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The test tube was then placed in an oil bath and heated up to the temperature desired (190–200 ◦C). After the reaction, the crude was cooled, diluted with HPLC acetone, filtered and analyzed. The reaction mixture was analyzed with a Thermo Focus from Thermo Fisher (Waltham, MA, USA) GC gas-chromatograph equipped with an FID detector and Agilent (Santa Clara, CA, USA) HP-5 column, using n-decane as the internal standard. The analysis conditions were: 60 ◦C for 0 min, 40 ◦C/min up to 280 ◦C, 2 min at 280 ◦C. 4. Conclusions Here, we report on the unprecedented reaction of phenol benzoylation with benzoic acid catalyzed by zeolites, which was carried out in the absence of solvent; this reaction is aimed at the production of hydroxybenzophenones, compounds of great interest for the chemical industry. H-beta zeolites offered a superior performance, in terms not only of activity, but also of selectivity to the desired compounds. The reaction network was found to consist of the primary reaction of phenol esterification with the formation of phenyl benzoate, which is then consecutively transformed into hydroxybenzophenones by means of an intermolecular reaction between the ester and phenol; conversely, the contribution of the Fries rearrangement seemed to be negligible. With H-beta zeolites, the Si/Al ratio significantly affected performance, especially in terms of the selectivity ratio between the two hydroxybenzophenone isomers. An important role was played by Lewis-type acid sites, which were most abundant with Al-richer zeolites. Conversely, in the case of H-Y zeolites, the transformation of the ester into the desired ketones was greatly inhibited. Author Contributions: G.G., S.P., F.B., P.M. and M.A. designed and performed experiments, and analyzed data. F.C. analyzed data and wrote the paper. Conflicts of Interest: The authors declare no conflict of interest. References 1. Sartori, G.; Maggi, R. Use of solid catalysts in Friedel-Crafts acylation reactions. Chem. Rev. 2006, 106, 1077–1104. 2. Bejblová, M.; Procházková, D.; Cˇejka, J. Acylation Reactions over Zeolites and Mesoporous Catalysts. ChemSusChem 2009, 2, 486–499. 3. Bolognini, M.; Cavani, F.; Cimini, M.; Pozzo, L.D.; Maselli, L.; Venerito, D.; Pizzoli, F.; Veronesi, G. An environmentally friendly synthesis of 2,4-dihydroxybenzophenone by the single-step o-mono-benzoylation of 1,3-dihydroxybenzene (resorcinol) and Fries rearrangement of intermediate resorcinol monobenzoate: the activity of acid-treated montmorillonite. Comptes Rendus Chim. 2004, 7, 143–150. 4. Singh, A.P.; Bhattacharya, D.; Sharma, S. Benzoylation of toluene with benzoyl chloride over zeolite catalysts. J. Mol. Catal. A 1995, 102, 139–145. 132PDF Image | Zeolite Catalysis
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