Synthesis of Crown Ethers from Saturated Urushiol and Separation of Their Positional Isomers

Saturated Urushiol, prepared by the catalytic hydrogenation of the Chinese lacquer was condensed with dichlorides of polyethylene glycol to give five dibenzo crown ethers with n-pentadecyl group on the two benzene rings. The crude products were purified by continuous extraction and fractional crystailization.The positional isomers of DSU18-C-6 were separatd by TLC.The structures of the new compounds were determined by infrared spectra, ultraviolet spectra,mass spectra,1HNMR spectra,X-ray crystallography and elementary analysis. The long alkyl chains on the benzene rings improved the lipophilicity of the crown ethers.They were soluble in various organic solvent,and showed improved activity as phase trafer catafer catalyst.DSU30-C-10 has been shown to be a very attractive neutral carrier for making potassium-selective PVC membrance electrode.