Development of Rapid Environment Degradable and Recyclable Poly(1,3-propylene glycol oxalate) <italic style="font-style: italic">via</italic> Ring-opening Polymerization of Seven-membered Cyclic Oxalate

Yue-Yuan Qian; Xiang-Bin Sun; Ya-Lei Liu; Zhi-Bo Li

doi:10.1007/s10118-026-3725-3

Your Location：

Home >

Browse articles >

Development of Rapid Environment Degradable and Recyclable Poly(1,3-propylene glycol oxalate) via Ring-opening Polymerization of Seven-membered Cyclic Oxalate

RESEARCH ARTICLE | Updated：2026-09-23

- Development of Rapid Environment Degradable and Recyclable Poly(1,3-propylene glycol oxalate) via Ring-opening Polymerization of Seven-membered Cyclic Oxalate
- Chinese Journal of Polymer Science Vol. 44, Issue 10, Pages: 3366-3374(2026)
- Affiliations：
  
  a.Shandong Key Laboratory of High Performance Polyolefin Materials and Recycling; College of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
  b.College of Chemistry, Chemical Engineering and Materials Science, Zaozhuang University, Zaozhuang 277160, China
  c.State Key Laboratory of Chemical Engineering and Low-carbon Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310058, China
- Author bio：
  
  sunxiangbinld@163.com (X.B.S.)
  zbli@qust.edu.cn, zbli@zju.edu.cn (Z.B.L.)
- Funds：
- DOI：10.1007/s10118-026-3725-3
  CLC：
- Received：23 March 2026，
  
  Revised：2026-04-15，
  
  Accepted：21 April 2026，
  
  Online First：20 July 2026，
  
  Published：05 October 2026
- Accepted：
Scan QR Code
Qian, Y. Y.; Sun, X. B.; Liu, Y. L.; Li, Z. B. Development of rapid environment degradable and recyclable poly(1,3-propylene glycol oxalate) via ring-opening polymerization of seven-membered cyclic oxalate. Chinese J. Polym. Sci. 2026, 44, 3366–3374

Yue-Yuan Qian, Xiang-Bin Sun, Ya-Lei Liu, et al. Development of Rapid Environment Degradable and Recyclable Poly(1,3-propylene glycol oxalate) via Ring-opening Polymerization of Seven-membered Cyclic Oxalate[J]. Chinese Journal of Polymer Science, 2026, 44(10): 3366-3374. DOI: 10.1007/s10118-026-3725-3.
Qian, Y. Y.; Sun, X. B.; Liu, Y. L.; Li, Z. B. Development of rapid environment degradable and recyclable poly(1,3-propylene glycol oxalate) via ring-opening polymerization of seven-membered cyclic oxalate. Chinese J. Polym. Sci. 2026, 44, 3366–3374 DOI： 10.1007/s10118-026-3725-3.

Yue-Yuan Qian, Xiang-Bin Sun, Ya-Lei Liu, et al. Development of Rapid Environment Degradable and Recyclable Poly(1,3-propylene glycol oxalate) via Ring-opening Polymerization of Seven-membered Cyclic Oxalate[J]. Chinese Journal of Polymer Science, 2026, 44(10): 3366-3374. DOI: 10.1007/s10118-026-3725-3. DOI：

摘要

Seven-membered cyclic oxalate (POx) is made from cheap dimethyl oxalate and bio-based 1

3-propanediol. The ring-opening polymerization of POx yields high-molecular-weight PPOx

which features rapid environmental degradation and recyclability.

