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Mechanistic Aspects of the Zeolite Catalyzed Methylation of Alkenes and Aromatics with Methanol: A Review

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Abstract

Alkylation and methylation are important reactions in industrial zeolite catalyzed hydrocarbon transformation processes. This contribution compiles the present knowledge concerning the reaction mechanism of zeolite catalyzed methylation of alkenes and aromatics, based on insights obtained using spectroscopy, quantum chemistry, and kinetic measurements. A central issue is to discuss the potential role surface bound methoxy group intermediates.

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References

  1. Stern DL, Brown SH, Beck JS (2008) In: Ertl G, Knözinger H, Schüth F, Weitkamp J (eds) Handbook of heterogeneous catalysis, second, completely revised and enlarged edition. Wiley, Weinham, pp 3168–3194

  2. Clark MC, Morris Smith C, Stern DL, Beck JS (2008) In: Ertl G, Knözinger H, Schüth F, Weitkamp J (eds) Handbook of Heterogeneous Catalysis, Second, Completely Revised and Enlarged Edition. Wiley, Weinham, pp 3153–3168

    Google Scholar 

  3. Millini R, Frigerio F, Bellussi G, Pazzuconi G, Perego C, Pollesel P, Romano U (2003) J Catal 217:298

    CAS  Google Scholar 

  4. Kvisle S, Fuglerud T, Kolboe S, Olsbye U, Lillerud KP, Vora BP (2008) In: Ertl G, Knözinger H, Schüth F, Weitkamp J (eds) Handbook of heterogeneous catalysis, second, completely revised and enlarged edition. Wiley, Weinham, pp 2950–2965

  5. Teketel S, Olsbye U, Lillerud KP, Beato P, Svelle S (2010) Microporous Mesoporous Mater 136:33

    Article  CAS  Google Scholar 

  6. Svelle S, Joensen F, Nerlov J, Olsbye U, Lillerud KP, Kolboe S, Bjørgen M (2006) J Am Chem Soc 128:14770

    Article  CAS  Google Scholar 

  7. Bjørgen M, Svelle S, Joensen F, Nerlov J, Kolboe S, Bonino F, Palumbo L, Bordiga S, Olsbye U (2007) J Catal 249:195

    Article  Google Scholar 

  8. Ahn JH, Temel B, Iglesia E (2009) Angew Chem Int Ed 48:1

    Article  Google Scholar 

  9. Claeyssens F, Harvey JN, Manby FR, Mata RA, Mulholland AJ, Ranaghan KE, Schütz M, Thiel S, Thiel W, Werner HJ (2006) Angew Chem Int Ed 45:6856

    Article  CAS  Google Scholar 

  10. Svelle S, Tuma C, Rozanska X, Kerber T, Sauer J (2009) J Am Chem Soc 131:816

    Article  CAS  Google Scholar 

  11. Van Speybroeck V, Van der Mynsbrugge J, Vandichel M, Hemelsoet K, Lesthaeghe D, Ghysels A, Marin GB, Waroquier M (2011) J Am Chem Soc 133:888

