Journal of Porous Materials

, Volume 20, Issue 4, pp 937–949 | Cite as

Porous silica supported Co2+-tetrachlorophthalocyanine (CoPcCl-APTES@SiO2): a novel and recyclable organic–inorganic hybrid catalyst for eco-friendly oxidation of secondary alcohols

  • R. K. Sharma
  • Shikha Gulati
  • Amit Pandey


A novel, selective and recyclable cobalt based catalyst has been synthesized by covalent grafting of Co2+-tetrachlorophthalocyanine (CoPcCl) onto porous silica functionalized with 3-aminopropyltriethoxysilane (APTES), and the resulting organic–inorganic hybrid porous material was found to be highly effective catalyst for peroxidative oxidation of secondary alcohols. The porous material was characterized by elemental analysis, diffuse reflectance UV–Visible spectroscopy, 13C CPMAS and 29Si CPMAS NMR spectroscopy, X-ray diffraction (XRD), Scanning electron microscopy (SEM), BET surface area analysis, Energy dispersive X-ray fluorescence (ED-XRF), Fourier transform Infrared (FT-IR) and Atomic absorption spectroscopy (AAS) techniques. High turnover frequency, mild reaction conditions, high selectivity for ketones, and easy recovery and reusability of the catalyst renders the present protocol highly essential to address the industrial needs and environmental concerns.


Co2+-tetrachlorophthalocyanine Porous support Silica Immobilization Recyclable catalyst Ketones 



The financial assistance from University Grant Commission, Delhi, India is acknowledged. Due thanks to AIRF, JNU, Delhi, India for SEM analysis and IISc, Bangalore, India for solid state NMR measurements.

Supplementary material

10934_2012_9671_MOESM1_ESM.doc (698 kb)
Supplementary material 1 (DOC 699 kb)