Abstract

As plastic pollution has become increasingly severe

the development of recyclable and rapidly degradable polyesters has significant practical value and significance. In this study

seven-membered cyclic 1

3-propylene glycol oxalate (POx) was successfully synthesized through a two-step polycondensation-depolymerization method using dimethyl oxalate (a low-cost and readily accessible bulk chemical) and bio-based 1

3-propylene glycol as the starting materials. Using Sn(Oct)

s the catalyst

high-molecular-weight poly(1

3-propylene oxalate) (PPOx) was efficiently prepared

via

ring-opening polymerization (ROP) of POx. This ROP demonstrated excellent reactivity

attaining a monomer conversion up to 95% within 10 min

and PPOx had a maximum intrinsic viscosity (

) of 1.06 dL/g. Furthermore

the prepared PPOx could be catalytically depolymerized to enable efficient recovery of the POx monomer

with a yield of 60% and a purity of 98%. The degradation performance tests indicated that PPOx exhibited rapid degradation

reaching a degradation rate of up to 99% within 50 days. Owing to the innovative selection of raw materials and the design of a closed-loop process

this study provides a new economical and sustainable strategy for reducing dependence on petroleum resources

offering valuable insights into the development of recyclable and rapidly degradable polyesters.

关键词

Keywords

references

Zhou, X.; Guo, B.; Zhang, L.; Hu, G. Progress in bio-inspired sacrificial bonds in artificial polymeric materials. Chem. Soc. Rev. 2017 , 46 , 6301−6329..

Wang, X.; Zhang, Z.; Hadjichristidis, N. Poly(amino esters) as an emerging synthetic biodegradable polymer platform: recent developments and future trends. Prog. Polym. Sci. 2023 , 136 , 101634..

Becker, M. L.; Burdick, J. A. Introduction: Polymeric biomaterials. Chem. Rev. 2021 , 121 , 10789−10791..

Wang, G. X.; Huang, D.; Ji, J. H.; Völker, C.; Wurm, F. R. Seawater-degradable polymers-fighting the marine plastic pollution. Adv. Sci. 2021 , 8 , 2001121..

Hu, H.; Chen, Y.; You, F.; Yao, J.; Yang, H.; Jiang, X.; Xia, B. Y. Recycling and upgrading utilization of polymer plastics. Chinese J. Chem. 2023 , 41 , 469−480..

Jambeck, J. R.; Geyer, R.; Wilcox, C.; Siegler, T. R.; Perryman, M.; Andrady, A.; Narayan, R.; Law, K. L. Plastic waste inputs from land into the ocean. Science 2015 , 347 , 768−771..

Li, N.; Liu, H.; Cheng, Z.; Yan, B.; Chen, G.; Wang, S. Conversion of plastic waste into fuels: A critical review. J. Hazard. Mater. 2022 , 424 , 127460..

Gontarek-Castro, E.; Haseler, M.; Narra, M. M.; Abiewska, A. G.; Trzebiatowska, P. J. Utilization routes of plastic waste from the marine environment: a review. Waste Manage. 2026 , 210 , 115221..

[Billiet, S.; Trenor, S. R. 100th anniversary of macromolecular science viewpoint: Needs for plastics packaging circularity. ACS Macro Lett . 2020 , 9 , 1376−1390..

Liu, Y.; Yin, F.; Hu, X.; Zhu, N.; Guo, K. Protecting-group-free synthesis of thiol-functionalized degradable polyesters. Polym. Chem. 2021 , 12 , 1749−1757..

Hayashi, S.; Hiraishi, T.; Sugimoto, M.; Abe, H. Marine-biodegradable alternating copoly(ester-amide)s from ( R )-3-hydroxybutyric acid and amino acid with high glass-transition temperature. Polym. Degrad. Stabil. 2026 , 244 , 111818..

Şucu, T.; Wang, M.; Shaver, M. P. Degradable and reprocessable resins from a dioxolanone cross-linker. Macromolecules 2023 , 56 , 1625−1632..

Liu, B.; Cheng, Z.; Xia, J.; Wang, M.; Zheng, Z.; Yang, S.; Shen, Y.; Dai, D.; Wang, J.; Yu, X.; Guo, C. Degradable carboxymethyl cellulose/chitosan sponge swabs for sustainable diagnostics. Carbohyd. Polym. 2025 , 363 , 123761..

