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Substrate Veratrole Phenylacetate Phenylacetate (gas-phase) Phenylacetate Phenylacetate, phenyl benzoate Acylating Reagent Acetic anhydride Fries rearrangement Fries rearrangement Fries rearrangement Fries rearrangement Table 1. Cont. Desired Product 3-4-dimethoxyacetophenone p- and o-hydroxyacetophenone p- and o-hydroxyacetophenone p- and o-hydroxyacetophenone p- and o-hydroxyacetophenone Catalyst Ref. Other non-zeolitic, but heterogeneous catalysts have also been used, such as: (i) montmorillonites of the K series for the acetylation of various aliphatic and aromatic substrates [47,48] and of aliphatic and aromatic alcohols [49], for the acylation of resorcinol with phenylacetic chloride [50] and after an exchange with various metals for the reaction between aromatic aldehydes and acetic anhydride to produce the corresponding 1,1-diacetates [51]; (ii) silica-supported phosphotungstic acid for the acylation of aromatic hydrocarbons with acrylic and crotonic acid [52,53], for the Fries rearrangement of phenyl benzoate [54] and for the acylation of anisole with acetic anhydride [55,56]; (iii) clay-supported Cs-phosphotungstic acid for the benzoylation of anisole with benzoyl chloride [57], for the benzoylation of p-xylene [58,59] and of phenol with benzoic acid (BA) to obtain p-hydroxybenzophenone (HBP) [60]; (iv) giant P/W heteropolyacids for the acetylation of phenol with acetic anhydride [61] (the reactivity of heteropolyacids for Friedel-Crafts acylation was reviewed by Kozhevnikov [62]), and other P/W polyoxometalates for the acetylation of alcohols and phenols [61]; (v) NaGa-Mg hydrotalcite for the benzoylation of toluene with benzoyl chloride [63,64]; (vi) EPZG® for the acylation of 1-methoxynaphthalene and anisole with various acyl chlorides and anhydrides [65]; (vii) sulfated zirconia, even promoted with other metal oxides or supported over MCM-41, for the benzoylation of anisole with benzoic anhydride [66–70] or benzoyl chloride [71], for the acylation of phenol, anisole and chlorobenzene with acetic anhydride or benzoic anhydride [72–74], for the acylation of veratrole with acetic anhydride [75] and for the Fries rearrangement of 4-methylphenylbenzoate [76]; (viii) borate zirconia for the benzoylation of anisole with benzoyl chloride [77]; (ix) Zr hydroxide functionalized with trifluoromethanesulfonic acid for the benzoylation of biphenyl [78]; (x) Sn-doped sulfated zirconia for the benzoylation of anisole with benzoyl chloride [79]; (xi) triflic acid-functionalized Zr-TMS (zirconium oxide with a mesostructured framework; TMS, transition metal oxide mesoporous molecular sieves) for the benzoylation of biphenyl [80], of diphenyl ether to 4-phenoxybenzophenone [81] and of toluene to 4,4′-dimethylbenzophenone [82]; (xii) Fe-Zr phosphate for the benzoylation of different arenes [83]; (xiii) mesoporous UDCaT-5 (a sulphated tetragonal zirconia-based catalyst) for the acylation of anisole with propionic anhydride [84]; 119 H-Y, H-beta H-beta [9,21] [23,27,46] H3PO4/ZSM-5 [28] H-beta, H-Y, H-ZSM5 [34] H-ZSM5, H-ZSM12 [35]PDF Image | Zeolite Catalysis
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