Skip to main content
SpringerLink
Log in

Zeolites for fine chemicals production

  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

The use of zeolitic catalysts in organic syntheses is reviewed with emphasis on recent developments in the areas of acid and redox catalysis and on their relationship with environmental issues. Examples of acid‐catalyzed reactions are chosen from the acylation, alkylation, hydroxyalkylation of aromatic and heterocyclic compounds and from rearrangement reactions. The epoxidation of olefins, the hydroxylation of arenes and the oxidation of O‐, S‐ and N‐functionalities with hydrogen peroxide on Ti‐zeolites illustrate catalyzed oxidations.

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

Similar content being viewed by others

References

  1. H.U. Blaser and M. Studer, Appl. Catal. A 189 (1999) 191.

    Article  CAS  Google Scholar 

  2. P.B. Venuto and P.S. Landis, in: Advances in Catalysis, Vol. 18, eds. D.D. Eley, H. Pines and P.B. Weisz (Academic Press, New York, 1968) pp. 259–371.

    Google Scholar 

  3. P.B. Venuto, Micropor. Mater. 2 (1994) 297.

    Article  CAS  Google Scholar 

  4. W. Hölderich, M. Hesse and F. Näumann, Angew. Chem. Int. Ed. Engl. 27 (1988) 226.

    Article  Google Scholar 

  5. W.F. Hoelderich and H. van Bekkum, in: Introduction in Surface Science and Catalysis, Stud. Surf. Sci. Catal., Vol. 58, eds. H. van Bekkum, E.M. Flanigen and J.C. Jansen (Elsevier, Amsterdam, 1991) p. 631.

    Google Scholar 

  6. A. Corma and H. Garcia, Catal. Today 38 (1997) 257.

    Article  CAS  Google Scholar 

  7. R.A. Sheldon and R.S. Downing, Appl. Catal. A 189 (1999) 163.

    Article  CAS  Google Scholar 

  8. B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Graille and D. Pioch, J. Org. Chem. 51 (1986) 2128.

    Article  CAS  Google Scholar 

  9. E.A. Gunnewegh, R.S. Downing and H. van Bekkum, in: A Refined Tool for Designing Catalytic Sites, Stud. Surf. Sci. Catal., Vol. 97, eds. L. Bonneviot and S. Kaliaguine (Elsevier, Amsterdam, 1995) p. 447.

    Google Scholar 

  10. A. Komarowski and S. Kostancki, Ber. 27 (1890) 1997.

    Google Scholar 

  11. French Patent 2 034 934 (1970), to Borsodi Vegyi.

  12. P. Slagan, South African Patent 76 02 667 (1977), to American Cyanamid.

  13. J.P. Beau, US Patent 5 629 453 (1997), to Great Lakes Chemical France.

  14. E.H. Dobratz and A.J. Kolka, US Patent 3 403 183, to Koppers.

  15. M.S. Whelen, US Patent 3 371 119 (1968), to Du Pont.

  16. A.J. Hoefnagel and H. van Bekkum, Appl. Catal. A 97 (1993) 87.

    Article  CAS  Google Scholar 

  17. H. van Bekkum, A.J. Hoefnagel, M.A. Vankoten, E.A. Gunnewegh, A.H.G. Vogt and H.W. Kouwenohoven, in: Zeolites and Microporous Crystals, Stud. Surf. Sci. Catal., Vol. 83, eds. T. Hattori and T. Yashima (Elsevier, Amsterdam, 1994) p. 379.

    Google Scholar 

  18. G. Harvey, A. Vogt, H.W. Kouwenhoven and R. Prins, in: Proc. 9th Int. Zeolite Conf., Vol. 2, eds. R. von Ballmoos, J.B. Higgins and M.M.J. Treacy (Butterworth-Heinemann, Boston, 1993) p. 363.

