Friedel–Crafts benzylation of toluene catalyzed by ZnCl2/SiO2 heterogeneous catalyst to para- and ortho-monobenzylated toluene

Iqbal, Anwar and Tan, Kok Hou and Shaari, U. S and Ahmad, Najwa I.N.B. and Adam, Farook and Lee, Hwei Voon and M. Yusop, Rahimi and Abu Bakar, Noor Hana Hanif and Lee, Hooi Ling and Pauzi, Hariy and Abd Malik, Muhammad Fadhirul Izwan and Jusoh, Ahmad Fadly and Wilson, Lee D. and Ahmad, Mohammad Norazmi and Hussin, Mohd. Hazwan and Mohamad Ibrahim, Mohamad Nasir (2020) Friedel–Crafts benzylation of toluene catalyzed by ZnCl2/SiO2 heterogeneous catalyst to para- and ortho-monobenzylated toluene. Journal of The Iranian Chemical Society, 17 (7). pp. 1615-1626. ISSN 1735-207X

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Abstract

A series of catalysts was prepared for the liquid-phase Friedel–Crafts benzylation of toluene with benzyl chloride (BC) by impregnating rice husk ash silica with ZnCl2 (3 wt%, 6 wt%, 9 wt%, and 12 wt%) via a wet impregnation method. The XRD analysis indicates that the catalysts were amorphous with ill-defined pore systems. The XPS analysis detected the coexistence of ZnO nanoparticles together with ZnCl2 on the catalyst surface, whereas the 29Si NMR analysis indicates the formation of Si–O–Zn bond. Quantitative conversion of benzyl chloride (100%) was achieved within 3 h at 353 K when a catalyst with 9 wt% ZnCl2 was used due to its narrow pore size and high surface area (635 m2 g−1). Para- and ortho-mono-benzylated toluene was obtained as the products. The reaction is proposed to take place via weak attraction between benzyl chloride and the Zn through its chlorine atom. The catalyst was recycled four times with minimum loss (8%) in activity. The benzylation of benzene, toluene, p-xylene, and anisole followed the classical mechanism of Friedel–Craft-type acid-catalyzed benzylation reaction. The BC conversion increased in the order of toluene = p-xylene > anisole > benzene. The catalyst was also screened to be active in the benzoylation of toluene with benzoyl chloride (BOC). The conversion of BOC was 45% with selectivity toward 2-methylbenzophenone (50%) and 3-methylbenzophenone (50%)

Item Type:	Article (Journal)
Additional Information:	7148/79765
Uncontrolled Keywords:	Rice husk · Rice husk ash silica · Friedel–Crafts benzylation · ZnCl2 · Para- and ortho-mono-benzylated toluene
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Science Kulliyyah of Science > Department of Chemistry
Depositing User:	Dr Mohammad Norazmi Ahmad
Date Deposited:	06 Apr 2020 18:08
Last Modified:	27 Nov 2020 15:38
URI:	http://irep.iium.edu.my/id/eprint/79765

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