取-高效液相色谱-四极杆飞行时间质谱法快速提取检测干燥恰特草中5种生物碱成分[J]. 色谱, 2023, 41(9): 771-780.
[2]	唐泽坤, 万慧慧, 李红, 陈绍云, 赵金凤, 孙玉明, 蔡蕊, 徐强, 张华. 亲水相互作用色谱-静电场轨道阱高分辨质谱法测定CO₂吸收液中9种有机胺类化合物[J]. 色谱, 2023, 41(9): 799-806.
[3]	赵芮, 黄晴雯, 余智颖, 韩铮, 范楷, 赵志辉, 聂冬霞. QuEChERS-超高效液相色谱-串联质谱法同时测定水果中36种真菌毒素[J]. 色谱, 2023, 41(9): 760-770.
[4]	刘宇, 邢家溧, 沈坚, 毕晓丽, 毛玲燕, 徐晓蓉, 张书芬, 娄永江, 吴希, 穆应花. 高效液相色谱-蒸发光散射检测法同时测定固态食品中6种稀有糖[J]. 色谱, 2023, 41(9): 781-788.
[5]	岳超, 赵超群, 毛思浩, 王展华, 施贝, 徐欣丰, 梁晶晶. 通过式固相萃取净化-超高效液相色谱-串联质谱法测定液体乳中10种氨基甲酸酯类农药残留[J]. 色谱, 2023, 41(9): 807-813.
[6]	周然锋, 张惠贤, 尹小丽, 彭西甜. 新型纳米材料在农产品安全分析中的应用进展[J]. 色谱, 2023, 41(9): 731-741.
[7]	钱正明, 吴梦奇, 谭国英, 金李玲, 李宁, 谢菊英. 高效液相色谱紫外等吸收波长法快速测定秦皮中秦皮甲素和秦皮乙素[J]. 色谱, 2023, 41(8): 690-697.
[8]	马超, 倪洪星, 戚羽霖. 超高效液相色谱-傅里叶变换离子回旋共振质谱法解析溶解性有机质的化学多样性[J]. 色谱, 2023, 41(8): 662-672.
[9]	吴萍萍, 林仁义, 黄丽英. 三相中空纤维液相微萃取-高效液相色谱法测定铁皮石斛和金线莲中3种植物生长调节剂[J]. 色谱, 2023, 41(8): 683-689.
[10]	孟二琼, 念琪循, 李峰, 张秋萍, 许茜, 王春民. 磺酸化磁性氮化碳固相萃取-超高液相色谱-串联质谱筛检淡水鱼中孔雀石绿和隐色孔雀石绿[J]. 色谱, 2023, 41(8): 673-682.
[11]	曹沁玲, 赵小丹, 沈国滨, 汪竹琴, 章弘扬, 张敏, 胡坪. 基于超高效液相色谱-电雾式检测的槐糖脂指纹图谱[J]. 色谱, 2023, 41(8): 722-729.
[12]	陈东洋, 张昊, 张磊, 王一红, 王小丹, 冯家力, 梁静, 钟旋. 固相萃取-超高效液相色谱-串联质谱法测定发酵食品中的曲酸[J]. 色谱, 2023, 41(7): 632-639.
[13]	王秋旭, 冯启言, 朱雪强. 加速溶剂萃取-固相萃取净化结合超高效液相色谱-串联质谱法测定沉积物中双酚类化合物[J]. 色谱, 2023, 41(7): 582-590.
[14]	杨哲, 吕建霞, 吴一荻, 蒋力维, 李冬梅. 超高效液相色谱法同时测定电子烟油中的5种吲哚/吲唑酰胺类合成大麻素[J]. 色谱, 2023, 41(7): 602-609.
[15]	夏宝林, 汪仕韬, 殷晶晶, 张维益, 杨娜, 刘强, 吴海晶. 自动上样固相萃取-超高效液相色谱-串联质谱法同时测定水中9类43种抗菌药物残留[J]. 色谱, 2023, 41(7): 591-601.