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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 4: 1241 - 1270

DOI: https://doi.org/10.6023/cjoc202209003

REVIEWS

Research Progress of Functional Polyacrylonitrile Fiber in Promoting Organic Reaction

  • Linsheng Bai ,
  • Peng Hong ,
  • Anguo Ying
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  • School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
* Corresponding author.

Received date: 2022-09-03

  Revised date: 2022-10-13

  Online published: 2022-11-15

Supported by

National Natural Science Foundation of China(21978154); National Natural Science Foundation of China(22278243)

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Abstract

Polyacrylonitrile fiber (PANF) has excellent mechanical strength, chemical resistance and good thermal stability, and it is easy to be modified. Physical modification can be achieved by adding additives or functional monomers into polyacrylonitrile spinning dope or heat treating PANF. Chemical surface modification of PANF includes amination, amidation, oxidation, reduction, cross-linking, hydrolysis, acid treatment and chemical grafting. Surface modification brings many special functional groups to PANF, which can be further used as carriers of organic compounds, organic ligands, enzymes and transition metals. Functionalized PANF with catalytic activity was obtained by loading the catalytic active sites. In recent years, functional PANF has been widely used as heterogeneous catalyst in the field of organic synthesis. The research achievements and progress of functional PANF catalyst in organic reactions are reviewed, including condensation reaction, coupling reaction, addition reaction, redox reaction and multi-component one-pot reaction. The synthesis and structure of fiber catalyst are introduced, the catalytic performance is discussed, and the possible catalytic mechanism is analyzed, which pave the way for the development of better functional PANF.

Key words： polyacrylonitrile fiber; carrier; modification; functionalization; catalysis; organic synthesis

Cite this article

Linsheng Bai , Peng Hong , Anguo Ying . Research Progress of Functional Polyacrylonitrile Fiber in Promoting Organic Reaction[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1241 -1270 . DOI: 10.6023/cjoc202209003

