Skip to main content
SpringerLink
Log in

Catalytic chemistry of dimethyl ether (review)

  • Published:
Petroleum Chemistry Aims and scope Submit manuscript

Abstract

Heterogeneous catalytic reactions of dimethyl ether (DME) with various compounds (alkenes, aromatic compounds, CO, etc.) are surveyed. Analysis of published data allows the conclusion that the formation of products generally involves surface intermediates produced by the interaction of DME with Brønsted acid sites. There is no formation of water in this case, suggesting that DME can be preferred to methanol in some cases. Surface intermediates CH*3 which are bound to the oxygen atoms of the zeolite lattice (methoxides) and retain their reactivity in the case of temperature elevation to 473 K have been identified using IR, UV, and in situ high-resolution solid-state NMR spectroscopy. Based upon the data on the state of intermediates that are formed from DME on the surface of heterogeneous catalysts, a series of catalytic reactions involving DME, namely, methylation of alkenes and aromatic compounds, carbonylation, synthesis of ethanol, and partial oxidation resulting in a set of compounds have been considered. Some reactions, such as carbonylation of DME by synthesis gas, synthesis of ethanol, and synthesis of dimethoxymethane and polyoxymethylene dimethyl ether, are of industrial interest.

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. P. Haro, F. Trippe, R. Stahl, and E. Henrich, Appl. Energy 108, 54 (2013).

    Article  CAS  Google Scholar 

  2. R. Fornell, T. Berntsson, and A. Åsblad, Energy 50, 83 (2013).

    Article  CAS  Google Scholar 

  3. S. Bhattacharya K. B. Kabir, and K. Hein, Prog. Energy Combust. Sci. 39, 577 (2013).

    Article  Google Scholar 

  4. S. N. Khadzhiev, M. V. Magomedova, and E. G. Peresypkina, Pet. Chem. 55, 7 (2015).

    Google Scholar 

  5. P. Tian, Y. Wei, M. Ye, and Z. Li, ACS Catal. 5, 1922 (2015).

    Article  CAS  Google Scholar 

  6. K. Hemelsoet, J. van der Mynsbrugge, K. de Wispelaere, et al., ChemPhysChem 14, 1526 (2013).

    Article  CAS  Google Scholar 

  7. S. Ilias and A. Bhan, ACS Catal. 3, 18 (2013).

    Article  CAS  Google Scholar 

  8. T. Mokrani and M. Scurrell, Catal. Rev. 51, 1 (2009).

    Article  CAS  Google Scholar 

  9. E. Ramos, L. Davin, I. Angurell, et al., Chem-CatChem 7, 2179 (2015).

    CAS  Google Scholar 

  10. M. Yang, Y. Men, S. Li, and G. Chen, Appl. Catal., A 433/434, 26 (2012).

    Article  CAS  Google Scholar 

  11. J. Lu, S. Zhou, K. Ma, M. Meng, Y. Tian, Chin. J. Catal. 36, 1295 (2015).

    Article  CAS  Google Scholar 

  12. S. N. Khadzhiev, M. V. Magomedova, and E. G. Peresypkina, Pet. Chem. 56, 181 (2016).

    Article  CAS  Google Scholar 

  13. T. R. Forester and R. F. Howe, J. Am. Chem. Soc. 109, 5076 (1987).

    Article  CAS  Google Scholar 

  14. S. Svelle, M. Visur, U. Olsbye, et al., Top. Catal. 54, 897 (2011).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. W. Wang, Y. Jiang, and M. Hunger, Catal. Today 113, 102 (2006).

    Article  CAS  Google Scholar 

  17. W. Wang, M. Seiler, and M. Hunger, J. Phys. Chem. B 105, 12553 (2001). 3 * CH

    Article  CAS  Google Scholar 

  18. W. Wang, A. Buchholz, A. Arnold, et al., Chem. Phys. Lett. 370, 88 (2003).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  20. V. Bosacek, J. Phys. Chem. 97, 10732 (1993).

