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2023 , Vol. 43 >Issue 1: 112 - 119

DOI: https://doi.org/10.6023/cjoc202206051

综述与进展

聚乳酸合成催化体系: 机遇与挑战

  • 孟祥坤 ,
  • 祁正源 ,
  • 俞磊 ,
  • 张亦旸
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  • a 扬州大学化学化工学院 江苏扬州 225002
    b 甘肃农业大学信息科学技术学院 兰州 730070
    c 扬州大学机械学院 江苏扬州 225127

收稿日期: 2022-06-28

  修回日期: 2022-07-26

  网络出版日期: 2022-09-09

基金资助

江苏省“六大”人才高峰高层次人才(XCL-090); 江苏省优势学科资助项目

收起

Catalytic System for Poly(lactic acid) Synthesis: Opportunities and Challenges

  • Xiangkun Meng ,
  • Zhengyuan Qi ,
  • Lei Yu ,
  • Yiyang Zhang
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  • a School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002
    b College of Information Science and Technology, Gansu Agricultural University, Lanzhou 730070
    c School of Mechanical Engineering, Yangzhou University, Yangzhou, Jiangsu 225127
* Corresponding authors. E-mail: ;

Received date: 2022-06-28

  Revised date: 2022-07-26

  Online published: 2022-09-09

Supported by

Jiangsu Provincial Six Talent Peaks Project(XCL-090); Priority Academic Program Development of Jiangsu Higher Education Institutions

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摘要

随着国家减塑令的发布, 开发聚乳酸(PLA)等生物可降解材料逐渐成为热门话题. 对合成聚乳酸的不同方法进行了讨论. 丙交酯开环聚合法已成为获得高分子量聚乳酸的最常用方法. 因此, 重点介绍了用于丙交酯开环聚合的催化剂设计, 并阐述了聚合的机理, 希望能为设计开发低毒性、高选择性的催化体系指明方向.

关键词： 减塑令; 聚乳酸; 生物可降解; 催化剂; 聚合

本文引用格式

孟祥坤 , 祁正源 , 俞磊 , 张亦旸 . 聚乳酸合成催化体系: 机遇与挑战[J]. 有机化学, 2023 , 43(1) : 112 -119 . DOI: 10.6023/cjoc202206051

Abstract

With the national plastic reduction order issued, the development of biodegradable materials such as poly(lactic acid) (PLA) has gradually become a hot topic. The different methods for synthesizing polylactic acid are discussed. Since the ring-opening polymerization of lactide has become the major method for preparing PLA, we focused on the catalyst design for the process, and clarified the related mechanisms. This short review may point out the direction for the design and development of low-toxicity and high-selectivity catalyst systems for application.

Key words： plastic reduction order; polylactic acid; biodegradable; catalysts; polymerization