References

[1]
Xu, G.; Wang, L.; Li, M. M.; Tao, M. L.; Zhang, W. Q. Green Chem. 2017, 19, 5818.
[2]
Cole-Hamilton, D. J. Science 2003, 299, 1702.
[3]
Wang, X. L.; Yang, M.; Zhu, L. J.; Zhu, X. N.; Wang, S. R. J. Fuel Chem. Technol. 2020, 48, 456.
[4]
Gogoi, P.; Dutta, A. K.; Saikia, S.; Borah, R. Appl. Catal., A 2016, 523, 321.
[5]
Schulze, J. S.; Migenda, J.; Becker, M.; Schuler, S. M.; Wende, R. C.; Schreiner, P. R.; Smarsly, B. M. J. Mater. Chem. A 2020, 8, 4107.
[6]
Liu, G. H.; Zong, Z. M.; Liu, Z. Q.; Liu, F. J.; Zhang, Y. Y.; Wei, X. Y. Fuel Process Technol. 2018, 179, 114.
[7]
Pan, S.; Yan, S.; Osako, T.; Uozumi, Y. ACS Sustainable Chem. Eng. 2017, 5, 10722.
[8]
Baran, T. J. Mol. Struct. 2017, 1141, 535.
[9]
Lu, X. T.; Li, S. N.; Wang, L. M.; Huang, S. J.; Liu, Z. Q.; Liu, Y. J.; Ying, A. G. Fuel 2022, 310, 122318.
[10]
Badoga, S.; Sohani, K.; Zheng, Y.; Dalai, A. K. Fuel Process. Technol. 2017, 168, 140.
[11]
McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
[12]
Zheng, Y. W.; Zhao, W.; Jia, D.; Cui, L.; Liu, J. Q. Chem. Eng. J. 2019, 364, 70.
[13]
Zhang, Y. Y.; Sun, Y. L.; Peng, L. F.; Yang, J. Q.; Jia, H. H.; Zhang, Z. R.; Shan, B.; Xie, J. Energy Storage Mater. 2019, 21, 287.
[14]
Xiao, J.; Wang, L.; Ran, J. R.; Zhao, J. Y.; Tao, M. L.; Zhang, W. Q. React. Funct. Polym. 2020, 146, 104394.
[15]
Xu, G.; Xu, W. S.; Tian, S.; Zheng, W. J.; Yang, T.; Wu, Y. X.; Xiong, Q. Z.; Kalkhajeh, Y. K.; Gao, H. J. Chem. Eng. J. 2021, 416, 127889.
[16]
Xing, X. L.; Yang, H. X.; Tao, M. L.; Zhang, W. Q. J. Hazard. Mater. 2015, 297, 207.
[17]
Li, Y.; Abedalwafa, M. A.; Ni, C. F.; Sanbhal, N.; Wang, L. React. Funct. Polym. 2019, 138, 18.
[18]
Hong, P.; Wang, L. M.; Bai, L. S.; Liu, Z. Q.; Liu, Y. J.; Yang J. G., Ying, A. G. Dyes Pigm. 2022, 197, 109902.
[19]
Liu, X. M.; Li, M. Y.; Han, G. Y.; Dong, J. H. Electrochim. Acta 2010, 55, 2983.
[20]
Shi, X. L.; Xing, X. L.; Lin, H. K.; Zhang, W. Q. Adv. Synth. Catal. 2014, 356, 2349.
[21]
Xu, C. Z.; Du, J. G.; Ma, L. C.; Li, G. W.; Tao, M. L.; Zhang, W. Q. Tetrahedron 2013, 69, 4749.
[22]
Liu, R. X.; Zhang, B. W.; Tang, H. X. React. Funct. Polym. 1999, 39, 71.
[23]
Moroi, G.; Bilba, D.; Bilba, N. Polym. Degrad. Stab. 2004, 84, 207.
[24]
Xiao, J.; Xu, G.; Wang, L.; Li, P. Y.; Zhang, W. Q.; Ma, N.; Tao, M. L. J. Ind. Eng. Chem. 2019, 77, 65.
[25]
Li, G. W.; Xiao, J.; Zhang, W. Q. Dyes Pigm. 2012, 92, 1091.
[26]
Zheng, L. S.; Li, P. Y.; Tao, M. L.; Zhang, W. Q. Catal. Commun. 2019, 118, 19.
[27]
