Revisiting the Knoevenagel condensations: A universal and flexible bis-ammoniated fiber catalyst for the mild synthesis of a,β-unsaturated compounds

Qianqian Hu; Xian-Lei Shi; Yongju Chen; Xuefeng Han; Peigao Duan; Wenqin Zhang

Journal of Industrial and Engineering Chemistry, Vol.54, 75-81, October, 2017

DOI10.1016/j.jiec.2017.05.020 Export Citation

Revisiting the Knoevenagel condensations: A universal and flexible bis-ammoniated fiber catalyst for the mild synthesis of a,β-unsaturated compounds

Qianqian Hu¹, Xian-Lei Shi^{1, 2, †}, Yongju Chen¹, Xuefeng Han¹, Peigao Duan¹, and Wenqin Zhang²

¹Henan Polytechnic University, Jiaozuo, Henan 454003, PR China
²Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, PR China

E-mail:

A universal fiber catalyst for the Knoevenagel condensations is presented. The detailed characterization by mechanical properties, elemental analysis, FTIR spectroscopy, and SEM confirmed the rangeability of the fiber catalyst during the full-course. Moreover, the mediated condensations proceeded smoothly with lower catalyst amount (1 mol%) in different solvents of varying polarities and the products were obtained in good to excellent yields (95-99%), and even with water as the solvent could also achieve a series of a,β-unsaturated compounds with nearly quantitative yields at room temperature. Furthermore, the catalyst exhibited excellent flexibility and could be easily recovered and recycled with prominent stability over 10 cycles, and the procedure was operationally convenient and effectively amenable to the gram scale on a simple fixed-bed reactor.

Keywords:Fiber catalyst;Knoevenagel condensations;Applicability;Recyclability;Fixed-bed reactor

[References]

