Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Dimethyl Glutarate from Cyclobutanone and Dimethyl Carbonate over Solid Base Catalysts

  • Zhi, Chen (Center of Analysis, Guangdong Medical College) ;
  • Dudu, Wu (School of Pharmacy, Guangdong Medical College)
  • Received : 2011.11.18
  • Accepted : 2012.02.28
  • Published : 2012.06.20
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Abstract

A facile route for the synthesis of dimethyl glutarate (DMG) from cyclobutanone and dimethyl carbonate (DMC) in the presence of solid base catalysts has been developed. It was found that the intermediate carbomethoxycyclobutanone (CMCB) was produced from cyclobutanone with DMC in the first step, and then CMCB was further converted to DMG by reacting with a methoxide group. The role of the basic catalysts can be mainly ascribed to the activation of cyclobutanone $via$ the abstraction of a proton in the ${\alpha}$-position by base sites, and solid bases with moderate strength, such as MgO, favor the formation of DMG.

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References

  1. Li, M.; Huang, J. Y.; Wang, X. L.; Yu, C. J.; Cheng, G. J. Petrochemical Technology & Application 2007, 4, 310-312.
  2. Huang, M. Q.; Sun, B. G.; Tian, H. Y.; Peng, Q. J. China Chemicals 2006, 1, 30-32.
  3. Sun, X. B.; Luan, X. H.; Mao, Z. B.; Liu, H.; Liu, G. J. Chemical World 2009, 5, 303-305, 311.
  4. Pacheco, M. A.; Marshall, C. L. Energy Fuels 1997, 11, 2-29. https://doi.org/10.1021/ef9600974
  5. Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Lemaire, M. Tetrahedron Lett. 2000, 41, 6347-6350. https://doi.org/10.1016/S0040-4039(00)01051-0
  6. Tundo, P.; Selva, M. Acc. Chem. Res. 2002, 35, 706-716. https://doi.org/10.1021/ar010076f
  7. Jyothi, T. M.; Raja. T.; Talawar, M. B.; Rao, B. S. Appl. Catal. A 2001, 211, 41-46. https://doi.org/10.1016/S0926-860X(00)00839-5
  8. Ono, Y.; Baba, T. Catal. Today 1997, 38, 321-337. https://doi.org/10.1016/S0920-5861(97)81502-5
  9. Tundo, P.; Moraglio. G.; Trotta, F. Ind. Eng. Chem. Res. 1989, 28, 881-890. https://doi.org/10.1021/ie00091a001
  10. Shivarkar, A. B.; Gupte, S. P.; Chaudhari, R. V. J. Mol. Catal. A 2005, 226, 49-56. https://doi.org/10.1016/j.molcata.2004.09.025
  11. Shieh, W. C.; Dell, S.; Bach, A.; Blacklock, T. J. J. Org. Chem. 2003, 68, 1954-1957. https://doi.org/10.1021/jo0266644
  12. Mei, F.; Pei, Z.; Li, G. X. Org. Process Res. Dev. 2004, 8, 372-375. https://doi.org/10.1021/op0302098
  13. Selva, M.; Marques, C. A.; Tundo, P. Gazz. Chim. It. 1993, 123, 515-518.
  14. Tundo, P.; Memoli, S.; Selva, M. WO Patent. 0 214 257, 2002.
  15. Fisher, R. US Patent. 5 453 535, 1995.
  16. Koehler, G.; Metz, J. US Patent. 5 786 502, 1998.
  17. Ono, Y.; Baba, T. Catal. Today 1997, 38, 321-337. https://doi.org/10.1016/S0920-5861(97)81502-5
  18. Hattori, H. Chem. Rev. 1995, 95, 537-558. https://doi.org/10.1021/cr00035a005
  19. Li, F.; Miao. J.; Wang, Y. J.; Zhao, X. Q. Ind. Eng. Chem. Res. 2006, 45, 4892-4897. https://doi.org/10.1021/ie060142n
  20. Cao, M.; Meng, Y. Z.; Lu, Y. X. Catalysis Communication 2005, 6, 802-807. https://doi.org/10.1016/j.catcom.2005.07.020
  21. Xiao, F. K.; Zhang, D. S.; Dong, Q. N.; Wei, W.; Sun, Y. H. Reaction Kinetics and Catalysis Letters 2006, 89, 131-138. https://doi.org/10.1007/s11144-006-0095-2
  22. Wu, D. D.; Fu, X.; Li, J. P.; Zhao, N.; Wei, W.; Sun, Y. H. Catalysis Communication 2008, 9, 680-684. https://doi.org/10.1016/j.catcom.2007.08.004
  23. Wu, D. D.; Chen, Z. Chemical. Papers 2010, 64, 758-766. https://doi.org/10.2478/s11696-010-0068-9
  24. Zhang, W. Y.; Wang, H.; Wei, W.; Sun, Y. H. J. Mol. Catal. A 2005, 231, 83-88. https://doi.org/10.1016/j.molcata.2004.12.025