An efficient cyclodepolymerization route for the chemical recycling of poly(ethylene adipate)

Li, Hongjuan; Yan, Xiangxiang; Huan, Jie; Sheng, Weidong; Li, Xiaohong; Wang, Yatao; Tu, Yingfeng; Li, Zhiping

doi:10.1039/d2py01613c

Cited by 8 publications

(6 citation statements)

References 52 publications

(68 reference statements)

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“…In 2023, Li and co-workers reported an efficient cyclodepolymerization method for the chemical recycling of poly(ethylene adipate) (PEA) into its cyclic oligomers as MLs, termed cyclic oligo(ethylene adipate)s (COEAs), achieving up to 99% yield . This process is catalyzed by 3% dibutyltin oxide in toluene (25 g/L), conducted at 110 °C over 96 h. Their findings highlighted the superior performance of toluene over chlorobenzene or dichlorobenzene as a solvent.…”

Section: Emerging Aliphatic Polyestersmentioning

confidence: 99%

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Shi,

Quinn,

Diment

et al. 2024

Chem. Rev.

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Polyesters carrying polar main-chain ester linkages exhibit distinct material properties for diverse applications and thus play an important role in today's plastics economy. It is anticipated that they will play an even greater role in tomorrow's circular plastics economy that focuses on sustainability, thanks to the abundant availability of their biosourced building blocks and the presence of the main-chain ester bonds that can be chemically or biologically cleaved on demand by multiple methods and thus bring about more desired end-of-life plastic waste management options. Because of this potential and promise, there have been intense research activities directed at addressing recycling, upcycling or biodegradation of existing legacy polyesters, designing their biorenewable alternatives, and redesigning future polyesters with intrinsic chemical recyclability and tailored performance that can rival today's commodity plastics that are either petroleum based and/or hard to recycle. This review captures these exciting recent developments and outlines future challenges and opportunities. Case studies on the legacy polyesters, poly(lactic acid), poly(3-hydroxyalkanoate)s, poly(ethylene terephthalate), poly(butylene succinate), and poly(butylene-adipate terephthalate), are presented, and emerging chemically recyclable polyesters are comprehensively reviewed.

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Section: Emerging Aliphatic Polyestersmentioning

confidence: 99%

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Shi,

Quinn,

Diment

et al. 2024

Chem. Rev.

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“…In contrast, in dilute conditions, translational entropy becomes more dominant, thereby shifting the equilibrium toward the monomers. 49,50 Given that polymers with an appropriate T f are anticipated to polymerize at elevated temperatures and depolymerize at lower temperatures or even at room temperature, a stark contrast to the behavior of T c -regulated recyclable polymers, we assert that transitioning to T f -regulated polymers could resolve at least three major challenges associated with low-T c chemically recyclable polymers. (1) T f -regulated polymers enable the polymerization of monomers at industrially feasible temperatures, avoiding the impractically low temperatures required by low T c polymers.…”

Section: ■ Introductionmentioning

confidence: 97%

“…Therefore, the ROP of MLs, similar to the polymerization of elemental sulfur and the ROP of octamethylcyclotetrasiloxane (D4) generally requires higher reaction temperatures to attain energetic favorability (Δ G p < 0). − Moreover, the entropy change is concentration-dependent, favoring polymerization at high monomer concentrations due to the conformational entropy benefits of the polymers. In contrast, in dilute conditions, translational entropy becomes more dominant, thereby shifting the equilibrium toward the monomers. , …”

Section: Introductionmentioning

confidence: 99%

Thermally Stable and Chemically Recyclable Poly(ketal-ester)s Regulated by Floor Temperature

Meng,

Zhou,

Yang

et al. 2024

J. Am. Chem. Soc.

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Chemical recycling to monomers (CRM) offers a promising closed-loop approach to transition from current linear plastic economy toward a more sustainable circular paradigm. Typically, this approach has focused on modulating the ceiling temperature (T c) of monomers. Despite considerable advancements, polymers with low T c often face challenges such as inadequate thermal stability, exemplified by poly(γ-butyrolactone) (PGBL) with a decomposition temperature of ∼200 °C. In contrast, floor temperature (T f)-regulated polymers, particularly those synthesized via the ring-opening polymerization (ROP) of macrolactones, inherently exhibit enhanced thermodynamic stability as the temperature increases. However, the development of those T f regulated chemically recyclable polymers remains relatively underexplored. In this context, by judicious design and efficient synthesis of a biobased macrocyclic diester monomer (HOD), we developed a type of T f -regulated closed-loop chemically recyclable poly(ketal-ester) (PHOD). First, the entropy-driven ROP of HOD generated high-molar mass PHOD with exceptional thermal stability with a T d,5% reaching up to 353 °C. Notably, it maintains a high T d,5% of 345 °C even without removing the polymerization catalyst. This contrasts markedly with PGBL, which spontaneously depolymerizes back to the monomer above its T c in the presence of catalyst. Second, PHOD displays outstanding closed-loop chemical recyclability at room temperature within just 1 min with t BuOK. Finally, copolymerization of pentadecanolide (PDL) with HOD generated high-performance copolymers (PHOD-co-PPDL) with tunable mechanical properties and chemical recyclability of both components.

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“…The cyclodepolymerization of polyesters to their corresponding cyclic oligoesters has attracted great research interest since Brunelle et al reported it, based on the ring-chain equilibrium in solution. [14][15][16][17][18][19][20][21][22] The obtained cyclic oligoesters were capable of repolymerizing to their linear polyester counterparts by ring-opening polymerization (ROP). [23][24][25][26][27][28][29] As the polymerization speed of ROP is faster than condensation polymerization (CP), the obtained PBT can achieve a high molecular weight (445 kg mol −1 ) that is hard to obtain by typical CP.…”

Section: Introductionmentioning

confidence: 99%

Chemical recycling of poly(butylene terephthalate) into value-added biodegradable poly(butylene adipate-co-terephthalate)

Yan,

Huang,

Huan

et al. 2024

Polym. Chem.

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An efficient cyclodepolymerization route for the chemical recycling of poly(ethylene adipate)

Abstract: Cyclodepolymerization is a special chemical recycling (upcycling) method for polyesters based on the ring-chain equilibria in solution, yet it is usually carried out in halogenated solvents at temperatures around 200...

Cited by 8 publications

References 52 publications

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Thermally Stable and Chemically Recyclable Poly(ketal-ester)s Regulated by Floor Temperature

Chemical recycling of poly(butylene terephthalate) into value-added biodegradable poly(butylene adipate-co-terephthalate)

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