    Article  CAS  Google Scholar 

  21. V. Bosacek, Z. Phys. Chem. 189, 241 (1995).

    Article  CAS  Google Scholar 

  22. V. Bosacek, H. Ernst, D. Freude, and T. Mildner, Appl. Spectrosc. 18, 196 (1997).

    CAS  Google Scholar 

  23. Y. Jiang, W. Wang, V. R. R. Marthala, et al., J. Catal. 238, 21 (2006).

    Article  CAS  Google Scholar 

  24. W. Wang and M. Hunger, Acc. Chem. Res. 41, 895 (2008).

    Article  CAS  Google Scholar 

  25. P. Cheung, A. Bhan, G. J. Sunley, et al., J. Catal. 245, 110 (2007).

    Article  CAS  Google Scholar 

  26. P. Cheung, A. Bhan, G. J. Sunley, and E. Iglesia, Angew. Chem., Int. Ed. Engl. 45, 1617 (2006).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. A. G. Stepanov, Usp. Khim. 68, 619 (1999).

    Article  Google Scholar 

  29. Proceedings of the 12th International Zeolite Conference, Ed. by M. M. J. Treacy, B. K. Marcus, M. E. Bisher, and J. B. Higgins (Materials Research Society, Warrendale, PA, 1999).

  30. M. W. Anderson and J. Klinowski, Nature 339, 200 (1989).

    Article  CAS  Google Scholar 

  31. M. W. Anderson and J. Klinowski, J. Am. Chem. Soc. 112, 10 (1990).

    Article  CAS  Google Scholar 

  32. P. O. Ronning, U. Olsbye, and S. Kolboe, J. Catal. 234, 385 (2005).

    Article  CAS  Google Scholar 

  33. S. Svelle, P. O. Ronning, and S. Kolboe, J. Catal. 224, 115 (2004).

    Article  CAS  Google Scholar 

  34. I. M. Hill, Y. S. Ng, and A. Bhan, ACS Catal. 2, 1742 (2012).

    Article  CAS  Google Scholar 

  35. I. M. Hill, S. A. Hashimi, and A. Bhan, J. Catal. 291, 155 (2012).

    Article  CAS  Google Scholar 

  36. V. van Speybroeck, J. van der Mynsbrugge, M. Vandichel, et al., J. Am. Chem. Soc. 133, 888 (2011).

    Article  CAS  Google Scholar 

  37. S. Svelle, C. Tuma, X. Rozanska, et al., J. Am. Chem. Soc. 131, 816 (2009).

    Article  CAS  Google Scholar 

  38. R. Y. Brogaard, R. Henry, Y. Schuurman, et al., J. Catal. 314, 159 (2014).

    Article  CAS  Google Scholar 

  39. A. M. Vos, K. H. L. Nulens, F. De Proft, et al., J. Phys. Chem. B 106, 2026 (2002).

    Article  CAS  Google Scholar 

  40. T. Maihom, B. Boefka, J. Sirijaraensre, et al., J. Phys. Chem. C 113, 6654 (2009).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  43. M. N. Mazar, S. Al-Hashimi, A. Bhan, and M. Cococcioni, J. Phys. Chem. C 116, 19385 (2012).

