Xin Wang, Sanguan Ma, Bihua Chen, Jingshun Zhang, Yongya Zhang, Guohua Gao. Swelling acidic poly(ionic liquid)s as efficient catalysts for the esterification of cyclohexene and formic acid. Green Energy&Environment, 2020, 5(2): 138-146. doi: 10.1016/j.gee.2020.04.013
Citation: Xin Wang, Sanguan Ma, Bihua Chen, Jingshun Zhang, Yongya Zhang, Guohua Gao. Swelling acidic poly(ionic liquid)s as efficient catalysts for the esterification of cyclohexene and formic acid. Green Energy&Environment, 2020, 5(2): 138-146. doi: 10.1016/j.gee.2020.04.013

Swelling acidic poly(ionic liquid)s as efficient catalysts for the esterification of cyclohexene and formic acid

doi: 10.1016/j.gee.2020.04.013
  • Acidic poly(ionic liquid)s (PILs) with swelling ability were synthesized by free radical copolymerization of N-vinylimidazolium ionic liquids, divinylbenzene (DVB) and sodium acrylate (NaAA), and further acidification by sulfuric acid. The swelling ability of acidic PILs was greatly affected by cross-linker content and chain length of 3-alkyl-substituents on imidazolium. Cross-linked network structures could be observed from the cryogenic scanning electron microscopy (cryo-SEM) images of the swollen acidic PILs in formic acid. Acidic PILs with network structures in swollen state exhibited excellent activities in the esterification of cyclohexene and formic acid, and the catalytic activities were in positive correlation with their swelling abilities. Acidic PIL with 3-octyl-substituent and 2.5 mol% DVB (PIL-C8-2.5DVB-HSO4) had the highest swelling ability in formic acid and exhibited comparable catalytic activities with homogeneous catalysts such as sulfuric acid and p-toluenesulfonic acid.

     

