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Characterization and use of MoO3 modified alumosilicates in Prins cyclization of isoprenol and isovaleraldehyde

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Abstract

MoO3 modified alumosilicates were prepared by impregnation method and used in Prins cyclization of isoprenol and isovaleraldehyde forming 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (important compound for fragrant industry). Alumosilicates of Siral type were chosen as supports and compared with pure silica and alumina. Prepared catalysts were characterized by available methods: XRD, XRF, solid UV–Vis, TGA, TPD of pyridine, nitrogen adsorption and SEM. It was found that impregnation of Siral by MoO3 gave homogeneous distribution of Mo species on the support. On the other side using pure silica as a support the crystallic structure of MoO3 was detected in the resulting material. Impregnation of pure alumina by MoO3 resulted in the formation of aluminum molybdate. All prepared materials were used in above mentioned reaction. With increasing amount of silica in alumosilicate the increase of reaction rate and selectivity was observed up to 40% of silica in the material. Comparable results (selectivity to substituted tetrahydropyranol up to 50%) were obtained using Siral 40 and silica as supports for MoO3. These materials may be also used repeatedly without loss of activity and selectivity.

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References

  1. E. Vyskocilova, L. Rezkova, E. Vrbkova, I. Paterova, L. Cerveny, Res. Chem. Intermed. 42(2), 725–733 (2016)

    Article  CAS  Google Scholar 

  2. P.H. Williams, S.A. Ballard, US Pat., 2 422 648 (1947)

  3. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, N. Niranjan, J. Mol. Catal. A 210(1–2), 99–103 (2004)

    Article  CAS  Google Scholar 

  4. U. Akira, A. Yochiharu, T. Shigeyoshi, N. Kazuki, M. Koji, Eur. Pat. 149 3737 (2005)

    Google Scholar 

  5. G.P. More, M. Rane, S.V. Bhat, Green Chem. Lett. Rev. 5, 13–17 (2012)

    Article  CAS  Google Scholar 

  6. G. Gralla, K. Beck, M. Klos, H. Griesbach, US Pat. 0306 779 (2011)

  7. G. Li, Y. Gu, Y. Ding, Z. Yong, W. Hanpeng, G. Jianming, Y. Qiang, S.J. Liang, J. Mol. Catal. A 218(2), 147–152 (2004)

    Article  CAS  Google Scholar 

  8. J.S. Yadav, B.V. Subba Reddy, G.G.K.S. Narayana Kumar, S. Aravind, Synthesis 2008(3), 395–400 (2008)

    Article  Google Scholar 

  9. J.S. Yadav, B.V. Subba Reddy, D.N. Chaya, G.G.K.S. Narayana Kumar, P. Naresh, B. Jagadeesh, Tetrahedron Lett. 50, 1799–1802 (2009)

    Article  CAS  Google Scholar 

  10. K. Tadpetch, S. Rychnovsky, Org. Lett. 10, 4839–4842 (2008)

    Article  CAS  Google Scholar 

  11. S. Telalović, A. Ramanthan, J. Fei Ng, R. Maheswari, C. Kwakernaak, F. Soulimani, H.C. Brouwer, G.K. Chuah, B.M. Weckhuzsen, U. Hanefeld, Chem. Eur. J. 17, 2077–2088 (2011)

    Article  Google Scholar 

  12. E. Vyskočilová, M. Krátká, M. Veselý, E. Vrbková, L. Červený, Res. Chem. Intermed. 42, 6691 (2016)

    Google Scholar 

  13. M. Breugst, R. Grée, K.N. Houk, J. Org. Chem. 78, 9892–9897 (2013)

    Article  CAS  Google Scholar 

  14. F.K. Chio, J. Warne, D. Gough, M. Penny, S. Green, S.J. Coles, M.B. Hursthouse, P. Jones, Tetrahedron 67, 5107–5124 (2011)

