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Catalysts 2015, 5(4), 2223-2243; doi:10.3390/catal5042223

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

Dipartimento di Chimica Industriale “Toso Montanari”, Viale Risorgimento 4, Università di Bologna, 40136 Bologna, Italy
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Academic Editor: Andreas Martin
Received: 14 November 2015 / Revised: 5 December 2015 / Accepted: 9 December 2015 / Published: 16 December 2015
(This article belongs to the Special Issue Zeolite Catalysis)
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Abstract

In this paper, we report on the reaction of phenol benzoylation with benzoic acid, which was carried out in the absence of solvent. The aim of this reaction is the synthesis of hydroxybenzophenones, which are important intermediates for the chemical industry. H-beta zeolites offered superior performance compared to H-Y, with a remarkably high conversion of phenol and high yields to the desired compounds, when using a stoichiometric amount of benzoic acid. It was found that the reaction mechanism did not include the intramolecular Fries rearrangement of the primary product phenyl benzoate, but indeed, the bimolecular reaction between phenyl benzoate and phenol mainly contributed to the formation of hydroxybenzophenones. The product distribution was greatly affected by the presence of Lewis-type acid sites in H-beta; it was suggested that the interaction between the aromatic ring and the electrophilic Al3+ species led to the preferred formation of o-hydroxybenzophenone, because of the decreased charge density on the C atom at the para position of the phenolic ring. H-Y zeolites were efficient than H-beta in phenyl benzoate transformation into hydroxybenzophenones. View Full-Text
Keywords: phenol; benzoic acid; hydroxybenzophenone; H-beta; benzoylation; acylation phenol; benzoic acid; hydroxybenzophenone; H-beta; benzoylation; acylation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Gliozzi, G.; Passeri, S.; Bortolani, F.; Ardizzi, M.; Mangifesta, P.; Cavani, F. Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones. Catalysts 2015, 5, 2223-2243.

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