화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.69, 387-396, January, 2019
DOI10.1016/j.jiec.2018.09.047  Export Citation
Fiber-polyquaterniums@Cu(I) as recyclable polymer-supported copper complex catalysts for alkyne coupling and cycloaddition reactions
Qianqian Hu1, 2, Xian-Lei Shi1, 3, †, Yongju Chen1, Feng Wang1, 3, Yujing Weng1, and Peigao Duan1, 3, †
  • 1Henan Polytechnic University, Jiaozuo, Henan 454003, PR China
  • 2Department of Pharmacy, School of Medicine, Henan Polytechnic University, Jiaozuo, Henan 454003, PR China
  • 3Henan Key Laboratory of Coal Green Conversion, Henan Polytechnic University, Jiaozuo, Henan 454003, PR China
E-mail:,
Herein, a newly designed and synthesized fiber-supported polyquaterniums@Cu(I) served as efficient and recyclable polymer-supported copper complex catalysts for alkyne coupling and cycloaddition reactions, is reported. The fiber-supported copper complex catalyst was prepared systematically from commercially available polyacrylonitrile fiber, and characterized detailedly by elemental analysis, FTIR spectroscopy, mechanical properties, and SEM during both of the preparation and utilization processes. Moreover, the fiber-supported polyquaterniums@Cu(I) has been verified to possess high catalytic activities for the homocoupling of terminal alkyne in ethyl acetate (10 samples yields 83-99%, 10 cycles from 98% to 95%), A3 coupling of alkyne, aldehyde and amine in toluene (10 samples yields 81-94%, 10 cycles from 94% to 90%), and click chemistry of CuAAC reactions in water (10 samples yields 82-99%, 21 cycles from 97% to 96%). Furthermore, the newly developed fiber catalyst in spinning basket reactor displayed excellent stability and recyclability, and the concise and effective gram-scalable operation has extensive application prospect on chemical productions.
Keywords:Supported catalyst;Fiber catalyst;Alkynes;Applicability;Recyclability
  1. Rothenberg G, Catalysis: Concepts and Green Applications, Second, Revised and Enlarged Edition, Wiley-VCH, p.1 2017.
  2. Afewerki S, Cordova A, Chem. Rev., 116(22), 13512 (2016)
  3. Tomioka K, Shioiri T, Sajiki H, New Horizons of Process Chemistry: Scalable Reactions and Technologies, Springer, Singapore, p.1 2017.
  4. Hagen J, Industrial Catalysis: A Practical Approach, Third Completely Revised and Enlarged Edition, Wiley-VCH, Weinheim, Germany, p.1 2015.
  5. Munnik P, de Jongh PE, de Jong KP, Chem. Rev., 115(14), 6687 (2015)
  6. Kaftan A, Schonweiz A, Nikiforidis I, Hieringer W, Dyballa KM, Franke R, Gorling A, Libuda J, Wasserscheid P, Laurin M, Haumann M, J. Catal., 321, 32 (2015)
  7. Zhang Y, Riduan SN, Chem. Soc. Rev., 41, 2083 (2012)
  8. Kallitsakis M, Loukopoulos E, Abdul-Sada A, Tizzard GJ, Coles SJ, Kostakis GE, Lykakis IN, Adv. Synth. Catal., 359, 138 (2017)
  9. Doustkhah E, Heidarizadeh M, Rostamnia S, Hassankhani A, Kazemi B, Liu X, Mater. Lett., 216, 139 (2018)
  10. Nasir Baig RB, Varma RS, Green Chem., 15, 1839 (2013)
  11. Zhao YJ, Guo ZY, Zhang HJ, Peng B, Xu YX, Wang Y, Zhang J, Xu Y, Wang SP, Ma XB, J. Catal., 357, 223 (2018)
  12. Dong X, Ma X, Xu H, Ge Q, Catal. Sci. Technol., 6, 4151 (2016)
  13. Hosseini HG, Doustkhah E, Kirillova MV, Rostamnia S, Mahmoudi G, Kirillov AM, Appl. Catal. A: Gen., 548, 96 (2017)
  14. Alonso F, Arroyo A, Martin-Garcia I, Moglie Y, Adv. Synth. Catal., 357, 3549 (2015)
