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Liquid-Phase Oligomerization of 1-Hexene Catalyzed by Macroporous Ion-Exchange Resins

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Abstract

Oligomerization of pure 1-hexene catalyzed by macroporous ion-exchange resins was performed in batch experiments at 350–390 K and 2 MPa. At 373 K, after 6 h, 1-hexene conversion was practically complete and the selectivity to dimers was 56%, that to trimers 0.8 and 43.2% to double-bond isomerization. By assuming an homogeneous kinetic model for olefin dimerization of second order reaction, a value of 64–68 kJ mol−1 for apparent activation energy was obtained.

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Abbreviations

A:

Preexponential factor of Arrhenius equation (mol kg−1 h−1)

A-15:

Macroporous ion-exchange resin Amberlyst 15

A-16:

Macroporous ion-exchange resin Amberlyst 16

A-35:

Macroporous ion-exchange resin Amberlyst 35

A-36:

Macroporous ion-exchange resin Amberlyst 36

A-39:

Macroporous ion-exchange resin Amberlyst 39

A-46:

Macroporous ion-exchange resin Amberlyst 46

A-48:

Macroporous ion-exchange resin Amberlyst 48

B:

Bisulfonated

C:

Conventionally sulfonated

cj :

Concentration of j (mol j L−1)

CT-175:

Macroporous ion-exchange resin Purolite CT-175

CT-252:

Macroporous ion-exchange resin Purolite CT-252

CT-275:

Macroporous ion-exchange resin Purolite CT-275

CT-276:

Macroporous ion-exchange resin Purolite CT-276

Ea :

Apparent activation energy (kJ mol−1)

MN500:

Macroporous ion-exchange resin Purolite MN500

GC/MS:

Gas chromatograph with mass detector

K:

Apparent rate constant (mol1-n Ln kg−1 h−1)

n:

Order of reaction (dimensionless)

\( n_{1hex}^{o} \) :

Initial mole of 1-hexene (mol)

\( n_{j}^{{}} \) :

mole of component j (mol)

O:

Oversulfonated

rj :

Reaction rate of component j (mol j kg−1 h−1)

\( S_{j} \) :

Selectivity to product j (%) (dimensionless)

SS:

Sulfonated only on surface

SQ:

Sum of square of the residuals

T:

Time (h)

Wcat :

Mass of dry resin (kg)

X1hex :

Conversion of 1-hexene (%) (dimensionless)

Dim:

Dimers

Hex:

Linear hexenes

1hex:

1-Hexene

2hex:

2-Hexene

j:

Component j

Trim:

Trimers

References

  1. Asinger F (1968) In: Mono-olefins chemistry and technology.(Chap 5 and 10). Pergamon Press, Oxford

  2. De Klerk A (2005) Ind Chem Eng Res 44:3887

    Article  Google Scholar 

  3. Quann RJ, Green LA, Tabak SA, Krambeck FJ (1988) Ind Eng Chem Res 27:565

    Article  CAS  Google Scholar 

  4. Köhler E, Schmidt F, Wernicke HJ, De Pontes M, Roberts HL (1995) Hydrocarbon Technol Int Summer:37

  5. Schmidt R, Welch MB, Randolph BB (2008) Energy Fuels 22:1148

    Article  CAS  Google Scholar 

  6. Cruz VJ, Izquierdo JF, Cunill F, Tejero J, Iborra M, Fité C (2005) React & Funct Polym 65:149

    Article  CAS  Google Scholar 

  7. Cruz VJ, Bringué R, Cunill F, Izquierdo JF, Tejero J, Iborra M, Fité C (2006) J Catal 238:330

    Article  CAS  Google Scholar 

  8. Schwarzer R, Du Toit E, Nicol W (2008) Appl Catal A 340:119

    Article  CAS  Google Scholar 

  9. Van Grieken R, Escola JM, Moreno J, Rodríguez R (2006) Appl Catal A 305:176

    Article  Google Scholar 

  10. Escola JM, Van Grieken R, Moreno J, Rodriguez R (2008) Ind Eng Chem Res 45:7409

    Article  Google Scholar 

  11. Van Grieken R, Escola JM, Moreno J, Rodriguez R (2008) Appl Catal A 337:173

    Article  Google Scholar 

  12. Lundquist EG, Beshsah K (1997) 213th In: ACS National Meeting, San Francisco

  13. Farcasiu D, Ghenciu A, Marino G, Rose KD (1997) J Am Chem Soc 119:11826

    Article  CAS  Google Scholar 

  14. Beck JW, Haw JF (1995) J Phys Chem 99:1076

    Article  CAS  Google Scholar 

  15. Pérez M, Cruz VJ, Tejero J, Iborra M, Cunill F, Izquierdo JF, Fité C (2003) In: Poster A3-068, EuropaCat-VI, August 31–September 4 ,Innsbruck, Austria

  16. Coleto I, Roldán R, Jimenez-Sanchidrián C, Gómez JP, Romero-Salguero FJ (2009) Catal Today 149:275

    Article  Google Scholar 

  17. Schwarzer R, Du Toit E, Nicol W (2009) Appl Catal A 369:83

    Article  CAS  Google Scholar 

  18. IJ Dijs, HLF van Ochten, HLF, AJM van der Heijden, JW Geus, LW Jenneskens (2003) Appl Catal A General 241:185

  19. Siril PF, Cross HE, Brown DR (2008) J Mol Catal A 279:63

    Article  CAS  Google Scholar 

  20. Hart M, Fuller G, Brown R, Parck C, Keane MA, Dale JA, Fougret CM, Cockman RW (2001) Catal Lett 72:135

    Article  CAS  Google Scholar 

  21. Cruz VJ, Izquierdo JF, Cunill F, Tejero J, Iborra M, Fité C, Bringué R (2007) React Funct Polym 67:210

    Article  CAS  Google Scholar 

  22. Fortini EM, González-Bóveda MC, Löffler D (1997) React Kinet Catal Lett 61:281

    Article  CAS  Google Scholar 

  23. Hauge M, Bergene E, Chen D, Fredriksen GR, Holmen A (2005) Catal Today 100:463

    Article  CAS  Google Scholar 

  24. NF Shah, MM Sharma (1993) React Polym 19:181

  25. Haag WO (1967) Chem Eng Prog Symp Ser 63:140

    CAS  Google Scholar 

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Acknowledgments

The authors thank Rohm and Haas, and Purolite for providing their catalysts. We are also grateful to Repsol YPF for the financial support to this research and for permission to publish this work.

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Authors and Affiliations

  1. Department of Chemical Engineering, University of Barcelona, Martí i Franquès 1, 08028, Barcelona, Spain

    Madelin Cadenas, Roger Bringué, Carles Fité, Eliana Ramírez & Fidel Cunill

Authors
  1. Madelin Cadenas
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  2. Roger Bringué
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  3. Carles Fité
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  4. Eliana Ramírez
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  5. Fidel Cunill
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Correspondence to Fidel Cunill.

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Cadenas, M., Bringué, R., Fité, C. et al. Liquid-Phase Oligomerization of 1-Hexene Catalyzed by Macroporous Ion-Exchange Resins. Top Catal 54, 998 (2011). https://doi.org/10.1007/s11244-011-9721-y

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