参考文献

[1]
(a) Wang, Y.; Ying, Z.; Xie, W.; Wu, D. Carbohydr. Polym. 2020, 233, 115845.
[1]
(b) Zhang, G.; Xie, W.; Wu, D. Carbohydr. Polym. 2020, 227, 115341.
[1]
(c) Qiu, Y.; Wanyan, Q.; Xie, W.; Wang, Z.; Chen, M.; Wu, D. Polymer 2019, 180, 121733.
[1]
(d) Lu, Y.; Huang, J.; Ge, L.; Xie, W.; Wu, D. Polymer 2018, 156, 136.
[1]
(e) Zhang, G.; Wu, D.; Xie, W.; Wang, Z.; Xu, C. Carbohydr. Polym. 2018, 195, 79.
[1]
(f) Xu, C.; Chen, C.; Wu, D. Carbohydr. Polym. 2018, 182, 115.
[1]
(g) Ji, L.; Gong, M.; Qiao, W.; Zhang, W.; Liu, Q.; Dunham, R. E.; Gu, J. J. Polym. Res. 2018, 25, 210.
[1]
(h) Lv, Q.; Wu, D.; Xie, H.; Peng, S.; Chen, Y.; Xu, C. RSC Adv. 2016, 6, 37721.
[1]
(i) Song, X.; You, J.; Wang, J.; Zhu, A.; Ji, L.; Guo, R. Chem. Res. Chin. Univ. 2014, 30, 326.
[1]
(j) Lu, L.; Wu, D.; Zhang, M.; Zhou, W. Ind. Eng. Chem. Res. 2012, 51, 3682.
[1]
(k) Meng, X.; Yu, L.; Cao, Y.; Zhang, X.; Zhang, Y. Org. Biomol. Chem. 2021, 19, 10288.
[1]
(l) Luo, S.-H.; Xiao, Y.; Lin, J.-Y.; Chen, Z.-H.; Lin, S.-T.; Wang, Z.-Y. Mater. Today Chem. 2022, 25, 100986.
[2]
(a) Inkinen, S.; Hakkarainen, M.; Albertsson, A.-C.; S?derg?rd, A. Biomacromolecules 2011, 12, 523.
[2]
(b) Garlotta, D. J. Polym. Environ. 2001, 9, 63.
[3]
(a) Saeidlou, S.; Huneault, M. A.; Li, H.; Park, C. B. Prog. Polym. Sci. 2012, 37, 1657.
[3]
(b) Tsuji, H. Macromol. Biosci. 2005, 5, 569.
[3]
(c) Yang, W.; Zhu, Y.; He, Y.; Xiao, L.; Xu, P.; Puglia, D.; Ma, P. Ind. Crops Prod. 2022, 183, 114965.
[3]
(d) Xu, H.; Ke, L.; Tang, M.; Shang, H.; Zhang, Z.-L.; Xu, W.; Fu, Y.-N.; Wang, Y.; Tang, D.; Huang, D.; Zhang, S.; Yang, H.-R.; He, X.; Gao, J. Int. J. Biol. Macromol. 2022, 216, 114.
[4]
Ajioka, M.; Enomoto, K.; Suzuki, K.; Yamaguchi, A. Bull. Chem. Soc. Jpn. 1995, 68, 2125.
[5]
(a) Moon, S. I.; Lee, C. W.; Miyamoto, M.; Kimura, Y. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1673.
[5]
(b) Moon, S. I.; Kimura, Y. Polym. Int. 2003, 52, 299.
[6]
Lei, Z.-Q.; Wang, S.-F.; Bai, Y.-B. J. Appl. Polym. Sci. 2007, 105, 3597.
[7]
Chafran, L. S.; Campos, J. M. C.; Santos, J. S.; Sales, M. J. A.; Dias, S. C. L.; Dias, J. A. J. Polym. Res. 2016, 23, 107.
[8]
Ren, H.-X.; Ying, H.-J.; Ouyang, P.-K.; Xu, P.; Liu, J. J. Mol. Catal. A: Chem. 2013, 366, 22.
[9]
Huang, W.; Cheng, N.; Qi, Y.; Zhang, T.; Jiang, W.; Li, H.; Zhang, Q. Polymer 2014, 55, 1491.
[10]
Penczek, S.; Szymanski, R.; Duda, A.; Baran, J. Macromol. Symp. 2003, 201, 261.
[11]
Madhavan Nampoothiri, K.; Nair, N. R.; John, R. P. Bioresour. Technol. 2010, 101, 8493.
[12]
Zhang, X.; MacDonald, D. A.; Goosen, M. F. A.; McAuley, K. B. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 2965.
[13]
Kricheldorf, H. R.; Kreiser-Saunders, I.; Stricker, A. Macromolecules 2000, 33, 702.
