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(xiv) KF/alumina for the benzoylation of phenolics with benzoyl chloride [85]; (xv) polystyrene-supported GaCl3 for the benzoylation of phenols with benzoic anhydride [86]; (xvi) Fe3O4 nanoparticles for the benzoylation of phenols with aryl aldehydes to obtain the substituted o-HBPs (xanthones) [87]; (xvii) ZnO for the o-benzoylation of alcohols (including phenol) with benzoyl chloride [88,89] and ZnAl2O4/SiO2 composites for the acetylation of alcohols and phenols with acetic anhydride [90]; (xviii) mesoporous Al-KIT-6 (a cubic mesoporous silica with Al incorporated) for the gas-phase acylation of phenol to phenyl acetate with acetic acid [91]; (xix) Al-MCM-41 for the acylation of phenol with acetic acid in the gas-phase [31]; (xx) yttria-zirconia for the acylation of alcohols, thiols and amines with carboxylic acids [92]; (xxi) nafion-in-silica composite for the Fries rearrangement of phenyl acetate [34] and for anisole acylation with acetic anhydride (also with expanded CO2 as the solvent) [55]; (xxii) WO3/ZrO2 for the acylation of veratrole with acetic anhydride and of anisole with benzoic anhydride [93]; and (xxiii) Ni/SiO2 for the acetylation of phenol, naphthol and other alcohols [94]. In regards to the synthesis of p- and o-HBP (or other substituted benzophenones) or benzyl benzoates via c- or o-benzoylation, respectively, papers in the literature describe the use of benzoyl chloride or benzyl trichloride also with various homogeneous catalysts: AlCl3 for phenol (and phenol derivatives containing 2,2,6,6,-tetramethylpiperidine) [95], Cu(OTf)2 and Sn(OTf)2 for anisole and veratrole [96,97], Bi(III) salts for phenol [98] and Hf(OTf)4 for phenol [99], even with carboxylic acids [100]. As shown in Table 1, there are no papers in the literature describing the use of zeolites for the benzoylation of phenol; there is only one paper reporting on phenol benzoylation with benzoic anhydride catalyzed by the H-beta zeolite [19] and one paper reporting about the benzoylation of phenol with BA using polyoxometalate catalyst [60]. In this latter case, Yadav et al. [60] reported that the first step of the reaction, catalyzed by Cs2.5H0.5PW12O40 supported over K-10 clay, is the esterification, which is followed by Fries rearrangement towards hydroxybenzophenones (HBPs). The best selectivity to p-HBP was 32.5% at 70% BA conversion, with a phenol/BA ratio of 7/1. In the paper of Chaube et al. [19], H-beta turned out to be the more active zeolite for the production of HBPs. The selectivity to p-HBP was found to increase with the increase of the strength of acid sites; HBPs formed by both Fries rearrangement and acylation of phenol by phenyl benzoate. Here, we report on a study aimed at finding zeolitic catalysts and conditions for the liquid-phase benzoylation of phenol with BA; the reaction was carried out in the absence of any solvent. Typically, the aim of this reaction is the production of HBPs, which are intermediates for dyes, pharmaceuticals and fragrances. In the current industrial production of HBPs, benzotrichlorides are produced first; they are then reacted with benzene in the presence of AlCl3, and afterwards, the adduct is 120PDF Image | Zeolite Catalysis
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