Sheldon RA, Chem. Soc. Rev., 41, 1437 (2012)
Jackson WR, Campi EM, Hearn MTW, Green Chem., 18, 4140 (2016)
Munnik P, de Jongh PE, de Jong KP, Chem. Rev., 115(14), 6687 (2015)
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)
Minakata S, Komatsu M, Chem. Rev., 109(2), 711 (2009)
Schlogl R, Angew. Chem.-Int. Edit., 54, 3465 (2015)
Simon MO, Li CJ, Chem. Soc. Rev., 41, 1415 (2012)
Abdel-Mageed AM, Eckle S, Widmann D, Behm RJ, J. Catal., 335, 79 (2016)
Jang HS, Kim YH, Kim YO, Lee SM, Kim JW, Chung WJ, Lee YS, J. Ind. Eng. Chem., 20(1), 29 (2014)
Speybroeck VV, Hemelsoet K, Joos L, Waroquier M, Bell RG, Catlow CRA, Chem. Soc. Rev., 44, 7044 (2015)
Kainz QM, Reiser O, Acc. Chem. Res., 47, 667 (2014)
Yan Y, Miao J, Yang Z, Xiao FX, Yang HB, Liu B, Yang Y, Chem. Soc. Rev., 44, 3295 (2015)
Chughtai AH, Ahmad N, Younus HA, Laypkov A, Verpoort F, Chem. Soc. Rev., 44, 6804 (2015)
Sun LB, Liu XQ, Zhou HC, Chem. Soc. Rev., 44, 5092 (2015)
Shekouhy M, Moaddeli A, Khalafi-Nezhad A, J. Ind. Eng. Chem., 50, 41 (2017)
Mowry DT, J. Am. Chem. Soc., 67, 1050 (1945)
Garrabou X, Wicky BIM, Hilvert D, J. Am. Chem. Soc., 138(22), 6972 (2016)
Polander LE, Barlow S, Seifried BM, Marder SR, J. Org. Chem., 77, 9426 (2012)
Kudirka RA, Barfield RM, McFarland JM, Drake PM, Carlson A, Banas S, Zmolek W, Garofalo AW, Rabuka D, ACS Med. Chem. Lett., 7, 994 (2016)
Liang F, Pu YJ, Kurata T, Kido J, Nishide H, Polymer, 46(11), 3767 (2005)
Mitra AK, De A, Karchaudhuri N, Synth. Commun., 29, 2731 (1999)
Ryabukhin SV, Plaskon AS, Volochnyuk DM, Pipko SE, Shivanyuk AN, Tolmachev AA, J. Comb. Chem., 9, 1073 (2007)
Zhang Y, Xia CG, Appl. Catal. A: Gen., 366(1), 141 (2009)
Tangale NP, Sonar SK, Niphadkar PS, Joshi PN, J. Ind. Eng. Chem., 40, 128 (2016)
Panchenko VN, Matrosova MM, Jeon J, Jun JW, Timofeeva MN, Jhung SH, J. Catal., 316, 251 (2014)
Wach A, Drozdek M, Dudek B, Szneler E, Kustrowski P, Catal. Commun., 64, 52 (2015)
Elhamifar D, Kazempoor S, Karimi B, Catal. Sci. Technol., 6, 4318 (2016)
Wang X, Zhang L, Du L, Zhou Y, Wang J, Catal. Sci. Technol., 6, 460 (2016)
Li CJ, Green Chem., 18, 1836 (2016)
Giraud RJ, Williams PA, Sehgal A, Ponnusamy E, Phillips AK, Manley JB, ACS Sustain. Chem. Eng., 2, 2237 (2014)
Vatutsina OM, Soldatov VS, Sokolova VI, Johann J, Bissen M, Weissenbacher A, React. Funct. Polym., 67(3), 184 (2007)
Moroi G, Bilba D, Bilba N, Polym. Degrad. Stabil., 84, 207 (2004)
Li G, Xiao J, Zhang W, Green Chem., 13, 1828 (2011)
Li G, Xiao J, Zhang W, Green Chem., 14, 2234 (2012)
Shi XL, Xing X, Lin H, Zhang W, Adv. Synth. Catal., 356, 2349 (2014)
Shi XL, Hu QQ, Wang F, Zhang WQ, Duan PG, J. Catal., 337, 233 (2016)
Shi XL, Zhang M, Li Y, Zhang W, Green Chem., 15, 3438 (2013)
Shi XL, Zhang M, Lin H, Tao M, Li Y, Zhang W, Chem.-Asian J., 10, 752 (2015)
Cheng XQ, Yang HY, Tatarchuk BJ, Catal. Today, 273, 62 (2016)
Lopatin S, Mikenin P, Pisarev D, Baranov D, Zazhigalov S, Zagoruiko A, Chem. Eng. J., 282, 58 (2015)

[1] Sheldon RA, Chem. Soc. Rev., 41, 1437 (2012)

[2] Jackson WR, Campi EM, Hearn MTW, Green Chem., 18, 4140 (2016)

[3] Munnik P, de Jongh PE, de Jong KP, Chem. Rev., 115(14), 6687 (2015)

[4] 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)

[5] Minakata S, Komatsu M, Chem. Rev., 109(2), 711 (2009)

[6] Schlogl R, Angew. Chem.-Int. Edit., 54, 3465 (2015)

[7] Simon MO, Li CJ, Chem. Soc. Rev., 41, 1415 (2012)

[8] Abdel-Mageed AM, Eckle S, Widmann D, Behm RJ, J. Catal., 335, 79 (2016)

[9] Jang HS, Kim YH, Kim YO, Lee SM, Kim JW, Chung WJ, Lee YS, J. Ind. Eng. Chem., 20(1), 29 (2014)

[10] Speybroeck VV, Hemelsoet K, Joos L, Waroquier M, Bell RG, Catlow CRA, Chem. Soc. Rev., 44, 7044 (2015)

[11] Kainz QM, Reiser O, Acc. Chem. Res., 47, 667 (2014)