Polander, L. E.; Barlow, S.; Seifried, B. M.; Marder, S. R. J. Org. Chem. 2012, 77, 9426.
[28]
Kudirka, R. A.; Barfield, R. M.; McFarland, J. M.; Drake, P. M.; Carlson, A.; Ban?as, S.; Zmolek, W.; Garofalo, A. W.; Rabuka, D. ACS Med. Chem. Lett. 2016, 7, 994.
[29]
Liang, F. S.; Pu, Y. J.; Kurata, T.; Kido, J. J.; Nishide, H. Polymer 2005, 46, 3767.
[30]
Zhu, H.; Xu, G.; Du, H. M.; Zhang, C. L.; Ma, N.; Zhang, W. Q. J. Catal. 2019, 374, 217.
[31]
Li, G. W.; Xiao, J.; Zhang, W. Q. Chin. Chem. Lett. 2013, 24, 52.
[32]
Li, G. W.; Xiao, J.; Zhang, W. Q. Green Chem. 2011, 13, 1828.
[33]
Li, G. W.; Xiao, J.; Zhang, W. Q. Green Chem. 2012, 14, 2234.
[34]
Xu, G.; Jin, M. C.; Kalkhajeh, Y. K.; Wang, L.; Tao, M. L.; Zhang, W. Q. J. Cleaner Prod. 2019, 231, 77.
[35]
Hu, Q. Q.; Shi, X. L.; Chen, Y. J.; Han, X. F.; Duan, P. G.; Zhang, W. Q. J. Ind. Eng. Chem. 2017, 54, 75.
[36]
Li, P. Y.; Liu, Y. Y.; Ma, N.; Zhang, W. Q. Catal. Lett. 2018, 148, 813.
[37]
Li, P. Y.; Mi, L. W.; Liu, Y. Y.; Zhang, W. Q.; Shi, X. L. J. Ind. Eng. Chem. 2020, 81, 323.
[38]
Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. 1985, 24, 1.
[39]
Liu, B. Y.; Zhao, D. S.; Xu, D. Q.; Xu, Z. Y. Chem. Res. Chin. Univ. 2007, 23, 549.
[40]
Xiao, J.; Li, G. W.; Zhang, W. Q. Chem. Res. Chin. Univ. 2013, 29, 256.
[41]
Zhu, H.; Zhang, C. L.; Ma, N.; Tao, M. L.; Zhang, W. Q. Appl. Catal., A 2020, 608, 117842.
[42]
Wang, L.; Xu, G.; Xiao, J.; Tao, M. L.; Zhang, W. Q. Ind. Eng. Chem. Res. 2019, 58, 12401.
[43]
Li, P. Y.; Liu, Y. Y.; Wang, L.; Tao, M. L.; Zhang, W. Q. J. Appl. Polym. Sci. 2018, 135, 45992.
[44]
Zhang, Z.; Wang, M.; Zhang, C. F.; Zhang, Z. X.; Lu, J. M.; Wang, F. Chem. Commun. 2015, 51, 9205.
[45]
Zhou, J. G.; Fang, J. J. Org. Chem. 2011, 76, 7730.
[46]
Modi, A.; Ali, W.; Mohanta, P. R.; Khatun, N.; Patel, B. K. ACS Sustainable Chem. Eng. 2015, 3, 2582.
[47]
Laha, J. K.; Patel, K. V.; Tummalapalli, K. S.; Dayal, N. Chem. Commun. 2016, 52, 10245.
[48]
De Vries, J. G. Can. J. Chem. 2001, 79, 1086.
[49]
Madasu, S. B.; Vekariya, N. A.; Kiran, M. H.; Gupta, B.; Islam, A.; Douglas, P. S.; Babu, K. R. Beilstein J. Org. Chem. 2012, 8, 1400.
[50]
Biffis, A.; Centomo, P.; Del Zotto, A.; Zecca, M. Chem. Rev. 2018, 118, 2249.
[51]
Jagtap, S. Catalysts 2017, 7, 267.
[52]
Mpungose, P. P.; Vundla, Z. P.; Maguire, G. E.; Friedrich, H. B. Molecules 2018, 23, 1676.
[53]
Xiao, J.; Wang, L.; Zhang, H. N.; Ma, N.; Tao, M. L.; Zhang, W. Q. Chem. Eng. Sci. 2022, 247, 117053.
[54]
Xiao, J.; Zhang, H. N.; Ejike, A. C.; Wang, L.; Tao, M. L.; Zhang, W. Q. React. Funct. Polym. 2021, 161, 104843.