[14]
Viamonte-Aristizábal, S.; García-Sancho, A.; Arrabal Campos, F. M.; Martínez-Lao, J. A.; Fernández, I. Eur. Polym. J. 2021, 161, 110818.
[15]
Wu, L.-M.; Wang, C.; He, L.-G.; Wang, Z.-J.; Tong, Z.; Song, F.; Tu, J.-F.; Qiu, W.-M.; Liu, J.-H.; Jiang, Y.-C.; Peng, S.-A. Plants 2020, 9, 95.
[16]
Schwach, G.; Coudane, J.; Engel, R.; Vert, M. J. Polym. Sci.,Part A: Polym. Chem. 1997, 35, 3431.
[17]
Dubois, P.; Jacobs, C.; Jér?me, R.; Teyssie, P. Macromolecules 1991, 24, 2266.
[18]
Hormnirun, P.; Marshall, E. L.; Gibson, V. C.; Pugh, R. I.; White, A. J. P. Proc. Natl. Acad. Sci. 2006, 103, 15343.
[19]
Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 11583.
[20]
Chotard, F.; Lapenta, R.; Bolley, A.; Trommenschlager, A.; Balan, C.; Bayardon, J.; Malacea-Kabbara, R.; Bonnin, Q.; Bodio, E.; Cattey, H.; Richard, P.; Milione, S.; Grassi, A.; Dagorne, S.; Le Gendre, P. Organometallics 2019, 38, 4147.
[21]
Fuchs, M.; Schmitz, S.; Sch?fer, P. M.; Secker, T.; Metz, A.; Ksiazkiewicz, A. N.; Pich, A.; K?gerler, P.; Monakhov, K. Y.; Herres-Pawlis, S. Eur. Polym. J. 2020, 122, 109302.
[22]
D’Auria, I.; Ferrara, V.; Tedesco, C.; Kretschmer, W.; Kempe, R.; Pellecchia, C. ACS Appl. Polym. Mater. 2021, 3, 4035.
[23]
Poirier, V.; Roisnel, T.; Carpentier, J.-F.; Sarazin, Y. Dalton Trans. 2009, 9820.
[24]
Ghosh, S.; Gl?ckler, E.; W?lper, C.; Tjaberings, A.; Gr?schel, A. H.; Schulz, S. Organometallics 2020, 39, 4221.
[25]
Liu, B.; Dorcet, V.; Maron, L.; Carpentier, J.-F.; Sarazin, Y. Eur. J. Inorg. Chem. 2012, 3023.
[26]
Liu, B.; Roisnel, T.; Sarazin, Y. Inorg. Chim. Acta 2012, 380, 2.
[27]
Zelikoff, A. L.; Kopilov, J.; Goldberg, I.; Coates, G. W.; Kol, M. Chem. Commun. 2009, 6804.
[28]
(a) Saha, T. K.; Ramkumar, V.; Chakraborty, D. Inorg. Chem. 2011, 50, 2720.
[28]
(b) El-Zoghbi, I.; Whitehorne, T. J. J.; Schaper, F. Dalton Trans. 2013, 42, 9376.
[29]
Sergeeva, E.; Kopilov, J.; Goldberg, I.; Kol, M. Inorg. Chem. 2010, 49, 3977.
[30]
Horeglad, P.; Szczepaniak, G.; Dranka, M.; Zachara, J. Chem. Commun. 2012, 48, 1171.
[31]
Pietrangelo, A.; Knight, S. C.; Gupta, A. K.; Yao, L. J.; Hillmyer, M. A.; Tolman, W. B. J. Am. Chem. Soc. 2010, 132, 11649.
[32]
Guo, J.; Haquette, P.; Martin, J.; Salim, K.; Thomas, C. M. Angew. Chem., Int. Ed. 2013, 52, 13584.
[33]
Wang, X.; Liao, K.; Quan, D.; Wu, Q. Macromolecules 2005, 38, 4611.
[34]
Whitehorne, T. J. J.; Schaper, F. Inorg. Chem. 2013, 52, 13612.
[35]
Daneshmand, P.; Schaper, F. Dalton Trans. 2015, 44, 20449.
[36]
Ding, L.; Jin, W.; Chu, Z.; Chen, L.; Lü, X.; Yuan, G.; Song, J.; Fan, D.; Bao, F. Inorg. Chem. Commun. 2011, 14, 1274.
[37]
Samantaray, M. K.; Katiyar, V.; Pang, K.; Nanavati, H.; Ghosh, P. J. Organomet. Chem. 2007, 692, 1672.