    Article  CAS  Google Scholar 

  44. I. Hill, PhD Dissertation (University of Minessota, Minessota, 2013).

    Google Scholar 

  45. A. Széchenyi and F. Solymosi, Catal. Lett. 127, 13 (2009).

    Article  CAS  Google Scholar 

  46. Y. W. Fang, J. Tang, X. C. Huang, et al., Chin. J. Catal 31, 264 (2010).

    Article  CAS  Google Scholar 

  47. H. Liu, H. Wei, W. Xin, et al., J. Energy Chem. 23, 617 (2014).

    Article  Google Scholar 

  48. B. Li, J. Xu, B. Han, et al., J. Phys. Chem. C 117, 5840 (2013).

    Article  CAS  Google Scholar 

  49. X. F. Wu and H. Neumann, ChemCatChem 4, 447 (2012).

    Article  CAS  Google Scholar 

  50. F. Li, B. Chen, Z. Huang, et al., Green Chem. 15, 1600 (2013).

    Article  CAS  Google Scholar 

  51. K. Fujimoto, T. Shikada, K. Omata, and H. Tominaga, Chem. Lett. 13, 2047 (1984).

    Article  Google Scholar 

  52. B. Ellis, M. J. Howard, R. W. Joyner, et al., Stud. Surf. Sci. Catal. 101, 771 (1996).

    Article  CAS  Google Scholar 

  53. W. J. Smith, US Patent No. 5420345 (1995).

    Google Scholar 

  54. A. G. Stepanov, M. V. Luzgin, V. N. Romannikov, et al., J. Catal. 164, 411 (1996).

    Article  CAS  Google Scholar 

  55. Q. Xu, S. Inoue, N. Tsumori, et al., J. Mol. Catal. A 170, 147 (2001).

    Article  CAS  Google Scholar 

  56. S. Kuba, P. Lukinskas, R. K. Grasselli, et al., J. Catal. 216, 353 (2003).

    Article  CAS  Google Scholar 

  57. A. Martinez, G. Prieto, M. A. Arribas, and P. Concepcion, Appl. Catal., A 309, 224 (2006).

    Article  CAS  Google Scholar 

  58. A. Bhan, A. D. Allian, G. J. Sunley, et al., J. Am. Chem. Soc. 129, 4919 (2007).

    Article  CAS  Google Scholar 

  59. M. Boronat, C. Martinez-Sanchez, D. Law, and A. Corma, J. Am. Chem. Soc. 130, 16316 (2008).

    Article  CAS  Google Scholar 

  60. S. Y. Park, C. Shin, and J. Bae, Catal. Commun. 75, 28 (2016).

    Article  CAS  Google Scholar 

  61. X. Li, X. San, Y. Zhang, et al., ChemSusChem 3, 1192 (2010).

    Article  CAS  Google Scholar 

  62. J. Liu, H. Xue, X. Huang, et al., Catal. Lett. 139, 33 (2010).

    Article  CAS  Google Scholar 

  63. P. M. Arvela, I. Kubickova, M. Snare, et al., Energy Fuels 21, 30 (2007).

    Article  CAS  Google Scholar 

  64. K. Faungnawakij, Y. Tanaka, N. Shimoda, et al., Appl. Catal., A 304, 40 (2006).

    Article  CAS  Google Scholar 

  65. T. A. Semelsberger, K. C. Ott, R. L. Borup, and H. L. Greene, Appl. Catal. B 61, 281 (2005).

    Article  CAS  Google Scholar 

  66. R. W. Wegman, J. Chem. Soc., Chem. Commun., 947 (1994).

  67. A. Sardesai, S. Lee, and T. Tartamella, Energy Sources 24, 301 (2002).

    Article  CAS  Google Scholar 

  68. G. G. Volkova, L. M. Plyasova, A. N. Salanov, et al., Catal. Lett. 80, 175 (2002).

    Article  CAS  Google Scholar 

  69. M. S. Kazantsev, M. V. Luzgin, G. G. Volkova, and A. G. Stepanov, J. Catal. 291, 9 (2012).

    Article  CAS  Google Scholar 

  70. M. V. Luzgin, M. S. Kazantsev, G. G. Volkova, et al., J. Catal. 277, 72 (2011).

    Article  CAS  Google Scholar 

  71. T. Ueda, T. Tatsumi, T. Eguchi, and N. Nakamura, J. Phys. Chem. B 105, 5391 (2001).