    Google Scholar 

  19. K. Smith, Z. Zhenhua and P.K.G. Hodgson, J. Mol. Catal. A 134 (1998) 121.

    Article  CAS  Google Scholar 

  20. B.M. Choudary, M. Sateesh, M.L. Kantam and K.V.R. Prasad, Appl. Catal. A 171 (1998) 155.

    Article  CAS  Google Scholar 

  21. Q.L. Wang, Y.D. Ma, X.D. Ji, H. Yan and Q. Qiu, J. Chem. Soc., Chem. Commun. (1995) 2307.

  22. U. Freese, F. Heinrich and F. Roessner, Catal. Today 49 (1999) 237.

    Article  CAS  Google Scholar 

  23. K. Gaare and D. Akporiaye, J. Mol. Catal. A 109 (1996) 177.

    Article  CAS  Google Scholar 

  24. D. Rohan, C. Canaff, E. Fromentin and M. Guisnet, J. Catal. 177 (1998) 296.

    Article  CAS  Google Scholar 

  25. E.G. Derouane, C.J. Dillon, D. Bethell and S.B. Derouane-Abd Hamid, J. Catal. 187 (1999) 209.

    Article  CAS  Google Scholar 

  26. M. Spagnol, L. Gilbert, E. Benazzi and C. Marcilly, US Patent 5 817 878 (1998), to Rhône-Poulenc.

  27. A. Corma, M.J. Climent, H. Garcia and J. Primo, Appl. Catal. 49 (1989) 109.

    Article  CAS  Google Scholar 

  28. P.J. Harrington and E. Lodewijk, Org. Process Res. Dev. 1 (1997) 72.

    Article  CAS  Google Scholar 

  29. G. Harvey and G. Maeder, Collect. Czech. Chem. Commun. 57 (1992) 863.

    Article  Google Scholar 

  30. E.A. Gunnewegh, S.S. Gopie and H. van Bekkum, J. Mol. Catal. A 106 (1996) 151.

    Article  CAS  Google Scholar 

  31. P.R. Reddy, M. Subrahmanyam and V.D. Kumar, Catal. Lett. 61 (1999) 207.

    Article  CAS  Google Scholar 

  32. A.P. Singh and A.K. Pandey, J. Mol. Catal. A 123 (1997) 141.

    Article  CAS  Google Scholar 

  33. A. Vogt, H.W. Kouwenhoven and R. Prins, Appl. Catal. A 123 (1995) 37.

    Article  CAS  Google Scholar 

  34. F. Richard, H. Carreyre and G. Pérot, J. Catal. 159 (1996) 427.

    Article  CAS  Google Scholar 

  35. A. Finiels, A. Calmette, P. Geneste and P. Moreau, in: Heterogeneous Catalysis and Fine Chemicals III, Stud. Surf. Sci. Catal., Vol. 78, eds. M. Guisnet, J. Barbier, J. Barrault, C. Bouchoule, D. Duprez, G. Pérot and C. Montassier (Elsevier, Amsterdam, 1993) p. 595.

