Synthesis, characterization of tetra substituted phthalocyanines and catalytic activities of their cobalt(II) complexes on cyclohexene oxidation

In this work, 4-[2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)ethoxy]phthalonitrile (3) and 4-(3,3-diphenylpropoxy)cyclohexa-3,5-dien-1,2-dicarbonitrile (8) compounds were synthesized by using 1-(2-hydroxyethyl)4-piperidon ethylene ketal (1) and 3,3-diphenylpropanol (7) and 4-nitrophthalonitrile (2) as starting compounds. The metal-free phthalocyanines (4) and (9) were synthesized by using dinitrile compounds (3) and (8) with n-pentanol, DBU. Zinc(II) phthalocyanines (5) and (10), cobalt(II) phthalocyanines (6) and (11) compounds were synthesized by the reaction of dinitrile compounds in the presence of dimethylaminoethanol by using dry Zn(CH3COO)2 and CoCl2 salts, respectively in microwave oven. In addition, catalytic activities of cobalt(II) phthalocyanines (6) and (11) were investigated on cyclohexene oxidation. Then, gas chromatography instrument was used for the evaluation of the results. The structures of the synthesized original compounds were identified by using elemental analysis, IR, 13C-NMR, 1H-NMR, UV-Vis and MS spectroscopic data.