Supported phosphotungstic acid catalyst on modified activated carbon for Friedel–Crafts alkenylation of diverse aromatics to their corresponding α-arylstyrenes

Abstract

The supported phosphotungstic acid catalysts on modified activated carbon (PTA/AC) prepared by a facile wet impregnation method were employed for Friedel–Crafts alkenylation of diverse aromatics with phenylacetylene to synthesize their corresponding α-arylstyrenes. Reaction results demonstrate that the fabricated PTA/AC catalyst with 30wt.% PTA loading exhibits outstanding catalytic performance. The 100% conversion of phenylacetylene with 95.7% selectivity towards α-(2,5-dimethylphenyl) styrene can be achieved over the developed 30wt.% PTA/AC catalyst under optimized reaction conditions, and no visible loss in catalytic performance can be observed after it suffers from several times recycling. The various characterization techniques including X-ray diffraction, N2 adsorption–desorption, Fourier transform infrared spectroscopy, and NH3 temperature-programmed desorption were employed to reveal the relationship between the catalysts nature and catalytic properties. Moreover, the results on the scope of aromatics for the Friedel–Crafts alkenylation illustrate that the developed PTA/AC alkenylation catalyst can be efficiently catalyze the diverse aromatics and even for the electron deficient chlorobenzene. The developed PTA/AC catalyst, using the modified low-cost and sustainable AC as support, may be a robust and promising candidate for highly-efficient and clean α-arylstyrenes production through Friedel–Crafts alkenylation of diverse aromatics including electron-donating and electron-withdrawing groups substituted benzene derivatives as well as heterocyclic and polypolycyclic arenes with phenylacetylene.