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Gas-phase propene epoxidation over coinage metal catalysts

Research on Chemical Intermediates volume 38, pages 1–24 (2012)Cite this article

Abstract

Propene oxide (PO) is a very important bulk chemical and is produced on a scale of about 7.5 million tons per year. In industry, PO is produced via multiple reaction steps in the liquid phase, using hazardous chlorine or costly organic hydroperoxides as oxidants. Accordingly, development of a simple and green process to produce PO has been desired. This paper presents an overview of one-step propene epoxidation in the gas phase over coinage metal catalysts with a mixture of O2 and H2 or with molecular O2 alone as oxidant. Silver (Ag) and gold (Au) catalysts can catalyze propene epoxidation with a mixture of O2 and H2, with high selectivity, whereas copper (Cu) catalysts cannot. In this reaction Au catalysts are much more active than Ag catalysts. All the coinage metals can catalyze propene epoxidation by molecular O2, but with selectivity usually below 60%. The valence states of Cu species and the sizes of Ag particles and Au particles are of crucial importance in PO synthesis.

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References

  1. F. Nees, Heterogeneous catalysis at BASF (available at http://basf.com/group/corporate/en/innovations/events-presentations/catalysis/papers, 2008)

  2. M. Ishino, J. Yamamoto, Shokubai 48, 511 (2006)

    CAS  Google Scholar 

  3. A. Tullo, Chem. Eng. News 82(36), 15 (2004)

    Article  Google Scholar 

  4. T.A. Nijhuis, M. Makkee, J.A. Moulijn, B.M. Weckhuysen, Ind. Eng. Chem. Res. 45, 3447 (2006)

    Article  CAS  Google Scholar 

  5. J.K. Edwards, G.J. Hutchings, Angew. Chem. Int. Ed. 47, 9192 (2008)

    Article  CAS  Google Scholar 

  6. J.M. Campos-Martin, G. Blanco-Brieva, J.L.G. Fierro, Angew. Chem. Int. Ed. 45, 6962 (2006)

    Article  CAS  Google Scholar 

  7. T. Hayashi, K. Tanaka, M. Haruta, J. Catal. 178, 566 (1998)

    Article  CAS  Google Scholar 

  8. R. Meiers, W.F. Höderich, Catal. Lett. 59, 161 (1999)

    Article  CAS  Google Scholar 

  9. G. Jenzer, T. Mallat, M. Maciejewski, F. Eigenmann, A. Baiker, Appl. Catal. A 208, 125 (2001)

    Article  CAS  Google Scholar 

  10. J. Jiang, S.M. Oxford, B. Fu, M.C. Kung, H.H. Kung, J. Ma, Chem. Commun. 3791 (2010)

  11. T. Thömmes, S. Zürcher, A. Wix, A. Reitzmann, B. Kraushaar-Czarnetzki, Appl. Catal. A 318, 160 (2007)

    Article  Google Scholar 

  12. B. Horváth, M. Hornec, Appl. Catal. A 347, 72 (2008)

    Article  Google Scholar 

  13. V. Duma, D. Hönicke, J. Catal. 191, 93 (2000)

    Article  CAS  Google Scholar 

  14. Q. Zhang, Q. Guo, X. Wang, T. Shishido, Y. Wang, J. Catal. 239, 105 (2006)

    Article  CAS  Google Scholar 

  15. B. Moens, H.D. Winne, S. Corthals, H. Poelman, R.D. Gryse, V. Meynen, P. Cool, B.F. Sels, P.A. Jacobs, J. Catal. 247, 86 (2007)

    Article  CAS  Google Scholar 

  16. S. Yang, W. Zhu, Q. Zhang, Y. Wang, J. Catal. 254, 251 (2008)

    Article  CAS  Google Scholar 

  17. J. Llorca, M. Domínguez, C. Ledesma, R.J. Chimentão, F. Medina, J. Sueiras, I. Angurell, J. Seco, O. Rossell, J. Catal. 258, 187 (2008)

