New soluble peripherally tetra-substituted Co(II), Fe(II) phthalocyanines: Synthesis, spectroscopic characterization and their catalytic activity in cyclohexene oxidation


SAKA E. T. , CAKIR D., BLYIKLIOGLU Z., KANTEKİN H.

DYES AND PIGMENTS, vol.98, no.2, pp.255-262, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 98 Issue: 2
  • Publication Date: 2013
  • Doi Number: 10.1016/j.dyepig.2013.02.021
  • Journal Name: DYES AND PIGMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.255-262
  • Keywords: Phthalocyanine, Iron, Cobalt, Cyclohexene, Oxidation, TBHP, IRON(III) PORPHYRIN COMPLEXES, MICROWAVE-ASSISTED SYNTHESIS, METAL-FREE PHTHALOCYANINE, HYDROGEN-PEROXIDE, TERT-BUTYLHYDROPEROXIDE, SELECTIVE OXIDATION, HOMOGENEOUS SOLUTION, BIPHASIC SYSTEM, IRON, PHENOLS
  • Karadeniz Technical University Affiliated: Yes

Abstract

New 4-{2[3-(diethylamino)phenoxy]ethoxy}phthalonitrile 3 was obtained from 2-[3-(diethylamino) phenoxy]ethanol 1 and 4-nitrophthalonitrile 2 with K2CO3 in DMF at 50 degrees C. The novel iron(II) and cobalt(II) phthalocyanine complexes 4 and 5 were prepared by the reaction of the phthalonitrile derivative 3 with n-pentanol in a standard Schlenk tube in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). These new phthalocyanine complexes were characterized by the spectroscopic methods (IR, H-1 NMR, C-13 NMR, UV-vis and mass spectroscopies) Complexes 4 and 5 are employed as catalyst for the oxidation of cyclohexene using tert-butyl hydroperoxide (TBHP), m-chloroperoxybenzoic acid (m-CPBA), aerobic oxygen and hydrogen peroxide (H2O2) as oxidant. It is observed that iron(II) phthalocyanine complex can selectively oxidize cyclohexene to give 2-cyclohexene-1-ol as major product, and 2-cyclohexene-1-one and cyclohexene oxide are minor products. TBHP was found to be the best oxidant since the minimal destruction of the catalyst, higher selectivity and conversion were observed in the products. (C) 2013 Elsevier Ltd. All rights reserved.