Skip to main content
SpringerLink
Log in

Behavior of Triazolylmolybdenum(VI) Oxide Hybrids as Oxidation Catalysts with Hydrogen Peroxide

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A family of molybdenum(VI) oxide hybrid solids with the general compositions [MoO3(tr)], [Mo2O6(tr)] and [Mo2O6(tr)(H2O)2] (tr = 1,2,4-triazole ligands bearing amine, pyrazole, 1H-tetrazole, and 1,2,4-triazole groups) have been shown to promote the epoxidation of cis-cyclooctene, the oxidative dehydrogenation of benzyl alcohol to give benzaldehyde, and the oxidation of benzaldehyde to give benzoic acid, using aqueous H2O2 as oxidant. All materials studied act as pre-catalysts and undergo chemical transformation in the presence of the oxidant to give the active oxidising species which, on the basis of characterisation data for recovered compounds, are either mononuclear or polynuclear oxo(peroxo)molybdenum(VI) complexes. Materials with one-dimensional (1D) structures led to homogeneous catalytic reactions with activities that were generally superior to those obtained with materials possessing more rigid 2D/3D structures containing bitriazole ligands. The latter were proposed to lead to interconverting mononuclear (poorly soluble) and dinuclear (soluble) species of the type [MoO(O2)2(L)] and [{MoO(O2)2(L)}2(μ-O)].

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 3
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Hagrman PJ, Hagrman D, Zubieta J (1999) Angew Chem Int Ed 38:2638

    Article  CAS  Google Scholar 

  2. Hagrman D, Hagrman PJ, Zubieta J (1999) Com Inorg Chem 21:225

    Article  CAS  Google Scholar 

  3. Hagrman PJ, Finn RC, Zubieta J (2001) Solid State Sci 3:745

    Article  CAS  Google Scholar 

  4. Zapf PJ, Haushalter RC, Zubieta J (1997) Chem Mater 9:2019

    Article  CAS  Google Scholar 

  5. Lu Y, Wang E, Yuan M, Li Y, Hu C (2003) J Mol Struct 649:191

    Article  CAS  Google Scholar 

  6. Kim J, Lim WT, Koo BK (2007) Inorg Chim Acta 360:2187

    Article  CAS  Google Scholar 

  7. Amarante TR, Neves P, Valente AA, Paz FAA, Fitch AN, Pillinger M, Gonçalves IS (2013) Inorg Chem 52:4618

    Article  CAS  Google Scholar 

  8. Zhang X, Hejazi M, Thiagarajan SJ, Woerner WR, Banerjee D, Emge TJ, Xu W, Teat SJ, Gong Q, Safari A, Yang R, Parise JB, Li J (2013) J Am Chem Soc 135:17401

    Article  CAS  Google Scholar 

  9. Zhou Y, Zhang L, Fun HK, You X (2000) Inorg Chem Commun 3:114

    Article  CAS  Google Scholar 

  10. Johnson JW, Jacobson AJ, Rich SM, Brody JF (1981) J Am Chem Soc 103:5246

    Article  CAS  Google Scholar 

  11. Hagrman PJ, LaDuca RL Jr, Koo HJ, Rarig R Jr, Haushalter RC, Whangbo MH, Zubieta J (2000) Inorg Chem 39:4311

    Article  CAS  Google Scholar 

  12. Chuang J, Ouellette W, Zubieta J (2008) Inorg Chim Acta 361:2357

    Article  CAS  Google Scholar 

  13. Xu Y, Lu J, Goh NK (1999) J Mater Chem 9:1599

    Article  CAS  Google Scholar 

  14. Zapf PJ, LaDuca RL Jr, Rarig R Jr, Johnson KM III, Zubieta J (1998) Inorg Chem 37:3411

    Article  CAS  Google Scholar 

  15. Amarante TR, Neves P, Coelho AC, Gago S, Valente AA, Paz FAA, Pillinger M, Gonçalves IS (2010) Organometallics 29:883

    Article  CAS  Google Scholar 

  16. Abrantes M, Amarante TR, Antunes MM, Gago S, Paz FAA, Margiolaki I, Rodrigues AE, Pillinger M, Valente AA, Gonçalves IS (2010) Inorg Chem 49:6865

    Article  CAS  Google Scholar 

  17. Abrantes M, Gonçalves IS, Pillinger M, Vurchio C, Cordero FM, Brandi A (2011) Tetrahedron Lett 52:7079

    Article  CAS  Google Scholar 

  18. Amarante TR, Neves P, Valente AA, Paz FAA, Pillinger M, Gonçalves IS (2016) J Catal 340:354

    Article  CAS  Google Scholar 

  19. Lysenko AB, Senchyk GA, Lincke J, Lässig D, Fokin AA, Butova ED, Schreiner PR, Krautscheid H, Domasevitch KV (2010) Dalton Trans 39:4223

    Article  CAS  Google Scholar 

  20. Lysenko AB, Senchyk GA, Domasevitch KV, Hauser J, Fuhrmann D, Kobalz M, Krautscheid H, Neves P, Valente AA, Gonçalves IS (2015) Inorg Chem 54:8327

    Article  CAS  Google Scholar 

  21. Neves P, Gomes AC, Paz FAA, Valente AA, Gonçalves IS, Pillinger M (2017) J Mol Catal A Chem. doi:10.1016/j.mcat.2017.01.016 (in press)