    Article  CAS  Google Scholar 

  72. J. Yang, M. J. Janik, D. Ma, et al., J. Am. Chem. Soc. 127, 18274 (2005).

    Article  CAS  Google Scholar 

  73. H. L. Zhang, A. M. Zheng, H. G. Yu, et al., J. Phys. Chem.C 112, 15765 (2008).

    Article  CAS  Google Scholar 

  74. M. V. Luzgin, M. S. Kazantsev, W. Wang, and A. G. Stepanov, J. Phys. Chem. C 113, 19639 (2009).

    Article  CAS  Google Scholar 

  75. M. V. Luzgin, V. A. Rogov, V. P. Shmachkova, et al., J. Phys. Chem. C 111, 10624 (2007).

    Article  CAS  Google Scholar 

  76. X. L. Pan and X. H. Bao, Chem. Commun. 47, 6271 (2008).

    Article  CAS  Google Scholar 

  77. J. J. Spivey and A. Egbebi, Chem. Soc. Rev. 36, 1514 (2007).

    Article  CAS  Google Scholar 

  78. V. Subramani and S. K. Gangwal, Energy Fuel 22, 814 (2008).

    Article  CAS  Google Scholar 

  79. M. Pijolat and V. Perrichon, Appl. Catal. 13, 321 (1985).

    Article  CAS  Google Scholar 

  80. K. Okabe, H. Yamada, T. Hanaoka, et al., Chem. Lett. 30, 904 (2001).

    Article  Google Scholar 

  81. X. Sun and R. G. Robert, Appl. Catal., A 247, 133 (2003).

    Article  CAS  Google Scholar 

  82. Y. Liu, K. Murata, M. Inaba, et al., J. Jpn. Pet. Inst. 53, 15318 (2010).

    Article  Google Scholar 

  83. Y. Liu, K. Murata, M. Inaba, et al., Fuel 104, 62 (2013).

    Article  CAS  Google Scholar 

  84. J. Bao, Z. Sun, Y. Fu, et al., Top. Catal. 52, 789 (2009).

    Article  CAS  Google Scholar 

  85. M. Xiang, D. Li, H. Qi, et al., Fuel 86, 1298 (2007).

    Article  CAS  Google Scholar 

  86. Y. Liu, K. Murata, M. Inaba, et al., Catal. Today 164, 308 (2011).

    Article  CAS  Google Scholar 

  87. J. Wang, Q. Zhang, and Y. Wang, Catal. Today 171, 257 (2011).

    Article  CAS  Google Scholar 

  88. X. San, Y. Zhang, W. Shen, and N. Tsubaki, Energy Fuel 23, 2843 (2009).

    Article  CAS  Google Scholar 

  89. Y. Zhang, X. San, N. Tsubaki, et al., Ind. Eng. Chem. Res. 49, 5485 (2010).

    Article  CAS  Google Scholar 

  90. X. Li, X. San, Y. Zhang, et al., ChemSusChem 3, 1192 (2010).

    Article  CAS  Google Scholar 

  91. G. Yang, X. San, N. Jiang, et al., Catal. Today 164, 425 (2011).

    Article  CAS  Google Scholar 

  92. X. San, G. Yang, Y. Zhang, et al., J. Jpn. Pet. Inst. 52, 357 (2009).

    Article  CAS  Google Scholar 

  93. N. Tsubaki, M. Ito, and K. Fujimoto, J. Catal. 197, 224 (2001).

    Article  CAS  Google Scholar 

  94. Y. Zhang, R. Q. Yang, and N. Tsubaki, Catal. Today 132, 93 (2008).

    Article  CAS  Google Scholar 

  95. D. Gao, Y. Feng, H. Yin, et al., Chem. Eng. J. 233, 349 (2013).

    Article  CAS  Google Scholar 

  96. D. Wang, G. Yang, Q. Ma, et al., Fuel 109, 54 (2013).

    Article  CAS  Google Scholar 

  97. T.-S. Zhao, T. Takemoto, and N. Tsubaki, Catal. Commun. 7, 647 (2006).

    Article  CAS  Google Scholar 

  98. P. Lu, G. Yang, Y. Tanaka, and N. Tsubaki, Catal. Today 232, 22 (2014).

    Article  CAS  Google Scholar 

  99. L. Lefferts, J. G. van Ommen, and J. R. H. Ross, Appl. Catal. 23, 385 (1986).

    Article  CAS  Google Scholar 