    Article  CAS  Google Scholar 

  18. R.J. Chimentão, F. Medina, J.L.G. Fierro, J. Llorca, J.E. Sueiras, Y. Cesteros, P. Salagre, J. Mol. Catal. A 274, 159 (2007)

    Article  Google Scholar 

  19. J. Lu, M. Luo, H. Lei, C. Li, Appl. Catal. A 237, 11 (2002)

    Article  CAS  Google Scholar 

  20. A. Takahashi, N. Hamakawa, I. Nakamura, T. Fujitani, Appl. Catal. A 294, 34 (2005)

    Article  CAS  Google Scholar 

  21. J. Lu, J.J. Bravo-Suárez, M. Haruta, S.T. Oyama, Appl. Catal. A 302, 283 (2006)

    Article  CAS  Google Scholar 

  22. O.P.H. Vaughan, G. Kyriakou, N. Macleod, M. Tikhov, R.M. Lambert, J. Catal. 236, 401 (2005)

    Article  CAS  Google Scholar 

  23. W. Su, S. Wang, P. Ying, Z. Feng, C. Li, J. Catal. 268, 165 (2009)

    Article  CAS  Google Scholar 

  24. W. Zhu, Q. Zhang, Y. Wang, J. Phys. Chem. C 112, 7731 (2008)

    Article  CAS  Google Scholar 

  25. Y. Liu, K. Murata, M. Inaba, N. Mimura, Appl. Catal. A 309, 91 (2006)

    Article  CAS  Google Scholar 

  26. Z. Song, N. Mimura, J.J. Bravo-Suárez, T. Akita, S. Tsubota, S.T. Oyama, Appl. Catal. A 316, 142 (2007)

    Article  CAS  Google Scholar 

  27. A. Held, P. Florczak, Catal. Today 142, 3329 (2009)

    Article  Google Scholar 

  28. N. Mimura, S. Tsubota, K. Murata, K.K. Bando, J.J. Bravo-Suárez, M. Haruta, S.T. Oyama, Catal. Lett. 110, 47 (2006)

    Article  CAS  Google Scholar 

  29. Z. Song, N. Mimura, S. Tsubota, T. Fujitani, S.T. Oyama, Catal. Lett. 121, 33 (2008)

    Article  CAS  Google Scholar 

  30. B.T. Pennington, M.C. Fullington, U.S. Patent No. 4,943,643 (1990)

  31. B.T. Pennington, U.S. Patent No. 4,883,889 (1989)

  32. B.T. Pennington, European Patent No. EP 0268870 (1988)

  33. T.A. Nijhuis, S. Musch, M. Makkee, J.A. Moulijn, Appl. Catal. A 196, 217 (2000)

    Article  CAS  Google Scholar 

  34. M. Haruta, M. Daté, Appl. Catal. A 222, 427 (2001)

    Article  CAS  Google Scholar 

  35. M. Haruta, Cattech 6, 102 (2002)

    Article  CAS  Google Scholar 

  36. M. Haruta, Chem. Rec. 3, 75 (2003)

    Article  CAS  Google Scholar 

  37. B.K. Min, C.M. Friend, Chem. Rev. 107, 2709 (2007)

    Article  CAS  Google Scholar 

  38. C. Qi, Gold Bull. 41, 224 (2008)

    Article  Google Scholar 

  39. J. Huang, T. Akita, J. Faye, T. Fujitani, T. Takei, M. Haruta, Angew. Chem. Int. Ed. 48, 7862 (2009)

    Article  CAS  Google Scholar 