    Google Scholar 

  36. A.P. Singh, D. Bhattacharya and S. Sharma, J. Mol. Catal. A 102 (1995) 139.

    Article  CAS  Google Scholar 

  37. A.K. Pandey and A.P. Singh, Catal. Lett. 44 (1997) 129.

    Article  CAS  Google Scholar 

  38. B. Jacob, S. Sugunan and A.P. Singh, J. Mol. Catal. A 139 (1999) 43.

    Article  CAS  Google Scholar 

  39. Yu. Isaev and J.J. Fripiat, J. Catal. 182 (1999) 257.

    Article  CAS  Google Scholar 

  40. G. Pazzuconi, C. Perego, R. Millini, F. Frigerio, R. Mansani and D. Rancati, EP950650 (1999), to Enichem.

  41. B. Coq, V. Gourves and F. Figéras, Appl. Catal. A 100 (1993) 69.

    Article  CAS  Google Scholar 

  42. B.S. Kwak and T.J. Kim, Appl. Catal. A 188 (1999) 99.

    Article  CAS  Google Scholar 

  43. B.S. Kwak and T.J. Kim, Catal. Lett. 59 (1999) 55.

    Article  CAS  Google Scholar 

  44. A.P. Singh, B. Jacob and S. Sugunan, Appl. Catal. A 174 (1998) 51.

    Article  CAS  Google Scholar 

  45. A.P. Singh and A.K. Pandey, Catal. Lett. 60 (1999) 157.

    Article  CAS  Google Scholar 

  46. A.J. Hoefnagel, E.A. Gunnewegh, R.S. Downing and H. van Bekkum, J. Chem. Soc., Chem. Commun. (1995) 225.

  47. E.A. Gunnewegh, A.J. Hoefnagel and H. van Bekkum, J. Mol. Catal. A 100 (1995) 87.

    Article  CAS  Google Scholar 

  48. E.A. Gunnewegh, A.J. Hoefnagel, R.S. Downing and H. van Bekkum, Recl. Trav. Chim. Pays-bas 115 (1996) 226.

    CAS  Google Scholar 

  49. S. Shimizu, N. Abe, A. Iguchi, M. Dohba, H. Sato and K. Hirose, Micropor. Mesopor. Mater. 21 (1998) 447.

    Article  CAS  Google Scholar 

  50. M.G. Clerici, G. Bellussi and U. Romano, US Patent 5 241 119 (1993), to Enichem.

  51. M.J. Climent, A. Corma, H. Garcia and J. Primo, Appl. Catal. A 51 (1989) 113.

    Article  CAS  Google Scholar 

  52. X. Wu and R.G. Anthony, J. Catal. 184 (1999) 294.

    Article  CAS  Google Scholar 

  53. C. Moreau, F. Fajula, A. Finiels, S. Razigade, L. Gilbert, R. Jacquot and M. Spagnol, Catal. Org. React. (Dekker) (1998) 51.

  54. J. Lecomte, A. Finiels, P. Geneste and C. Moreau, Appl. Catal. A 168 (1998) 235.

    Article  CAS  Google Scholar 

  55. J. Lecompte, A. Finiels, P. Geneste and C. Moreau, J. Mol. Catal. A 123 (1998) 283.

    Article  Google Scholar 

  56. M.J. Climent, A. Corma, R. Guil-Lopez, S. Iborra and J. Primo, J. Catal. 175 (1998) 70.

    Article  CAS  Google Scholar 

  57. A. Corma, S. Iborra, S. Miquel and J. Primo, J. Catal. 180 (1998) 218.

    Article  CAS  Google Scholar 

  58. A. Severino, A. Esculcas, J. Rocha, J. Vital and L.S. Lobo, Appl. Catal. A 142 (1996) 255.

    Article  CAS  Google Scholar 

  59. W.F. Hölderich and G. Heitmann, Catal. Today 38 (1997) 227.

    Article  Google Scholar 

  60. P.J. Kunkeler, J. van der Waal, J. Bremmer, B.J. Zuurdeeg, R.S. Dowing and H. van Bekkum, Catal. Lett. 53 (1998) 135.

    Article  CAS  Google Scholar 

  61. G. Langhendries, D.E. De Vos, G.V. Baron and P.A. Jacobs, J. Catal. 187 (1999) 453.

    Article  CAS  Google Scholar 

  62. M.G. Clerici and P. Ingallina, J. Catal. 140 (1993) 71.

    Article  CAS  Google Scholar 

  63. A. Corma, P. Esteve, A. Martínez and S. Valencia, J. Catal. 152 (1995) 18.

    Article  CAS  Google Scholar 

  64. J.C. van der Waal, M.S. Rigutto and H. van Bekkum, Appl. Catal. A 167 (1998) 331.

    Article  CAS  Google Scholar 

  65. G. Bellussi, A. Carati, M.G. Clerici, G. Maddinelli and R. Millini, J. Catal. 133 (1992) 220.

    Article  CAS  Google Scholar 

  66. D. Swern, Organic Peroxides, Vol. 2 (Wiley, New York, 1971) p. 452.

    Google Scholar 

  67. I. Tabushi and A. Yazaki, J. Am. Chem. Soc. 103 (1981) 7371.

    Article  CAS  Google Scholar 

  68. J.C. van der Waal, P. Lin, M.S. Rigutto and H. van Bekkum, in: Progress in Zeolite and Microporous Materials, Stud. Surf. Sci. Catal., Vol. 105, eds. H. Chon, S.K. Ihm and Y.S. Uh (Elsevier, Amsterdam, 1997) p. 1093.

