Skip to main content
Log in

Synthesis and catalytic activities in cyclohexane hydroxylation of metalloporphyrins supported on styrene-methylacrylic acid copolymer microspheres

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

Through a new synthetic strategy, metalloporphyrins (M = Fe(III), Mn(III) or Co(II)) were covalently immobilized on styrene-methylacrylic acid copolymer microspheres. These copolymer-immobilized metalloporphyrins were found to be more efficient catalysts than the analogous non-supported metalloporphyrins for cyclohexane hydroxylation in metalloporphyrin–O2–ascrobate mixtures. The catalytic activities of the immobilized catalysts follow the order Fe>Mn>Co.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Miguel YRD, Bampos N, Silva KMN, Richards SA, Sanders JKM (1998) Chem Commun 3:2267. doi:10.1039/a806034g

    Article  Google Scholar 

  2. Senkan S (2001) Angew Chem Int Ed 40:312. doi: 10.1002/1521-3773(20010119)40:2<312::AID-ANIE312>3.0.CO;2-I

    Google Scholar 

  3. Leadbeater NE, Marco M (2002) Chem Rev 102:3217. doi:10.1021/cr010361c

    Article  CAS  Google Scholar 

  4. Mirkhani V, Moghadam M, Tangestaninejad S, Kargar H (2006) Appl Catal A General 221:303

    Google Scholar 

  5. Mansuy D (2007) C R Chim 10:392

    CAS  Google Scholar 

  6. McNamara CA, Dixon MJ, Bradley M (2002) Chem Rev 102:3275. doi:10.1021/cr0103571

    Article  CAS  Google Scholar 

  7. Herron N (1988) Coord Chem Rev 19:25

    CAS  Google Scholar 

  8. Skrobot FC, Rosa ILV, Marques APA, Martins PR, Rocha J, Valente AA, Iamamoto Y (2005) J Mol Catal A Chem 237:86. doi:10.1016/j.molcata.2005.05.001

    Article  CAS  Google Scholar 

  9. Farrall MJ, Fre’chet JMJ (1976) J Org Chem 41:3877. doi:10.1021/jo00886a023

    Article  CAS  Google Scholar 

  10. Wang RM, Wang YP, Lei ZQ (1998) Rev Roum Chim 43:51

    CAS  Google Scholar 

  11. Mathew T, Kuriakose SJ (1999) J Porphyrin Phthalocyanines 3:316. doi:10.1002/(SICI)1099-1409(199904)3:4<316::AID-JPP136>3.0.CO;2-Z