[55]
Sruthi, P. R.; Anjali, S.; Varghese, N.; Anas, S. J. Organomet. Chem. 2020, 921, 121354.
[56]
Sruthi, P. R.; Sarika, V.; Suku, A.; Krishnan, A.; Anas, S. Inorg. Chim. Acta 2020, 502, 119305.
[57]
Xing, G. Y. Fibers Polym. 2016, 17, 194.
[58]
Shao, L. J.; Liu., J.; Ye, Y. H.; Zhang, X. M.; Qi, C. Z. Appl. Organomet. Chem. 2011, 25, 699.
[59]
Shao, L. J.; Qi, C. Z. Appl. Catal., A 2013, 468, 26.
[60]
Shao, L. J.; Qi, C. Z. Fibers Polym. 2014, 15, 2233.
[61]
Guo, L. P.; Bai, J.; Wang, J. Z.; Liang, H. O.; Li, C. P.; Sun, W. Y.; Meng, Q. R. J. Mol. Catal. A: Chem. 2015, 400, 95.
[62]
Han, F. S. Chem. Soc. Rev. 2013, 42, 5270.
[63]
Zhong, L.; Chokkalingam, A.; Cha, W. S.; Lakhi, K. S.; Su, X. Y.; Lawrence, G.; Vinu, A. Catal. Today 2015, 243, 195.
[64]
Kundu, D.; Patra, A. K.; Sakamoto, J.; Uyama, H. React. Funct. Polym. 2014, 79, 8.
[65]
Marziale, A. N.; Jantke, D.; Faul, S. H.; Reiner, T.; Herdtweck, E.; Eppinger, J. Green Chem. 2011, 13, 169.
[66]
Yu, D. D.; Bai, J.; Wang, J. Z.; Li, C. P. J. Inorg. Organomet. Polym. Mater. 2016, 26, 914.
[67]
Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790.
[68]
Huo, X.; Liu, J.; Wang, B. D.; Zhang, H. L.; Yang, Z. Y.; She, X. G.; Xi, P. X. J. Mater. Chem. A 2013, 1, 651.
[69]
Hashmi, A. S. K. Pure Appl. Chem. 2010, 82, 657.
[70]
Jaimes, M. C. B.; Rominger, F.; Pereira, M. M.; Carrilho, R. M. B.; Carabineiro, S. A. C.; Hashmi, A. S. K. Chem. Commun. 2014, 50, 4937.
[71]
Cao, J.; Xu, G.; Li, P. Y.; Tao, M. L.; Zhang, W. Q. ACS Sustainable Chem. Eng. 2017, 5, 3438.
[72]
Cao, J.; Li, P. Y.; Xu, G.; Tao, M. L.; Ma, N.; Zhang, W. Q. Chem. Eng. J. 2018, 349, 456.
[73]
Hu, Q. Q.; Shi, X. L.; Chen, Y. J.; Wang, F.; Weng, Y. J.; Duan, P. G. J. Ind. Eng. Chem. 2019, 69, 387.
[74]
Shi, X. L.; Sun, B. Y.; Chen, Y. J.; Hu, Q. Q.; Li, P. Y.; Meng, Y. L.; Duan, P. G. J. Catal. 2019, 372, 321.
[75]
Trost, B. M.; Masters, J. T. Chem. Soc. Rev. 2016, 45, 2212.
[76]
Zhang, B.; Wang, Y.; Yang, S. P.; Zhou, Y.; Wu, W. B.; Tang, W.; Zuo, J. P.; Li, Y.; Yue, J. M. J. Am. Chem. Soc. 2012, 134, 20605.
[77]
Gholami, M.; Tykwinski, R. R. Chem. Rev. 2006, 106, 4997.
[78]
Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666.
[79]
Shi, X. L.; Hu, Q. Q.; Wang, F.; Zhang, W. Q.; Duan, P. G. J. Catal. 2016, 337, 233.
[80]
Zhang, C. L.; Zhu, H.; Gang, K. Y.; Tao, M. L.; Ma, N.; Zhang, W. Q. React. Funct. Polym. 2021, 160, 104831.
[81]
Cao, J.; Tian, H. Q. Chem.-Asian J. 2018, 13, 1561.
[82]
Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
[83]
Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 113, 623.
[84]
Toyota, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110.
[85]
Li, J. Z.; Ambroise, A.; Yang, S. I.; Diers, J. R.; Seth, J.; Wack, C. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Am. Chem. Soc. 1999, 121, 8927.
[86]
Strachan, J. P.; Gentemann, S.; Seth, J.; Kalsbeck, W. A.; Lindsey, J. S.; Holten, D.; Bocian, D. F. Inorg. Chem. 1998, 37, 1191.
[87]
Wang, W. S.; Shangguan, S. H.; Qiu, N.; Hu, C. Q.; Zhang, L.; Hu, Y. Z. Bioorg. Med. Chem. 2013, 21, 2879.
[88]
Fu, T. L.; Wang, I. J. Dyes Pigm. 2008, 76, 590.
[89]
Puterová, Z.; Romiszewski, J.; Mieczkowski, J.; Gorecka, E. Tetrahedron 2012, 68, 8172.
[90]
Narlawar, R.; Lane, J. R.; Doddareddy, M.; Lin, J.; Brussee, J.; IJzerman, A. P. J. Med. Chem. 2010, 53, 3028.
[91]
Li, P. Y.; Du, J. G.; Xie, Y. J.; Tao, M. L.; Zhang, W. Q. ACS Sustainable Chem. Eng. 2016, 4, 1139.
[92]
Du, J. G.; Shuai, B.; Tao, M. L.; Wang, G. W.; Zhang, W. Q. Green Chem. 2016, 18, 2625.
[93]
Yuan, X. Y.; Du, H. M.; Zhao, J. Y.; Chima, A. E.; Ma, N.; Tao, M. L.; Zhang, W. Q. Catal. Lett. 2021, 151, 832.
[94]
Song, Q. W.; Zhou, Z. H.; He, L. N. Green Chem. 2017, 19, 3707.
[95]
Lang, X. D.; He, L. N. Chem. Rec. 2016, 16, 1337.
[96]
Shi, X. L.; Chen, Y. J.; Duan, P. G.; Zhang, W. Q.; Hu, Q. Q. ACS Sustainable Chem. Eng. 2018, 6, 7119.
[97]
Geng, H.; Zhang, C. L.; Tao, M. L.; Ma, N.; Zhang, W. Q. J. CO2 Util. 2021, 49, 101559.
[98]
Li, P. Y.; Liu, Y. Y.; Mi, L. W.; Shi, X. L.; Duan, P. G.; Cao, J. L.; Zhang, W. Q. Catal. Today 2020, 355, 162.
[99]
Shi, X. L.; Chen, Y. J.; Hu, Q. Q.; Zhang, W. Q.; Luo, C. X.; Duan, P. G. J. Ind. Eng. Chem. 2017, 53, 134.
[100]
Liu, H.; Bai, J.; Wang, S.; Li, C. P.; Guo, L. P.; Liang, H. O.; Xu, T.; Sun, W. Y.; Li, H. Q. Colloids Surf., A 2014, 448, 154.
[101]
Du, J. G.; Xu, G.; Lin, H.; Wang, G. W.; Tao, M. L.; Zhang, W. Q. Green Chem. 2016, 18, 2726.
[102]
Arslan, O.; Eren, H.; Biyikli, N.; Uyar, T. ChemistrySelect 2017, 2, 8790.
[103]
Wang, M. L.; Jiang, T. T.; Lu, Y.; Liu, H. J.; Chen, Y. J. Mater. Chem. A 2013, 1, 5923.
[104]
Xiao, J.; Wu, Z. Y.; Li, K. L.; Zhao, Z. B.; Liu, C. Y. RSC Adv. 2022, 12, 1051.
[105]
Shi, X. L.; Chen, Y. J.; Hu, Q. Q.; Wang, F.; Duan, P. G. J. Ind. Eng. Chem. 2018, 60, 333.
[106]
Zhen, Y. Z.; Lin, H. K.; Wang, S. Y.; Tao, M. L. RSC Adv. 2014, 4, 26122.
[107]
Li, P. Y.; Yang, Y.; Mi, L. W.; Gao, K.; Tao, M. L.; Chen, W. H. Catal. Lett. 2021, 151, 2056.