  1. 1.
    Q.H. Xia, H.Q. Ge, C.P. Ye, Z.M. Liu, K.X. Su, Chem. Rev. 105, 160 (2005)CrossRefGoogle Scholar
  2. 2.
    K.N. Bhagya, V. Gayathri, J. Porous Mater. (2012). doi: 10.1007/s10934-012-9595-9 Google Scholar
  3. 3.
    S.M.S. Chauhan, A. Kumar, K.A. Srinivas, Chem. Commun. 18, 2348–2349 (2003)CrossRefGoogle Scholar
  4. 4.
    N. Grootboom, T. Nyokong, J. Mol. Catal. A Chem. 179, 113 (2002)CrossRefGoogle Scholar
  5. 5.
    Q.H. Fan, Y.M. Li, A.S.C. Chan, Chem. Rev. 102, 3385 (2002)CrossRefGoogle Scholar
  6. 6.
    D. Brunel, N. Belloq, P. Sutra, A. Cauvel, M. Lasperas, P. Moreau, F.D. Renzo, A. Galarneau, F. Fajula, Coord. Chem. Rev. 1085, 178 (2008)Google Scholar
  7. 7.
    A. Corma, H. Garcia, Chem. Rev. 102, 3837 (2002)CrossRefGoogle Scholar
  8. 8.
    R. Sharma, S. Dhingra. Designing and synthesis of functionalized silica gels and their applications as metal scavengers, sensors, and catalysts: a green chemistry approach, (LAP Lambert Academic Publishing LAP Lambert Academic Publishing, Germany, 2011)Google Scholar
  9. 9.
    G. Strukul (ed.), Catalytic oxidations with hydrogen peroxide as oxidant (Kluwer Academic Publishers, Dordrecht, 1992)Google Scholar
  10. 10.
    K. Sato, M. Aoki, T. Hashimoto, R. Noyori, J. Org. Chem. 61, 8310 (1996)CrossRefGoogle Scholar
  11. 11.
    K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Panyella, R. Noyon, Bull. Chem. Soc. Jpn. 70, 905 (1997)CrossRefGoogle Scholar
  12. 12.
    M. Menger, C. Lee, J. Org. Chem. 44, 3446 (1979)CrossRefGoogle Scholar
  13. 13.
    A.N. Kharat, A. Bakhoda, B.T. Jahromi, Polyhedron 30, 2768 (2011)CrossRefGoogle Scholar
  14. 14.
    W. Zhao, Y. Zhang, B. Ma, Y. Ding, W. Qiu, Catal. Commun. 11, 527 (2010)CrossRefGoogle Scholar
  15. 15.
    H. Golchoubian, S.E. Babaei, Chin. J. Catal. 31, 615 (2010)CrossRefGoogle Scholar
  16. 16.
    P. Wang, Z. Dong, Y. Lei, Y. Du, H. Li, H. Yang, Y. Nie, J. Ma, J. Porous Mater. (2012). doi: 10.1007/s10934-012-9597-7 Google Scholar
  17. 17.
    P. Tundo, G.P. Romanelli, P.G. Vazquez, F. Arico, Catal. Commun. 11, 1181 (2010)CrossRefGoogle Scholar
  18. 18.
    G.B. Shul’pin, M.V. Kirillova, Y.N. Kozlov, L.S. Shul’pin, A.R. Kudinov, A.J.L. Pombeiro, J. Catal. 277, 164 (2011)CrossRefGoogle Scholar
  19. 19.
    Y. Yu, B. Lu, X. Wang, J. Zhao, X. Wang, Q. Cai, Chem. Eng. J. 162, 738 (2010)CrossRefGoogle Scholar
  20. 20.
    S. Zhang, S. Gao, S. Xi, J. Xu, Catal. Commun. 8, 531 (2007)CrossRefGoogle Scholar
  21. 21.
    S.L. Jain, B. Sain, Appl. Catal. A: Gen. 301, 259 (2006)CrossRefGoogle Scholar
  22. 22.
    A. Rezaeifard, M. Jafarpour, A. Naeimi, M. Salimi, Inorg. Chem. Commun. 15, 230 (2012)CrossRefGoogle Scholar
  23. 23.
    S. Zhanga, G. Zhaoa, S. Gao, Z. Xi, J. Xu, J. Mol. Catal. A: Chem. 289, 22 (2008)CrossRefGoogle Scholar
  24. 24.
    R.K. Sharma, S. Gulati, J. Mol. Catal. A: Chem. (2012). doi: 10.1016/j.molcat.2012.07.004 Google Scholar
  25. 25.
    E. Kockrick, T. Lescouet, E.V. Kudrik, A.B. Sorokin, D. Farrusseng, D. Chem, Communication 47, 1562 (2011)Google Scholar
  26. 26.
    R.K. Sharma, C. Sharma, Tetrahedron Lett. 51, 4415–4418 (2010)CrossRefGoogle Scholar
  27. 27.
    H. Liu, E. Min, Green Chem. 8, 657 (2006)CrossRefGoogle Scholar
  28. 28.
    A.B. Sorokin, E.V. Kudrik, Catal. Today 159, 37 (2011)CrossRefGoogle Scholar
  29. 29.
    R.K. Sharma, S. Gulati, S. Sachdeva, Green Chem. Lett. Rev. 5, 83 (2012)CrossRefGoogle Scholar
  30. 30.
    R.K. Sharma, A. Pandey, S. Gulati, A. Adholeya, J. Hazard. Mater. 209–210, 285 (2012)CrossRefGoogle Scholar
  31. 31.
    R.K. Sharma, A. Goel, Anal. Chim. Acta 534, 137 (2005)CrossRefGoogle Scholar
  32. 32.
    R.K. Sharma, A. Pandey, S. Gulati, Appl. Catal. A: Gen. 431–432, 33 (2012)CrossRefGoogle Scholar
  33. 33.
    R.K. Sharma, D. Rawat, Inorg. Chem. Commun. 17, 58 (2012)CrossRefGoogle Scholar
  34. 34.
    R.K. Sharma, D. Rawat, G. Gaba, Catal. Commun. 19, 31 (2012)CrossRefGoogle Scholar
  35. 35.
    R.K. Sharma, S. Gulati, A. Pandey, Polyhedron (2012). doi: 10.1016/j.poly.2012.07.065 Google Scholar
  36. 36.
    A.M. Donia, A.A. Atia, W.A. Al-amrani, A.M. El-Nahas, J. Hazard. Mater. 161, 1544 (2009)CrossRefGoogle Scholar
  37. 37.
    J.L. Liu, S. Xu, B. Yan Coll, Surf. A Physicochem. Eng. Aspects 373, 116 (2011)CrossRefGoogle Scholar
  38. 38.
    M. Kruk, M. Jaroniec, Y. Sakamoto, O. Terasaki, R. Ryoo, C.H. Ko, J. Phys. Chem. B 104, 292 (2000)CrossRefGoogle Scholar
  39. 39.
    S.B. Hartono, S.Z. Qiao, J. Liu, K. Jack, B.P. Ladewig, Z. Hao, G.Q.M. Lu, J. Phys. Chem. C 114, 8353 (2010)CrossRefGoogle Scholar
  40. 40.
    A.B. Sorokin, P. Buisson, A.C. Pierre, Microporous Mater. 46, 87 (2001)CrossRefGoogle Scholar
  41. 41.
    E. DeOliveira, C.R. Neri, A.O. Ribeiro, V.S. Garcia, L.L. Costa, A.O. Moura, A.G.S. Prado, O.A. Serra, Y. Iamamoto, J. Colloid Interface Sci. 323, 98 (2008)CrossRefGoogle Scholar
  42. 42.
    R. Kureshy, I. Ahmad, N.H. Khan, S. Abdi, S. Singh, P. Pandia, P.R. Jasra, J. Catal. 235, 28 (2005)CrossRefGoogle Scholar
  43. 43.
    S. Shylesh, A.P. Singh, J. Catal. 228, 333 (2004)CrossRefGoogle Scholar
  44. 44.
    R.K. Sharma, S. Gulati, A. Pandey, A. Adholeya, Appl. Catal. B: Environ. 125, 247 (2012)CrossRefGoogle Scholar
  45. 45.
    P. Karandhikar, A.J. Chandwadkar, M. Agashe, N.S. Ramgir, S. Sivasanker, Appl. Catal. A Gen. 297, 220 (2006)CrossRefGoogle Scholar
  46. 46.
    D.J. Upadhyaya, S.D. Samant, Appl. Catal. A Gen. 340, 42 (2008)CrossRefGoogle Scholar
  47. 47.
    H.F. Hoefnagels, D. Wu, G.D. With, W. Ming, Langmuir 23, 13158 (2007)CrossRefGoogle Scholar
  48. 48.
    S. Das, T. Punniyamurthy, Tetrahedron Lett. 44, 6033 (2003)Google Scholar
  49. 49.
    V.B. Sharma, S.L. Jain, B. Sain, Tetrahedron Lett. 44, 383–386 (2003)CrossRefGoogle Scholar
  50. 50.
    V.B. Sharma, S.L. Jain, B. Sain, J. Mol. Catal. A: Chem. 212, 55 (2004)CrossRefGoogle Scholar
  51. 51.
    F. Rajabi, B. Karimi, J. Mol. Catal. A: Chem. 232, 95 (2005)CrossRefGoogle Scholar
  52. 52.
    J. He, T. Wu, T. Jiang, X. Zhou, B. Hu, B. Han, Catal. Commun. 9, 2239 (2008)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  1. 1.Department of Chemistry, Green Chemistry Network CentreUniversity of DelhiDelhiIndia

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