  40. M. Haruta, Nature 437, 1098 (2005)

    Article  CAS  Google Scholar 

  41. A.L. Oliveira, A. Wolf, F. Schüth, Catal. Lett. 73, 157 (2001)

    Article  Google Scholar 

  42. X. Guo, R. Wang, X. Wang, J. Hao, Catal. Today 93–95, 211 (2004)

    Article  Google Scholar 

  43. R. Wang, X. Guo, X. Wang, J. Hao, G. Li, J. Xiu, Appl. Catal. A 261, 7 (2004)

    Article  CAS  Google Scholar 

  44. C. Wang, X. Guo, X. Wang, R. Wang, J. Hao, Catal. Lett. 96, 79 (2004)

    Article  CAS  Google Scholar 

  45. R. Wang, X. Guo, X. Wang, J. Hao, Catal. Today 93–95, 217 (2004)

    Article  Google Scholar 

  46. E.E. Stangland, B. Taylor, R.P. Andres, W.N. Delgass, J. Phys. Chem. B 109, 2321 (2005)

    Article  CAS  Google Scholar 

  47. E.E. Stangland, K.B. Stavens, R.P. Andres, W.N. Delgass, J. Catal. 191, 332 (2000)

    Article  CAS  Google Scholar 

  48. T.A. Nijhuis, B.M. Weckhuysen, Chem. Commun. 6002 (2005)

  49. T.A. Nijhuis, B.M. Weckhuysen, Catal. Today 117, 84 (2006)

    Article  CAS  Google Scholar 

  50. T.A. Hijhuis, T.Q. Gardner, B.M. Weckhuysen, J. Catal. 236, 153 (2005)

    Article  Google Scholar 

  51. T.A. Nijhuis, T. Visser, B.M. Weckhuysen, Angew. Chem. Int. Ed. 44, 1115 (2005)

    Article  CAS  Google Scholar 

  52. T.A. Nijhuis, T. Visser, B.M. Weckhuysen, J. Phys. Chem. B 109, 19309 (2005)

    Article  CAS  Google Scholar 

  53. B. Chowdhury, J.J. Bravo-Suárez, M. Daté, S. Tsubota, M. Haruta, Angew. Chem. Int. Ed. 45, 412 (2006)

    Article  CAS  Google Scholar 

  54. J.J. Bravo-Suárez, K.K. Bando, J. Lu, M. Haruta, T. Fujitani, S.T. Oyama, J. Phys. Chem. C 112, 1115 (2008)

    Article  Google Scholar 

  55. A.K. Sinha, S. Seelan, S. Tsubota, M. Haruta, Angew. Chem. Int. Ed. 43, 1546 (2004)

    Article  CAS  Google Scholar 

  56. A.K. Sinha, S. Seelan, M. Okumura, T. Akita, S. Tsubota, M. Haruta, J. Phys. Chem. B 109, 3956 (2005)

    Article  CAS  Google Scholar 

  57. A.K. Sinha, S. Seelan, S. Tsubota, M. Haruta, Top. Catal. 29(3–4), 95 (2004)

    Article  CAS  Google Scholar 

  58. C. Qi, T. Akita, M. Okumura, K. Kuraoka, M. Haruta, Appl. Catal. A 253, 75 (2003)

    Article  CAS  Google Scholar 

  59. C. Qi, T. Akita, M. Okumura, M. Haruta, Appl. Catal. A 218, 81 (2001)

    Article  CAS  Google Scholar 

  60. B. Chowdhury, J.J. Bravo-Suárez, N. Mimura, J. Lu, K.K. Bando, S. Tsubota, M. Haruta, J. Phys. Chem. B 110, 22995 (2006)