  100. J. M. Tatibouet, Appl. Catal., A 148, 213 (1997).

    Article  Google Scholar 

  101. H. C. Liu, P. Cheung, and E. Iglesia, PhysChem-ChemPhys 5, 3795 (2003).

    CAS  Google Scholar 

  102. H. C. Liu, P. Cheung, and E. Iglesia, J. Catal. 217, 222 (2003).

    CAS  Google Scholar 

  103. H. C. Liu, P. Cheung, and E. Iglesia, J. Phys. Chem. B 107, 4118 (2003).

    Article  CAS  Google Scholar 

  104. H. C. Liu and E. Iglesia, J. Catal. 208, 1 (2002).

    Article  CAS  Google Scholar 

  105. P. Cheung, H. Liu, and E. Iglesia, J. Phys. Chem. B 108, 18650 (2004).

    Article  CAS  Google Scholar 

  106. X. Huang, Y. Li, Y. Xu, and W. Shen, Catal. Lett. 97, 185 (2004).

    Article  CAS  Google Scholar 

  107. S. Wang, T. Ishihara, and Y. Takita, Appl. Catal., A 228, 167 (2002).

    Article  CAS  Google Scholar 

  108. G. Liu, Q. Zhang, Y. Han, et al., J. Fuel Chem. Technol. 41, 223 (2013).

    Article  CAS  Google Scholar 

  109. N. V. Pavlenko, Yu. N. Kochkin, N. V. Vlasenko, et al., Teor. Eksp. Khim. 36, 111 (2000).

    Google Scholar 

  110. N. V. Vlasenko and Yu. N. Kochkin, Russ. J. Appl. Chem. 76, 1615 (2003).

    Article  CAS  Google Scholar 

  111. Y. Z. Yuan, H. C. Liu, H. Imoto, et al., J. Catal. 195, 51 (2000).

    Article  CAS  Google Scholar 

  112. Y. Yuan and Y. Iwasawa, J. Phys. Chem. B 106, 4441 (2002).

    Article  CAS  Google Scholar 

  113. H. C. Liu and E. Iglesia, J. Phys. Chem. B 107, 10840 (2003).

    Article  CAS  Google Scholar 

  114. Q. Zhang, Y. Tan, C. Yang, and Y. Han, J. Mol. Catal. A: Chem. 263, 149 (2007).

    Article  CAS  Google Scholar 

  115. J. Chen, Z. Tang, C. Xia, et al., CN Patent No. 101182367 (2008); US Patent No. 7560599 (2009).

    Google Scholar 

  116. H. Schelling, E. Stroefer, R. Pinkos, et al., CN Patent No. 101048357 (2007).

    Google Scholar 

  117. G. P. Hagen and M. J. Spangler, US Patent No. 5959156 (1999).

    Google Scholar 

  118. G. P. Hagen and M. J. Spangler, US Patent No. 6392102 (2002).

    Google Scholar 

  119. E. Stroefer, H. Schelling, and H. Hasse, DE Patent No. 102005027690 (2006).

    Google Scholar 

  120. H. Li, H. Song, L. Chen, and C. Xia, Appl. Catal., B 165, 466 (2015).

    Article  CAS  Google Scholar 

  121. H. Zhou, W. Zhu, L. Shi, et al., J. Mol. Catal. A: Chem. 417, 1 (2016).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russia

    E. A. Volnina, M. A. Kipnis & S. N. Khadzhiev

Authors
  1. E. A. Volnina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. Kipnis
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. N. Khadzhiev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. A. Kipnis.

Additional information

Original Russian Text © E.A. Volnina, M.A. Kipnis, S.N. Khadzhiev, 2017, published in Neftekhimiya, 2017, Vol. 57, No. 3, pp. 243–262.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Volnina, E.A., Kipnis, M.A. & Khadzhiev, S.N. Catalytic chemistry of dimethyl ether (review). Pet. Chem. 57, 353–373 (2017). https://doi.org/10.1134/S0965544117050139

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0965544117050139

Keywords

Search

Navigation