화학공학소재연구정보센터
Korean Journal of Chemical Engineering, Vol.31, No.8, 1377-1383, August, 2014
Tetrabutylphosphonium amino acid ionic liquids as efficient catalysts for solvent-free Knoevenagel condensation reactions
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Five tetrabutylphosphonium amino acid ionic liquids ([P4444][AA]) were prepared, characterized, and used as catalysts for solvent-free Knoevenagel condensation reactions. The tetrabutylphosphonium prolinate ([P4444][Pro]) showed excellent catalytic activity and selectivity in Knoevenagel condensation reactions of active methylene compounds with various aromatic aldehydes, and all the yields of corresponding products were more than 85% under mild conditions. Furthermore, a plausible reaction mechanism for the excellent performance of [P4444][Pro] has been proposed, and [P4444][Pro] could be used repetitively at least six times without obvious decrease in activity and quantity.
  1. Freeman F, Chem. Rev., 80, 329 (1980)
  2. Tietze LF, Chem. Rev., 96(1), 115 (1996)
  3. Kraus GA, Krolski ME, J. Org. Chem., 51, 3347 (1986)
  4. Tietze LF, Rackelmann N, Pure Appl. Chem., 76, 1967 (2004)
  5. Liang F, Pu YJ, Kurata T, Kido J, Nishide H, Polymer, 46(11), 3767 (2005)
  6. Zahouily M, Salah M, Bahlaouane B, Rayadh A, Houmam A, Hamed EA, Sebti S, Tetrahedron, 60, 1631 (2004)
  7. Jackson DB, Macquarrie DJ, Clark JH, in Proceedings of the 4th International Symposium on Supported Reagents and Catalyts in Chemistry, RSC, Cambridge (2001).
  8. Kohki E, Ken M, Kohsuke M, Tomoo M, Kiyotomi K, J. Org. Chem., 71, 5440 (2006)
  9. Angelescu E, Pavel OD, Birjega R, Zavoianu R, Costentin G, Che M, Appl. Catal. A: Gen., 308, 13 (2006)
  10. Chen XQ, Arruebo M, Yeung KL, Catal. Today, 204, 140 (2012)
  11. Reddy BM, Patil MK, Rao KN, Reddy GK, J. Mol. Catal. A-Chem., 258(1-2), 302 (2006)
  12. Khan FA, Dash J, Satapathy R, Tetrahedron Lett., 45, 3055 (2004)
  13. Goa Y, Wu P, Tatsumi T, J. Catal., 224(1), 107 (2004)
  14. Tran UPN, Le KKA, Phan NTS, ACS Catal., 1, 120 (2011)
  15. Jiang H, Wang M, Song ZG, Gong H, Prep. Biochem. Biotechnol., 39, 194 (2009)
  16. Varadwaj GBB, Rana S, Parida KM, J. Chem. Soc.-Dalton Trans., 42, 5122 (2013)
  17. Parvin MN, Jin H, Ansari MB, Oh SM, Park SE, Appl. Catal. A: Gen., 413-414, 205 (2012)
  18. Pineda A, Balu AM, Campelo JM, Romero AA, Luque R, Catal. Commun., 33, 1 (2013)
  19. Ali E, Alnashef I, Ajbar A, Mulyono S, Hizaddin HF, Hadj-Kali MK, Korean J. Chem. Eng., 30(11), 2068 (2013)
  20. Benzagouta MS, AlNashef IM, Karnanda W, Al-Khidir K, Korean J. Chem. Eng., 30(11), 2108 (2013)
  21. Fazlali A, Koranian P, Beigzadeh R, Rahimi M, Korean J. Chem. Eng., 30(9), 1681 (2013)
  22. Mai NL, Kim SH, Ha SH, Shin HS, Koo YM, Korean J. Chem. Eng., 30(9), 1804 (2013)
  23. Wang A, Jiang Y, Chen W, Yin H, Liu Y, Shen Y, Jiang T, Wu Z, J. Ind. Eng. Chem., 18(1), 237 (2012)
  24. Jiang YQ, Chen WG, Liu YJ, Yin HB, Shen YT, Wang AL, Yu LB, Jiang TS, Ind. Eng. Chem. Res., 50(4), 1893 (2011)
  25. Chen W, Yin H, Zhang Y, Lu Z, Wang A, Shen Y, Jiang T, Yu L, J. Ind. Eng. Chem., 16(5), 800 (2010)
  26. Shen LQ, Yin HB, Wang AL, Lu XF, Zhang CH, Chen F, Wang YT, Chen HJ, J. Ind. Eng. Chem., http://dx.doi.org/10.1016/j.jiec.2013.06.004, In Press.
  27. Hui W, Zhang FR, Yu W, Ye L, Lett. Org. Chem., 5, 209 (2008)
  28. Yuan XH, Chen M, Dai QX, Cheng XN, Chem. Eng. J., 146(2), 266 (2009)
  29. Singh A, Kumar A, J. Org. Chem., 77, 8775 (2012)
  30. Wei Z, Li F, Xing H, Deng S, Ren Q, Korean J. Chem. Eng., 26(3), 666 (2009)
  31. Mancini PME, Rosa CDD, Ormachea CM, Kneeteman MN, Domingo LR, RSC Adv., 3, 13825 (2013)
  32. Guo H, Li X, Wang JL, Jin XH, Lin XF, Tetrahedron, 66, 8300 (2010)
  33. Ranu BC, Jana R, Eur. J. Org. Chem.
  34. Wang CM, Luo HM, Li HR, Zhu X, Yu B, Dai S, Chem.-Eur. J., 18, 2153 (2012)
  35. Tao DJ, Ouyang F, Li ZM, Hu N, Yang Z, Chen XS, Ind. Eng. Chem. Res., DOI:10.1021/ie402250e. (2013)
  36. Zhu AL, Liu RX, Li LJ, Li LY, Wang L, Wang JJ, Catal. Today, 200, 17 (2013)
  37. Xu J, Shen K, Xue B, Li YX, J. Mol. Catal. A-Chem., 372, 105 (2013)
  38. Chen XQ, Arruebo M, Yeung KL, Catal. Today, 204, 140 (2013)
  39. Mangala K, Sreekumar K, Appl. Organomet. Chem., 27, 73 (2013)
  40. Wang H, Li L, Bai XF, Deng WF, Zheng ZJ, Yang KF, Xu LW, Green Chem., 15, 2349 (2013)
  41. Zhao SH, Wang XJ, Zhang LW, RSC Adv., 3, 11691 (2013)
  42. Burgoyne AR, Meijboom R, Catal. Lett., 143(6), 563 (2013)
  43. Ansari MB, Jin HL, Parvin MN, Park SE, Catal. Today, 185, 2119 (2012)