Abstract
Polylactic acid (PLA), as a biodegradable plastic, is considered a potential alternative to alleviate the environmental problems caused by the accumulation of petroleum-based plastic wastes. However, PLA is relatively expensive and naturally degrades very slowly. Therefore, compared to disposal, recycling PLA is more conducive to sustainable development. In this study, a novel immobilized deep eutectic solvent (DES) ChCl–2ZnCl2@ZIF-8 was developed and used for the methanolysis of PLA to produce a valuable product methyl lactate (ML). The synthesized heterogeneous catalyst exhibits excellent thermal and chemical stability, as well as excellent catalytic performance. For example, the reaction temperature significantly decreased, the dosage of the catalyst decreased, and the PLA conversion and the ML yield were both improved, reaching 98.2% and 96.3%. After the reaction, the catalyst can be recovered through simple filtration, and reused for five times with negligible loss of catalytic activity. The catalyst was characterized by FT-IR, SEM, BET, TGA and XRD. Based on the experimental results, a possible reaction mechanism of PLA methanolysis was proposed. In addition, the kinetics of the PLA methanolysis catalyzed by ChCl–2ZnCl2@ZIF-8 was examined and the activation energy was obtained. This work mainly provided a way of recovering catalysts and promoted the development of PLA methanolysis into ML.
Similar content being viewed by others
References
Kakanuru P, Pochiraju K (2020) Addit Manuf 36:101529
Hamad K, Kaseem M, Ayyoob M, Joo J, Deri F (2018) Prog Polym Sci 85:83–127
Swetha TA, Bora A, Mohanrasu K, Balaji P, Raja R, Ponnuchamy K, Muthusamy G, Arun A (2023) Int J Biol Macromol 234:123715
Shen H, Li Y, Yao W, Yang S, Yang L, Pan F, Chen Z, Yin X (2021) Compos B Eng 222:109042
Tyler B, Gullotti D, Mangraviti A, Utsuki T, Brem H (2016) Adv Drug Deliver Rev 107:163–175
Ferreira RTL, Amatte IC, Dutra TA, Bürger D (2017) Compos B Eng 124:88–100
Li Y, Lin Z, Wang X, Duan Z, Lu P, Li S, Ji D, Wang Z, Li G, Yu D, Liu W (2021) Sep Purif Technol 270:118794
He Y, Fang C, Xu WH, Tan LC, Qin S, Yin XC, Feng YH, Park CB, Qu JP (2023) Chem Eng J 457:141371
Beltrán FR, Infante C, de la Orden MU, Martínez Urreaga J (2019) J Clean Prod 219:46–56
Vasile C, Pamfil D, Rapa M, Darie-Nita RN, Mitelut AC, Popa EE, Popescu PA, Draghici MC, Popa ME (2018) Compos Part B-Eng 142:251–262
Santulli F, Lamberti M, Mazzeo M (2021) Chemsuschem 14:5470–5475
Elsawy MA, Kim KH, Park JW, Deep A (2017) Renew Sust Energ Rev 79:1346–1352
Song X, Bian Z, Hui Y, Wang H, Liu F, Yu S (2019) Polym Degrad Stab 168:108937
Yan YF, Liang XB, Feng YL, Shi LF, Chen RP, Guo JZ, Guan Y (2023) Carbohydr Polym 320:121251
Lin HY, Tsai SY, Yu HT, Lin CP (2017) J Polym Environ 26:122–131
Karimi-Avargani M, Bazooyar F, Biria D, Zamani A, Skrifvars M (2021) Chemosphere 278:130443
Xie S, Sun Z, Liu T, Zhang J, Li T, Ouyang X, Qiu X, Luo S, Fan W, Lin H (2021) J Catal 402:61–71
Leibfarth FA, Moreno N, Hawker AP, Shand JD (2012) J Polym Sci Part A: Polym Chem 50:4814–4822
