Synthesis and Ring-opening Polymerization of Benzoxy Substituted Oxa-lactones

Dong-fang Zhao; Zheng Li; Yong Shen; Zhi-bo Li

doi:10.11777/j.issn1000-3304.2023.23061

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Synthesis and Ring-opening Polymerization of Benzoxy Substituted Oxa-lactones

Research Article | 更新时间：2023-08-21

- Synthesis and Ring-opening Polymerization of Benzoxy Substituted Oxa-lactones
  增强出版
- ACTA POLYMERICA SINICA Vol. 54, Issue 9, Pages: 1303-1311(2023)
- 作者机构：
  
  1.青岛科技大学，高分子科学与工程学院山东省教育厅生物基高分子材料重点实验室，青岛 266042
  2.青岛科技大学，化工学院，青岛 266042
- 作者简介：
  
  Yong Shen, E-mail: shenyong@qust.edu.cn
  Zhi-bo Li, E-mail: zbli@qust.edu.cn
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2023.23061
  CLC：
- Published：20 September 2023，
  
  Published Online：26 May 2023，
  
  Received：14 March 2023，
  
  Accepted：28 March 2023
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赵东方,李峥,沈勇等.苯甲氧基氧杂环内酯的合成及开环聚合研究[J].高分子学报,2023,54(09):1303-1311.

Zhao Dong-fang,Li Zheng,Shen Yong,et al.Synthesis and Ring-opening Polymerization of Benzoxy Substituted Oxa-lactones[J].ACTA POLYMERICA SINICA,2023,54(09):1303-1311.
赵东方,李峥,沈勇等.苯甲氧基氧杂环内酯的合成及开环聚合研究[J].高分子学报,2023,54(09):1303-1311. DOI： 10.11777/j.issn1000-3304.2023.23061.

Zhao Dong-fang,Li Zheng,Shen Yong,et al.Synthesis and Ring-opening Polymerization of Benzoxy Substituted Oxa-lactones[J].ACTA POLYMERICA SINICA,2023,54(09):1303-1311. DOI： 10.11777/j.issn1000-3304.2023.23061.

摘要

从聚(3-羟基丁酸酯) (P3HB)的醇解产物(

)-3-羟基丁酸甲酯出发，高效地合成了2个氧杂环内酯非对映异构体单体((3

和(3

). 苯氧甲基的引入使2个非对映异构体有较大极性差异，因而可以通过柱层析分离. 以MeAl[salen]为催化剂，BnOH为引发剂实现了单体的可控开环聚合，得到了分子量(

)可控和末端官能团明确的P((3

)和P((3

)聚合物. 利用基质辅助激光解吸/电离飞行时间质谱(MALDI-TOF MS)和核磁共振氢谱(

H-NMR)表征聚合物的链结构，示差扫描量热法(DSC)表征证明了P((3

)为半结晶聚酯. 在1

5-均三甲苯的稀溶液中，使用辛酸亚锡(Sn(Oct)

)催化解聚实现了P((3

)的化学回收. 这种化学回收策略实现了P3HB的升级回收，延长了材料的生命周期，并拓展了高价值可闭环回收聚醚酯的种类.

Abstract

This study described the efficient synthesis of two oxolactone monomers ((3

and (3

). The monomers were synthesized using (

)-methyl-3-hydroxybutyrate

which is an alcoholysis product of poly(3-hydroxybutyrate) (P3HB). The introduction of phenoxymethyl resulted in diastereoisomers with different polarity that could be separated by column chromatography. The monomers were polymerized

via

ring-opening polymerization using MeAl[salen] as the catalyst

and the polymerization behaviour was investigated. P((3

) and P((3

) with controlled molecular weights and chain-end groups were prepared. The linear structure of the polymers was further confirmed using matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy (MALDI-TOF MS) and

H nuclear magnetic resonance (

H-NMR). P((3

) is a semi-crystalline polyester. Additionally

stannous octanoate (Sn(Oct)

was used as a catalyst to achieve the depolymerization and recovery of the P((3

) in a dilute solution of 1

5-mono-trimethylbenzene. This strategy enables P3HB upcycling

extending the material's life cycle and expanding the range of high-value closed-loop recyclable polyether esters.

关键词

开环聚合闭合循环可降解聚酯聚醚酯聚(3-羟基丁酸酯)

Keywords

Ring-opening polymerizationClosed-loop recyclingDegradable polyesterPoly(ether-ester)Poly(3-hydroxybutyrate)

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Key Laboratory of Biobased Polymer Materials, Shandong Provincial Education Department, College of Polymer Science and Engineering, Qingdao University of Science and Technology

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Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education

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