Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Long Chain Dicationic Phase Transfer Catalysts in the Condensation Reactions of Aromatic Aldehydes in Water Under Ultrasonic Effect

  • Esen, Ilker (Department of Chemistry, Yildiz Technical University) ;
  • Yolacan, Cigdem (Department of Chemistry, Yildiz Technical University) ;
  • Aydogan, Feray (Department of Chemistry, Yildiz Technical University)
  • Received : 2010.05.15
  • Accepted : 2010.06.23
  • Published : 2010.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

Long chain dicationic ammonium salts were used successfully as phase transfer catalyst in the condensation reactions of aromatic aldehydes in water under ultrasonic irradiation for the first time. The quaternary salt having longer distance between the cation centers was more effective than the mono- and dicationic ones having short chain.

Keywords

References

  1. Anastas, P. T.; Warner, J. C. In Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
  2. Sanghi, R. Curr. Sci. 2000, 79, 1662.
  3. Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis, 3rd ed.; Wiley-VCH Verlag: Weinheim, 2008.
  4. Starks, C. M.; Liotta, E. L.; Halpern, M. In Phase Transfer Catalysis Fundamentals, Applications and Industrial Perspectives; Chapman and Hall: New York, 1994.
  5. Makosza, M. Pure Appl. Chem. 2000, 72, 1399. https://doi.org/10.1351/pac200072071399
  6. Jones, R. A. In Quaternary Ammonium Salts Their Use in Phase Transfer Catalysis; Academic Press:Trowbridge, 2001.
  7. Ahmed, B.; Khan, R. A.; Keshari, M. Tetrahedron Lett. 2009, 50, 2889. https://doi.org/10.1016/j.tetlet.2009.03.177
  8. Han, Z.; Yamaguchi, Y.; Kitamura, M.; Maruoka, K. Tetrahedron Lett. 2005, 46, 8555. https://doi.org/10.1016/j.tetlet.2005.09.185
  9. O’Reilly, E.; Lestini, E.; Balducci, D.; Paradisi, F. Tetrahedron Lett. 2009,50, 1748. https://doi.org/10.1016/j.tetlet.2009.01.146
  10. Vivekanand, P. A.; Balakrishnan, T. Catal. Commun. 2009, 10,687. https://doi.org/10.1016/j.catcom.2008.11.020
  11. Ali, H. S. Catal. Commun. 2007, 8, 855. https://doi.org/10.1016/j.catcom.2006.09.013
  12. Murugan, E.; Gopinath, P. J. Mol. Catal. A-Chem. 2009, 309, 12. https://doi.org/10.1016/j.molcata.2009.04.009
  13. Park, H.; Jeong, B.; Yoo, M.; Park, M.; Huh, H.; Jew, S. Tetrahedron Lett.2001, 42, 4645. https://doi.org/10.1016/S0040-4039(01)00809-7
  14. Murugan, E.; Siva, A. J. Mol. Catal. A-Chem. 2005, 235, 220. https://doi.org/10.1016/j.molcata.2005.03.029
  15. Sekhon, B. S. Resonance 2004, 42.
  16. Bagha, A. R. T.; Bahrami, H.; Movassagh, B.; Arami, M.; Menger, F. M. Dyes Pigm. 2007, 72, 331. https://doi.org/10.1016/j.dyepig.2005.09.011
  17. Li, F.; Rosen, M. J. J. Colloid. Interface Sci. 2000, 224, 265. https://doi.org/10.1006/jcis.2000.6721
  18. Shukla, D.; Tyagi, V. K. J. Oleo. Sci. 2006, 55, 381. https://doi.org/10.5650/jos.55.381
  19. Buwalda, R. T.; Engberts, B. F. N. Langmuir 2001, 17, 1054. https://doi.org/10.1021/la001277f
  20. Villemin, D.; Jullien, A.; Bar, N. J. Mol. Catal. A- Chem. 2003,5, 467.
  21. Loupy, A.; Pellet, M.; Petit, A.; Vo-Thanh, G. Org. Biomol. Chem. 2005, 3, 1534. https://doi.org/10.1039/b418156e
  22. Peach, P.; Cross, D. J.; Kenny, J. A.; Mann, I.; Houson, I.; Campbell, L.; Walsgroveb, T.; Willsa, M. Tetrahedron 2006, 62, 1864. https://doi.org/10.1016/j.tet.2005.11.036
  23. Jayachandran, J. P.; Wheeler, C.; Eason, B. C.; Liotta, C. L.; Eckert,C. A. J. Supercrit. Fluid 2003, 27, 179. https://doi.org/10.1016/S0896-8446(02)00238-3

Cited by

  1. Sonolytic and Silent Polymerization of Methacrlyic Acid Butyl Ester Catalyzed by a New Onium Salt with bis-Active Sites in a Biphasic System — A Comparative Investigation vol.18, pp.2, 2013, https://doi.org/10.3390/molecules18022419
  2. Manganese Catalyzed α-Olefination of Nitriles by Primary Alcohols vol.139, pp.34, 2017, https://doi.org/10.1021/jacs.7b06993
  3. ChemInform Abstract: Long Chain Dicationic Phase Transfer Catalysts in the Condensation Reactions of Aromatic Aldehydes in Water under Ultrasonic Effect. vol.41, pp.50, 2010, https://doi.org/10.1002/chin.201050054
  4. Synthesis and Characterization of Double‐Salt Herbicidal Ionic Liquids Comprising both 4‐Chloro‐2‐methylphenoxyacetate and trans ‐Cinnamate Anions vol.85, pp.10, 2010, https://doi.org/10.1002/cplu.202000546