Mesoporous MFI Zeolite Nanosponge as a High-Performance Catalyst in the Pechmann Condensation Reaction

ACS Catalysis

Volumn 5, Issue 4, 2015, Pages 2596-2604

  Kim, Jeong Chul ^a,b   Ryoo, Ryong ^a,b   Opanasenko, Maksym V ^c,d   Shamzhy, Mariya V ^c,d   Čejka, Jiří ^c  

^a Institute for Basic Science   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^d L V PISARZHEVSKII INSTITUTE OF PHYSICAL CHEMISTRY   (Ukraine)

Author keywords

external acidity; hierarchical zeolite; mesoporous material; MFI; nanomorphic zeolite; Pechmann reaction

Indexed keywords

CONDENSATION; MESOPOROUS MATERIALS; SURFACE REACTIONS; SYNTHESIS (CHEMICAL);

CATALYTIC PERFORMANCE; CONVENTIONAL ZEOLITES; DISORDERED NETWORKS; HIERARCHICAL ZEOLITES; MFI; PECHMANN CONDENSATION; PECHMANN REACTION; STRUCTURE DIRECTING AGENTS;

CONDENSATION REACTIONS;

EID: 84926430380     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs502021a     Document Type: Article

References (42)

1. Sethna, S.; Phadke, R. In Organic Reactions; Denmark, S. E., Aubé, J., Cha, J. K., Farina, V., Feldman, P., Hall, D., Hergenrother, P. J., Johnson, J. S., Kozlowski, M. C., Molander, G., Montgomery, J., Rovis, T., Weinreb, S. M., Eds.; John Wiley & Sons, Inc.: New York, 2011; pp 1 - 58.
2. Gunnewegh, E. A.; Hoefnagel, A. J.; Downing, R. S.; vanBekkum, H. Recl. Trav. Chim. Pays-Bas 1996, 115, 226 - 230 10.1002/recl.19961150407
3. Sun, W. C.; Gee, K. R.; Haugland, R. P. Bioorg. Med. Chem. Lett. 1998, 8, 3107 - 3110 10.1016/S0960-894X(98)00578-2
4. Oyamada, J.; Jia, C. G.; Fujiwara, Y.; Kitamura, T. Chem. Lett. 2002, 31, 380 - 381 10.1246/cl.2002.380
5. Daru, J.; Stirling, A. J. Org. Chem. 2011, 76, 8749 - 8755 10.1021/jo201439u
6. Woods, L. L.; Sapp, J. J. Org. Chem. 1962, 27, 3703 - 3705 10.1021/jo01057a519
7. Gupta, A. K. D.; Chatterje, R. M.; Das, K. R.; Green, B. J. Chem. Soc. C 1969, 29 - 33 10.1039/j39690000029
8. Canter, F. W.; Curd, F. H.; Robertson, A. J. Chem. Soc. 1931, 1245 - 1255 10.1039/jr9310001245
9. Horning, E. C.; Horning, M. G.; Dimmig, D. A. In Organic Syntheses; John Wiley & Sons, Inc.: New York, 2003.
10. Gunnewegh, E. A.; Hoefnagel, A. J.; vanBekkum, H. J. Mol. Catal. A: Chem. 1995, 100, 87 - 92 10.1016/1381-1169(95)00156-5
11. Chaudhari, D. D. Chem. Ind. 1983, 568 - 569
12. Sabou, R.; Hoelderich, W. F.; Ramprasad, D.; Weinand, R. J. Catal. 2005, 232, 34 - 37 10.1016/j.jcat.2005.02.002
13. Torviso, R.; Mansilla, D.; Belizan, A.; Alesso, E.; Moltrasio, G.; Vazquez, P.; Pizzio, L.; Blanco, M.; Caceres, C. Appl. Catal., A 2008, 339, 53 - 60 10.1016/j.apcata.2008.01.020
14. Sudha, S.; Venkatachalam, K.; Priya, S. V.; Mabel, J. H.; Palanichamy, M.; Murugesan, V. J. Mol. Catal. A: Chem. 2008, 291, 22 - 29 10.1016/j.molcata.2008.04.021
15. Tyagi, B.; Mishra, M. K.; Jasra, R. V. J. Mol. Catal. A: Chem. 2007, 276, 47 - 56 10.1016/j.molcata.2007.06.003
16. Shamzhy, M.; Opanasenko, M.; Shvets, O.; Cejka, J. Front. Chem. 2013, 1, 1 - 11 10.3389/fchem.2013.00011
17. Opanasenko, M.; Shamzhy, M.; Cejka, J. ChemCatChem 2013, 5, 1024 - 1031 10.1002/cctc.201200232