    Article  Google Scholar 

  12. Ivanova II, Corma A (1997) J Phys Chem B 101:547

    Article  CAS  Google Scholar 

  13. Vos AM, Nulens KHL, De Proft F, Schoonheydt RA, Geerlings P (2002) J Phys Chem B 106:2026

    Article  CAS  Google Scholar 

  14. Svelle S, Kolboe S, Olsbye U, Swang O (2003) J Phys Chem B 107:5251

    Article  CAS  Google Scholar 

  15. Stich I, Gale JD, Terakura K, Payne MC (1999) J Am Chem Soc 121:3292

    Article  CAS  Google Scholar 

  16. Shah R, Gale JD, Payne MC (1996) J Phys Chem 100:11688

    Article  CAS  Google Scholar 

  17. Haase F, Sauer J (2000) Microporous Mesoporous Mater 35–36:379

    Article  Google Scholar 

  18. Mihaleva VV, van Santen RA, Jansen APJ (2001) J Phys Chem B 105:6874

    Article  CAS  Google Scholar 

  19. Haase F, Sauer J (1995) J Am Chem Soc 117:3780

    Article  CAS  Google Scholar 

  20. Bandiera J, Naccache C (1991) Appl Catal 69:139

    Article  CAS  Google Scholar 

  21. Shah R, Gale JD, Payne MC (1997) J Phys Chem B 101:4787

    Article  CAS  Google Scholar 

  22. Blaszkowski SR, van Santen RA (1995) J Phys Chem 99:11728

    Article  CAS  Google Scholar 

  23. Blaszkowski SR, van Santen RA (1997) J Phys Chem 101:2292

    CAS  Google Scholar 

  24. Payne MC, Hytha M, Stich I, Gale JD, Terakura K (2001) Microporous Mesoporous Mater 48:375

    Article  CAS  Google Scholar 

  25. Sandre E, Payne MC, Gale JD (1998) Chem Commun 2445

  26. Blaszkowski SR, van Santen RA (1996) J Am Chem Soc 118:5152

    Article  CAS  Google Scholar 

  27. Svelle S, Kolboe S, Swang O, Olsbye U (2005) J Phys Chem B 109:12874

    Article  CAS  Google Scholar 

  28. Maihom T, Boefka B, Sirijaraensre J, Nanok T, Probst M, Limtrakul J (2009) J Phys Chem C 113:6654

    Article  CAS  Google Scholar 

  29. Vos AM, Rozanska X, Schoonheydt RA, van Santen RA, Hutschka F, Hafner J (2001) J Am Chem Soc 123:2799

    Article  CAS  Google Scholar 

  30. Lesthaeghe D, Van Speybroeck V, Marin GB, Waroquier M (2006) Angew Chem Int Ed 45:1714

    Article  CAS  Google Scholar 

  31. Arstad B, Kolboe S, Swang O (2002) J Phys Chem B 106:12722

    Article  CAS  Google Scholar 

  32. Svelle S, Arstad B, Kolboe S, Swang O (2003) J Phys Chem B 107:9281

    Article  CAS  Google Scholar 

  33. Bleken F, Svelle S, Lillerud KP, Olsbye U, Arstad B, Swang O (2010) J Phys Chem A 114:7391

    Article  CAS  Google Scholar 

  34. Moon SH, Windawl H, Katzer JR (1981) Ind Eng Chem Fundam 20:396

    Article  CAS  Google Scholar 

  35. Wang W, Hunger M (2008) Acc Chem Res 41:895

    Article  CAS  Google Scholar 

  36. Haw JF, Song W, Marcus DM, Nicholas JM (2003) Acc Chem Res 36:317

    Article  CAS  Google Scholar 

  37. Haw JF, Nicholas JB, Xu T, Beck LW, Ferguson DB (1996) Acc Chem Res 29:259

    Article  CAS  Google Scholar 

  38. Jiang Y, Hunger M, Wang W (2006) J Am Chem Soc 128:11679

    Article  CAS  Google Scholar 

  39. Forester TR, Howe RF (1987) J Am Chem Soc 109:5076

    Article  CAS  Google Scholar 

  40. Campbell SH, Jiang X-Z, Howe RF (1999) Microporous Mesoporous Mater 29:91

    Article  CAS  Google Scholar 

  41. Datka J, Rakoczy J, Zadrozna G (1999) In: Treacy MMJ, Marcus BK, Bisher ME, Higgins JB (eds) Proceedings of the 12th international zeolite conference. Materials Research Society, Warrendale, pp 2601–2608

