Synthesis of chiral binaphthyl Schiff-base ligand and metal complexes and their application in alkene epoxidation in supercritical carbon dioxide

In this study, new chiral Schiff base ligand have been synthesised by condensation of 2,2?-diamino-1,1?-binaphthalene and various salicylaldehydes. In order that products are preferentially soluble in supercritical carbondioxide, various chiral ligands with perfluoroalkyl chains attached have been synthesised and studied. The use of perfluoroalkyl chains not only raise solubility but also achieve original quality to these ligands. Effects of their perfluorinated derivatives and soluble on the activity and selectivity of the catalysts are herein discussed. The chiral binaphthyl Schiff-base manganese complexes have been prepared. The complete FT-IR, LC-MS, 1H and 19F NMR characterization of the ligands and complexes are analyzed, solubility is determined under 2250 psi CO2 constant pressure at 40oC.Their catalytic abilities in asymmetric epoxidation of styrene as a catalyst and the effects of organic solvents or scCO2 as a reaction area have been studied. Also, the effects of reaction conditions such as time, catalyst/substrat rate, various oxidant, solvent, temperature, substitute groups and position have been investigated.