  12. Evans S, Lindsay-Smith JR (2001) J Chem Soc Perkin Trans 2:174. doi:10.1039/b007326 l

    Google Scholar 

  13. Du CP, Li ZK, Wen XM, Wu J, Yu XQ, Yang M, Xie RG (2004) J Mol Catal A Chem 216:7

    CAS  Google Scholar 

  14. Sonia MR, Armenio CS, Rocha Gonsalves AMd’A (2007) Tetrahedron 63:7885. doi:10.1016/j.tet.2007.05.084

  15. Liu ZL, Huang JW, Ji LN (1996) J Mol Catal A Chem 104:193. doi:10.1016/1381-1169(95)00253-7

    Article  Google Scholar 

  16. Huang JW, Mei WJ, Liu J, Ji LN (2001) J Mol Catal A Chem 170:261. doi:10.1016/S1381-1169(01)00071-1

    Article  CAS  Google Scholar 

  17. Oh KC, Kim KA, Paeng IR, Baek D, Paeng KJ (1999) J Electroanal Chem 468:98. doi:10.1016/S0022-0728(99)00151-5

    Article  CAS  Google Scholar 

  18. Oh KC, Lim SM, Paeng IR, Paeng KJ (2001) J Electroanal Chem 42:506

    Google Scholar 

  19. Huang JW, Huang WZ, Mei WJ, Liu J, Hu SG, Ji LN (2000) J Mol Catal A Chem 156:275. doi:10.1016/S1381-1169(99)00447-1

    Article  CAS  Google Scholar 

  20. Ji LN, Liu M, Hsieh AK, Hor TSA (1991) J Mol Catal 70:247. doi:10.1016/0304-5102(91)80166-Z

    Article  CAS  Google Scholar 

  21. Ren QZ, Huang JW, Liu ZL, Luo GT, Ji LN (1997) S Afr J Chem 50:181

    CAS  Google Scholar 

  22. Ren QZ, Huang JW, Peng XB, Ji LN (1999) J Mol Catal A Chem 9:148

    Google Scholar 

  23. He LN, Fang BS, Huang JW, Ji LN (2000) Transition Met Chem 25:352. doi:10.1023/A:1007010312674

    Article  CAS  Google Scholar 

  24. Mei WJ, Huang JW, Hu SG, Ji LN (2000) Acta Sci Nat Unvis Sun Yet-Sen 39:125

    CAS  Google Scholar 

  25. Ren QZ, Zhu ZA, Huang JW, Ji LN, Chen YT (2001) J Porphyr Phthalocyanines 5:449. doi:10.1002/jpp.337

    Article  CAS  Google Scholar 

  26. Yu HC, Chen XL, Li XX, Huang JW, Ji LN (2007) Front Chem Eng Chin 1:65. doi:10.1007/s11705-007-0013-9

    Article  Google Scholar 

  27. Doro FG, Smith JRL, Ferreira AG, Assis MD (2000) J Mol Catal A Chem 164:97. doi:10.1016/S1381-1169(00)00352-6

    Article  CAS  Google Scholar 

  28. Schiavon MA, Iamamoto Y, Nascimento OR, Assis MD (2001) J Mol Catal A Chem 174:213. doi:10.1016/S1381-1169(01)00176-5

    Article  CAS  Google Scholar 

  29. Nakagaki S, Machado AM, Wypych F, Drechsel SM (2002) J Colloid Interface Sci 254:158. doi:10.1006/jcis.2002.8488

    Article  Google Scholar 

  30. Assis MD, Smith JRL (1998) J Chem Soc Perkin Trans 2:2221. doi:10.1039/a804679d

    Google Scholar 

  31. Lee J, Isobe T, Senna M (1996) J Colloid Interface Sci 177:490. doi:10.1006/jcis.1996.0062

    Article  CAS  Google Scholar 

  32. Yu XQ, Huang JS, Yu WY, Che CM (2000) J Am Chem Soc 122:5337. doi:10.1021/ja000461k

    Article  CAS  Google Scholar 

  33. Buchler JW (1978) In: Dolphin D (ed) The porphyrins, 1st edn. Academe, New York

  34. Rovira C, Kunc K, Hutter J, Ballone P, Parrinello M (1997) J Phys Chem A 101:8914. doi:10.1021/jp9722115

    Article  CAS  Google Scholar 

  35. DeAngelis F, Car RS (2003) J Am Chem Soc 125:15710. doi:10.1021/ja037373v

    Article  CAS  Google Scholar 

  36. Tsuda M, Dy ES, Kasai H (2005) J Chem Phys 122:244719. doi:10.1063/1.1947187

    Article  Google Scholar 

  37. Tsuda M, Dy ES, Kasai H (2006) Eur Phys J D 38:139. doi:10.1140/epjd/e2005-00253-y

    Article  CAS  Google Scholar 

  38. Vogel KM, Kozlowski PM, Zgierski MZ, Spiro TG (1999) J Am Chem Soc 121:9915. doi:10.1021/ja990042r

    Article  CAS  Google Scholar 

  39. Shi Z, Zhang JJ (2007) J Phys Chem C 111:7084. doi:10.1021/jp0671749

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the supports of Guangzhou Municipality Science & Technology Bureau of China, the National Natural Science Foundation of China and National Key Foundation Research Development Project (973) Item of China (No. 2007 CB815306).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jin-Wang Huang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fu, B., Yu, HC., Huang, JW. et al. Synthesis and catalytic activities in cyclohexane hydroxylation of metalloporphyrins supported on styrene-methylacrylic acid copolymer microspheres. Transition Met Chem 33, 803–807 (2008). https://doi.org/10.1007/s11243-008-9114-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-008-9114-7

Keywords

Navigation