Crown Ether Used As Chiral Separation Material

With the increasing demand for chiral drugs in the pharmaceutical field,the search for an efficient and low-cost separation method of chiral drugs has become a research hot spot in the pharmaceutical field.In recent years,researchers have paid much attention to the enantiomer obtained from the separation of chiral membrane,which has the advantages of low energy consumption,continuous operation,low cost and easy industrial production.The main work of this dissertation is as follows:?1?R-?3,3-dibromo-1,1-dinaphthalene?-20-crown-6 and R-?3,3-diphenyl-1,1-dinaphthalene?-20-crown-6 were synthesized from R-binaphthol as raw materials,and nine crown+C₁₈8 chiral stationary phases of high performance liquid chromatography were prepared to detect phenylglycine and p-hydroxyphenylglycine for membrane dialysis.The results showed that the mixed R-?3,3-dibromo-1,1-dinonyl?-20-crown-6column could be preferred for determination,and the mixed R-?3,3-diphenyl-1,1-dinonyl?-20-crown-6 column could be used for auxiliary verification.This method provides a low cost,high efficiency and accurate analyses for membrane separation of phenylglycine and p-hydroxyphenylglycine.?2?Using the method of solution casting film,the enantioselective membrane of R-?3,3-diphenyl-1,1-dinaphthyl?-20-crown-6 was prepared for enantiomer dialysis of phenylglycine or p-hydroxy phenylglycine.The effects of the reliability of the membrane,dialysate,impurity,thickness,drying temperature,drying time,content of chiral recognition agent,dialysate time,dialysate concentration and stability on the separation performance of the membrane were investigated.The value of e.e.%on the membrane could reach about 77%for phenylglycine,24%for p-hydroxy phenylglycine.?3?R-?3,3-dibromo-1,1-dinaphthalene?-20-crown-6 was used as chiral recognition agent to make the membrane by solution casting method,which was used for selective dialysis of phenylglycine enantiomers.The influence of factors on the membrane separation performance including reliability,which were thickness,chiral recognition agent content,dialysis time,dialysis concentration and stability was investigated.The experimental results showed that the membrane had a certain separation ability to phenylglycine,and the value of e.e.%could reach about 43%.