SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

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

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

REVIEWS

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

  • Xiangkun Meng ,
  • Zhengyuan Qi ,
  • Lei Yu ,
  • Yiyang Zhang
Expand
  • 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

Fold

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

Cite this article

Xiangkun Meng , Zhengyuan Qi , Lei Yu , Yiyang Zhang . Catalytic System for Poly(lactic acid) Synthesis: Opportunities and Challenges[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 112 -119 . DOI: 10.6023/cjoc202206051

References

[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.
Options
Outlines

/

〈 〉