    Google Scholar 

  69. R.A. Sheldon, M. Wallau, I.W.C.E. Arends and U. Schuchardt, Acc. Chem. Res. 31 (1998) 485.

    CAS  Google Scholar 

  70. J.S. Reddy, P. Liu and A. Sayari, Appl. Catal. A 148 (1996) 7.

    Article  Google Scholar 

  71. L.Y. Chen, G.K. Chuah and S. Jaenicke, Catal. Lett. 50 (1998) 107.

    Article  CAS  Google Scholar 

  72. K.A. Koyano and T. Tatsumi, Micropor. Mater. 10 (1997) 259.

    Article  Google Scholar 

  73. G.J. Hutchings and D.F. Lee, J. Chem. Soc., Chem. Commun. (1994) 1095.

  74. G.J. Hutchings, D.F. Lee and A.R. Minihan, Catal. Lett. 39 (1996) 83.

    Article  CAS  Google Scholar 

  75. T. Tatsumi, M. Yako, M. Nakamura, Y. Yuhara and H. Tominaga, J. Mol. Catal. 78 (1993) L41.

    Article  CAS  Google Scholar 

  76. R. Kumar, G.C.G. Pais, B. Pandey and P. Kumar, J. Chem. Soc., Chem. Commun. (1995) 1315.

  77. W. Adam, A. Corma, T.I. Reddy and M. Renz, J. Org. Chem. 62 (1997) 3631.

    Article  CAS  Google Scholar 

  78. W. Adam, A. Corma, A. Martínez, C.M. Mitchell, T.I. Reddy, M. Renz and A.K. Smerz, J. Mol. Catal. A 117 (1997) 357.

    Article  CAS  Google Scholar 

  79. F. Maspero and U. Romano, J. Catal. 146 (1994) 476.

    Article  CAS  Google Scholar 

  80. S.B. Kumar, S.P. Mirajkar, G.C.G. Pais, P. Kumar and R. Kumar, J. Catal. 156 (1995) 163.

    Article  CAS  Google Scholar 

  81. A. Corma, M.A. Camblor, P. Esteve, A. Martínez and J. Pérez-Pariente, J. Catal. 145 (1994) 151.

    Article  CAS  Google Scholar 

  82. E.R. Derouane, G.J. Hutchings, W.F. Mbafor and S.M. Roberts, New J. Chem. (1998) 797.

  83. A. Bhaumik and T. Tatsumi, J. Catal. 182 (1999) 349.

    Article  CAS  Google Scholar 

  84. A. Bhaumik and T. Tatsumi, J. Catal. 176 (1998) 305.

    Article  CAS  Google Scholar 

  85. A. Corma, M. Iglesia and F. Sanchez, J. Chem. Soc., Chem. Commun. (1995) 1635.

  86. A. Corma, M.T. Navarro, J. Pérez-Pariente and F. Sanchez, in: Zeolites and Related Microporous Materials: State of Art 1994, Stud. Surf. Sci. Catal., Vol. 84, eds. J. Weitkamp, H.G. Karge, H. Pfeifer and W.F. Hölderich (Elsevier, Amsterdam, 1994) p. 69.

    Google Scholar 

  87. H. Gao, G. Lu, J. Suo and S. Li, Appl. Catal. A 138 (1996) 27.

    Article  CAS  Google Scholar 

  88. M.G. Clerici, in: Fine Chemicals through Heterogeneous Catalysis, eds. R.A. Sheldon and H. van Bekkum (Wiley-VCH, Weinhneim, 2000).

