Catalytic performance of Metal-Organic-Frameworks vs. Extra-large pore zeolite UTL in condensation reactions

Frontiers in Chemistry

Volumn 1, Issue , 2013, Pages

  Shamzhy, Mariya ^a,b   Opanasenko, Maksym ^a,b   Shvets, Oleksiy ^a,b   Cejka, Jirí ^a  

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

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

Author keywords

Condensation reactions; MOFs; Prins reaction; UTL; Zeolites

Indexed keywords

EID: 84987617352     PISSN: None     EISSN: 22962646     Source Type: Journal    
DOI: 10.3389/fchem.2013.00011     Document Type: Article

References (66)

1. Alarcon, E. A., Correa, L., Montes, C., and de Villa, A. L. (2010). Nopol production over Sn-MCM-41 synthesized by different procedures-Solvent effects. Micropor. Mesopor. Mater. 136, 59-67. doi: 10.1016/j.micromeso.2010.07.021
2. Andersen, N. H., Hadley, S. W., Kelly, J. D., and Bacon, E. R. (1985). Intramolecular olefinic aldehyde Prins reactions for the construction of 5-membered rings. J. Org. Chem. 50, 4144-4151. doi: 10.1021/jo00221a034
3. 2O-NaI system as promoter in the synthesis of functionalized trisubstituted alkenes via Knoevenagel condensation. Tetrahedron Lett. 47, 6501-6504. doi: 10.1016/j.tetlet.2006.07.031
4. Bennazha, J., Zahouilly, M., Boukhari, A., and Hol, E. A. (2003). Investigation of the basis of catalytic activity of solid state phosphate complexes in the Knoevenagel condensation. J. Mol. Catal. A Chem. 202, 247-252. doi: 10.1016/S1381-1169(03)00208-5
5. Bigi, F., Chesini, L., Maggi, R., and Sartori, G. (1999). Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids. J. Org. Chem. 64, 1033-1035. doi: 10.1021/jo981794r
6. Bledsoe, J. O. (1997). "Terpenoids," in Kirk-Othmer Encyclopedia of Chemical Technology, eds J. I. Kroschwitz and M. Howe-Grant (New York, NY: Wiley), 833-882.
7. Borah, H. N., Deb, M. L., Boruah, R. C., and Bhuyan, P. J. (2005). Stereoselective intramolecular hetero Diels-Alder reactions of 1-oxa-1, 3-butadienes: synthesis of novel annelated pyrrolo[1, 2-a]indoles. Tetrahedron Lett. 46, 3391-3393. doi: 10.1016/j.tetlet.2005.03.091
8. Calvino-Casilda, V., Martin-Aranda, R. M., Lopez-Peinado, A. J., Sobczak, I., and Ziolek, M. (2009). Catalytic properties of alkali metal-modified oxide supports for the Knoevenagel condensation: kinetic aspects. Catal. Tod. 142, 278-282. doi: 10.1016/j.cattod.2008.08.023
9. Calvino-Casilda, V., Pérez-Mayoral, E., Martín-Aranda, R. M., Zienkiewicz, Z., Sobczak, I., and Ziolek, M. (2010). Isomerization of Eugenol under ultrasound activation catalyzed by alkali modified mesoporous NbMCM-41. Top. Catal. 53, 179-186. doi: 10.1007/s11244-009-9422-y
10. Canter, F. W., Curd, F. H., and Robertson, A. (1931). Hydroxy-carbonyl compounds. Part, I. I. I. The preparation of coumarines and 1 4-benzopyrones from phloroglucinol and resorcinol. J. Chem. Soc. 1, 1255-1265. doi: 10.1039/jr9310001255
11. Chae, H. K., Siberio-Perez, D. Y., Kim, J., Go, Y. B., Eddaoudi, M., Matzger, A. J., et al. (2004). A route to high surface area, porosity and inclusion of large molecules in crystals. Nature 427, 523-527. doi: 10.1038/nature02311
12. 2O)(3)](n). Science 283, 1148-1150. doi: 10.1126/science.283.5405.1148
13. Corma, A., Díaz-Cabañas, M. J., and Rey, F. (2004). ITQ-15: the first ultralarge pore zeolite with a bi-directional pore system formed by intersecting 14-and 12-ring channels, and its catalytic implications. Chem. Commun. 40, 1356-1357. doi: 10.1039/b406572g
14. Corma, A., Fornes, V., Martin-Aranda, R. M., Garcia, H., and Primo, J. (1990). Zeolites as base catalysts: condensation of aldehydes with derivatives of malonic esters. Appl.Catal. 59, 237-248. doi: 10.1016/S0166-9834(00)82201-0
