Chinese Journal of Organic Chemistry >
Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis
Received date: 2022-08-19
Revised date: 2022-09-21
Online published: 2022-11-15
Supported by
Fundamental Research Funds for the Central Universities(2572020AW45); Natural Science Foundation of Heilongjiang Province(ZD2021C001); Program of Introducing Talents of Discipline to Universities(B20088)
The attention of biomass-based catalysts has been continuously increased due to the proposal of carbon neutralization development concept. The use of lignin as a support for transition metal catalysts for the preparation of heterogeneous catalysts in the field of organic synthesis can greatly improve the utilization value of lignin. The extensive presence of oxygen-containing functionalities in the lignin structure provides a variety of binding sites for the loading of metal catalysts, and metal particles can be efficiently captured by physical adsorption/deposition, ion exchange, and electrostatic complexation with hydroxyl functional groups. The structure of lignin is firstly introduced, and the methods for preparing heterogeneous catalysts are then described. Lignin and its derivatives supported metal catalysts catalyzed Click reaction, Glaser reaction, Huisgen [3＋2] cycloaddition reaction, Heck reaction, Suzuki reaction, Sonogashira reaction, Stille coupling, Michael addition/dehydration tandem, Electrophilic ring-opening reaction, Fridel-Crafts type reaction, ethylene polymerization and other reactions. Thus, at the end of this review, the existing problems and development trends are prospected.
Baichuan Mo , Chunxia Chen , Jinsong Peng . Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1215 -1240 . DOI: 10.6023/cjoc202207013
| [1] | Schulze, F. Chem. Zentralbl. 1857, 21, 321. |
| [2] | Adler, E. Wood Sci. Technol. 1977, 11, 169. |
| [3] | Pan, X. J.; Kadla, J. F.; Ehara, K.; Gilkes, N.; Saddler, J. N. J. Agric. Food Chem. 2006, 54, 5806. |
| [4] | Liew, R. K.; Nam, W. L.; Chong, M. Y.; Phang, X. Y.; Su, M. H.; Yek, P. N. Y.; Ma, N. L.; Cheng, C. K.; Chong, C. T.; Lam, S. S. Process Saf. Environ. Prot. 2018, 115, 57. |
| [5] | Anderson, E. M.; Katahira, R.; Reed, M.; Resch, M. G.; Karp, E. M.; Beckham, G. T. ACS Sustainable Chem. Eng. 2016, 4, 6940. |
| [6] | Gioia, C.; Re, L. G.; Lawoko, M.; Berglund, L. J. Am. Chem. Soc. 2018, 140, 4054. |
| [7] | Pu, Y. Q.; Cao, S. L.; Ragauskas, A. J. Energy Environ. Sci. 2011, 4, 3154. |
| [8] | Freudenberg, K. Nature 1959, 183, 1152. |
| [9] | Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552. |
| [10] | Wang, Y. P.; Dai, L. L.; Fan, L. L.; Shan, S. Q.; Liu, Y. H.; Roger, R. J. Anal. Appl. Pyrolysis 2016, 119, 104. |
| [11] | Wang, C.; Kelley, S. S.; Venditti, R. A. ChemSusChem 2016, 9, 770. |
| [12] | Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F. C.; Kim, H.; Schatz1, P. F.; Marita, J. M.; Hatfield, R. D.; Ralph, S. A.; Christensen, J. H.; Boerjan,, W. Phytochem. Rev. 2004, 3, 29. |
| [13] | Boeriu, C. G.; Bravo, D.; Gosselink, R. J. A.; Dam, J. E. G. V. Ind. Crops Prod. 2004, 20, 205. |
