膜科学与技术

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Study of chiral transport properties of cellulose acetoacetate membranes

Authors： WANG Tao1, LIU Xuyang1, LIU Dongqing1, YOU Meng2, MENG Jianqiang1

Units： 1. State Key Laboratory of Separation Membranes and Membrane Processes, School of Materials Science and Engineering, Tiangong University 2.1. State Key Laboratory of Separation Membranes and Membrane Processes, School of Materials Science and Engineering, Tiangong University

KeyWords： chiral separation; cellulose acetoacetate membrane; ester exchange reaction; chiral transport properties; D,L-tryptophan

ClassificationCode：TQ028

year,volume(issue):pagination： 2024,44(5):82-89

Abstract：

In this study, the less expensive and readily available microcrystalline cellulose was chosen as the experimental raw material, and the reaction of tert-butyl acetoacetate with ester exchange method was used to prepare cellulose acetoacetate (CAA) with different degrees of substitution by controlling the reaction time, and the solvent evaporation method was used to obtain the CAA membrane. The chemical structure, morphology and thermal stability of CAA membranes were tested by 1H NMR, FTIR, SEM and TGA. The permeation splitting property of CAA membranes for D,L-tryptophan was tested using a dialyser, and the concentration of D-tryptophan and L-tryptophan in the permeate was tested using binary high-pressure gradient high-performance liquid chromatography (HPLC). The mechanism of D,L-tryptophan splitting by CAA membranes with different degree of substitution was investigated with respect to the chiral transport property. It was found that CAA membranes with low substitution degree had better chiral splitting performance, while CAA membranes with high substitution degree had lower separation performance due to the increase of free volume after contacting with aqueous solution, and the tryptophan could easily pass through the permeation periplasm. After analysing the permeation, partitioning and diffusion coefficients of D-tryptophan and L-tryptophan, it was concluded that the chiral splitting performance of CAA membranes with high substitution degree was mainly controlled by diffusion. The enantiomeric excess percentage of CAA membranes with low substitution degree (DS=0.57) remained 100% for 6 h, decreased slightly beyond 6 h, and then stabilised. In this study, chiral separation membranes with certain splitting performance were prepared by simply modulating the substitution degree of CAA, which provides ideas for the design of chiral separation membranes.

Funds：

国家自然科学基金项目（22075206）

AuthorIntro：

王涛（1998-），男，山东滨州人，硕士生，从事改性膜对手性分子分离性能的研究.*通讯作者,尤蒙,E-mail： youmeng125@163.com; 孟建强,E-mail：jianqiang.meng@hotmail.com

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