18. Choi, M.; Na, K.; Kim, J.; Sakamoto, Y.; Terasaki, O.; Ryoo, R. Nature 2009, 461, 246 - 249 10.1038/nature08288
19. Jo, C.; Cho, K.; Kim, J.; Ryoo, R. Chem. Commun. 2014, 50, 4175 - 4177 10.1039/c4cc01070a
20. Jo, C.; Seo, Y.; Cho, K.; Kim, J.; Shin, H. S.; Lee, M.; Kim, J.-C.; Kim, S. O.; Lee, J. Y.; Ihee, H.; Ryoo, R. Angew. Chem., Int. Ed. 2014, 53, 5117 - 5121 10.1002/anie.201310748
21. Kim, J.-C.; Lee, S.; Cho, K.; Na, K.; Lee, C.; Ryoo, R. ACS Catal. 2014, 4, 3919 - 3927 10.1021/cs500784v
22. Kim, J.-C.; Cho, K.; Ryoo, R. Appl. Catal., A 2014, 470, 420 - 426 10.1016/j.apcata.2013.11.019
23. Opanasenko, M. V.; Shamzhy, M. V.; Jo, C.; Ryoo, R.; Cejka, J. ChemCatChem 2014, 6, 1919 - 1927 10.1002/cctc.201402007
24. Ramos, F. S. O.; de Pietre, M. K.; Pastore, H. O. RSC Adv. 2013, 3, 2084 - 2111 10.1039/C2RA21573J
25. Roth, W. J.; Nachtigall, P.; Morris, R. E.; Čejka, J. Chem. Rev. 2014, 114, 4807 - 4837 10.1021/cr400600f
26. Diaz, U.; Corma, A. Dalton Trans. 2014, 43, 10292 - 10316 10.1039/c3dt53181c
27. Na, K.; Choi, M.; Park, W.; Sakamoto, Y.; Terasaki, O.; Ryoo, R. J. Am. Chem. Soc. 2010, 132, 4169 - 4177 10.1021/ja908382n
28. Na, K.; Park, W.; Seo, Y.; Ryoo, R. Chem. Mater. 2011, 23, 1273 - 1279 10.1021/cm103245m
29. Zhang, X.; Liu, D.; Xu, D.; Asahina, S.; Cychosz, K. A.; Agrawal, K. V.; Al Wahedi, Y.; Bhan, A.; Al Hashimi, S.; Terasaki, O.; Thommes, M.; Tsapatsis, M. Science 2012, 336, 1684 - 1687 10.1126/science.1221111
30. Emeis, C. A. J. Catal. 1993, 141, 347 - 354 10.1006/jcat.1993.1145
31. Camblor, M. A.; Corma, A.; García, H.; Semmer-Herlédan, V.; Valencia, S. J. Catal. 1998, 177, 267 - 272 10.1006/jcat.1998.2110
32. Tao, Y. S.; Kanoh, H.; Abrams, L.; Kaneko, K. Chem. Rev. 2006, 106, 896 - 910 10.1021/cr040204o
33. Kruk, M.; Jaroniec, M.; Kim, J. H.; Ryoo, R. Langmuir 1999, 15, 5279 - 5284 10.1021/la990179v
34. Imperor-Clerc, M.; Davidson, P.; Davidson, A. J. Am. Chem. Soc. 2000, 122, 11925 - 11933 10.1021/ja002245h
35. Cranston, R. W.; Inkley, F. A. Adv. Catal. 1957, 9, 143 - 154 10.1016/S0360-0564(08)60163-7
36. Newsam, J. M.; Treacy, M. M. J.; Koetsier, W. T.; Degruyter, C. B. Proc. R. Soc. London, Ser. A 1988, 420, 375 - 405 10.1098/rspa.1988.0131
37. Janssen, A. H.; Koster, A. J.; de Jong, K. P. J. Phys. Chem. B 2002, 106, 11905 - 11909 10.1021/jp025971a
38. Derouane, E. G.; Detremmerie, S.; Gabelica, Z.; Blom, N. Appl. Catal. 1981, 1, 201 - 224 10.1016/0166-9834(81)80007-3
39. Corma, A.; Fornes, V.; Forni, L.; Marquez, F.; Martinez-Triguero, J.; Moscotti, D. J. Catal. 1998, 179, 451 - 458 10.1006/jcat.1998.2233
40. Kunkeler, P. J.; Downing, R. S.; Bekkum, H. v. In Stud. Surf. Sci. Catal.; H. van Bekkum, E. M. F. P. A. J.; Jansen, J. C., Eds.; Elsevier: 2001; Vol. 137, pp 987 - 1001.
41. In Name Reactions in Heterocyclic Chemistry II; Li, J. J.; Corey, E. J., Eds.; John Wiley & Sons, Inc.: New York, 2011; pp 457 - 458.
42. Liu, D.; Zhang, X.; Bhan, A.; Tsapatsis, M. Microporous Mesoporous Mater. 2014, 200, 287 - 290 10.1016/j.micromeso.2014.06.029