    Article  CAS  Google Scholar 

  61. M.P. Kapoor, A.K. Sinha, S. Seelan, S. Inagaki, S. Tsubota, H. Yoshida, M. Haruta, Chem. Commun. 2902 (2002)

  62. J.J. Bravo-Suárez, J. Lu, C.G. Dallos, T. Fujitani, S.T. Oyama, J. Phys. Chem. C 111, 17427 (2007)

    Article  Google Scholar 

  63. J. Lu, X. Zhang, J.J. Bravo-Suárez, S. Tsubota, J. Gaudet, S.T. Oyama, Catal. Today 123, 189 (2007)

    Article  CAS  Google Scholar 

  64. J. Lu, Z. Zhang, J.J. Bravo-Suárez, K.K. Bando, T. Fujitani, S.T. Oyama, J. Catal. 250, 350 (2007)

    Article  CAS  Google Scholar 

  65. E. Sacaliuc-Parvulescu, H. Friedrich, R. Palkovits, B.M. Weckhuysen, T.A. Nijhuis, J. Catal. 259, 43 (2008)

    Article  CAS  Google Scholar 

  66. E. Sacaliuc, A.M. Beale, B.M. Weckhuysen, T.A. Nijhuis, J. Catal. 248, 235 (2007)

    Article  CAS  Google Scholar 

  67. H. Yang, D. Tang, X. Lu, Y. Yuan, J. Phys. Chem. C 113, 8186 (2009)

    Article  CAS  Google Scholar 

  68. L. Cumaranatunge, W.N. Delgass, J. Catal. 232, 38 (2005)

    Article  CAS  Google Scholar 

  69. J. Huang, T. Takei, T. Akita, H. Ohashi, M. Haruta, Appl. Catal. B 95, 430 (2010)

    Article  CAS  Google Scholar 

  70. B.S. Uphade, S. Tsubota, T. Hayashi, M. Haruta, Chem. Lett. 27, 1277 (1998)

    Article  Google Scholar 

  71. J. Lu, X. Zhang, J.J. Bravo-Suárez, T. Fujitani, S.T. Oyama, Catal. Today 147, 186 (2009)

    Article  CAS  Google Scholar 

  72. S.T. Oyama, X. Zhang, J. Lu, Y. Gu, T. Fujitani, J. Catal. 257, 1 (2008)

    Article  CAS  Google Scholar 

  73. T.A. Nijhuis, B.J. Huizinga, M. Makkee, J.A. Moulijn, Ind. Eng. Chem. Res. 38, 884 (1999)

    Article  CAS  Google Scholar 

  74. N. Yap, R.P. Andres, W.N. Delgass, J. Catal. 226, 156 (2004)

    Article  CAS  Google Scholar 

  75. B. Taylor, J. Lauterbach, W.N. Delgass, Appl. Catal. A 291, 188 (2005)

    Article  CAS  Google Scholar 

  76. B. Taylor, J. Lauterbach, G.E. Blau, W.N. Delgass, J. Catal. 242, 142 (2006)

    Article  CAS  Google Scholar 

  77. B. Taylor, J. Lauterbach, W.N. Delgass, Catal. Today 123, 50 (2007)

    Article  CAS  Google Scholar 

  78. C. Qi, J. Huang, S. Bao, H. Su, T. Akita, M. Haruta, J. Catal. 281, 12 (2011)

    Article  CAS  Google Scholar 

  79. M. Haruta, B.S. Uphade, S. Tsubota, A. Miyamoto, Res. Chem. Intermed. 24, 329 (1998)

    Article  CAS  Google Scholar 

  80. F. Wang, C. Qi, J. Ma, Catal. Commun. 8, 1947 (2007)

    Article  CAS  Google Scholar 

  81. A.M. Joshi, W.N. Delgass, K.T. Thomson, J. Phys. Chem. C 111, 7841 (2007)

    Article  CAS  Google Scholar 

  82. A.M. Joshi, W.N. Delgass, K.T. Thomson, J. Phys. Chem. B 110, 2572 (2006)

    Article  CAS  Google Scholar 

  83. J. Huang, E. Lima, T. Akita, A. Guzmán, C. Qi, T. Takei, M. Haruta, J. Catal. 278, 8 (2011)

    Article  CAS  Google Scholar 

  84. R.A. Van Santen, H.P.C.E. Kuipers, Adv. Catal. 35, 265 (1987)

    Article  Google Scholar 

  85. M. Ojeda, E. Iglesia, Chem. Commun. 352 (2009)

  86. S. Lee, L.M. Molina, M.J. López, J.A. Alonso, B. Hammer, B. Lee, S. Seifert, R.E. Winans, J.W. Elam, M.J. Pellin, S. Vajda, Angew. Chem. Int. Ed. 48, 1467 (2009)

    Article  CAS  Google Scholar 

  87. R.L. Cropley, F.J. Williams, A.J. Urquhart, O.P.H. Vaughan, M.S. Tikhov, R.M. Lambert, J. Am. Chem. Soc. 127, 6069 (2005)

