Investigation of catalytic activity of new Co(II) phthalocyanine complexes in cyclohexene oxidation using different type of oxidants


AKTAS A., SAKA E. T., BIYIKLIOĞLU Z., ACAR İ., KANTEKİN H.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.745, pp.18-24, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 745
  • Publication Date: 2013
  • Doi Number: 10.1016/j.jorganchem.2013.07.013
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.18-24
  • Keywords: Phthalocyanine, Cobalt(II), Cyclohexene oxidation, Oxidant, m-Chloroperoxybenzoic acid, TETRA-SUBSTITUTED CO(II), METAL-FREE, SPECTROELECTROCHEMICAL PROPERTIES, TERT-BUTYLHYDROPEROXIDE, MICROWAVE IRRADIATION, AEROBIC OXIDATION, COBALT, METALLOPHTHALOCYANINES, IRON, METALLOMACROCYCLES
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this work, the new phthalonitrile derivatives 4, 5 bearing 1,3-bis(naphthalen-1-yloxy)propan-2-ol and 1,3-bis(naphthalen-2-yloxy)propan-2-ol, cobalt phthalocyanine complexes have been synthesized. The new cobalt phthalocyanines have been prepared by cyclotetramerization of phthalonitrile derivatives 4, 5 in the presence of the corresponding CoCl2 salt in DMAE by using a microwave oven. The new compounds have been characterized by IR, H-1 NMR, C-13 NMR and MS spectral data. The new complexes have been 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 DMF. m-CPBA is also found as the most successful oxidant in the other oxygen sources. In this sense, the substrate/catalyst ratio, the influence of temperature, oxidant/cat ratio and type of oxidant have been studied. It is observed three oxidation products. First one is 2-cyclohexene-1-ol as dominant product and the others are 2-cyclohexene-1-one and cyclohexene oxide as minor product. (C) 2013 Elsevier B. V. All rights reserved.