Skip to main content
SpringerLink
Log in

Oxidative Coupling and Hydroxylation of Phenol over Transition Metal and Acidic Zeolites: Insights into Catalyst Function

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Reaction of phenol with hydrogen peroxide over H-MFI, Fe-MFI, H-BEA, Fe-BEA and TS-1 zeolite catalysts was investigated. Over H-BEA, biphenyl product was observed. It is suggested, that the larger pore size of H-BEA facilitates coupling of two phenol molecules. Two distinct reaction mechanisms are proposed for acid and redox catalysts.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Demirbaş A (2003) Energy Convers Manag 44:1465–1479

    Article  Google Scholar 

  2. Gogebakan Z, Gogebakan Y, Selçuk N, Selçuk E (2009) Bioresour Technol 100:1033–1036

    Article  CAS  Google Scholar 

  3. Chagger HK, Jones JM, Pourkashanian M, Williams A (1997) Fuel 76:861–864

    Article  CAS  Google Scholar 

  4. Chagger HK, Jones JM, Pourkashanian M, Williams A, Owen A, Fynes G (1999) Fuel 78:1527–1538

    Article  CAS  Google Scholar 

  5. Mandalakis M, Gustafsson Ö, Alsberg T, Egebäck A-L, Reddy CM, Xu L, Klanova J, Holoubek I, Stephanou EG (2005) Environ Sci Technol 39:2976–2982

    Article  CAS  Google Scholar 

  6. Yee LD, Kautzman KE, Loza CL, Schilling KA, Coggon MM, Chhabra PS, Chan MN, Chan AWH, Hersey SP, Crounse JD, Wennberg PO, Flagan RC, Seinfeld JH (2013) Atmos Chem Phys Discuss 13:3485–3532

    Article  Google Scholar 

  7. Bruce RM, Santodonato J, Neal MW (1987) Toxicol Ind Health 3:535–568

    Article  CAS  Google Scholar 

  8. Huang JP, Pearce EM, Reiser A, Kwei TK (1989) Dissolution of phenolic resins and their blends, polymers in microlithography. American Chemical Society, Washington, DC, pp 364–384

    Google Scholar 

  9. Kobayashi S, Higashimura H (2003) Prog Polym Sci 28:1015–1048

    Article  CAS  Google Scholar 

  10. Hudnall PM (2000) Hydroquinone, Ullmann’s Encyclopedia of Industrial Chemistry. Wiley, Weinheim

    Google Scholar 

  11. Fiege H, Voges H-W, Hamamoto T, Umemura S, Iwata T, Miki H, Fujita Y, Buysch H-J, Garbe D, Paulus W (2000) Phenol Derivatives, Ullmann’s Encyclopedia of Industrial Chemistry. Wiley, Weinheim

    Google Scholar 

  12. R. Noyori (2005) Chem Commun 1807–1811

  13. Germain A, Allian M, Figueras F (1996) Catal Today 32:145–148

    Article  CAS  Google Scholar 

  14. Herron N (1988) J Coord Chem 19:25–38

    Article  CAS  Google Scholar 

  15. Allian M, Germain A, Cseri T, Figueras F (1993) Catalytic hydroxylation of phenol by hydrogen peroxide. Kinetic study and comparison between solid acids and titanosilicates, studies in surface science and catalysis. Elsevier, Amsterdam, pp 455–462

    Google Scholar 

  16. Zhu K, Liu C, Ye X, Wu Y (1998) Appl Catal A 168:365–372

    Article  CAS  Google Scholar 

  17. Adán C, Carbajo J, Bahamonde A, Martínez-Arias A (2009) Catal Today 143:247–252

    Article  Google Scholar 

  18. Sundaram S, Annamalai SK (2012) Electrochim Acta 62:207–217

    Article  CAS  Google Scholar 

  19. Fajerwerg K, Debellefontaine H (1996) Appl Catal B 10:L229–L235

    Article  CAS  Google Scholar 

  20. Atoguchi T, Kanougi T, Yamamoto T, Yao S (2004) J Mol Catal A 220:183–187

    Article  CAS  Google Scholar 

  21. Kerton OJ, McMorn P, Bethell D, King F, Hancock F, Burrows A, Kiely CJ, Ellwood S, Hutchings G (2005) Phys Chem Chem Phys 7:2671–2678

    Article  CAS  Google Scholar 

  22. Bellussi G, Carati A, Clerici MG, Maddinelli G, Millini R (1992) J Catal 133:220–230

    Article  CAS  Google Scholar 

  23. Durgakumari V, Subrahmanyam M, Subba Rao KV, Ratnamala A, Noorjahan M, Tanaka K (2002) Appl Catal A 234:155–165

    Article  CAS  Google Scholar 

  24. Z. Kang, G. Fang, Q. Ke, J. Hu, T. Tang (2013) ChemCatChem 5:2191–2194

  25. Liu C, Shan Y, Yang X, Ye X, Wu Y (1997) J Catal 168:35–41

    Article  CAS  Google Scholar 

  26. Mohamed MM, Eissa NA (2003) Mater Res Bull 38:1993–2007

    Article  CAS  Google Scholar 

  27. Choi J-S, Yoon S–S, Jang S-H, Ahn W-S (2006) Catal Today 111:280–287

    Article  CAS  Google Scholar 

  28. Wu C, Kong Y, Gao F, Wu Y, Lu Y, Wang J, Dong L (2008) Microporous Mesoporous Mater 113:163–170

    Article  CAS  Google Scholar 

  29. Yu J, Taylor KE, Zou H, Biswas N, Bewtra JK (1994) Environ Sci Technol 28:2154–2160

    Article  CAS  Google Scholar 

  30. Huang Q, Tang J, Weber WJ Jr (2005) Water Res 39:3021–3027

    Article  CAS  Google Scholar 

  31. Nakamoto S, Machida N (1992) Water Res 26:49–54

    Article  CAS  Google Scholar 

  32. Tohma H, Morioka H, Takizawa S, Arisawa M, Kita Y (2001) Tetrahedron 57:345–352

    Article  CAS  Google Scholar 

  33. Murugadoss A, Goswami P, Paul A, Chattopadhyay A (2009) J Mol Catal A 304:153–158

    Article  CAS  Google Scholar 

  34. Rege SU, Yang RT, Cain CA (1998) AIChE J 44:1519–1528

    Article  CAS  Google Scholar 

  35. Atoguchi T, Kanougi T (2004) J Mol Catal A 222:253–257

    Article  CAS  Google Scholar 

  36. Ivanov DP, Sobolev VI, Panov GI (2003) Appl Catal A 241:113–121

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to acknowledge the University of Newcastle Australia for their support.

Author information

Authors and Affiliations

  1. PRCfE, Chemical Engineering, School of Engineering, Faculty of Engineering & Built Environment, University of Newcastle, Callaghan, NSW, 2308, Australia

    Jerry Pui Ho Li, Eric Kennedy & Michael Stockenhuber

Authors
  1. Jerry Pui Ho Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Eric Kennedy
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Michael Stockenhuber
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Michael Stockenhuber.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, J.P.H., Kennedy, E. & Stockenhuber, M. Oxidative Coupling and Hydroxylation of Phenol over Transition Metal and Acidic Zeolites: Insights into Catalyst Function. Catal Lett 144, 9–15 (2014). https://doi.org/10.1007/s10562-013-1142-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-013-1142-z

Keywords

Search

Navigation