  • Xin Wang and Sanguan Ma contributed equally to this work.
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  • [1]
    H. Shen, X. Lu, K.Z. Jiang, K.F. Yang, Y. Lu, Z.J. Zheng, G.Q. Lai, L.W. Xu, Tetrahedron 68 (2012) 8916-8923.
    [2]
    K. Niknam, M.A. Zolfigol, D. Saberi, M. Khonbazi, Chin. J. Chem. 27 (2009) 1548-1552.
    [3]
    Y. Gu, F. Shi, Y. Deng, J. Mol. Catal. A: Chem. 212 (2004) 71-75.
    [4]
    G. Zheng, X. Li, Synth. Commun. 49 (2019) 933-941.
    [5]
    G.D. Yadav, P.K. Goel, Green Chem. 2 (2000) 71-77.
    [6]
    F. Steyer, K. Sundmacher, Ind. Eng. Chem. Res. 46 (2007) 1099-1104.
    [7]
    B. Lu, Z. Wu, L. Ma, X. Yuan, J. Taiwan Inst. Chem. Eng. 88 (2018) 1-7.
    [8]
    D.R. Cova, C.W. Roos, Ind. Eng. Chem. Proc. Des. Dev. 7 (1968) 301-302.
    [9]
    L.O. Raether, A.J. Lauck, H.R. Gamrath, Ind. Eng. Chem. Prod. Res. Dev. 2 (1963) 133-138.
    [10]
    B. Saha, M.M. Sharma, React. Funct. Polym. 28 (1996) 263-278.
    [11]
    W. Xue, H. Zhao, J. Yao, F. Li, Y. Wang, Chin. J. Catal. 37 (2016) 769-777.
    [12]
    W. Qian, J. Texter, F. Yan, Chem. Soc. Rev. 46 (2017) 1124-1159.
    [13]
    B. Wang, L. Qin, T. Mu, Z. Xue, G. Gao, Chem. Rev. 117 (2017) 7113-7131.
    [14]
    S. Ren, Y. Hou, K. Zhang, W. Wu, Green Energy Environ. 3 (2018) 179-190.
    [15]
    Z. Chen, J. Zeng, J. Di, D. Zhao, M. Ji, J. Xia, H. Li, Green Energy Environ. 2 (2017) 124-133.
    [16]
    Y. Zhang, X. Deng, L. Zhang, B. Chen, T. Ding, B. Ni, G. Gao, ACS. Appl. Mater. Interfaces 11 (2019) 14347-14353.
    [17]
    F. Liu, L. Wang, Q. Sun, L. Zhu, X. Meng, F.S. Xiao, J. Am. Chem. Soc. 134 (2012) 16948−16950.
    [18]
    L. Qin, B. Wang, Y. Zhang, L. Chen, G. Gao, Chem. Commun. 53 (2017) 3785−3788.
    [19]
    S. Hayano, K. Ota, H.T. Ban, Polym. Chem. 9 (2018) 948−960.
    [20]
    C. Gao, G. Chen, X. Wang, J. Li, Y. Zhou, J. Wang, Chem. Commun. 51 (2015) 4969−4972.
    [21]
    Z. Guo, Q. Jiang, Y. Shi, J. Li, X. Yang, W. Hou, Y. Zhou, J. Wang, ACS Catal. 7 (2017) 6770−6780.
    [22]
    A. Dani, E. Groppo, C. Barolo, J.G. Vitillo, S. Bordiga, J. Mater. Chem. A 3 (2015) 8508−8518.
    [23]
    Y. Xie, Q. Sun, Y. Fu, L. Song, J. Liang, X. Xu, H. Wang, J. Li, S. Tu, X. Lu, J. Li, J. Mater. Chem. A 5 (2017) 25594-25600.
    [24]
    Y.F. Wang, B.H. Xu, Y.R. Du, S.J. Zhang, Mol. Catal. 457 (2018) 59-66.
    [25]
    A.S. Amarasekara, Chem. Rev. 116 (2016) 6133-6183.
    [26]
    J. Yuan, D. Mecerreyes, M. Antonietti, Prog. Polym. Sci. 38 (2013) 1009-1036.
    [27]
    Z. Wu, C. Chen, Q. Guo, B. Li, Y. Que, L. Wang, H. Wan, G. Guan, Fuel 184 (2016) 128-135.
    [28]
    D.J. Tao, F. Liu, L. Wang, L. Jiang, Appl. Catal. A: Gen. 564 (2018) 56-63.
    [29]
    H. Gao, Y. Zhou, X. Sheng, S. Zhao, C. Zhang, J. Fang, B. Wang, Appl. Catal. A: Gen. 552 (2018) 138-146.
    [30]
    Y. Zhang, B. Wang, E. H. M. Elageed, L. Qin, B. Ni, X. Liu, G. Gao, ACS Macro Lett. 5 (2016) 435-438.
    [31]
    Y. Zhang, Y. Zhang, B. Chen, L. Qin, G. Gao, ChemistrySelect 2 (2017) 9443-9449.
    [32]
    Y. Zhang, B. Chen, Y. Zhang, L. Qin, B. Liu, B. Ni, G. Gao, Green Chem. 20 (2018) 1594-1601.
    [33]
    H. Zhou, J. Song, X. Kang, J. Hu, Y. Yang, H. Fan, Q. Meng, B. Han, RSC Adv. 5 (2015) 15267-15273.
    [34]
    D. Zeng, S. Liu, W. Gong, G. Wang, J. Qiu, H. Chen, Appl. Catal. A: Gen. 469 (2014) 284-289.
    [35]
    F. Liu, W. Kong, C. Qi, L. Zhu, F.S. Xiao, ACS Catal. 2 (2012) 565-572.
    [36]
    H. Tokuda, K. Hayamizu, K. Ishii, M.A.B.H Susan, M. Watanabe, J. Phys. Chem. B. 109 (2005) 6103-6110.
    [37]
    J. Yang, L. Fang, T. Tan, J. Appl. Polym. Sci. 102 (2006) 550-557.
    [38]
    W.J. Horne, M.A. Andrews, K.L. Terrill, S.S. Hayward, J. Marshall, K.A. Belmore, M.S. Shannon, J.E. Bara, ACS. Appl. Mater. Interfaces 7 (2015) 8979-8983.
    [39]
    G.A. Becht, M. Sofos, S. Seifert, M.A. Firestone, Macromolecules 44 (2011) 1421-1428.
    [40]
    T. Ono, T. Sugimoto, S. Shinkai, K. Sada. Adv. Funct. Mater. 18 (2008) 3936-3940.
    [41]
    H.P. Liang, A. Acharjya, D.A. Anito, S. Vogl, T.X. Wang, A. Thomas, B.H. Han, ACS Catal. 9 (2019) 3959-3968.
    [42]
    J. Wu, Y. Gao, W. Zhang, A. Tang, Y. Tan, Y. Men, B. Tang, Chem. Eng. Process. 93 (2015) 61-65.
    [43]
    Q. Sun, Z. Dai, X. Meng, L. Wang, F.S. Xiao, ACS Catal. 5 (2015) 4556-4567.
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