[12] Yan Y, Miao J, Yang Z, Xiao FX, Yang HB, Liu B, Yang Y, Chem. Soc. Rev., 44, 3295 (2015)

[13] Chughtai AH, Ahmad N, Younus HA, Laypkov A, Verpoort F, Chem. Soc. Rev., 44, 6804 (2015)

[14] Sun LB, Liu XQ, Zhou HC, Chem. Soc. Rev., 44, 5092 (2015)

[15] Shekouhy M, Moaddeli A, Khalafi-Nezhad A, J. Ind. Eng. Chem., 50, 41 (2017)

[16] Mowry DT, J. Am. Chem. Soc., 67, 1050 (1945)

[17] Garrabou X, Wicky BIM, Hilvert D, J. Am. Chem. Soc., 138(22), 6972 (2016)

[18] Polander LE, Barlow S, Seifried BM, Marder SR, J. Org. Chem., 77, 9426 (2012)

[19] Kudirka RA, Barfield RM, McFarland JM, Drake PM, Carlson A, Banas S, Zmolek W, Garofalo AW, Rabuka D, ACS Med. Chem. Lett., 7, 994 (2016)

[20] Liang F, Pu YJ, Kurata T, Kido J, Nishide H, Polymer, 46(11), 3767 (2005)

[21] Mitra AK, De A, Karchaudhuri N, Synth. Commun., 29, 2731 (1999)

[22] Ryabukhin SV, Plaskon AS, Volochnyuk DM, Pipko SE, Shivanyuk AN, Tolmachev AA, J. Comb. Chem., 9, 1073 (2007)

[23] Zhang Y, Xia CG, Appl. Catal. A: Gen., 366(1), 141 (2009)

[24] Tangale NP, Sonar SK, Niphadkar PS, Joshi PN, J. Ind. Eng. Chem., 40, 128 (2016)

[25] Panchenko VN, Matrosova MM, Jeon J, Jun JW, Timofeeva MN, Jhung SH, J. Catal., 316, 251 (2014)

[26] Wach A, Drozdek M, Dudek B, Szneler E, Kustrowski P, Catal. Commun., 64, 52 (2015)

[27] Elhamifar D, Kazempoor S, Karimi B, Catal. Sci. Technol., 6, 4318 (2016)

[28] Wang X, Zhang L, Du L, Zhou Y, Wang J, Catal. Sci. Technol., 6, 460 (2016)

[29] Li CJ, Green Chem., 18, 1836 (2016)

[30] Giraud RJ, Williams PA, Sehgal A, Ponnusamy E, Phillips AK, Manley JB, ACS Sustain. Chem. Eng., 2, 2237 (2014)

[31] Vatutsina OM, Soldatov VS, Sokolova VI, Johann J, Bissen M, Weissenbacher A, React. Funct. Polym., 67(3), 184 (2007)

[32] Moroi G, Bilba D, Bilba N, Polym. Degrad. Stabil., 84, 207 (2004)

[33] Li G, Xiao J, Zhang W, Green Chem., 13, 1828 (2011)

[34] Li G, Xiao J, Zhang W, Green Chem., 14, 2234 (2012)

[35] Shi XL, Xing X, Lin H, Zhang W, Adv. Synth. Catal., 356, 2349 (2014)

[36] Shi XL, Hu QQ, Wang F, Zhang WQ, Duan PG, J. Catal., 337, 233 (2016)

[37] Shi XL, Zhang M, Li Y, Zhang W, Green Chem., 15, 3438 (2013)

[38] Shi XL, Zhang M, Lin H, Tao M, Li Y, Zhang W, Chem.-Asian J., 10, 752 (2015)

[39] Cheng XQ, Yang HY, Tatarchuk BJ, Catal. Today, 273, 62 (2016)

[40] Lopatin S, Mikenin P, Pisarev D, Baranov D, Zazhigalov S, Zagoruiko A, Chem. Eng. J., 282, 58 (2015)