| [14] | Chakar, F. S.; Ragauskas, A. J. Ind. Crops Prod. 2004, 20. 131. |
| [15] | Wikberg, H.; Ohra-aho, T.; Pileidis, F.; Titirici, M. M. ACS Sustainable Chem. Eng. 2015, 3, 2737. |
| [16] | Río, J. C. D.; Rencoret, J.; Marques, G.; Gutiérrez, A.; Ibarra, D.; Santos, J. I.; Jiménez-Barbero, J.; Zhang, L. M.; Martínez, á. T. J. Agric. Food Chem. 2008, 56, 9525. |
| [17] | Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552. |
| [18] | Vanholme, R.; Morreel, K.; Ralph, J.; Boerjan, W. Curr. Opin. Plant Biol. 2008, 11, 278. |
| [19] | Nada, A. A. M. A.; El-sakhawy, M.; Kamel, S. Int. J. Polym. Mater. Polym. Biomater. 2000, 46, 121. |
| [20] | Boerjan, W.; Ralph, J.; Baucher, M. Annu. Rev. Plant Biol. 2003, 54, 519. |
| [21] | Hatakeyama, H.; Hatakeyama, T. Adv. Polym. Sci. 2010, 232, 1. |
| [22] | Li, C. Z.; Zhao, X. C.; Wang, A. Q.; Huber, G. W.; Zhang, T. Chem. Rev. 2015, 115, 11559. |
| [23] | Kai, D.; Tan, M. J.; Chee, P. L.; Chua, Y. K.; Yap, Y. L.; Loh X. J. ; Green Chem. 2016, 18, 1175. |
| [24] | Saito, T.; Brown, R. H.; Hunt, M. A.; Pickel, D. L.; Pickel, J. M.; Messman, J. M.; Baker, F. S.; Keller, M.; Naskar, A. K. Green Chem. 2012, 14, 3295. |
| [25] | Culebras, M.; Geaney, H.; Beaucamp, A.; Upadhyaya, P.; Dalton E. Ryan, K. M.; Collins, M. N. ChemSusChem 2019, 12, 4516. |
| [26] | Sun, S. H.; Bai, R. X.; Gu, Y. L. Chem.-Eur. J. 2014, 20, 549. |
| [27] | Lai, B. B.; Bai, R. X.; Gu, Y. L. ACS Sustainable Chem. Eng. 2018, 6, 17076. |
| [28] | Zhou, Z. D.; Peng, X. W.; Zhong, L. X.; Li, X. H.; Sun, R. C. Polymers 2018, 10, 724. |
| [29] | Wang, Y. L.; Ren, K.; Sun, J.; Li, W.; Zhao, S. L.; Chen, Z. H.; Guan, J. G. Compos. Sci. Technol. 2017, 140, 89. |
| [30] | Lu, C.; Qi, L.; Yang, J.; Wang, X.; Zhang, D.; Xie, J.; Ma, J. Adv. Mater. 2005, 17, 2562. |
| [31] | Lai, B. B.; Ye, M.; Liu, P.; Li, M. H.; Bai, R. X.; Gu, Y. L. Beilstein J. Org. Chem. 2020, 16, 2888. |
| [32] | Akhtar, K.; Ali, F.; Sohni, S.; Kamal, T.; Asiri, A. M.; Bakhsh, E. M.; Khan, S. B. Environ. Sci. Pollut. Res. 2020, 27, 823. |
| [33] | Ahmadpoor, F.; Nasrollahzadeh, M.; Mohammad, M. Sep. Purif. Technol. 2021, 272, 118864. |
| [34] | Huang, Y. J.; Kang, Y.; El-kott, A.; Ahmed, A. E.; Khames, A.; Zein, M. A. Arabian J. Chem. 2021, 14, 103299. |
| [35] | Nasrollahzadeh, M.; Soleimani, F.; Nezafat, Z.; Orooji, Y.; Ah-madpoor, F. Biomass Conv. Bioref. 2021, 12, 1. |
| [36] | Nasrollahzadeh, M.; Bidgoli, N. S. S.; Karimkhani, M. M. Biomass Convers. Biorefin. 2021, https://doi.org/10.1007/s13399-021-01841-y. |
| [37] | Chanda, D.; Tufa, R. A.; Aili, D.; Basu, S. Nanotechnology 2022, 33, 055403. |
| [38] | Mohami, R.; Shakeri, A.; Nasrollahzadeh, M. Sep. Purif. Technol. 2022, 285, 120373. |
| [39] | Wu, Y. F.; Cui, Y. C. J. Mol. Catal. 2008, 6, 526. (in Chinese) |
| [39] | (吴玉锋, 崔元臣, 分子催化, 2008, 6, 526.) |
| [40] | Guillén, E.; Rico, R.; López-Romero, J. M.; Bedia, J.; Rosas, J. M.; Rodríguez-Mirasol, J.; Cordero, T. Appl. Catal., A 2009, 368, 113. |
| [41] | Wu, Y. F.; Zhang, L.; Cui, Y. C.; Liu, J. S.; Yang, S. Petrochem. Technol. 2009, 38, 733. (in Chinese) |
