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Selective Production of 2-Phenylhexane from Benzene and n-Hexane Over Pt- and Ga-Modified Zeolites

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Abstract

Alkylation of benzene with n-hexane was performed over H-ZSM-5 and monometallic Ga- and Pt- and bimetallic Ga- and Pt-modified ZSM-5. The influence of the particle size and the method of incorporation of Ga (during hydrothermal synthesis, by solid-state ion exchange, or by liquid-state ion exchange) was determined. The presence of Pt and well-dispersed extraframework Ga in H-ZSM-5 increased the selectivity in alkylation and suppressed cracking reactions. Well-dispersed Pt particles led to better catalytic performance. The method of Ga incorporation played an important role in obtaining higher selectivity to alkylation products and in the suppression of side reactions. Up to 93% selectivity in alkylation (of which >95% was to 2-phenylhexane) was reached over 2 wt% Pt/H-GafZSM5, in which Ga occupied framework positions. We propose that the close proximity of very small Pt nanoparticles and Ga–(OH)–Si acid sites results in the optimal bifunctional catalyst for selective production of 2-phenylhexane from benzene and n-hexane. During the reaction, the catalyst deactivated, most probably due to the sintering of the Pt particles.

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References

  1. Kocal JA, Vora BV, Imai T (2001) Appl Catal A 221:295

    Article  CAS  Google Scholar 

  2. Borutskii PN, Kozlova EG, Podkletnova NM, Gil`chenok ND, Sokolov BG, Zuev VA, Shatovkin AA (2007) Petrol Chem 47:250

    Article  Google Scholar 

  3. Pujado PR (1996) In: Meyers RA (ed) Linear alkylbenzene manufacturer: handbook of petroleum refining processes. McGraw-Hill, New York, p 1.53

    Google Scholar 

  4. Kocal JA (1993) US Patent 5,196,574 to UOP

  5. Olah GA, Schilling P, Staral JS, Halpern Y, Olah JA (1975) J Am Chem Soc 97:6807

    Article  CAS  Google Scholar 

  6. Smirniotis PG, Ruckenstein E (1995) Ind Eng Chem Res 34:1517

    Article  CAS  Google Scholar 

  7. Ivanova I, Blom N, Derouane EG (1996) J Mol Catal A 109:157

    Article  CAS  Google Scholar 

  8. Smirnov A, Mazin E, Yuschenko V, Knyazeva E, Nesterenko S, Ivanova I, Galperin L, Jensen R, Bradley S (2000) J Catal 194:194

    Article  Google Scholar 

  9. Abasov SI, Babayeva FA, Zarbaliyev RR, Abbasova GG, Tagiyev DB, Rustamov MI (2003) Appl Catal A 251:267

    Article  CAS  Google Scholar 

  10. Todorova S, Su B (2004) Catal Today 93–95:417

    Article  Google Scholar 

  11. Bigey C, Su B (2004) J Mol Catal A 209:179

    Article  CAS  Google Scholar 

  12. Sealy S, Traa Y (2005) Appl Catal A 294:273

    Article  CAS  Google Scholar 

  13. Huang X, Sun X, Zhu S, Liu Z (2007) Catal Lett 119:332

    Article  CAS  Google Scholar 

  14. Bressel A, Donauer T, Sealy S, Traa Y (2008) Microporous Mesoporous Mater 109:278

    Article  CAS  Google Scholar 

  15. Lukyanov DB, Vazhnova T (2008) J Catal 257:382

    Article  CAS  Google Scholar 

  16. Lukyanov DB, Vazhnova T (2008) J Mol Catal A 279:128

    Article  CAS  Google Scholar 

  17. Danilina N, Payrer EL, van Bokhoven JA (2010) Chem Commun 46:1509

    Article  CAS  Google Scholar 

  18. Kato S, Nakagawa K, Ikenaga N, Suzuki T (1999) Chem Lett 207

  19. Alireza S, Rezai S, Traa Y (2008) Catal Lett 122:91

    Article  CAS  Google Scholar 

  20. Bayence CR, van Hooff JHC, Kentgens APM, de Haan JE, van de Ven LJM (1989) Chem Commun 1292

  21. Timken HKC, Oldfield E (1987) J Am Chem Soc 109:7669

    Article  CAS  Google Scholar 

  22. O’Dell LA, Savin SLP, Chadwick AV, Smith ME (2007) Appl Magn Reson 32:527

    Article  Google Scholar 

  23. Post MFM, Huizinga T, Emeis CA (1989) In: Karge HG, Weitkamp J (eds) Zeolites as catalysts, sorbents and detergent builders. Elsevier, Amsterdam

    Google Scholar 

  24. Slaugh LH (1968) Tetrahedron 24:4523

    Article  Google Scholar 

  25. Borodina IB, Ponomareva OA, Fajula F, Bousquet J, Ivanova II (2007) Microporous Mesoporous Mater 105:181

    Article  CAS  Google Scholar 

  26. Jun Q, Komura K, Kubota Y, Sugi Y (2007) Chin J Catal 28:246

    Article  Google Scholar 

  27. Fricke R, Kosslick H, Lischke G, Richter M (2000) Chem Rev 100:2303

    Article  CAS  Google Scholar 

  28. Shpiro ES, Shecchenko DP, Tkachenko OP, Dmitriev RV (1994) Appl Catal A 107:147

    Article  CAS  Google Scholar 

  29. Shpiro ES, Shecchenko DP, Dmitriev RV, Tkachenko OP, Minachev KM (1994) Appl Catal A 107:165

    Article  CAS  Google Scholar 

  30. Iwasa N, Takezawa N (2003) Top Catal 22:215

    Article  CAS  Google Scholar 

  31. Vieira A, Tovar MA, Pfaff C, Betancourt P, Mendez B, Lopez CM, Machado FJ, Goldwasser J, Ramirez de Agudelo MM (2000) Stud Surf Sci Catal 130:269

    Article  Google Scholar 

  32. Cao YC, Jiang XZ (2005) J Mol Catal A 242:119

    Article  CAS  Google Scholar 

  33. Todorova S, Su B (2003) J Mol Catal A 201:223

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The work was supported by the Swiss National Science Foundation. The authors thank Dr. Frank Krumeich and the Electron Microscopy Centre of the ETH Zurich (EMEZ).

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Authors and Affiliations

  1. Institute for Chemical and Bioengineering, ETH Zurich, Wolfgang-Pauli-Str. 10, 8093, Zurich, Switzerland

    Nadiya Danilina, Elisabeth L. Payrer, Ekaterina Troussard & Jeroen A. van Bokhoven

  2. Laboratory for Energy and Environment, Paul Scherrer Institute, WLGA/135, 5232, Villigen, Switzerland

    Ekaterina Troussard & Jeroen A. van Bokhoven

Authors
  1. Nadiya Danilina
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  2. Elisabeth L. Payrer
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  3. Ekaterina Troussard
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  4. Jeroen A. van Bokhoven
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Corresponding author

Correspondence to Jeroen A. van Bokhoven.

Electronic supplementary material

Below is the link to the electronic supplementary material.

10562_2010_511_MOESM1_ESM.doc

Additional information about characterization of the material and figures related to the reported findings. Supplementary material 1 (DOC 215 kb)

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Danilina, N., Payrer, E.L., Troussard, E. et al. Selective Production of 2-Phenylhexane from Benzene and n-Hexane Over Pt- and Ga-Modified Zeolites. Catal Lett 141, 391–399 (2011). https://doi.org/10.1007/s10562-010-0511-0

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  • DOI: https://doi.org/10.1007/s10562-010-0511-0

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