Synthesis of cyclic carbonates and dimethyl carbonate using CO₂ as a building block catalyzed by MOF-5/KI and MOF-5/KI/K₂CO₃

Abstract

The synthesis of cyclic carbonates or dimethyl carbonate (DMC) using CO₂ as a building block is a very interesting topic. In this work, we found that the metal-organic framework-5 (MOF-5)/KI was an active and a selective catalytic system for the synthesis of cyclic carbonates from CO₂ and epoxides, and MOF-5/KI/K₂CO₃ was efficient for the preparation of DMC from CO₂, propylene, and methanol by a sequential route. The impacts of temperature, pressure, and reaction time length on the reactions were investigated, and the mechanism of the reactions is proposed on the basis of the experimental results.

Keywords

carbon dioxide / cyclic carbonates / dimethyl carbonate (DMC) / metal-organic framework-5 (MOF-5) / sequential route / propylene oxide

References

[1] Tundo, P., Pure Appl. Chem. 2001, 73, 1117–1124

[2] Tundo, P.; Selva, M., Acc. Chem. Res. 2002, 35, 706–716

[3] Pacheco, M. A.; Marshall, C. L., Energy Fuels 1997, 11, 2–29

[4] Romano, U.; Tesei, R.; Mauri, M. M.; Rebora, P., Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 396–403

[5] King, S. T., Catal. Today 1997, 33, 173–182

[6] Sakakura, T.; Choi, J. C.; Yasuda, H., Chem. Rev. 2007, 107, 2365–2387

[7] Song, C. S., Catal. Today 2006, 115, 2–32

[8] Gibson, D. H., Chem. Rev. 1996, 96, 2063–2096

[9] Fang, S.; Fujimoto, K., Appl. Catal. A Gen. 1996, 142, L1–L3

[10] Tomishige, K.; Sakaihori, S.; Ikeda, Y.; Fujimoto, K., Catal. Lett. 1999, 58, 225–229

[11] Choi, J. C.; He, L. N.; Yasuda, H.; Sakakura, T., Green Chem. 2002, 4, 230–234

[12] Sakakura, T.; Saito, Y.; Okano, M.; Choi, J. C.; Sako, T., J. Org. Chem. 1998, 63, 7095–7096

[13] Sakakura, T.; Choi, J. C.; Saito, Y.; Masuda, T.; Sako, T.; Oriyama, T., J. Org. Chem. 1999, 64, 4506–4508

[14] Fujita, S.; Bhanage, B. M.; Ikushima, Y.; Arai, M., Green Chem. 2001, 3, 87–91

[15] Choi, J. C.; Sakakura, T.; Sako, T., J. Am. Chem. Soc. 1999, 121, 3793–3794

[16] Ikeda, Y.; Sakaihori, T.; Tomishige, K.; Fujimoto, K., Catal. Lett. 2000, 66, 59–62

[17] Kishimoto, Y.; Ogawa, I., Ind. Eng. Chem. Res. 2004, 43, 8155–8162

[18] Bhanage, B. M.; Fujita, S. I.; Ikushima, Y.; Torii, K.; Arai, M., Green Chem. 2003, 5, 71–75

[19] Cui, H. Y.; Wang, T.; Wang, F. J.; Gu, C. R.; Wang, P. L.; Dai, Y. Y., Ind. Eng. Chem. Res. 2003, 42, 3865–3870

[20] Chang, Y. H.; Jiang, T.; Han, B. X.; Liu, Z. M.; Wu, W. Z.; Gao, L.; Li, J. C.; Gao, H. X.; Zhao, G. Y.; Huang, J., Appl. Catal. A Gen. 2004, 263, 179–186

[21] Bhanage, B. M.; Fujita, S. I.; Ikushima, Y.; Arai, M., Appl. Catal. A Gen. 2001, 219, 259–266

[22] Li, Y.; Zhao, X. Q.; Wang, Y. J., Appl. Catal. A Gen. 2005, 279, 205–208

[23] Jagtap, S. R.; Bhor, M. D.; Bhanage, B. M., Catal. Commun. 2008, 9, 1928–1931

[24] Tian, J. S.; Miao, C. X.; Wang, J. Q.; Cai, F.; Du, Y.; Zhao, Y.; He, L. N., Green Chem. 2007, 9, 566–571