| [41] | (吴玉锋, 张磊, 崔元臣, 刘降生, 杨帅, 石油化工, 2009, 38, 733.) |
| [42] | Xue, M.; Zhang, S. Z.; Wu, Y. F.; Liu, J.; Cui, Y. C. Chin. J. Appl. Chem. 2010, 27, 787. (in Chinese) |
| [42] | (薛蔓, 张士真, 吴玉锋, 刘剑, 崔元臣, 应用化学, 2010, 27, 787.) |
| [43] | Coccia, F.; Tonucci, L.; d'Alessandro, N.; D'Ambrosio, P.; Bressan, M. Inorg. Chim. Acta 2013, 399, 12. |
| [44] | Marulasiddeshwara, M. B.; Kumar, P. R. Int. J. Biol. Macromol. 2016, 83, 326. |
| [45] | Marulasiddeshwara, M. B.; Kumar, P. R. Mater. Today: Proc. 2018, 5, 20811. |
| [46] | Nasrollahzadeh, M.; Issaabadi, Z.; Varma, R. S. ACS Omega 2019, 4, 14234. |
| [47] | Chao, M.; Zhang, G. W.; Li, Z. Y.; Liu, L. H.; Yan, S. Q.; Chen, Y.; Shi, Y. H.; Yan, X.; Cao, C. S. ChemistrySelect 2019, 4, 766. |
| [48] | Nasrollahzadeh, M.; Bidgoli, N. S. S.; Issaabadi, Z.; Ghavamifar, Z.; Baran, T.; Luque, R. Int. J. Biol. Macromol. 2020, 148, 265. |
| [49] | Bharamanagowda, M. M.; Panchangam, R. K. Appl. Organomet. Chem. 2020, 34, 5837. |
| [50] | Baran, T.; Sargin, I. Int. J. Biol. Macromol. 2020, 155, 814. |
| [51] | Chen, S. L.; Wang, G. H.; Sui, W. J.; Parvez, A. M.; Dai, L.; Si, C. L. Ind. Crops Prod. 2020, 145, 112164. |
| [52] | Orooji, Y.; Pakzad, K.; Nasrollahzadeh, M.; Tajbakhsh, M. Int. J. Biol. Macromol. 2021, 182, 564. |
| [53] | Ji, T.; Chen, L.; Schmitz, M.; Bao, F. S.; Zhu, J. H. Green Chem. 2015, 17, 2515. |
| [54] | Gao, C.; Wang, X. L.; Zhai, S. R.; An, Q. D. Int. J. Biol. Macromol. 2019, 134, 202. |
| [55] | Gao, C.; Wang, X. L.; Wang, H. S.; Zhou, J. H.; Zhai, S. R.; An, Q. D. Int. J. Biol. Macromol. 2020, 144, 947. |
| [56] | Chen, S. L.; Wang, G. H.; Pang, T. R.; Sui, W. J.; Chen, Z. C.; Si, C. L. Int. J. Biol. Macromol. 2021, 166, 893. |
| [57] | Yang, J.; Liu, L. Q.; An, X. Y.; Seta, F. T.; Li, C. X.; Zhang, H.; Luo, B. Y.; Hu, Q.; Zhang, R. Q.; Nie, S. X.; Cao, H. B.; Cheng, Z. B.; Liu, H. B. Ind. Crops Prod. 2021, 169, 113644. |
| [58] | Zazo, J. A.; Bedia, J.; Fierro, C. M.; Pliego, G.; Casas, J. A.; Rodriguez, J. J. Catal. Today 2012, 187, 115. |
| [59] | Yan, Q. G.; Wan, C. X.; Liu, J.; Gao, J. S.; Yu, F.; Zhang, J. L.; Cai, Z. Y. Green Chem. 2013, 15, 1631. |
| [60] | Chieffi, G.; Fechler, N.; Esposito, D. RSC Adv. 2015, 5, 63691. |
| [61] | Song, K. P.; Tang, C.; Zou, Z. J.; Wu, Y. D. Transition Met. Chem. 2020, 45, 111. |
| [62] | Chen, X. Y.; Yuan, B.; Yu, F. L.; Liu, Y. X.; Xie, C. X.; Yu, S. T. ACS Omega 2020, 5, 8902. |
| [63] | Zhang, J. R.; Yao, R. X.; Chen, J. Z.; Li, T.; Xu, Y. S. iScience 2021, 24, 103045. |
| [64] | Wang, S. W.; Feng, N.; Zheng, J. L.; Yoon, K. B.; Lee, D.; Qu, M. J.; Zhang, X. Q.; Zhang, H. X. Polym. Adv. Technol. 2016, 27, 1351. |
| [65] | Zhang, X. P.; Lu, G. P.; Wang, K.; Lin, Y. M.; Wang, P. C.; Yi, W. B. Nano Res. 2022, 15, 1874. |
| [66] | Zhu, Y. C.; Wu, H.; Fang, Z.; Yang, X. B.; Guo, K.; He, W. Mol. Catal. 2021, 514, 111765. |
| [67] | Chen, D. W.; Liang, F. B.; Feng, D. X.; Du, F. L.; Zhao, G.; Liu, H. Z.; Xian, M. Catal. Commun. 2016, 84, 159. |
| [68] | Zimmerman, J. B.; Anastas, P. T.; Erythropel, H. C.; Leitener, W. Science 2020, 367, 397. |
/
| 〈 |
|
〉 |