    Google Scholar 

  89. U. Romano, A. Esposito, F. Maspero, C. Neri and M.G. Clerici, Chim. Ind. (Milan) 72 (1990) 610.

    CAS  Google Scholar 

  90. M.G. Clerici, Appl. Catal. 68 (1991) 249.

    Article  CAS  Google Scholar 

  91. A.V. Ramaswamy, S. Sivasanker and P. Ratnasamy, Micropor. Mesopor. Mater. 2 (1994) 451.

    CAS  Google Scholar 

  92. R. Kumar and A. Bhaumik, Micropor. Mesopor. Mater. 21 (1998) 497.

    Article  CAS  Google Scholar 

  93. P.R. Hari Prasad Rao and A.V. Ramaswamy, Appl. Catal. A 93 (1993) 123.

    Article  Google Scholar 

  94. C.B. Khouw, C.B. Dartt, J.A. Labinger and M.E. Davis, J. Catal. 149 (1994) 195.

    Article  CAS  Google Scholar 

  95. P. Wu, T. Komatsu and T. Yashima, J. Phys. Chem. B 102 (1998) 9297.

    Article  CAS  Google Scholar 

  96. A.J.H. van der Pol and J.H.C. van Hooff, Appl. Catal. 106 (1993) 97.

    Article  CAS  Google Scholar 

  97. A. Corma, P. Esteve and A. Martínez, J. Catal. 161 (1996) 11.

    Article  CAS  Google Scholar 

  98. R.A. Sheldon and J. Dakka, Erdöl Erdgas Kohle 109 (1993) 520.

    CAS  Google Scholar 

  99. H. Hayashi, K. Kikawa, Y. Murai, N. Shigemoto, S. Sugiyama and K. Kawashioro, Catal. Lett. 36 (1996) 99.

    Article  Google Scholar 

  100. M. Sasidharan, S. Suresh and A. Sudalai, Tetrahedron Lett. 36 (1995) 9071.

    Article  CAS  Google Scholar 

  101. A. Bhaumik, P. Kumar and R. Kumar, Catal. Lett. 40 (1996) 47.

    Article  CAS  Google Scholar 

  102. S. Gontier and A. Tuel, J. Catal. 157 (1995) 124.

    Article  CAS  Google Scholar 

  103. S. Suresh, R. Joseph, B. Jayachandran, A.V. Pol, M.P. Vinod, A. Sudalai, H.R. Sonawane and T. Ravindranathan, Tetrahedron 51 (1995) 11305.

    Article  CAS  Google Scholar 

  104. T. Selvan and A.V. Ramaswamy, J. Chem. Soc., Chem. Commun. (1996) 1215.

  105. J.S. Reddy and P.A. Jacobs, J. Chem. Soc. Perkin Trans. I (1993) 2665.

    Article  Google Scholar 

  106. J.S. Reddy and A. Sayari, Appl. Catal. A 128 (1995 231.

    Article  Google Scholar 

  107. J. Reni, A. Sudalai and T. Ravindranathan, Synlett. (1995) 1177.

  108. J.S. Reddy and P. Jacobs, Catal. Lett. 37 (1996) 213.

    Article  CAS  Google Scholar 

  109. P. Roffia, G. Leofanti, A. Cesana, M. Mantegazza, M. Padovan, G. Petrini, S. Tonti, V. Gervasutti and R. Varagnolo, Chim. Ind. (Milan) 72 (1990) 598.

    CAS  Google Scholar 

  110. J. Le Bars, J. Dakka and R. Sheldon, Appl. Catal. A 136 (1996) 69.

    Article  CAS  Google Scholar 

  111. P. Wu, T. Komatsu and T. Yashima, J. Catal. 168 (1997) 400.

    Article  CAS  Google Scholar 

  112. R. Joseph, A. Sudalai and T. Ravindranathan, Tetrahedron Lett. 35 (1994) 5493.

    Article  CAS  Google Scholar 

  113. P. Kumar, V.R. Hegde, B. Pandey and T. Ravindranathan, J. Chem. Soc., Chem. Commun. (1993) 1553.

  114. R. Reddy, J.S. Reddy, R. Kumar and P. Kumar, J. Chem. Soc., Chem. Commun. (1992) 84.

  115. V. Hulea, P. Moreau and F. Di Renzo, J. Mol. Catal. A 111 (1996) 325.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. EniTecnologie, Via F. Maritano 26, I‐20097, San Donato Milanese (Milano), Italy

    Mario G. Clerici

Authors
  1. Mario G. Clerici
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Clerici, M.G. Zeolites for fine chemicals production. Topics in Catalysis 13, 373–386 (2000). https://doi.org/10.1023/A:1009063106954

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1009063106954

Search

Navigation