Synthesis, characterization and catalytic activity of novel Co(II) and Pd(II)-perfluoroalkylphthalocyanine in fluorous biphasic system; benzyl alcohol oxidation

ÖZER M., YILMAZ F., Erer H., KANİ İ., Bekaroglu O.

APPLIED ORGANOMETALLIC CHEMISTRY, vol.23, no.2, pp.55-61, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23 Issue: 2
  • Publication Date: 2009
  • Doi Number: 10.1002/aoc.1471
  • Journal Name: APPLIED ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.55-61
  • Istanbul Technical University Affiliated: Yes

Abstract

Tetra kis[heptadecafluorononyl] substituted phthalocyanine complexes were prepared by template synthesis from 4-(heptadecafluorononyloxy)phthalonitrile with Co(CH3COO)(2)center dot 4H(2)O or PdCl2 in 2-N,N-dimethylaminoethanol. The corresponding phthalonitrile was obtained from heptadecafluorononan-1-ol and 4-nitrophthalonitrile with K2CO3 in DMF at 50 degrees C. The structures of the compounds were characterized by elemental analysis, FTIR, UV-vis and MALDI-TOF MS spectroscopic methods. Metallophthalocyanines are soluble in fluoroalkanes such as perfluoromethylcyclohexane (PFMCH). The complexes were tested as catalysts for benzyl alcohol oxidation with tert-butylhydroperoxide (TBHP) in an organic-fluorous biphasic system (n-hexane-PFMCH).The oxidation of benzyl alcohol was also tested with different oxidants, such as hydrogen peroxide, m-chloroperoxybenzoic acid, molecular oxygen and oxone in n-hexane-PFMCH. TBHP was found to be the best oxidant for benzyl alcohol oxidation since higher conversion and selectivity were observed when this oxidant was used. Copyright (c) 2008 John Wiley & Sons, Ltd.