[108]
Xie, Y. J.; Liu, X. X.; Tao, M. L. J. Chem. Educ. 2016, 93, 2074.
[109]
Shi, X. L.; Lin, H. K.; Li, P. Y.; Zhang, W. Q. ChemCatChem 2014, 6, 2947.
[110]
Xiao, J.; Wang, L.; Ran, J. R.; Zhao, J. Y.; Ma, N.; Tao, M. L.; Zhang, W. Q. J. Cleaner Prod. 2020, 274, 122473.
[111]
Xu, G.; Cao, J.; Zhao, Y. L.; Zheng, L. S.; Tao, M. L.; Zhang, W. Q. Chem.-Asian J. 2017, 12, 2565.
[112]
Li, P. Y.; Liu, Y. Y.; Cao, J.; Tao, M. L.; Zhang, W. Q. ChemCatChem 2017, 9, 3725.
[113]
Shi, X. L.; Sun, B. Y.; Hu, Q. Q.; Liu, K.; Li, P. Y.; Liu, B. Z. Chem. Eng. J. 2020, 395, 125084.
[114]
Shi, X. L.; Sun, B. Y.; Hu, Q. Q.; Chen, Y. J.; Duan, P. G. Green Chem. 2019, 21, 3573.
[115]
Wu, J.; Du, X. L.; Ma, J.; Zhang, Y. P.; Shi, Q. C.; Luo, L. J.; Song, B. A.; Yang, S.; Hu, D. Y. Green Chem. 2014, 16, 3210.
[116]
Chen, J. X.; Su, W. K.; Wu, H. Y.; Liu, M. C.; Jin, C. Green Chem. 2007, 9, 972.
[117]
Wu, Z. C.; Wu, Q.; Chen, M.; Tao, T. X. Asian J. Chem. 2013, 25, 5783.
[118]
Bergbreiter, D. E.; Osburn, P. L.; Frels, J. D. J. Am. Chem. Soc. 2001, 123, 5783.
[119]
Hwang, Y. K.; Hong, D. Y.; Chang, J. S.; Jhung, S. H.; Seo, Y. K.; Kim, J.; Vimont, A.; Daturi, M.; Serre, C.; Férey, G. Angew. Chem., Int. Ed. 2008, 120, 4212.
[120]
Tabatabaei Rezaei, S. J.; Shamseddin, A.; Ramazani, A.; Mashhadi Malekzadeh, A.; Azimzadeh Asiabi, P. Appl. Organomet. Chem. 2017, 31, e3707.
[121]
Kaneko, T.; Tanaka, S.; Asao, N.; Yamamoto, Y.; Chen, M. W.; Zhang, W.; Inoue, A. Adv. Synth. Catal. 2011, 353, 2927.
[122]
Modak, A.; Mondal, J.; Sasidharan, M.; Bhaumik, A. Green Chem. 2011, 13, 1317.
[123]
Ju, P. Y.; Wu, S. J.; Su, Q.; Li, X. D.; Liu, Z. Q.; Li, G. H.; Wu, Q. L. J. Mater. Chem. 2019, 7, 2660.
[124]
Zhan, K.; You, H. H.; Liu, W. Y.; Lu, J.; Lu, P.; Dong, J. React. Funct. Polym. 2011, 71, 756.
[125]
Liu, P.; Li, P. H.; Wang, L. Synth. Commun. 2012, 42, 2595.
[126]
Islam, S. M.; Salam, N.; Mondal, P.; Roy, A. S.; Ghosh, K.; Tuhina, K. J. Mol. Catal. 2014, 387, 7.
[127]
Altman, R. A.; Koval, E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190.
[128]
Devarajan, N.; Suresh, P. ChemCatChem 2016, 8, 2953.
[129]
Anbu, N.; Dhakshinamoorthy, A. J. Ind. Eng. 2018, 65, 120.
[130]
Dutta, M. M.; Phukan, P. Catal. Commun. 2018, 109, 38.
[131]
Mu?oz, A.; Leo, P.; Orcajo, G.; Martínez, F.; Calleja, G. ChemCatChem 2019, 11, 3376.
[132]
Borah, R. K.; Raul, P. K.; Mahanta, A.; Shchukarev, A.; Mikkola, J. P.; Thakur, A. J. Synlett 2017, 28, 1177.
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