Synthesis, characterization of metal-free, metallophthalocyanines and catalytic activity of cobalt phthalocyanine in cyclohexene oxidation

In this work, the new phthalonitrile derivative (3) bearing 4-pentylphenol (1), metal-free phthalocyanine (4), metallophthalocyanines (5) and (6) have been synthesized. . The metal-free phthalocyanine (4) was synthesized by using dinitrile compound (3) with n-pentanol, DBU. Zinc(II) phthalocyanine (5) compound was synthesized by the reaction of dinitrile compound in the presence of dimethylaminoethanol by using dry Zn(CH3COO)2 salt, respectively in microwave oven. Cobalt(II) phthalocyanine (6) compound was synthesized under nitrogen atmosphere by the reaction of dinitrile compound in the presence of dimethylaminoethanol by using dry CoCl2 salt. The new compounds have been characterized by IR, 1H NMR, 13C NMR and MS spectra data. The new cobalt(II) phthalocyanine (6) has tested as a catalyst for the oxidation of cyclohexene with different oxidants, such as tert-butylhydroperoxide (TBHP), m-chloroperoxybenzoic acid (m-CPBA) and hydrogen peroxide (H2O2), in organic solvent Then, gas chromatography instrument was used for the evaluation of the results.