  15. Li GN, Vassilev P, Sanchez-Sanchez M, Lercher JA, Hensen EJM, Pidko EA, J. Catal., 338, 305 (2016)
  16. Nia AS, Rana S, Dohler D, Noirfalise X, Belfiore A, Binder WH, Chem. Commun., 50, 15374 (2014)
  17. Reddy VH, Reddy YVR, Sridhar B, Reddy BVS, Adv. Synth. Catal., 358, 1088 (2016)
  18. Zhou J, Guo L, Guo X, Mao J, Zhang S, Green Chem., 12, 1835 (2010)
  19. Wang JJ, Chernavskii PA, Khodakov AY, Wang Y, J. Catal., 286, 51 (2012)
  20. Yadav A, Verma N, J. Ind. Eng. Chem., 67, 448 (2018)
  21. Yu B, Xie JN, Zhong CL, Li W, He LN, ACS Catal., 5, 3940 (2015)
  22. Kaboudin B, Mostafalu R, Yokomatsu T, Green Chem., 15, 2266 (2013)
  23. Ren J, Hao PP, Sun W, Shi RN, Liu SS, Chem. Eng. J., 328, 673 (2017)
  24. Su CY, Liu BH, Lin TH, Chi YM, Kei CC, Wang KW, Perng TP, J. Mater. Chem. A, 3, 18983 (2015)
  25. Dang GH, Lam HQ, Nguyen AT, Le DT, Truong T, Phan NTS, J. Catal., 337, 167 (2016)
  26. Sharma RK, Gaur R, Yadav M, Goswami A, Zboril R, Gawande MB, Sci. Rep., 8, 1901 (2018)
  27. Shi XL, Hu QQ, Wang F, Zhang WQ, Duan PG, J. Catal., 337, 233 (2016)
  28. Shi XL, Chen Y, Hu Q, Zhang W, Luo C, Duan P, J. Ind. Eng. Chem., 53, 134 (2017)
  29. Sirion U, Bae YJ, Lee BS, Chi DY, Synlett, 15, 2326 (2008)
  30. Li H, Yang M, Zhang X, Yan L, Li J, Qi Y, New J. Chem., 37, 1343 (2013)
  31. Shi XL, Xing X, Lin H, Zhang W, Adv. Synth. Catal., 356, 2349 (2014)
  32. Shi XL, Chen Y, Duan P, Zhang W, Hu Q, ACS Sustain. Chem. Eng., 6, 7119 (2018)
  33. Shi XL, Chen YJ, Hu Q, Wang F, Duan P, J. Ind. Eng. Chem., 60, 333 (2018)
  34. Trost BM, Masters JT, Chem. Soc. Rev., 45, 2212 (2016)
  35. Luo Z, Cetegen SA, Miao R, Jiang T, Chen SY, Jafari T, Zhang YS, Suib SL, J. Catal., 338, 94 (2016)
  36. Panthama N, Kanokmedhakul S, Kanokmedhakul K, J. Nat. Prod., 73, 1366 (2010)
  37. Zhang B, Wang Y, Yang SP, Zhou Y, Wu WB, Tang W, Zuo JP, Li Y, Yue JM, J. Am. Chem. Soc., 134(51), 20605 (2012)
  38. Lu Y, Yang Y, Sellinger A, Lu M, Huang J, Fan H, Haddad R, Lopez G, Burn AR, Sasaki DY, Shelnutt J, Brinker CJ, Nature, 410, 913 (2001)
  39. Yang Y, Lu YF, Lu MC, Huang JM, Haddad R, Xomeritakis G, Liu NG, Malanoski AP, Sturmayr D, Fan HY, Sasaki DY, Assink RA, Shelnutt JA, van Swol F, Lopez GP, Burns AR, Brinker CJ, J. Am. Chem. Soc., 125(5), 1269 (2003)
  40. Liu JZ, Lam JWY, Tang BZ, Chem. Rev., 109(11), 5799 (2009)
  41. Eisler S, Slepkov AD, Elliott E, Luu T, McDonald R, Hegmann FA, Tykwinski RR, J. Am. Chem. Soc., 127(8), 2666 (2005)
  42. Peshkov VA, Pereshivkoa OP, Van der Eycken EV, Chem. Soc. Rev., 41, 3790 (2012)
  43. Gao J, Song WQ, He LN, Yang ZZ, Dou XY, Chem. Commun., 48, 2024 (2014)
  44. Gallagher DA, Schrag A, CNS Drugs, 22, 563 (2008)
  45. Yamamoto Y, Hayashi H, Saigoku T, Nishiyama H, J. Am. Chem. Soc., 127(31), 10804 (2005)
  46. Cho EA, Jeong DH, Dindulkar SD, Jung SH, J. Ind. Eng. Chem., 59, 372 (2018)
  47. Tiwari VK, Mishra BB, Mishra KB, Mishra N, Singh AS, Chen X, Chem. Rev., 116(5), 3086 (2016)
  48. Alonso F, Moglie Y, Radivoy G, Accounts Chem. Res., 48, 2516 (2015)
  49. Jumde RP, Evangelisti C, Mandoli A, Scotti N, Psaro R, J. Catal., 324, 25 (2015)
  50. Kacprzak K, Skiera I, Piasecka M, Paryzek Z, Chem. Rev., 116(10), 5689 (2016)
  51. Glassford I, Teijaro CN, Daher SS, Weil A, Small MC, Redhu SK, Colussi DJ, Jacobson MA, Childers WE, Buttaro B, Nicholson AW, MacKerell AD, Cooperman BS, Andrade RB, J. Am. Chem. Soc., 138(9), 3136 (2016)