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Chiral Membrane Chromatography Study Based on Amylose-tris-(3, 5-dimethylphenylcarbamate)-Polyethersulfone
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摘要: 以直链淀粉三(3, 5-二甲基苯基氨基甲酸酯)为材料，利用相转化法制备直链淀粉三(3, 5-二甲基苯基氨基甲酸酯)-聚醚砜手性高分子膜. 使用自制的手性膜色谱装置与高效液相色谱仪结合，对手性物质盐酸普萘洛尔和美托洛尔进行了手性膜色谱分离研究. 研究了进样量、流速、膜尺寸对分离效果的影响. 在优选分离效果的条件下，手性膜色谱以纯水为流动相，测得盐酸普萘洛尔的分离因子（α）和分离度（Rs）分别为3.00和0.95，美托洛尔的α和Rs分别为1.65和0.46. 为手性化合物的分离分析开拓了新的途径.Abstract: The chiral membrane of amylose-tris-(3, 5-dimethylphenylcarbamate)-polyethersulfone was prepared by phase conversion method using the amylose-tris-(3, 5-dimethylphenylcarbamate) as the material. The chiral membrane chromatographic separation of propranolol hydrochloride and metoprolol were studied by using the self-made chiral membrane chromatographic device combined with a high performance liquid chromatograph. The effects of injection volume, flow rate and membrane size on the separation of membrane were studied. Under the optimal conditions, the separation factors (α) and resolution (Rs) with water as mobile phase were 3.00 and 0.95 for propranolol hydrochloride, 1.65 and 0.46 for metoprolol, respectively. The study opens up a new way for the isolation and analysis of chiral compounds.
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图 2 膜色谱装置（左）正面及（右）截面示意图
Figure 2. Schematic views of (left) front and (right) cross-section of membrane chromatography device
图 3 （a）PES膜，（b）AD-PES手性膜的傅里叶红外光谱图
Figure 3. FT-IR spectra of (a) PES membrane, (b) AD-PES chiral membrane
图 4 AD-PES手性膜的SEM图
（a）AD-PES手性膜表面,（b）AD-PES手性膜截面
Figure 4. SEM images of AD-PES chiral membrane
(a) surface of AD-PES chiral membrane, (b) cross-section of AD-PES chiral membrane
图 5 盐酸普萘洛尔分离色谱图及其结构式
Figure 5. Chromatogram and structural formula of propranolol hydrochloride
表 1 三种膜色谱装置具体参数
Table 1. Specific parameters of three membrane chromatography devices
/mm 型号 凹槽直径 凹槽
深度过滤芯
厚度过滤芯
直径孔道
直径整体
高度大号 33 1 2.0 33 0.5 25 中号 22 1 1.5 22 0.5 25 小号 13 1 1.5 13 0.5 27 
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表 2 不同进样量条件下盐酸普萘洛尔的分离结果
Table 2. Separation results of propranolol hydrochloride under different injection volumes
进样量/μL k1 k2 α Rs 1 4.20 11.53 2.75 0.68 2 3.99 11.06 2.77 0.82 3 3.50 10.50 3.00 0.95 4 3.27 10.06 3.08 0.88 5 3.54 10.16 2.87 0.74
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表 3 不同流速下盐酸普萘洛尔的分离结果
Table 3. Separation results of propranolol hydrochloride under different flow rates
流速/ (mL/min) k1 k2 α Rs 0.01 14.46 34.25 2.37 0.78 0.02 6.75 18.00 2.67 0.80 0.03 3.50 10.50 3.00 0.95 0.04 3.40 8.83 2.60 0.84 0.05 2.46 6.20 2.52 0.77
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表 4 不同膜尺寸下盐酸普萘洛尔的分离结果
Table 4. Separation results of propranolol hydrochloride under different membrane sizes
膜尺寸/mm k1 k2 α Rs 33 5.17 12.83 2.48 0.88 22 3.50 10.50 3.00 0.95 13 3.64 9.66 2.65 0.87
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表 5 不同进样量条件下美托洛尔的分离结果
Table 5. Separation results of metoprolol under different injection volumes
进样量/μL k1 k2 α Rs 1 2.43 3.44 1.42 0.38 2 2.39 3.41 1.43 0.43 3 1.70 2.80 1.65 0.46 4 2.34 3.43 1.46 0.37 5 2.45 3.43 1.40 0.25
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表 6 不同流速下美托洛尔的分离结果
Table 6. Separation results of metoprolol under different flow rates
流速/ (mL/min) k1 k2 α Rs 0.01 6.55 8.69 1.33 0.38 0.02 4.84 6.59 1.36 0.40 0.03 1.70 2.80 1.65 0.46 0.04 1.61 2.41 1.49 0.43 0.05 0.50 0.94 1.88 0.33
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表 7 不同膜尺寸下美托洛尔的分离结果
Table 7. Separation results of metoprolol under different membrane sizes
膜尺寸/mm k1 k2 α Rs 33 — — — — 22 1.70 2.80 1.65 0.46 13 1.48 2.13 1.44 0.41
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