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

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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