[38]
Zhou, Y.; Hu, D.; Li, D.; Jiang, X. JACS Au 2021, 1, 1141.
[39]
Rajashekhar, B.; Chakraborty, D. Polym. Bull. 2014, 71, 2185.
[40]
Balasanthiran, V.; Chatterjee, C.; Chisholm, M. H.; Harrold, N. D.; RajanBabu, T. V.; Warren, G. A. J. Am. Chem. Soc. 2015, 137, 1786.
[41]
Kim, Y.; Kapoor, P. N.; Verkade, J. G. Inorg. Chem. 2002, 41, 4834.
[42]
Roymuhury, S. K.; Mandal, M.; Chakraborty, D.; Ramkumar, V. Polym. Chem. 2021, 12, 3953.
[43]
Choe, S.; Lee, H.; Nayab, S. Appl. Organomet. Chem. 2021, 35, e6204.
[44]
Mandal, M.; Chakraborty, D. J. Polym. Res. 2021, 28, 52.
[45]
(a) Deng, X.; Qian, R.; Zhou, H.; Yu, L. Chin. Chem. Lett. 2021, 32, 1029.
[45]
(b) Wang, F.; Yang, C.; Shi, Y.; Yu, L. Mol. Catal. 2021, 514, 111849.
[45]
(c) Wang, F.; Chen, T.; Shi, Y.; Yu, L. Asian J. Org. Chem. 2021, 10, 614.
[45]
(d) Ou, W.; Zou, R.; Han, M.; Yu, L.; Su, C. Chin. Chem. Lett. 2020, 31, 1899.
[45]
(e) Liu, M.; Li, Y.; Yu, L.; Xu, Q.; Jiang, X. Sci. China Chem. 2018, 61, 294.
[46]
(a) Yu, L.; Huang, Y.; Wei, Z.; Ding, Y.; Su, C.; Xu, Q. J. Org. Chem. 2015, 80, 8677.
[46]
(b) Yu, L.; Han, Z.; Ding, Y. Org. Process Res. Dev. 2016, 20, 2124.
[46]
(c) Liu, Y.; Tang, D.; Cao, K.; Yu, L.; Han, J.; Xu, Q. J. Catal. 2018, 360, 250.
[46]
(d) Sun, H.; Shi, Y.; Fu, W.; Yu, L. ChemistrySelect 2021, 6, 7599.
[46]
(e) Li, W.; Wang, F.; Shi, Y.; Yu, L. Chin. Chem. Lett. 2023, 34, 107505.
[47]
(a) Xiao, X.; Guan, C.; Xu, J.; Fu, W.; Yu, L. Green Chem. 2021, 23, 4647.
[47]
(b) Xiao, X.; Shao, Z.; Yu, L. Chin. Chem. Lett. 2021, 32, 2933.
[47]
(c) Chen, C.; Cao, Y.; Wu, X.; Cai, Y.; Liu, J.; Xu, L.; Ding, K.; Yu, L. Chin. Chem. Lett. 2020, 31, 1078.
[47]
(d) Cao, H.; Qian, R.; Yu, L. Catal. Sci. Technol. 2020, 10, 3113.
[47]
(e) Zheng, Y.; Wu, A.; Ke, Y.; Cao, H.; Yu, L. Chin. Chem. Lett. 2019, 30, 937.
[47]
(f) Cao, H.; Zhu, B.; Yang, Y.; Xu, L.; Yu, L.; Xu, Q. Chin. J. Catal. 2018, 39, 899.
[48]
Nederberg, F.; Connor, E. F.; M?ller, M.; Glauser, T.; Hedrick, J. L. Angew. Chem., Int. Ed. 2001, 40, 2712.
[49]
Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R. M.; Hedrick, J. L. Macromolecules 2006, 39, 8574.
[50]
Zhi, X.; Liu, J.; Li, Z.; Wang, H.; Wang, X.; Cui, S.; Chen, C.; Zhao, C.; Li, X.; Guo, K. Polym. Chem. 2016, 7, 339.
[51]
Guan, X.; Shen, Y.; Li, Z. Acta Polym. Sin. 2020, 51, 1121. (in Chinese)
[51]
(寇新慧, 沈勇, 李志波, 高分子学报, 2020, 51, 1121.)
[52]
(a) D’Alterio, M. C.; D’Auria, I.; Gaeta, L.; Tedesco, C.; Brenna, S.; Pellecchia, C. Macromolecules 2022, 55, 5115.
[52]
(b) Santulli, F.; Gravina, G.; Lamberti, M.; Tedesco, C.; Mazzeo, M. Mol. Catal. 2022, 528, 112480.
[53]
Vink, E. T. H.; Davies, S. Ind. Biotechnol. 2015, 11, 167.
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