CYCLOALKYLATION OF PARA-CHLOROPHENOL WITH 1-METHYL-CYCLOALKENES IN THE PRESENCE OF A ZEOLITE-CONTAINING CATALYST

Abstract

The results of alkylation reactions of para-chlorophenol with 1-methylcyclopentene and 1-methylcyclohexene in the presence of zeolite-containing catalyst Seokar-2 (TU38-101483-77) are presented in the paper. Para-chlorophenol (PCP) interacted with 1-methylcycloalkenes on a laboratory batch setup. The reaction products were separated from the catalyst by hot filtration (40-50 °C) and undergone to distillation. Methylcyclene was distilled off at atmospheric pressure, then unreacted para-chlorophenol and the target reaction product were isolated under vacuum (10 mm Hg). Optimal conditions ensuring maximum yield of 2-cycloalkyl-4-chlorophenols were determined by studying effect of temperature, reaction time, molar ratio of PCP to 1-methylcycloalkenes, and amount of catalyst on the yield and selectivity. The reaction temperature was varied from 80 to 140 °C, duration of the experiments was from 2 to 8 h, molar ratio of PCP to 1-methylcycloalkenes was from 2:1 to 1:2 mol/mol, amount of catalyst was from 5 to 15% mas. It resulted in determining of the optimal conditions for alkylation reaction of para-chlorophenol with 1-methylcyclopentene and 1-methylcyclohexene in the presence of the zeolite-containing catalyst Seokar-2: reaction temperature 110-120 °C, duration 4-6 h, molar ratio of PCP to 1-methylcycloalkenes 1:1, catalyst amount 12-15% (on the taken PCP). These conditions allow having 68.2-73.6% yield of theory for 2-cycloalkyl-4-chlorophenols for the taken PCP, and 89.3-91.8% of selectivity for the target product. The physicochemical properties, elemental composition and structure were determined by 1H NMR and IR spectroscopy after separation of the target products from alkylate by distillation.