Study On The Synthesis Of Calixarenes And Their Behavior As PTC In Fluoridation

A series of calix[6]arene derivatives have been synthesized and their performance as PTC in the fluorination of halogenated aromatic compounds has been studied. p-Tertbutylcalix[6]arene is synthesized by p-tertbutylphenol and 37% formaldehyde, in the presence of KOH. The yield of this reaction is 65.8%. The tertbutyl groups of p-tertbutylcalix[6]arene are removed to phenol by an AlCl3 catalyzed transalkylation reaction to produce calix[6]arene. The yield of this reaction is 62.0%. The hexasodium salt of calix[6]arene-p-hexasulfonate is synthesized by the sulfonation reaction between calix[6]arene and 98% sulfuric acid. The yield of this reaction is 58.4%. All products are characterized with 1H-NMR. The products are used as PTC in the fluoridation of p-chloronitrobenzene, tetrachloroterephthaloyl chloride and N-benzyltetrachloridephthalimide to detect the performance of the different PTCs. The catalytic activities of calix[6]arenes for these three reactions are proved and the result indicates that hexasodium salt of calix[6]arene-p-hexasulfonate has the best catalysis performance. In addition, the relationship between structure and performance of the catalyst is obtained. The yields of reaction with varieties of catalysts, reaction times and reaction temperatures are compared and the optimum condition is found.