PREPARATION OF BUTYLATED PHENOL DERIVATIVES USING ACIDIC HETEROGENEOUS CATALYSTS

Abstract

Propyl sulfonic acid functionalized SBA-15 and proton MCM-22 catalysts were synthesized by using hydrothermal method. The structure morphology and acidity of synthesized materials were characterized by X-ray powder diffraction, nitrogen sorption analysis, scanning electron microscopy and acidity measurement. Propyl sulfonic acid fuctionalized SBA-15 (SBA-15-Pr-SO3H) was tested catalytic activities in BisphenolA butylation and compared catalytic activity with Amberlyst-15 and other porous catalysts. The optimized condition when using SBA-15-Pr-SO3H was mole ratio of BisphenolA to MTBE of 1: 10, catalytic amount 15 wt% based on BisphenolA at 120oC for 8 hrs. The reaction mixture gave the highest total yield of products compared to those of other mesoporous catalysts. Moreover, the catalytic efficiency of HMCM-22 of butylation of BisphenolA was tested. Suitable reaction condition that gave the highest total product was optimized to be mole ratio of BisphenolA to tert-butanol as 1: 15, catalytic amount 10 wt% based on BisphenolA at 120oC for 8 hrs. The reaction mixture exhibited the highest total yield of alkylated products as 32.8%. In addition, the condition of continuous flow process to prepare 2,6-di-tert-butyl p-cumylphenol was optimized to be mole ratio of p-cumylphenol to MTBE of 1: 5, LHSV = 0.02 h-1, at 100oC. The results illustrated the highest 2,6-di-tert-butyl p-cumylphenol yield as 28.19%. The radical scavenging capacity of purified and reaction mixtures were measured to compare with their starting materials. It was found that antioxidant activity was increased as following order; BisphenolA < p-cumylphenol < 2-tert-butyl p-cumylphenol < BisphenolA products < 2,6-di-tert-butyl p-cumylphenol.