15. Corma, A., García, H., and Llabrési Xamena, F. X. (2010). Engineering metal organic frameworks for heterogeneous catalysis. Chem. Rev. 110, 4606-4655. doi: 10.1021/cr9003924
16. Corma, A., and Martin-Aranda, R. M. (1993). Application of solid base catalysts in the preparation of prepolymers by condensation of ketones and malononitrile. Appl. Catal. A Gen. 105, 271-279. doi: 10.1016/0926-860X(93)80252-L
17. Corma, A., and Renz, M. (2007). Water-resistant Lewis-acid sites: carbonyl-ene reactions catalyzed by tin-containing, hydrophobic molecular sieves. ARKIVOC 8, 40-48.
18. Das Gupta, A. K., Chatterje, R. M., Das, K. R., and Green, B. (1969). Coumarins and related compounds. 4. Aluminium chloride-catalysed reaction of phenols with methyl acrylate-a new approach to synthesis of hydroxycoumarins. J. Chem. Soc. C 1, 29-33. doi: 10.1039/j39690000029
19. de Villa, A. L., and Alarcon, P. E. (2002). Synthesis of nopol over MCM-41 catalysts. Chem. Commun. 22, 2654-2655. doi: 10.1039/b206239a
20. de Villa, A. L., Alarcon, P. E., and de Monteas, C. (2005). Nopol synthesis over Sn-MCM-41 and Sn-kenyaite catalysts. Catal. Tod. 107-108, 942-948. doi: 10.1016/j.cattod.2005.07.049
21. Dhakshinamoorthy, A., Alvaro, M., Horcajada, P., Gibson, E., Vishnuvarthan, M., Vimont, A., et al. (2012). Comparison of porous iron trimesates Basolite F300 and MIL-100(Fe) as heterogeneous catalysts for Lewis acid and oxidation reactions: roles of structural defects and stability. ACS Catal. 2, 2060-2065. doi: 10.1021/cs300345b
22. Dhakshinamoorthy, A., Opanasenko, M., Cejka, J., and Garcia, H. (2013). Metal organic frameworks as solid catalysts in condensation reactions of carbonyl groups. Adv. Synth. Cat. 355, 247-268.
23. Eddaoudi, M., Kim, J., Rosi, N., Vodak, D., Wachter, J., O'Keeffe, M., et al. (2002). Systematic design of pore size and functionality in isoreticular MOFs and their application in methane storage. Science 295, 469-472. doi: 10.1126/science.1067208
24. Emeis, C. A. (1993). Determination of integrated molar extinction coefficients for infrared-absorption bands of pyridine adsorbed on solid acid catalysts. J. Catal. 141, 347-354. doi: 10.1006/jcat.1993.1145
25. Freeman, F. (1981). Properties and reactions of ylidenemalononitriles. Chem. Rev. 80, 329-350. doi: 10.1021/cr60326a004
26. Green, B., Crane, R. I., Khaidem, I. S., Leighton, R. S., Newaz, S. S., and Smyser, T. E. (1985). Synthesis of steroidal 16, 17-fused unsaturated delta-lactones. J. Org. Chem. 50, 640-644. doi: 10.1021/jo00205a016
27. Hoefnagel, A. J., Gunnewegh, E. A., Downing, R. S., and van Bekkum, H. (1995). Synthesis of 7-hydroxycoumarins catalyzed by solid acid catalysts. J. Chem. Soc. Chem. Commun. 225-226. doi: 10.1039/c39950000225
28. Jiang, J., Yu, J., and Corma, A. (2010). Extra-large-pore zeolites: bridging the gap between micro and mesoporous structures. Angew. Chem. Int. Ed. Engl. 49, 3120-3145. doi: 10.1002/anie.200904016
29. Joshi, U. D., Joshi, P. N., Tamhankar, S. S., Joshi, V. V., Rode, C. V., and Shiralkar, V. P. (2003). Effect of nonframework cations and crystallinity on the basicity of NaX zeolites. Appl. Catal. A Gen. 239, 209-220. doi: 10.1016/S0926-860X(02)00391-5
30. Kalita, P., Sathyaseelan, B., Mano, A., Javaid Zaidi, S. M., Chari, M. A., and Vinu, A. (2010). Synthesis of superacid-functionalized mesoporous nanocages with tunable pore diameters and their application in the synthesis of coumarins. Chem. Eur. J. 16, 2843-2851. doi: 10.1002/chem.200902531
31. Karimi, B., and Behzadnia, H. (2011). Periodic mesoporous silica chloride (PMSCl) as an efficient and recyclable catalyst for the Pechmann reaction. Catal. Commun. 12, 1432-1436. doi: 10.1016/j.catcom.2011.05.019
