DOI QR코드

DOI QR Code

Synthesis, Characterization and Application of Poly(4-Methyl Vinylpyridinium Hydroxide)/SBA-15 Composite as a Highly Active Heterogeneous Basic Catalyst for the Knoevenagel Reaction

  • 투고 : 2010.06.18
  • 심사 : 2010.07.30
  • 발행 : 2010.09.20

초록

In this paper poly (4-methyl vinylpyridinium hydroxide)/SBA-15 composite was prepared as a highly efficient heterogeneous basic catalyst by in situ polymerization method for the first time. It was characterized by XRD, FT-IR, BET, TGA, SEM and back titration using NaOH. This catalyst exhibited the excellent catalytic activities for the Knoevenagel condensation of various aldehydes with ethyl cyanoacetate. Over this catalyst, ${\alpha},{\beta}$-unsaturated carbonyl compounds were obtained in the reasonable yield at $95^{\circ}C$ in 10 - 30 min in $H_2O$ as a solvent with a 100% selectivity to the condensation products. Catalyst could be easily recycled after the reaction and it could be reused without the significant loss of activity/selectivity performance. No by-product formation, high yields, short reaction times, mild reaction conditions and operational simplicity with reusability of the catalyst were the salient features of the present synthetic protocol. Presence of $H_2O$ as a solvent was also recognized as a "green method".

키워드

참고문헌

  1. Seki, T.; Onaka, M. J. Mol. Catal. A: Chem. 2007, 263, 115. https://doi.org/10.1016/j.molcata.2006.08.049
  2. Saravanamurugan, S.; Palanichamy, M.; Hartmann, M.; Murugesan, V. Appl. Catal. A: Gen. 2006, 298, 8. https://doi.org/10.1016/j.apcata.2005.09.014
  3. Wirz, R.; Ferri, D.; Baiker, A. Langmuir 2006, 22, 3698. https://doi.org/10.1021/la053145y
  4. Martin-Aranda, R. M.; Ortega-Cantero, E.; Rojas-Cervantes, M. L.; Vicente-Rodriguez, M. A.; Banares-Munoz, M. A. J. Chem. Technol. Biotechnol. 2005, 80, 234. https://doi.org/10.1002/jctb.1174
  5. Climent, M. J.; Corma, A.; Dominguez, I.; Iborra, S.; Sabater, M. J.; Sastre, G. J. Catal. 2007, 246, 136. https://doi.org/10.1016/j.jcat.2006.11.029
  6. Rodriguez, I.; Sastre, G.; Corma, A.; Iborra, S. J. Catal. 1999, 183, 14. https://doi.org/10.1006/jcat.1998.2380
  7. Jones, G. Org. React. 1967, 15, 204.
  8. Lehnert, W. Tet. Lett. 1970, 54, 4723.
  9. Cabello, J. A.; Campelo, J. M.; Garcia, A.; Luna, D.; Marina, J. M. J. Org. Chem. 1984, 49, 5195. https://doi.org/10.1021/jo00200a036
  10. Shanthan, R. P.; Venkataratnam, R. V. Tet. Lett. 1991, 41, 5821.
  11. Bennazha, J.; Zabouily, M.; Sbeti, S.; Boukhari, A.; Holt, E. M. Catal. Commun. 2001, 2, 101. https://doi.org/10.1016/S1566-7367(01)00015-2
  12. Zhang, M.; Zhang, A. Q.; Tang, X. H. Chin. J. Org. Chem. 2004, 24, 1106.
  13. Xu, X. M.; Li, Y. Q.; Zhou, M. Y. Chin. J. Org. Chem. 2004, 24, 1253.
  14. Yi, H.; Jue, C.; Zhang, G. L. Synth. Commun. 2005, 35, 739. https://doi.org/10.1081/SCC-200050380
  15. Chen, X.; Li, X.; Song, H.; Lu, Y.; Wang, F.; Hu, A. Chin. J. Catal. 2008, 29, 957. https://doi.org/10.1016/S1872-2067(08)60078-9
  16. Zhang, Y.; Zhao, Y.; Xia, C. J. Mol. Catal. A: Chem. 2009, 306, 107. https://doi.org/10.1016/j.molcata.2009.02.032
  17. Cai, Y.; Peng, Y.; Song, G. Catal. Lett. 2006, 109, 61. https://doi.org/10.1007/s10562-006-0057-3
  18. Sheldon, R. A. Pure Appl. Chem. 2000, 72, 1233. https://doi.org/10.1351/pac200072071233
  19. Weitkamp, J.; Hunger, M.; Rymsa, U. Micropor. Mesopor. Mater. 2001, 48, 255. https://doi.org/10.1016/S1387-1811(01)00366-3
  20. Tamami, B.; Fadavi, A. Iranian Poly. J. 2006, 15, 331.
  21. Jerome, F.; Kharchafi, G.; Adam, I.; Barrault, J. Green Chem. 2004, 6, 72. https://doi.org/10.1039/b315413k
  22. Corma, A.; Iborra, S.; Rodriguez, I.; Sanchez, F. J. Catal. 2002, 211, 208.
  23. Corma, A.; Hamid, S. B. A.; Iborra, S.; Velty, A. J. Catal. 2005, 234, 340. https://doi.org/10.1016/j.jcat.2005.06.023
  24. Corma, A. J. Catal. 2003, 216, 298. https://doi.org/10.1016/S0021-9517(02)00132-X
  25. Zhao, D. Y.; Huo, Q. S.; Feng, J. L.; Chmelka, B. F.; Stucky, G. D. J. Am. Chem. Soc. 1998, 120, 6024. https://doi.org/10.1021/ja974025i
  26. Zhao, D. Y.; Feng, J. L.; Huo, Q. S.; Melosh, N.; Fredrickson, G. H.; Chmelka, B. F.; Stucky, G. D. Science 1998, 279, 548. https://doi.org/10.1126/science.279.5350.548
  27. Kralik, M.; Biffis, A. J. Mol. Catal. A: Chem. 2001, 177, 113. https://doi.org/10.1016/S1381-1169(01)00313-2
  28. Malynych, S.; Luzinov, I.; Chumanov, G. J. Phys. Chem. B 2002, 106, 1280. https://doi.org/10.1021/jp013236d
  29. Tamami, B.; Borujeni, K. P. Iranian Poly. J. 2009, 18, 191.
  30. Goettmann, F.; Sanchez, C.; Parvanak Borujeni, K. J. Mater. Chem. 2007, 17, 24. https://doi.org/10.1039/b608748p
  31. Colilla, M.; Balas, F.; Manzano, M.; Vallet-Regi, M. Chem. Mater. 2007, 19, 3099. https://doi.org/10.1021/cm071032p
  32. Agarwal, G. K.; Titman, J. J.; Percy, M. J.; Armes, S. P. J. Phys. Chem. B 2003, 107, 12497. https://doi.org/10.1021/jp036065g
  33. Kumbhare, R. M.; Sridhar, M. Catal. Commun. 2008, 9, 403. https://doi.org/10.1016/j.catcom.2007.07.027
  34. Flitsch, W.; Kahner-Grone, S. Chemische Berichte 1982, 115(3), 871. https://doi.org/10.1002/cber.19821150305
  35. Krishnan, G. R.; Sreekumar, K. Euro. J. Org. Chem. 2008, 4763.
  36. Fan, X.; Hu, X.; Zhang, X.; Wang, J. Aust. J. Chem. 2004, 57, 1067. https://doi.org/10.1071/CH04060
  37. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Visali, B.; Narsaiah, A. V.; Nagaiah, K. Eur. J. Org. Chem. 2004, 546.