Sun, P.; Wang, S.; Huang, Z.; Zhang, L.; Dong, F.; Xu, X.; Liu, H. Water-resistan t, strong, degradable and recyclable rosin-grafted cellulose composite paper. Green Chem. 2022 , 24 , 7519−7530..

Wheeler, B. P.; Medd, K.; Woodworth, K. E.; Huyer, L. D. Molecular and macroscopic considerations for degradable aliphatic polyester biomaterial design. Biomacromolecules 2025 , 26 , 4784−4811..

Schneiderman, D. K.; Hillmyer, M. A. Aliphatic polyester block polymer design. Macromolecules 2016 , 49 , 2419−2428..

Chu, B.; Zhang, H.; Chen, K.; Liu, B.; Yu, Q. L.; Zhang, C. J.; Sun, J.; Yang, Q.; Zhang, X. H.; Tang, B. Z. Aliphatic polyesters with white-light clusteroluminescence. J. Am. Chem. Soc. 2022 , 144 , 15286−15294..

Hu, C.; Zhang, Y.; Pang, X.; Chen, X. Poly(lactic acid): Recent stereochemical advances and new materials engineering. Adv. Mate. 2025 , 37 , 2412185..

Barletta, M.; Aversa, C.; Ayyoob, M.; Gisario, A.; Hamad, K.; Mehrpouya, M.; Vahabi, H. Poly(butylene succinate) (PBS): Materials, processing, and industrial applications. Prog. Polym. Sci. 2022 , 132 , 101579..

Dou, Y.; Tian, N.; Ning, Z.; Jiang, N.; Gan, Z. Facile method for the synthesis of PCL-b-PA6-b-PCL using amino-terminated PA6 as a macroinitiator and its characterization. Macromolecules 2022 , 55 , 10090−10099..

Lee, D.; Bae, S.; Ke, Q.; Lee, J.; Song, B.; Karumanchi, S. A.; Khang, G.; Choi, H.; Kang, P. M. Hydrogen peroxide-responsive copolyoxalate nanoparticles for detection and therapy of ischemia-reperfusion injury. J. Control Release 2013 , 172 , 1102−1110..

Kim, S.; Seong, K.; Kim, O.; Kim, S.; Seo, H.; Lee, M.; Khang, G.; Lee, D. Polyoxalate nanoparticles as a biodegradable and biocompatible drug delivery vehicle. Biomacromolecules 2010 , 11 , 555−560..

Luan, Q.; Hu, H.; Jiang, X.; Lin, C.; Zhang, X.; Wang, Q.; Dong, Y.; Wang, J.; Zhu, J. Melt polycondensation of poly (butylene oxalate-co-succinate) with great potential in curbing marine plastic pollution. J. Hazard. Mater. 2023 , 457 , 131801..

Murcia Valderrama, M. A.; van Putten, R. J.; Gruter, G. J. M. The potential of oxalic - and glycolic acid based polyesters (review). Towards CO 2 as a feedstock (Carbon Capture and Utilization - CCU). Eur. Polym. J. 2019 , 119 , 445−468..

Chang, S. H.; Lee, H. J.; Park, S.; Kim, Y.; Jeong, B. Fast degradable polycaprolactone for drug delivery. Biomacromolecules 2018 , 19 , 2302−2307..

Tu, Z.; Lu, Y.; Sang, L.; Zhang, Y.; Li, Y.; Wei, Z. Kilogram-scale preparation of poly(ethylene oxalate) toward marine-degradable plastics. Macromolecules 2023 , 56 , 3149−3159..

Tu, Z.; Wang, B.; Lu, Y.; Wang, L.; Li, Y.; Sang, L.; Zhang, Y.; Wei, Z. Incorporation of large-scale prepared poly(ethylene oxalate) into biodegradable poly(butylene adipate- co -terephthalate) blown films with enhanced mechanical and barrier performance. ACS Sustainable Chem. Eng. 2023 , 11 , 9833−9845..