32. Karimi, B., and Zareyee, D. (2008). Design of a highly efficient and water-tolerant sulfonic acid nanoreactor based on tunable ordered porous silica for the von Pechmann reaction. Org. Lett. 10, 3989-3992. doi: 10.1021/ol8013107
33. Kumbhare, R. M., and Sridhar, M. (2008). Magnesium fluoride catalyzed Knoevenagel reaction: an efficient synthesis of electrophilic alkenes. Catal. Comm. 9, 403-405. doi: 10.1016/j.catcom.2007.07.027
34. Lai, M., Ng, C. P., Martin-Aranda, R., and Yeung, K. L. (2003). Knoevenagel condensation reaction in zeolite membrane microreactor. Micropor.Mesopor. Mater. 66, 239-252. doi: 10.1016/j.micromeso.2003.09.014
35. Lau, W. N., Yeung, K. L., and Martin-Aranda, R. (2008). Knoevenagel condensation reaction between benzaldehyde and ethyl acetoacetate in microreactor and membrane microreactor. Micropor. Mesopor. Mater. 115, 156-163. doi: 10.1016/j.micromeso.2007.12.036
36. Li, C.-J. (2005). Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem. Rev. 105, 3095-3166. doi: 10.1021/cr030009u
37. Li, G. X., Gu, Y. L., Ding, Y., Zhang, H. P., Wang, J. M., Gao, Q., et al. (2004). Wells-Dawson type molybdovanadophosphoric heteropolyacids catalyzed Prins cyclization of alkenes with paraformaldehyde under mild conditions-a facile and efficient method to 1, 3-dioxane derivatives. J. Mol. Catal. A: Chem. 218, 147-152. doi: 10.1016/j.molcata.2004.04.021
38. Li, H., Eddaoudi, M., O'Keeffe, M., and Yaghi, O. M. (1999). Design and synthesis of an exceptionally stable and highly porous metal-organic framework. Nature 402, 276-279. doi: 10.1038/46248
39. Li, T. S., Zhang, Z. H., Yang, F., and Fu, C. G. (1998). Montmorillonite clay catalysis. Part 7.1 an environmentally friendly procedure for the synthesis of coumarins via Pechmann condensation of phenols with ethyl acetoacetate. J. Chem. Res. (S) 1, 38-39.
40. Opanasenko, M., Dhakshinamoorthy, A., Shamzhy, M., Nachtigall, P., Horacek, M., Garcia, H., et al. (2013a). Comparison of the catalytic activity of MOFs and zeolites in Knoevenagel condensation. Catal. Sci. Technol. 3, 500-507. doi: 10.1039/c2cy20586f
41. Opanasenko, M., Shamzhy, M., and Cejka, J. (2013b). Solid acid catalysts for coumarin synthesis by the Pechmann reaction: MOFs versus zeolites. ChemCatChem 5, 1024-1031. doi: 10.1002/cctc.201200232
42. Paillaud, J.-L., Harbuzaru, B., and Patarin, J. (2004). Extra-large-pore zeolites with two-dimensional channels formed by 14 and 12 rings. Science 304, 990-992. doi: 10.1126/science.1098242
43. Patil, M. V., Yadav, M. K., and Jasra, R. V. (2007). Prins condensation for synthesis of nopol from P-pinene and paraformaldehyde on novel Fe-Zn double metal cyanide solid acid catalyst. J. Mol. Catal. A Chem. 273, 39-47. doi: 10.1016/j.molcata.2007.03.054
44. Pérez-Mayoral, E., Musilová, Z., Gil, B., Marszalek, B., Položij, M., Nachtigall, P., et al. (2012). Synthesis of quinolines via Friedlander reaction catalyzed by CuBTC metal-organic-framework. Dalton Trans. 44, 4036-4044. doi: 10.1039/c2dt11978a
45. Pillai, U. R., and Sahle-Demessie, E. (2004). Mesoporous iron phosphate as an active, selective and recyclable catalyst for the synthesis of nopol by Prins condensation. Chem. Commun. 7, 826-827. doi: 10.1039/b313747c
46. 2 supported heterogeneous catalysts: an environmentally benign approach. Catal. Comm. 10, 365-369. doi: 10.1016/j.catcom.2008.09.021
47. Reddy, T. I., and Verma, R. S. (1997). Rare-earth (RE) exchanged NaY zeolite promoted Knoevenagel condensation. Tetrahedron Lett. 38, 1721-1724. doi: 10.1016/S0040-4039(97)00180-9
48. Russell, A., and Frye, J. R. (1955). 2, 6-dihydroxyacetophenone. Org. Synth. 3, 281-283.
49. Sabou, R., Hoelderich, W. F., Ramprasad, D., and Weinand, R. (2005). Synthesis of 7-hydroxy-4-methyleoumarin via the Pechmann reaction with Amberlyst ion-exchange resins as catalysts. J. Catal. 232, 34-37. doi: 10.1016/j.jcat.2005.02.002
