An efficient, recyclable and large-scalable fiber-supported Fe(III) catalytic system on a simple fixed-bed reactor verified in the Biginelli reactions

Xian-Lei Shi; Yongju Chen; Qianqian Hu; Feng Wang; Peigao Duan

Journal of Industrial and Engineering Chemistry, Vol.60, 333-340, April, 2018

DOI10.1016/j.jiec.2017.11.019 Export Citation

An efficient, recyclable and large-scalable fiber-supported Fe(III) catalytic system on a simple fixed-bed reactor verified in the Biginelli reactions

Xian-Lei Shi^†, Yongju Chen, Qianqian Hu¹, Feng Wang, and Peigao Duan^†

College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, Henan 454003, PR China
¹Department of Pharmacy, School of Medicine, Henan Polytechnic University, Jiaozuo, Henan 454003, PR China

E-mail:,

An efficient, recyclable and large-scalable fiber-supported Fe(III) catalytic system verifed in the one-pot multicomponent Biginelli reactions, is presented. The fiber catalyst was prepared conveniently from commercially available polyacrylonitrile fiber according to a simple two-step procedure by amination and chelation in water, and characterized detailedly with ICP analysis, morphology, mechanical properties, elemental analysis, FTIR spectroscopy, and SEM during the modification and utilization processes. Moreover, the = fiber catalyst-mediated reactions showed broad applicability and proceeded smoothly to afford a series of substituted 3,4-dihydropyrimidin-2-(1H)-ones/-thiones (yields 81-94%) in ethanol under mild conditions. Furthermore, the newly developed fiber catalyst held high strength, good flexibility and exhibited excellent stability and recyclability (over 10 cycles), and the procedure was operationally concise and effectively amenable to the gram-scale on a simple fixed-bed reactor with potential industrialization prospect.

Keywords:Fiber catalyst;Supported-iron catalyst;Biginelli reaction;Recyclability;Fixed-bed reactor

[References]

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[Referenced By]

[1] Tomioka K, Shioiri T, Sajiki H, Scalable Reactions and Technologies, Springer, Singapore, pp.1 (2017).

[2] 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)

[3] Lup ANK, Abnisa F, Daud WMAW, Aroua MK, J. Ind. Eng. Chem., 56, 1 (2017)

[4] Das S, Asefa T, ACS Catal., 1, 502 (2011)

[5] Gan PP, Li SFY, Chem. Eng. J., 229, 351 (2013)

[6] Stathi P, Deligiannakis Y, Avgouropoulos G, Louloudi M, Appl. Catal. A: Gen., 498, 176 (2015)

[7] Rey A, Hungria AB, Duran-Valle CJ, Faraldos M, Bahamonde A, Casas JA, Rodriguez JJ, Appl. Catal. B: Environ., 181, 249 (2016)

[8] Liu X, Yin H, Lin A, Guo Z, J. Environ. Chem. Eng., 5, 870 (2017)

[9] Galvis HMT, Bitter JH, Khare CB, Ruitenbeek M, Dugulan AI, de Jong KP, Science, 335(6070), 835 (2012)

[10] Xu JD, Chang ZY, Zhu KT, Weng XF, Weng WZ, Zheng YP, Huang CJ, Wan HL, Appl. Catal. A: Gen., 514, 103 (2016)

[11] Sarioglan A, Durak-Cetin Y, Okutan H, Akgun F, Chem. Eng. Sci., 171, 440 (2017)

[12] Li CM, Sayaka I, Chisato F, Fujimoto K, Appl. Catal. A: Gen., 509, 123 (2016)

[13] Shi Q, Li A, Qing Z, Li Y, J. Ind. Eng. Chem., 25, 308 (2015)

[14] Wu J, Qin L, Wang C, Lv B, Wang L, Chena J, Xu Y, RSC Adv., 6, 38356 (2016)

[15] Biginelli P, Ber. Dtsch. Chem. Ges., 24, 1317 (1891)

[16] Alvim HGO, Lima TB, de Oliveira AL, de Oliveira HCB, Silva FM, Gozzo FC, Souza RY, da Silva WA, Neto BAD, J. Org. Chem., 79, 3383 (2014)

[17] Gasse C, Douguet D, Huteau V, Marchal G, Munier-Lehmanna H, Pochet S, Bioorg. Med. Chem., 16, 6075 (2008)

[18] Lin R, Johnson SG, Connolly PJ, Wetter SK, Binnun E, Hughes TV, Murray WV, Pandey NB, Moreno-Mazza SJ, Adams M, Fuentes-Pesquera AR, Middleton SA, Bioorg. Med. Chem. Lett., 19, 2333 (2009)

[19] Mondal J, Sen T, Bhaumik A, Dalton Trans., 41, 6173 (2012)

[20] Elhamifar D, Nasr-Esfahani M, Karimi B, Moshkelgosha R, Shabani A, ChemCatChem, 6, 2593 (2014)

[21] Jain SL, Prasad VVDN, Sain B, Catal. Commun., 9, 499 (2008)

[22] Kouachi K, Lafaye G, Pronier S, Bennini L, Menad S, J. Mol. Catal. A-Chem., 395, 210 (2014)

[23] Shen P, Xu M, Yin D, Xie S, Zhou C, Li F, Catal. Commun., 77, 18 (2016)

[24] Heirati SZD, Shirini F, Shojaei AF, RSC Adv., 6, 67072 (2016)

[25] Kolvari E, Koukabi N, Armandpour O, Tetrahedron, 70, 1383 (2014)

[26] Safari J, Zarnegar Z, RSC Adv., 3, 17962 (2013)

[27] Rostamnia S, Morsali A, RSC Adv., 4, 10514 (2014)

[28] Wang K, Jia Z, Yang X, Wang L, Gu Y, Tan B, J. Catal., 348, 168 (2017)

[29] Shi XL, Yang H, Tao M, Zhang W, RSC Adv., 3, 3939 (2013)

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

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

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

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

[34] Shi XL, Chen Y, Hu Q, Zhang W, Luo C, Duan P, J. Ind. Eng. Chem., 53, 134 (2017)

[35] Lu J, Bai Y, Synthesis, 4, 466 (2002)

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

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

[38] Clark JH, Macquarrie DJ, Sherwood J, Chem. Eur. J., 19, 5174 (2013)