Alberti C, Damps N, Meißner RRR, Enthaler S (2019) ChemistrySelect 4:6845–6848
Song XY, Zhang XJ, Wang H, Liu FS, Yu ST, Liu SW (2013) Polym Degrad Stab 98:2760–2764
Song X, Wang H, Zheng X, Liu F, Yu S (2014) J Appl Polym Sci 131:40817
Liu HQ, Zhao RY, Song XY, Liu FS, Yu ST, Liu SW, Ge XP (2017) Catal Lett 147:2298–2305
Agostinho B, Silvestre AJD, Sousa AF (2022) Green Chem 24:3115–3119
Kaur H, Singh M, Singh H, Kaur M, Singh G, Sekar K, Kang TS (2022) Green Chem 24:2953–2961
Ribeiro BD, Florindo C, Iff LC, Coelho MAZ, Marrucho IM (2015) ACS Sustain Chem Eng 3:2469–2477
Płotka-Wasylka J, de la Guardia M, Andruch V, Vilková M (2020) Microchem J 159:105539
Yuan Y, Wang J, Liu H, Li Z (2023) J Mater Chem A 11:24127–24135
Wan M, Zhang X, Li M, Chen B, Yin J, Jin H, Lin L, Chen C, Zhang N (2017) Small 13:1701395
Hao L, Stoian SA, Weddle LR, Zhang Q (2020) Green Chem 22:6351–6356
Wang R, Lu K, Zhang J, Li X, Zheng Z (2022) ACS Catal 12:14290–14303
Bohigues B, Rojas-Buzo S, Moliner M, Corma A (2021) ACS Sustain Chem Eng 9:15793–15806
Zanon A, Verpoort F (2017) Coord Chem Rev 353:201–222
Lin L, Liu H, Zhang X (2017) Chem Eng J 328:124–132
Wang Q, Zhang X, Huang L, Zhang Z, Dong S (2017) Angew Chem Int Ed 56:16082–16085
Wang R, Wang T, Yu G, Chen X (2021) Polym Degrad Stab 183:109463
Hoop M, Walde CF, Riccò R, Mushtaq F, Terzopoulou A, Chen X-Z, deMello AJ, Doonan CJ, Falcaro P, Nelson BJ, Puigmartí-Luis J, Pané S (2018) Appl Mater Today 11:13–21
Mohammadi A, Nakhaei Pour A (2023) J CO2 Util 69:102424
Liu F, Guo J, Zhao P, Gu Y, Gao J, Liu M (2019) Polym Degrad Stab 167:124–129
Wang Q, Yao X, Tang S, Lu X, Zhang X, Zhang S (2012) Green Chem 14:2559–2566
Al-Sabagh AM, Yehia FZ, Eissa AMF, Moustafa ME, Eshaq G, Rabie AM, ElMetwally AE (2014) Polym Degrad Stab 110:364–377
Huang W, Wang H, Zhu X, Yang D, Yu S, Liu F, Song X (2021). Appl Clay Sci. https://doi.org/10.1016/j.clay.2021.105986
Wang Y, Yang R, Xu G, Guo X, Dong B, Zhang Q, Li R, Wang Q (2023) Polym Degrad Stab 214:110413
Acknowledgements
The authors acknowledge the financial support of the National Natural Science Foundation of China (No. 22271170 and 22178191).
Funding
National Natural Science Foundation of China (Grant Nos. 22271170, 22178191).
Author information
Authors and Affiliations
Contributions
Xiaoxu Zhu and Huimin Zhao were responsible for the experimental operation and data analysis together, and Xiaoxu Zhu also wrote the main manuscript text. Hui Wang provided the experimental plan, while Daoshan Yang and Fusheng Liu provided funding. Xiuyan Song reviewed the project and provided laboratory resources. All authors provided review and supervision.
Corresponding author
Ethics declarations
Competing interests
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Zhu, X., Zhao, H., Wang, H. et al. Immobilized Deep Eutectic Solvent ChCl–2ZnCl2@ZIF-8 Composite as an Efficient and Reusable Catalyst for the Methanolysis of Poly(lactic Acid). J Polym Environ (2024). https://doi.org/10.1007/s10924-024-03302-9
Accepted:
Published:
DOI: https://doi.org/10.1007/s10924-024-03302-9