50. Selvaraj, M., and Choe, Y. (2010). Well ordered two-dimensional SnSBA-15 catalysts synthesized with high levels of tetrahedral tin for highly efficient and clean synthesis of nopol. Appl. Catal. A Gen. 373, 186-191. doi: 10.1016/j.apcata.2009.11.014
51. Selvaraj, M., and Sinha, P. K. (2010). Highly selective and clean synthesis of nopol over well-ordered mesoporous tin silicate catalysts. New J. Chem. 34, 1921-1929. doi: 10.1039/c0nj00080a
52. Shamzhy, M. V., Shvets, O. V., Opanasenko, M. V., Kurfirtova, L., Kubicka, D., and Cejka, J. (2013). Extra-large-pore zeolites with UTL topology: control of the catalytic activity by variation in the nature of the active sites. Chem. Cat. Chem. 5, 1891-1898.
53. Shamzhy, M. V., Shvets, O. V., Opanasenko, M. V., Yaremov, P. S., Sarkisyan, L. G., Chlubná, P., et al. (2012). Synthesis of isomorphously substituted extra-large pore UTL zeolites. J. Mater. Chem. 22, 15793-15803. doi: 10.1039/c2jm31725g
54. Shanthan, R. P., and Venkataratnam, R. V. (1991). Zinc chloride as a new catalyst for Knoevenagel condensation. Tetrahedron Lett. 32, 5821-5822. doi: 10.1016/S0040-4039(00)93564-0
55. Shvets, O. V., Kasian, N., Zukal, A., Pinkas, J., and Cejka, J. (2010). The role of template structure and synergism between inorganic and organic structure directing agents in the synthesis of UTL zeolite. Chem. Mater. 22, 3482-3495. doi: 10.1021/cm1006108
56. Shvets, O. V., Shamzhy, M. V., Yaremov, P. S., Musilová, Z., Procházková, D., and Cejka, J. (2011). Isomorphous introduction of boron in germanosilicate zeolites with UTL topology. Chem. Mater. 23, 2573-2585. doi: 10.1021/cm200105f
57. Shvets, O. V., Zukal, A., Kasian, N., Žilková, N., and Cejka, J. (2008). The role of crystallization parameters for the synthesis of germanosilicate with UTL Topology. Chem. Eur. J. 14, 10134-10140. doi: 10.1002/chem.200800416
58. Sudha, S., Venkatachalam, K., Vishnu Priya, S., Herbert Mabel, J., Palanichamy, M., and Murugesan, V. (2008). Single step synthesis of coumarin derivatives over Al-MCM-41 and its supported catalysts under solvent-free condition. J. Mol. Catal. A. 291, 22-29. doi: 10.1016/j.molcata.2008.04.021
59. Tietze, L. F., and Beifuss, U. (1991). "The Knoevenagel reaction," in Comprehensive Organic Synthesis, eds B. M. Trost and I. Fleming (Oxford: Pergamon Press), 341-394.
60. Torviso, R., Mansilla, D., Belizán, A., Alesso, E., Moltrasio, G., Vázquez, P., et al. (2008). Catalytic activity of Keggin heteropolycompounds in the Pechmann reaction. Appl. Catal. A 339, 53-60. doi: 10.1016/j.apcata.2008.01.020
61. Tyagi, B., Mishra, M. K., and Jasra, R. V. (2007). Synthesis of 7-substituted 4-methyl coumarins by Pechmann reaction using nano-crystalline sulfated-zirconia. J. Mol. Catal. A 276, 47-56. doi: 10.1016/j.molcata.2007.06.003
62. Weinmann, I. (1997). "History of the development and applications of coumarin and coumarin-related compounds," in Coumarins: Biology, Applications and Mode of Action, eds R. O. Kennedy and R. D. Thornes (Chichester: Wiley Press), 1-22.
63. Williams, J. T., Bahia, P. S., and Snaith, J. S. (2002). Synthesis of 3, 4-disubstituted piperidines by carbonyl ene and prins cyclizations: a switch in diastereoselectivity between Lewis and Bronsted acid catalysts. Org. Lett. 4, 3727-3730. doi: 10.1021/ol0266929
64. Woods, L. L., and Sapp, J. (1962). A new one-step synthesis of substituted coumarins. J. Org. Chem. 27, 3703-3705. doi: 10.1021/jo01057a519
65. Yadav, J. S., Reddy, B. V. S., and Bhaishya, G. (2003). InBr3-[bmim]PF6: a novel and recyclable catalytic system for the synthesis of 1, 3-dioxane derivatives. Green Chem. 5, 264-266. doi: 10.1039/b212044p
66. 2 impregnated Indian Montmorillonite. Catal. Commun. 7, 889-895. doi: 10.1016/j.catcom.2006.04.002