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通过对映选择性渗透实现高效手性拆分的静电纺丝纤维素膜

Electrospun Cellulosic Membranes toward Efficient Chiral Resolutions via Enantioselective Permeation.

作者信息

Otsuka Issei, Pandey Kritika, Ahmadi-Nohadani Hamed, Nono-Tagne Steve

机构信息

Université Grenoble Alpes, CNRS, CERMAV, Grenoble 38000, France.

出版信息

ACS Macro Lett. 2021 Jul 20;10(7):921-925. doi: 10.1021/acsmacrolett.1c00349. Epub 2021 Jun 28.

DOI:10.1021/acsmacrolett.1c00349
PMID:35549183
Abstract

Cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC), known as one of the most versatile chiral selectors packed in columns for chiral chromatography, is electrospun for the first time. The electrospun nanofibers with a mean diameter of 329 nm form a self-standing nonwoven textile with a specific surface area of 5.6 m/g. The textile is sandwiched between commercially available polytetrafluoroethylene membrane filters as a support material to fabricate a CDMPC membrane system for the chiral resolution of a racemic mixture, (,)-1-(1-naphthyl)ethanol. A vacuum filtration of the racemic mixture through the membrane system using a mixed solvent of -hexane/2-propanol = 9/1 (v/v) enriches the -enantiomer in the filtrate due to an enantioselective sorption of the -enantiomer. The sorption capacity can be regenerated repeatedly via extractions of the adsorbed enantiomers from the membrane system after the filtrations. By repeating the vacuum filtration-extraction process for 15 cycles, the enantiomeric excess () of the -isomer in the filtrate increases up to 32.9%.

摘要

纤维素三(3,5-二甲基苯基氨基甲酸酯)(CDMPC),作为用于手性色谱柱填充的最通用的手性选择剂之一,首次进行了电纺丝。平均直径为329nm的电纺纳米纤维形成了一种具有5.6m/g比表面积的自立式非织造织物。该织物夹在市售的聚四氟乙烯膜过滤器之间作为支撑材料,以制造用于外消旋混合物(±)-1-(1-萘基)乙醇手性拆分的CDMPC膜系统。使用正己烷/2-丙醇=9/1(v/v)的混合溶剂通过膜系统对外消旋混合物进行真空过滤,由于对映体对映体的对映选择性吸附,滤液中富含对映体。在过滤后,通过从膜系统中萃取吸附的对映体,可以反复再生吸附容量。通过将真空过滤-萃取过程重复15个循环,滤液中对映体的对映体过量(ee)增加至32.9%。

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