Issue
Korean Journal of Chemical Engineering,
Vol.36, No.2, 197-202, 2019
Metal- and halide-free solid-type multifunctional alkanolamines as catalysts for cycloaddition of CO2
Although the production of cyclic carbonates from CO2 and epoxides can be promoted by eco-friendly halogen- and metal-free organic catalysts, its homogeneity complicates the catalyst reuse. Herein, we synthesized solid multifunctional alkanolamines using simple epoxy and amine reactions, and analyzed their structures by IR and 13CNMR. Then, we employed these as catalysts for CO2 cycloaddition with propylene oxide, obtaining propylene carbonate in 98% yield after 3 h at 120 °C. Moreover, at 60 °C, the reaction was successfully repeated five times and a product yield of 50% was maintained throughout.
[References]
  1. Anderson TR, Hawkins E, Jones PD, Endeavour, 40, 178, 2016
  2. Alper E, Orhan OY, Petroleum, 3, 109, 2017
  3. North M, Pasquale R, Young C, Green Chem., 12, 1514, 2010
  4. Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kuhn FE, Angew. Chem.-Int. Edit., 50, 8510, 2011
  5. North M, Pasquale R, Angew. Chem.-Int. Edit., 48, 2946, 2009
  6. Dai WL, Luo SL, Yin SF, Au CT, Appl. Catal. A: Gen., 366(1), 2, 2009
  7. Cokoja M, Wilhelm ME, Anthofer MH, Herrmann WA, Kuhn FE, ChemSusChem, 8, 2436, 2015
  8. Martin C, Fiorani G, Kleij AW, ACS Catal., 5, 1353, 2015
  9. Shaikh AA, Sivaram S, Chem. Rev., 96(3), 951, 1996
  10. Sakakura T, Kohno K, Chem. Commun., 1312 (2009).
  11. Huang SY, Liu SG, Li JP, Zhao N, Wei W, Sun YH, Fuel Chem. Technol., 35, 701, 2007
  12. Bhanage BM, Fujita S, Ikushima Y, Arai M, Appl. Catal. A: Gen., 219(1-2), 259, 2001
  13. Bai D, Duan S, Hai L, Jing H, ChemCatChem, 4, 1752, 2012
  14. Zhang J, Cheng X, Zhang B, Shi J, Zheng L, Zhang J, Shao D, Tan X, Han B, Yang G, ChemCatChem, 10, 1, 2018
  15. Song J, Zhang Z, Han B, Hu S, Li W, Xie Y, Green Chem., 10, 1337, 2008
  16. He LN, Yasuda H, Sakakura T, Green Chem., 5, 92, 2003
  17. Decortes A, Castilla AM, Kleij AW, Angew. Chem.-Int. Edit., 49, 9822, 2010
  18. Zhang Y, Chan JYG, Energy Environ. Sci., 3, 408, 2010
  19. Vieira MO, Monteiro WF, Neto BS, Ligabue R, Chaban VV, Einloft S, Catal. Lett., 148, 108, 2018
  20. Wasserscheid P, Welton T, Ionic Liquids in Synthesis, 2nd Ed., Wiley-VCH (2008).
  21. Kim HG, Lim CS, Kim DW, Cho DH, Lee DK, Chung JS, Mol. Catal., 438, 121, 2017
  22. Chen J, Zhong M, Tao L, Liu L, Jayakumar S, Li C, Li H, Yang Q, Green Chem., 20, 903, 2018
  23. Wu S, Teng C, Cai S, Jiang B, Wang Y, Meng H, Tao H, Nanoscale Res. Lett., 12, 1, 2017
  24. Wu LX, Yang HP, Guan YB, Yang MP, Wang H, Lu JX, Int. J. Electrochem. Sci., 12, 8963, 2017
  25. Lan DH, Gong YX, Tan NY, Wu SS, Shen J, Yao KC, Yi B, Au CT, Yin SF, Carbon, 127, 245, 2018
  26. Lan DH, Wang HT, Chen L, Au CT, Yin SF, Carbon, 100, 81, 2016
  27. Lan DH, Chen L, Au CT, Yin SF, Carbon, 93, 22, 2015
  28. Lan DH, Yang FM, Luo SL, Au CT, Yin SF, Carbon, 73, 351, 2014
  29. Yang ZZ, Zhao YN, He LN, RSC Adv., 1, 545, 2011
  30. Sun J, Cheng WG, Fan W, Wang YH, Meng ZY, Zhang SJ, Catal. Today, 148(3-4), 361, 2009
  31. Jadhav AH, Thorat GM, Lee K, Lim AC, Kang H, Seo JG, Catal. Today, 265, 56, 2016
  32. Sammelson RE, Kurth MJ, Chem. Rev., 101(1), 137, 2001
  33. Chen A, Zhang Y, Chen J, Chen L, Yu Y, J. Mater. Chem. A, 3, 9807, 2015
  34. Meng XL, Nie Y, Sun J, Cheng WG, Wang JQ, He HY, Zhang SJ, Green Chem., 16, 2771, 2014
  35. Talapaneni SN, Buyukcakir O, Je SH, Srinivasan S, Seo Y, Polychronopoulou K, Coskun A, Chem. Mater., 27, 6818, 2015
  36. Roeser J, Kailasam K, Thomas A, ChemSusChem, 5, 1793, 2012
  37. Skelton R, Dubois F, Zenobi R, Anal. Chem., 72, 1707, 2000
  38. Rangel-Vazquez NA, Sanchez-Lopez C, Felix FR, Polimeros, 24, 453, 2014
  39. Mathers NJ, Xu Z, Geoderma, 114, 19, 2003
  40. Ochiai B, Endo T, Prog. Polym. Sci, 30, 183, 2005
  41. Tomalia DA, Swanson DR, Huang B, Svenson S, Reyna LA, Michael A, DeMattei CR, Heinzelmann JR, US Patent, 0298006A1 (2007).
  42. Roshan KR, Kim BM, Kathalikkattil AC, Tharun J, Won YS, Park DW, Chem. Commun., 50, 13664, 2014