  22. Gamelas CA, Gomes AC, Bruno SM, Paz FAA, Valente AA, Pillinger M, Romão CC, Gonçalves IS (2012) Dalton Trans 41:3474

    Article  CAS  Google Scholar 

  23. Calhorda MJ, Costa PJ (2012) Curr Org Chem 16:65

    Article  CAS  Google Scholar 

  24. Costa PJ, Calhorda MJ, Kühn FE (2010) Organometallics 29:303

    Article  CAS  Google Scholar 

  25. Veiros LF, Prazeres A, Costa PJ, Romão CC, Kühn FE, Calhorda MJ (2006) Dalton Trans 21:1383

  26. Kühn FE, Groarke M, Bencze E, Herdtweck E, Prazeres A, Santos AM, Calhorda MJ, Romão CC, Gonçalves IS, Lopes AD, Pillinger M (2002) Chem Eur J 8:2370

    Article  Google Scholar 

  27. Comas-Vives A, Lledos A, Poli R (2010) Chem Eur J 16:2147

    Article  CAS  Google Scholar 

  28. Thiel WR, Priermeier T (1995) Angew Chem Int Ed Engl 34:1737

    Article  CAS  Google Scholar 

  29. Thiel WR, Eppinger J (1997) Chem Eur J 3:696

    Article  CAS  Google Scholar 

  30. Dinoi C, Ciclosi M, Manoury E, Maron L, Perrin L, Poli R (2010) Chem Eur J 16:9572

    Article  CAS  Google Scholar 

  31. Gisdakis P, Yudanov IV, Rçsch N (2001) Inorg Chem 40:3755

    Article  CAS  Google Scholar 

  32. Morlot J, Uyttebroeck N, Agustin D, Poli R (2013) ChemCatChem 5:601

    Article  CAS  Google Scholar 

  33. Soezen-Aktas P, Manoury E, Demirhan F, Poli R (2013) Eur J Inorg Chem 2728

  34. Dinoi C, Poli R, Perrin L, Maron L (2012) Dalton Trans 41:1131

    Article  CAS  Google Scholar 

  35. Sharma RV, Soni KK, Dalai AK (2012) Catal Commun 29:87

    Article  CAS  Google Scholar 

  36. Jia L, Zhang S, Gu F, Ping Y, Guo X, Zhong Z, Su F (2012) Micropor Mesopor Mater 149:158

    Article  CAS  Google Scholar 

  37. Behera GC, Parida KM (2012) Appl Catal A: Gen 413:245

    Article  Google Scholar 

  38. Brauer HD, Eilers B, Lange A (2002) J Chem Soc Perkin Trans 2:1288

    Article  Google Scholar 

  39. Grigoropoulou G, Clark JH, Elings JA (2003) Green Chem 5:1

    Article  CAS  Google Scholar 

  40. Rajagopalan B, Wei M, Musie GT, Subramaniam B, Busch DH (2003) Ind Eng Chem Res 42:6505

    Article  CAS  Google Scholar 

  41. Amarante TR, Neves P, Paz FAA, Valente AA, Pillinger M, Gonçalves IS (2014) Dalton Trans 43:6059

    Article  CAS  Google Scholar 

  42. Amarante TR, Paz FAA, Gago S, Gonçalves IS, Pillinger M, Rodrigues AE, Abrantes M (2009) Molecules 14:3610

    Article  CAS  Google Scholar 

  43. Grzywa M, Nitek W, Łasocha W (2008) J Mol Struct 888:318

    Article  CAS  Google Scholar 

  44. Zhou MD, Liu MJ, Huang LL, Zhang J, Wang JY, Li XB, Kühn FE, Zang SL (2015) Green Chem 17:1186

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was developed in the scope of the project CICECO-Aveiro Institute of Materials, POCI-01-0145-FEDER-007679 [FCT (Fundação para a Ciência e a Tecnologia) Ref. UID/CTM/50011/2013], financed by national funds through the FCT/MEC and when applicable co-financed by FEDER (Fundo Europeu de Desenvolvimento Regional) under the PT2020 Partnership Agreement. The FCT and the European Union are acknowledged for post-doctoral grants to P.N. (SFRH/BPD/110530/2015) and A.C.G. (SFRH/BPD/108541/2015) co-funded by MCTES and the European Social Fund through the program POPH of QREN.

Author information

Authors and Affiliations

  1. Department of Chemistry, CICECO - Aveiro Institute of Materials, University of Aveiro, Campus Universitário de Santiago, 3810-193, Aveiro, Portugal

    Patrícia Neves, Ana C. Gomes, Martyn Pillinger, Isabel S. Gonçalves & Anabela A. Valente

  2. Inorganic Chemistry Department, Taras Shevchenko National University of Kyiv, Volodimirska Str. 64, Kyiv, 01033, Ukraine

    Andrey B. Lysenko

Authors
  1. Patrícia Neves
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Andrey B. Lysenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ana C. Gomes
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Martyn Pillinger
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Isabel S. Gonçalves
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Anabela A. Valente
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Andrey B. Lysenko or Anabela A. Valente.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Neves, P., Lysenko, A.B., Gomes, A.C. et al. Behavior of Triazolylmolybdenum(VI) Oxide Hybrids as Oxidation Catalysts with Hydrogen Peroxide. Catal Lett 147, 1133–1143 (2017). https://doi.org/10.1007/s10562-017-1991-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-017-1991-y

Keywords

Search

Navigation