    Article  CAS  Google Scholar 

  88. D. Torres, N. Lopez, F. Illas, R.M. Lambert, Angew. Chem. Int. Ed. 46, 2055 (2007)

    Article  CAS  Google Scholar 

  89. H. Chu, L. Yang, Q. Zhang, Y. Wang, J. Catal. 241, 225 (2005)

    Article  Google Scholar 

  90. Y. Wang, H. Chu, W. Zhu, Q. Zhang, Catal. Today 131, 496 (2008)

    Article  CAS  Google Scholar 

  91. J. Lu, M. Luo, H. Lei, X. Bao, C. Li, J. Catal. 211, 552 (2002)

    Article  CAS  Google Scholar 

  92. L. Yang, J. He, Q. Zhang, Y. Wang, J. Catal. 276, 76 (2010)

    Article  CAS  Google Scholar 

  93. A. Seubsai, M. Kahn, S. Senkan, ChemCatChem 3, 174 (2011)

    Article  CAS  Google Scholar 

  94. R.M. Lambert, F.J. Williams, R.L. Cropley, A. Palermo, J. Mol. Catal. A 228, 27 (2005)

    Article  CAS  Google Scholar 

  95. M. Luo, J. Lu, C. Li, Catal. Lett. 86(1–3), 43 (2003)

    Article  CAS  Google Scholar 

  96. G. Jin, G. Lu, Y. Guo, Y. Guo, J. Wang, W. Kong, X. Liu, J. Mol. Catal. A 232, 165 (2005)

    Article  CAS  Google Scholar 

  97. A. Palermo, A. Husain, M.S. Tikhov, R.M. Lambert, J. Catal. 207, 331 (2002)

    Article  CAS  Google Scholar 

  98. F.W. Zemichael, A. Palermo, M.S. Tikhov, R.L. Lambert, Catal. Lett. 80(3–4), 93 (2002)

    Article  CAS  Google Scholar 

  99. Y. Lei, F. Mehmood, S. Lee, J. Greeley, B. Lee, S. Seifert, R.E. Winans, J.W. Elam, R.J. Meyer, P.C. Redfern, D. Teschner, R. Schlögl, M.J. Pellin, L.A. Curtiss, S. Vajda, Science 328, 224 (2010)

    Article  CAS  Google Scholar 

  100. M.G. Clerici, G. Bellussi, U. Romano, J. Catal. 129, 159 (1991)

    Article  CAS  Google Scholar 

  101. J.J. Bravo-Suárez, K.K. Bando, T. Akita, T. Fujitani, T.J. Fuhrer, S.T. Oyama, Chem. Commun. 3272 (2008)

  102. J. Lu, J.J. Bravo-Suárez, A. Takahashi, M. Haruta, S.T. Oyama, J. Catal. 232, 85 (2005)

    Article  CAS  Google Scholar 

  103. C. Chang, Y. Wang, J. Li, Nano. Res. 4(1), 131 (2011)

  104. T.A. Nijhuis, J. Chen, S.M.A. Kriescher, J.C. Schouten, Ind. Eng. Chem. Res. 49, 10479 (2010)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-osawa, Hachioji, Tokyo, 192-0397, Japan

    Jiahui Huang & Masatake Haruta

  2. Japan Science and Technology Agency (JST), CREST, 4-1-8 Hon-cho, Kawaguchi, Saitama, 332-0012, Japan

    Jiahui Huang & Masatake Haruta

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  1. Jiahui Huang
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  2. Masatake Haruta
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Correspondence to Masatake Haruta.

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Huang, J., Haruta, M. Gas-phase propene epoxidation over coinage metal catalysts. Res Chem Intermed 38, 1–24 (2012). https://doi.org/10.1007/s11164-011-0424-6

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Keywords

  • Propene epoxidation
  • Propene oxide
  • O2 and H2 mixture
  • H2 efficiency
  • Molecular O2
  • Coinage metal catalysts
  • Copper
  • Silver
  • Gold