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  3. ChemInform Abstract: Synthesis, Characterization and Application of Poly(4-methyl vinylpyridinium hydroxide)/SBA-15 Composite as a Highly Active Heterogeneous Basic Catalyst for the Knoevenagel Reaction. vol.42, pp.8, 2011, https://doi.org/10.1002/chin.201108083
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  13. Preparation, characterization and catalyst application of ternary interpenetrating networks of poly 4-methyl vinyl pyridinium hydroxide-SiO2-Al2O3 vol.184, pp.8, 2010, https://doi.org/10.1016/j.jssc.2011.05.035
  14. Synthesis and characterization of polymer/microporous molecular sieve nanocomposite as a shape-selective basic catalyst vol.14, pp.11, 2010, https://doi.org/10.1016/j.crci.2011.05.001
  15. Synthesis and characterization of Pd-poly(N-vinyl-2-pyrrolidone)/KIT-5 nanocomposite for Heck reaction vol.47, pp.1, 2010, https://doi.org/10.1016/j.materresbull.2011.09.018
  16. Synthesis, characterization, and application of a manganese Schiff base complex containing salicylaldehyde-poly(vinylamine)/SBA-15 as a novel heterogeneous hybrid catalyst vol.3, pp.31, 2013, https://doi.org/10.1039/c3ra22579h
  17. Synthesis and characterization of mesoporous poly (4-methylvinylpyridinium hydroxide) as an efficient heterogeneous organocatalyst vol.138, pp.2, 2010, https://doi.org/10.1016/j.matchemphys.2012.12.009
  18. Synthesis and properties of alkaline stable pyridinium containing anion exchange membranes vol.4, pp.85, 2010, https://doi.org/10.1039/c4ra07616h
  19. Isomerization of Alkanes over Ionic Liquids Supported on SBA-15 vol.34, pp.11, 2010, https://doi.org/10.1021/acs.energyfuels.0c02331