[25] Moulton, B.; Zaworotko, M. J., Chem. Rev. 2001, 101, 1629–1658

[26] Kitagawa, S.; Kitaura, R.; Noro, S., Angew. Chem. Int. Ed. 2004, 43, 2334–2375

[27] Wang, Z.; Cohen, S. M., J. Am. Chem. Soc. 2007, 129, 12368–12369

[28] Song, Y. F.; Cronin, L., Angew. Chem. Int. Ed. 2008, 47, 4635–4637

[29] Natarajan, S.; Mandal, S., Angew. Chem. Int. Ed. 2008, 47, 4798–4828

[30] Li, Y.; Yang, R. T., Langmuir 2007, 23, 12937–12944

[31] Morris, R. E.; Wheatley, P. S., Angew. Chem. Int. Ed. 2008, 47, 4966–4981

[32] Zlotea, C.; Campesi, R.; Cuevas, F.; Leroy, E.; Dibandjo, P.; Volkringer, C.; Loiseau, T.; Férey, G.; Latroche, M., J. Am. Chem. Soc. 2010, 132, 2991–2997

[33] Chen, B.; Liang, C.; Yang, J.; Contreras, D. S.; Clancy, Y. L.; Lobkovsky, E. B.; Yaghi, O. M.; Dai, S., Angew. Chem. Int. Ed. 2006, 45, 1390–1393

[34] Procopio, E. Q.; Linares, F.; Montoro, C.; Colombo, V.; Maspero, A.; Barea, E.; Navarro, J. A. R., Angew. Chem. Int. Ed. 2010, 49, 1–5

[35] Lor, B. G.; Puebla, G.; Iglesias, M.; Monge, M. A.; Valero, C. R.; Snejko, N., Chem. Mater. 2005, 17, 2568–2573

[36] Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K., Nature 2000, 404, 982–986

[37] Pan, L.; Liu, H.; Lei, X.; Huang, X.; Olson, D. H.; Turro, N. J.; Li, J., Angew. Chem. Int. Ed. 2003, 42, 542–546

[38] Alaerts, L.; Séguin, E.; Poelman, H.; Thibault-Starzyk, F.; Jacobs, P. A.; De Vos, D. E., Chemistry 2006, 12, 7353–7363

[39] Gándara, F.; Gomez-Lor, B.; Gutiérrez-Puebla, E.; Iglesias, M.; Monge, M. A.; Proserpio, D. M.; Snejko, N., Chem. Mater. 2008, 20, 72–76

[40] Wu, C. D.; Hu, A.; Zhang, L.; Lin, W., J. Am. Chem. Soc. 2005, 127, 8940–8941

[41] Xamena, F. X. L. i.; Casanova, O.; Tailleyr, R. G.; Garcia, H.; Corma, A., J. Catal. 2008, 255, 220–227

[42] Dewa, T.; Saiki, T.; Aoyama, Y., J. Am. Chem. Soc. 2001, 123, 502–503

[43] Hasegawa, S.; Horike, S.; Matsuda, R.; Furukawa, S.; Mochizuki, K.; Kinoshita, Y.; Kitagawa, S., J. Am. Chem. Soc. 2007, 129, 2607–2614

[44] Horcajada, P.; Surblé, S.; Serre, C.; Hong, D. Y.; Seo, Y. K.; Chang, J. S.; Grenéche, J. M.; Margiolaki, I.; Férey, G., Chem. Comm. 2007, 2820–2822

[45] Liu, H.; Liu, Y.; Li, Y.; Tang, Z.; Jiang, H., J. Phys. Chem. C 2010, 114, 13362–13369

[46] Park, Y. K.; Choi, S. B.; Nam, H. J.; Jung, D. Y.; Ahn, H. C.; Choi, K.; Furukawa, H.; Kim, J., Chem. Commun. 2010, 46, 3086–3088

[47] Leus, K.; Muylaert, I.; Vandichel, M.; Marin, G. B.; Waroquier, M.; Van Speybroeck, V.; Van der Voort, P., Chem. Commun. 2010, 46, 5085–5087

[48] Huang, L.; Wang, H.; Chen, J.; Wang, Z.; Sun, J.; Zhao, D.; Yan, Y., Microporous Mesoporous Mater. 2003, 58, 105–114

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag Berlin Heidelberg