Tu, Z.; Wang, L.; Lu, Y.; Li, Y.; Sang, L.; Zhang, Y.; Wei, Z. Rapid marine degradable poly(butylene oxalate) by introducing promotion building blocks. J. Hazard. Mater. 2024 , 462 , 132791..

Tu, Z.; Lu, Y.; Zhang, Y.; Li, Y.; Wei, Z. Development of poly(n-alkylene oxalate)s toward a new kind of seawater degradable plastics. Mater. Today Sustain. 2023 , 22 , 100378..

Li, Z.; Shen, Y.; Li, Z. Ring-opening polymerization of lactones to prepare closed-loop recyclable polyesters. Macromolecules 2024 , 57 , 1919−1940..

Smith, M. L.; McGuire, T. M.; Kerr, R. W. F.; Williams, C. K. From polymers to rings and back again: Chemical recycling of polyesters to macrolactones. Angew. Chem. Int. Ed. 2025 , 64 , e202423478..

Naumann, S.; Scholten, P. B. V.; Wilson, J. A.; Dove, A. P. Dual catalysis for selective ring-opening polymerization of lactones: evolution toward simplicity. J. Am. Chem. Soc. 2015 , 137 , 14439−14445..

Yuan, P.; Sun, Y.; Xu, X.; Luo, Y.; Hong, M. Towards high-performance sustainable polymers via isomerization-driven irreversible ring-opening polymerization of five-membered thionolactones. Nat. Chem. 2022 , 14 , 294−303..

Sun, Y.; An, Z.; Gao, Y.; Hu, R.; Liu, Y.; Lu, H.; Lu, X. B.; Pang, X.; Qin, A.; Shen, Y.; Tao, Y.; Wang, Y. Z.; Wang, J.; Wu, G.; Wu, G. P.; Xu, T. Q.; Zhang, X. H.; Zhang, Y.; Zhang, Z. Zhu, J. B.; Hong, M.; Li, Z. New sustainable polymers with on-demand depolymerization property. Sci. China Chem. 2024 , 67 , 2803−2841..

Qin, B.; Zhang, X. On depolymerization. CCS Chem. 2024 , 6 , 297−312..

Liu, Y.; Li, Z.; Zhao, D.; Shen, Y.; Li, Z. A polycondensation-depolymerization strategy enables closed-loop recyclable polyoxalates via ring-opening polymerization of six-membered cyclic oxalates. Chem. Sci. 2026 , 17 , 3733−3742..

Lu, B.; Wang, G. X.; Huang, D.; Ren, Z. L.; Wang, X. W.; Wang, P. L.; Zhen, Z. C.; Zhang, W.; Ji, J. H. Comparison of PCL degradation in different aquatic environments: Effects of bacteria and inorganic salts. Polym. Degrad. Stabil. 2018 , 150 , 133−139..

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Synthesis of Sulfur/Selenium-containing Polyester with Recyclability and Controllable Hydrophilicity and Glass Transition Temperature

Urea-welded Anionic Vinyl-addition and Ring-opening Polymerizations for One-pot Hybrid Block Copolymer Synthesis

Readily Degradable and Recyclable High Molecular Weight Thiosalicylic Acid-based Copolyesters

Molecular Segregation and Melt Memory in Dilute Polycaprolactone with Reduced Entanglements

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers

Related Author

Wen-Jing Li

Xiang-Qiang Pan

Jian Zhu

Zheng-Biao Zhang

Heng Li

Ye-Ning Xia

Li-Jun Liu

Jun-Peng Zhao

Related Institution

Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University

Faculty of Materials Science and Engineering, South China University of Technology

College of Chemistry, Xiangtan University

Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, South China University of Technology

State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University

⁰

Development of Rapid Environment Degradable and Recyclable Poly(1,3-propylene glycol oxalate) via Ring-opening Polymerization of Seven-membered Cyclic Oxalate

DOI：10.1007/s10118-026-3725-3

摘要

Abstract

关键词

Keywords

references