    Article  CAS  Google Scholar 

  15. P. Borkar, P. Weghe, B.V.S. Reddy, J.S. Yadav, R. Grée, Chem. Commun. 48, 9316–9318 (2012)

    Article  CAS  Google Scholar 

  16. K. Yheng, X. Liu, S. Qin, M. Xie, L. Lin, Ch. Hu, X. Feng, J. Am. Chem. Soc. 134, 17564–17573 (2012)

    Article  Google Scholar 

  17. K.R.K.K. Reddy, I.M.L. Rosa, A.C. Doriguetto, E.L. Bastos, L.F. Silva Jr, Molecules 18, 11100–11130 (2013)

    Article  Google Scholar 

  18. E. Vyskočilová, M. Krátká, L. Červený, ICCT 2015, Mikulov, Czech Republic, ISBN: 978-80-86238-82-1, 27

  19. A. Auroux, A. Gervasini, J. Phys. Chem. 94, 6371–6379 (1990)

    Article  CAS  Google Scholar 

  20. M.A. Banares, H. Hu, I.E. Wachs, J. Catal. 150, 407–420 (1994)

    Article  CAS  Google Scholar 

  21. W. Zhang, S.T. Oyama, J. Phys. Chem. 100, 10759–10767 (1996)

    Article  CAS  Google Scholar 

  22. H. Lu, E. Iglesia, J. Catal. 208, 1–5 (2002)

    Article  Google Scholar 

  23. M.A. Banares, N.D. Spencer, M.D. Jones, I.E. Wachs, J. Catal. 146, 204–210 (1994)

    Article  CAS  Google Scholar 

  24. K. Chen, A.T. Bell, E. Iglesia, J. Catal. 209, 35–42 (2002)

    Article  CAS  Google Scholar 

  25. Z. Song, N. Mimura, J.J. Bravo-Suarez, T. Akita, S. Tsubota, S.T. Oyama, Appl. Catal. A 316, 142–151 (2007)

    Article  CAS  Google Scholar 

  26. C.C. Williams, J.G. Ekerdt, J.M. Jehng, F.D. Hardcastle, A.M. Turek, I.E. Wachs, J. Phys. Chem. 95, 8781–8791 (1991)

    Article  CAS  Google Scholar 

  27. M. Carbucicchio, F. Trifiro, J. Catal. 62, 13–18 (1980)

    Article  CAS  Google Scholar 

  28. K. Bruckman, B. Grzybowska, M. Che, J.M. Tatibouet, Appl. Catal. A 96, 279–288 (1993)

    Article  Google Scholar 

  29. T. Ono, H. Miyata, Y. Kubokawa, J. Chem. Soc. Faraday Trans. 83(6), 1761–1770 (1987)

    Article  CAS  Google Scholar 

  30. X. Ma, J. Gong, S. Wang, N. Gao, D. Wang, X. Yang, F. He, Catal. Commun. 5, 101–106 (2004)

    Article  CAS  Google Scholar 

  31. A.P. Amrute, S. Sahoo, A. Bordoloi, Y.K. Hwang, J.S. Hwang, S.B. Halligudi, Catal. Commun. 10, 1404–1409 (2009)

    Article  CAS  Google Scholar 

  32. V.S. Karakatti, D. Mumbaraddi, G.V. Shanbhag, A.B. Halgeri, S.P. Maradur, RSC Adv. 5, 93452–93462 (2015)

    Article  Google Scholar 

  33. A.N. Desikan, W. Zhang, S.T. Oyama, J. Catal. 157, 740–748 (1995)

    Article  CAS  Google Scholar 

  34. G. Tsilomelekis, A. Christodoulakis, S. Boghosian, Catal. Today 127, 139–147 (2007)

    Article  CAS  Google Scholar 

  35. T. Ono, H. Kamisuki, H. Hisashi, H. Miyata, J. Catal. 116, 303–307 (1989)

    Article  CAS  Google Scholar 

  36. DOPED ALUMINAS, Sasol Performance Chemicals (2016), http://www.sasolgermany.de/fileadmin/doc/alumina/0271.SAS-BR-Inorganics_Siral_Siralox_WEB.pdf. Accessed 17 June 2016

  37. M. Stekrova, H. Minarikova, E. Vyskocilova, J. Kolena, L. Cerveny, J. Porous Mater. 21(5), 757–767 (2014)

    Article  CAS  Google Scholar 

  38. L. Sekerová, E. Vyskočilová, L. Červený, React. Kinet. Mech. Catal. (2017). doi:10.1007/s11144-016-1131-5

    Google Scholar 

  39. J. Chang, A. Wang, J. Liu, X. Li, Y. Hu, Catal. Today 149(1–2), 122–126 (2010)

    Article  CAS  Google Scholar 

  40. E. Vyskočilová, M. Malý, A. Aho, J. Krupka, L. Červený, React. Kinet. Mech. Catal. 118(1), 235–246 (2016)

    Article  Google Scholar 

  41. M. McMillan, J.S. Brinen, G.L. Haller, J. Catal. 97(1), 243–247 (1986)

    Article  CAS  Google Scholar 

  42. J.P. Thielemann, G. Weinberg, C. Hess, ChemCatChem 3, 1814–1821 (2011)

    Article  CAS  Google Scholar 

  43. J.P. Thielemann, T. Ressler, A. Walter, G. Tzolova-Mueller, C. Hess, Appl. Catal. A 399, 28–34 (2011)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was realized within the Operational Programme Prague—Competitiveness (CZ.2.16/3.1.00/24501) and “National Program of Sustainability” (NPU I LO1613) MSMT-43760/2015. We also acknowledge grant project GACR 16-25747S. M. Lhotka is kindly acknowledged for BET measurement.

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Authors and Affiliations

  1. Department of Organic Technology, University of Chemistry and Technology Prague, Technicka 5, 166 28, Prague 6, Czech Republic

    Eliška Vyskočilová, Lada Sekerová, Iva Paterová, Jiří Krupka, Martin Veselý & Libor Červený

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  1. Eliška Vyskočilová
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  2. Lada Sekerová
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Correspondence to Eliška Vyskočilová.

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Vyskočilová, E., Sekerová, L., Paterová, I. et al. Characterization and use of MoO3 modified alumosilicates in Prins cyclization of isoprenol and isovaleraldehyde. J Porous Mater 25, 273–281 (2018). https://doi.org/10.1007/s10934-017-0440-z

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