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Benzene was hydroxylated with hydrogen peroxide (H 2 O 2 ) in the presence of catalytic amounts of copper complexes in acetone to yield phenol at 298 K. At higher temperature, phenol was further hydroxylated with H 2 O 2 by catalysis of copper complexes to yield p -benzoquinone. The kinetic study revealed that the rate was proportional to concentrations of benzene and H 2 O 2 , but to the square root of concentration of a copper(II) complex ([Cu(tmpa)] 2+ : tmpa = tris(2-pyridylmethyl)amine). The addition of a spin trapping reagent resulted in formation of a spin adduct of hydroperoxyl radical (HO 2  • ), as observed by EPR spectroscopy, inhibiting phenol formation. HO 2  • produced by the reaction of [Cu(tmpa)] 2+ with H 2 O 2 acts as a chain carrier for the radical chain reactions for formation of phenol. When [Cu(tmpa)] 2+ was incorporated into mesoporous silica-alumina (Al-MCM-41) by a cation exchange reaction, the selectivity to production of phenol was much enhanced by prevention of hydroxylation of phenol, which was not adsorbed to Al-MCM-41. The high durability with turnover number of 4320 for the hydroxylation of benzene to phenol with H 2 O 2 was achieved using [Cu(tmpa)] 2+ incorporated into Al-MCM-41 as an efficient and selective catalyst.

One-step selective hydroxylation of benzene to phenol with hydrogen peroxide catalysed by copper complexes incorporated into mesoporous silica–alumina