  42. Forester TR, Wong S-T, Howe RF (1986) J Chem Soc Chem Commun 1611

  43. Rakocky J, Romotowski T (1993) Zeolites 13:256

    Article  Google Scholar 

  44. Mirth G, Lercher JA (1991) J Phys Chem 95:3736

    Article  CAS  Google Scholar 

  45. Cheung P, Bhan A, Sunley GJ, Law DJ, Iglesia E (2007) J Catal 245:110

    Article  CAS  Google Scholar 

  46. Ono Y, Mori T (1981) J Chem Soc Faraday Trans 77:2209

    Article  CAS  Google Scholar 

  47. Wang W, Buchholz A, Seiler M, Hunger M (2003) J Am Chem Soc 125:15260

    Article  CAS  Google Scholar 

  48. Salehirad F, Anderson MW (1996) J Catal 164:301

    Article  CAS  Google Scholar 

  49. Ivanova II, Pomakhina EB, Rebrov AI, Hunger M, Kolyagin YG, Weitkamp J (2001) J Catal 203:375

    Article  CAS  Google Scholar 

  50. Hunger M, Horvath T (1996) J Am Chem Soc 118:12302

    Article  CAS  Google Scholar 

  51. Bosacek V, Klik R, Genoni F, Spano G, Rivetti F, Figueras F (1999) Magn Reson Chem 37:S135

    Article  CAS  Google Scholar 

  52. Beschmann K, Riekert L (1993) J Catal 141:548

    Article  CAS  Google Scholar 

  53. Mikkelsen Ø, Rønning PO, Kolboe S (2000) Microporous Mesoporous Mater 40:95

    Article  CAS  Google Scholar 

  54. Vinek H, Lercher JA (1991) J Mol Catal 64:23

    Article  CAS  Google Scholar 

  55. Bhat YS, Halgeri AB, Prasado Rao TSR (1989) Ind Eng Chem Res 28:890

    Article  CAS  Google Scholar 

  56. Mantha R, Bhatia S, Rao MS (1991) Ind Eng Chem Res 30:281

    Article  CAS  Google Scholar 

  57. Sotelo JL, Uguina MA, Valverde JL, Serrano DP (1993) Ind Eng Chem Res 32:2548

    Article  CAS  Google Scholar 

  58. Al-Khattaf S, Rabiu S, Tukur NM, Alnaizy R (2008) Chem Eng J 139:622

    Article  CAS  Google Scholar 

  59. Rabiu S, Al-Khattaf S (2008) Ind Eng Chem Res 47:39

    Article  CAS  Google Scholar 

  60. Saepurahman, Visur M, Olsbye U, Bjørgen M, Svelle S (2011) Top Catal (submitted)

  61. Svelle S, Rønning PO, Kolboe S (2004) J Catal 224:115

    Article  CAS  Google Scholar 

  62. Svelle S, Rønning PO, Olsbye U, Kolboe S (2005) J Catal 234:385

    Article  CAS  Google Scholar 

  63. Cheung P, Bhan A, Sunley GJ, Iglesia E (2006) Angew Chem Int Ed 45:1617

    Article  CAS  Google Scholar 

  64. Bhan A, Allian AD, Sunley GJ, Law DJ, Iglesia E (2007) J Am Chem Soc 129:4919

    Article  CAS  Google Scholar 

  65. Bhan A, Iglesia E (2008) Acc Chem Res 41:559

    Article  CAS  Google Scholar 

  66. Zhu Q, Kondo JN, Setoyama T, Yamaguchi M, Domen K, Tatsumi T (2008) Chem Commun 5164

  67. Unneberg E, Kolboe S (1995) Appl Catal A 124:345

    Article  CAS  Google Scholar 

  68. Svelle S, Aravinthan S, Bjørgen M, Lillerud KP, Kolboe S, Dahl IM, Olsbye U (2006) J Catal 241:243

    Article  CAS  Google Scholar 

  69. Murray DK, Chang JW, Haw JF (1993) J Am Chem Soc 115:4732

    Article  CAS  Google Scholar 

  70. Bosacek V (1993) J Phys Chem 97:10732

    Article  CAS  Google Scholar 

  71. Nilsen MH, Svelle S, Aravinthan S, Olsbye U (2009) Appl Catal A 367:23

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This publication forms a part of the inGAP Center of Research-based Innovation, which receives financial support from the Research Council of Norway under contract no. 174893.

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Authors and Affiliations

  1. inGap Center of Research Based Innovation, Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, 0315, Oslo, Norway

    Stian Svelle, Melina Visur & Unni Olsbye

  2. Department of Chemistry, Norwegian University of Science and Technology, Høgskoleringen 5, 7491, Trondheim, Norway

    Saepurahman & Morten Bjørgen

Authors
  1. Stian Svelle
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  2. Melina Visur
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  3. Unni Olsbye
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  4. Saepurahman
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  5. Morten Bjørgen
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Corresponding authors

Correspondence to Stian Svelle or Morten Bjørgen.

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Svelle, S., Visur, M., Olsbye, U. et al. Mechanistic Aspects of the Zeolite Catalyzed Methylation of Alkenes and Aromatics with Methanol: A Review. Top Catal 54, 897 (2011). https://doi.org/10.1007/s11244-011-9697-7

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