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Development of Synthesis and Preparation Methods of the Membranes Capable of Recognizing Chiral Structure for the Separation of Optical Isomers

用于光学异构体分离的手性结构识别膜的合成与制备方法研究进展

基本信息

批准号：
04555224
负责人：
TONE Setsuji
金额：
$ 3.9万
依托单位：
Osaka University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Developmental Scientific Research (B)
财政年份：
1992
资助国家：
日本
起止时间：
1992 至 1993
项目状态：
已结题

项目摘要

For the purpose of developing a technology in the preparation of ultrafiltration membranes for the effective separation of optical isomers such as the highly functionalized polymers and enzymes that are capable of recognizing chiral stereostructures, studies on membranes for optical resolution were performed and the following findings were obtained.1. Amino acid fixed membrane : Amino acid fixed membranes were prepared by introducing the condensate derived from the reaction of glutaraldehyde and L-phenylglycine into the polysulfone matrix by phase inversion method. It was found that the separation factor changed significantly with the types of membrane prepared under different conditions. Under the conditions of solvent evaporation period = 65 minutes at 60。C, a separation factor of 9.1 was obtained for the phenylglycine racemate. It was also found that the L-phenylglycine fixed membrane could be applied to the optical resolution of aromatic compounds with amino acid moiety.2. Plasma p … More olymerized l-menthol membrane : l-Menthol was fixed on the porous support membranes of cellulose acetate with different pore diameters by plasma polymerization. Constant fixation rates of l-menthol were obtained up to 60, 75 and 150 min of plasma irradiation time for cellulose acetate membranes with pore diameter = 0.2, 0.45 and 0.8 mum, respectively, and the pure water permeability of each membrane prepared over those times was proportionally related to the square of pore radii. However, it was seen that beyond these indicated times of plasma irradiation, the fixation rate of l-menthol on each membrane decreased. The separation factor of racemic tryptophan was the largest in the optical resolution of racemic tryptophan, phenylalanine and tyrosine. It was found that the steric configuration contributed to the separation factor.3. Terpene-fixed membranes : The fixation of optically active terpenes such as l-menthol, S-citronellol, R-limonene and S-borneol on the cellulose acetate membrane with pore diameter = 0.2 mum was performed by plasma polymerization. Different membranes were prepared under various conditions of plasma polymerization. It was revealed that the amount of terpene fixed on the membrane increased with increasing time of plasma irradiation, and the large separation factor resulted in a decrease in permeation flux. Further, it was shown that the optical resolution of amino acid was feasible irrespective of the types of membrane used, and the separation factor of S-citronellol fixed membrane was the largest among the prepared membranes. Less

为了开发一种制备超滤膜的技术，以有效分离光学异构体，如能够识别手性立体结构的高度官能化的聚合物和酶，对光学拆分膜进行了研究，获得了以下结果1。氨基酸固定膜：将戊二醛与L-苯甘氨酸反应生成的缩合物引入到聚砜基质中，采用相转化法制备了氨基酸固定膜。研究发现，不同条件下制备的膜的分离因子随膜的类型不同而发生显著变化。在溶剂挥发时间=65分钟、温度为60℃的条件下。C，苯甘氨酸外消旋体的分离系数为9.1。研究还发现，L-苯甘氨酸固定膜可用于含氨基酸结构的芳香族化合物的光学拆分。血浆p-…进一步聚合的L-薄荷醇膜：采用等离子体聚合的方法将L-薄荷醇固定在不同孔径的醋酸纤维素多孔支撑膜上。对于孔径分别为0.2um、0.45和0.8um的醋酸纤维素膜，在60、75和150min的等离子体辐照时间下，L薄荷脑的固定率保持不变，且在此时间内制得的膜的纯水透过率与孔径的平方成正比。但是，超过这些指示的等离子体照射次数后，L薄荷脑在每一膜上的固定率都下降了。外消旋色氨酸、苯丙氨酸和酪氨酸的光学拆分中，外消旋色氨酸的分离因子最大。研究发现，立体构型对分离因子有贡献。萜类固定膜：采用等离子体聚合的方法，将光学活性的L-薄荷醇、S-香茅醇、R-柠檬烯和S-冰片等光学活性萜类化合物固定在孔径为0.2um的醋酸纤维素膜上。在不同的等离子体聚合条件下制备了不同的膜。结果表明，随着等离子体辐照时间的延长，膜上固定的萜烯含量增加，分离因子越大，膜的渗透通量越小。进一步研究表明，无论使用何种膜，氨基酸的光学拆分都是可行的，其中S-香茅醇固定膜的分离因子最大。较少