Chemically Recyclable Polyester Thermosets from Activated Adipic Acid and Renewable Polyols

Journal Article · Mon Jun 30 00:00:00 EDT 2025 · ChemSusChem

DOI:https://doi.org/10.1002/cssc.202500880· OSTI ID:2588447

Rigo, Davide ^[1]; Lorenzon, Matteo ^[1]; Simon, Jonas ^[2]; Addison, Bennett ^[3]; Perosa, Alvise ^[1]; Selva, Maurizio ^[1]

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1. Ca Foscari University of Venice
2. University of Natural Resources & Life Sciences
3. National Renewable Energy Lab., Golden, CO (United States)

This study outlines a method for producing chemically recyclable crosslinked polyesters using renewable polyols-glycerol and sorbitol-combined with adipic acid (AA), which is transformed/activated into a polyanhydride mixture prior to use. A three-step procedure has been designed: 1) an acid-catalyzed reaction of AA with nontoxic isopropenyl acetate or acetic anhydride to form a crosslinking mixture (CLM) made of adipic-acetic mixed polyanhydrides; 2) a solvent- and additive-free process where glycerol or sorbitol, or a combination thereof, is reacted with the CLM to achieve a prepolymer, and 3) a casting/molding of the liquid viscous prepolymer to yield a thermoset as the end product. Different thermosets (eight examples) are prepared by changing the reagents ratio. These solids are thoroughly characterized by tensile tests, DMA, high-resolution magic angle spinning and solid-state NMR, thermal gravimetric analysis, DSC, and fourier transformed infra red (FT-IR) spectroscopy. The formation of cross-linked polyesters is confirmed in all cases, but mechanical properties varied significantly from one specimen to another. Interestingly, a tensile strength up to 18 MPa-approximately an order of magnitude higher than similar polymers-is achieved when sorbitol and the CLM are used in a 1:1 wt% ratio. The chemical recycle of the resulting polymers is achieved via methanolysis with quantitative recovery of the monomeric units.

• Research Organization: National Renewable Energy Laboratory (NREL), Golden, CO (United States)
• Sponsoring Organization: USDOE National Renewable Energy Laboratory (NREL)
• Grant/Contract Number: AC36-08GO28308
• OSTI ID: 2588447
• Report Number(s): NREL/JA-2800-97045
• Journal Information: ChemSusChem, Journal Name: ChemSusChem Journal Issue: 19 Vol. 18
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
bioplastics
chemical recycling
isopropenyl acetate
solvent-free
upcycling