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DOE OSTI2025

Re-directing mixed-feed deconstruction products to hybrid polyesters: Tolerance windows for commodity plastics reconstruction

Solvolysis is a promising strategy for mixed-feed polyester recycling, but little attention has been given to downstream product separations or the impact of using imperfectly separated monomer mixtures in recycled polymer reconstruction. Here, we challenge the traditional need for high-purity monomers in polycondensation synthesis of engineering thermoplastics. Monomer mixtures are derived from catalyzed methanolysis of polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polybutylene adipate-co-terephthalate (PBAT), with separation scenarios ranging from high (99:1) to low (90:10) purity. We focus on challenging-to-separate products like ethylene glycol and 1,4-butanediol and evaluate tolerance for comonomer incorporation in recycled hybrid polyesters: polybutylene-co-ethylene terephthalate (PBET) and polybutylene ethylene adipate-co-terephthalate (PBEAT). Evaluations are made between “contaminant” monomer incorporation, and the resulting materials’ thermal properties, crystalline structure, tensile toughness, and rheology. Ultimately, we highlight that despite incorporation of contaminant monomer, high-performance hybrid polyesters of PET, PBT, and PBAT are obtained while reducing the strain of high-throughput separations.

36 MATERIALS SCIENCE↗

DOE OSTI2023

Evaluation of enzymatic depolymerization of PET, PTT, and PBT polyesters

Millions of tons of waste polyester plastics, including polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), and polybutylene terephthalate (PBT), end up in the environment as soil and water contaminants. Recent advances in enzymatic polyester degradation have motivated researchers toward biorecycling of plastic wastes. Leaf-branch compost cutinase (LCC) enzymes have been proven to be effective in the biodegradation of PET. This study focuses on enzymatic depolymerization of waste PET, PTT, and PBT materials by using an ICCG variant of LCC (LCC ICCG ) produced from Escherichia coli BL21(DE3). The degradation efficiency of the polyesters was determined by the monomer terephthalic acid (TPA) released from the depolymerization reaction. It was found that the most efficient depolymerization was achieved for PET, followed by PTT and PBT. A kinetic model based on Langmuir adsorption and the Michaelis-Menten equation was developed to describe the enzymatic depolymerization of PET, PTT, and PBT with various enzyme and substrate loadings. The model simulation results revealed that the LCCICCG enzyme loading should be linearly increased as the work capacity of the polyester substrate increases. A specific enzyme loading of 0.91 mg/g PET is suggested to achieve 90% depolymerization of PET within three days. Furthermore, the experimental data and model simulation results can be used to help further engineer the enzyme and process to achieve a complete biodegradation of polyester wastes at large scale.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

DOE OSTI2021

Efficient Polyester Hydrogenolytic Deconstruction via Tandem Catalysis

Abstract Using a mechanism‐based solvent‐free tandem catalytic approach, commodity polyester plastics such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polyethylene naphthalate (PEN) are rapidly and selectively deconstructed by combining the two air‐ and moisture‐stable catalysts, Hf(OTf) 4 and Pd/C, under 1 atm H 2 , affording terephthalic acid (or naphthalene dicarboxylic acid for PEN) and ethane (or butane for PBT) in essentially quantitative yield. This process is effective for both laboratory grade and waste plastics, and comingled polypropylene remains unchanged. Combined experimental and DFT mechanistic analyses indicate that Hf(OTf) 4 catalyzes a mildly exergonic retro‐hydroalkoxylation reaction in which an alkoxy C−O bond is first cleaved, yielding a carboxylic acid and alkene, and this process is closely coupled to an exergonic olefin hydrogenation step, driving the overall reaction forward.

Kratish, Yosi↗

DOE OSTI2021

Efficient Polyester Hydrogenolytic Deconstruction via Tandem Catalysis

Using a mechanism-based solvent-free tandem catalytic approach, commodity polyester plastics such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polyethylene naphthalate (PEN) are rapidly and selectively deconstructed by combining the two air- and moisture-stable catalysts, Hf(OTf) 4 and Pd/C, under 1 atm H 2 , affording terephthalic acid (or naphthalene dicarboxylic acid for PEN) and ethane (or butane for PBT) in essentially quantitative yield. This process is effective for both laboratory grade and waste plastics, and comingled polypropylene remains unchanged. Combined experimental and DFT mechanistic analyses indicate that Hf(OTf) 4 catalyzes a mildly exergonic retro-hydroalkoxylation reaction in which an alkoxy C-O bond is first cleaved, yielding a carboxylic acid and alkene, and this process is closely coupled to an exergonic olefin hydrogenation step, driving the overall reaction forward.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

DOE OSTI2025

Thermodynamically leveraged solventless aerobic deconstruction of polyethylene-terephthalate plastics over a single-site molybdenum-dioxo catalyst

Here, we describe the solventless catalytic deconstruction of polyethylene-terephthalate (PET) under an aerobic atmosphere, mediated by an earth-abundant, low-cost activated carbon (AC)-supported single-site molybdenum-dioxo catalyst (AC/MoO 2 ). Catalytic amounts of AC/MoO 2 selectively convert waste PET into its monomer, terephthalic acid (TPA), within 4 h at 265 °C with yields as high as 94% under 1 atm air. Pure crystalline TPA product sublimes from the reaction hot zone, crystallizing on the reactor cold zone, thus avoiding the need for separation and purification steps. This process does not employ any hazardous/toxic reducing agents or solvents, and the catalyst can be recycled multiple times without loss of activity, rendering this process highly atom-efficient. According to computational and experimental mechanistic studies, the AC/MoO 2 catalyst mediates a thermoneutral metal-catalyzed β-scission step, followed by an exothermic step that converts the vinyl benzoate intermediate to TPA and acetaldehyde using trace amounts of moisture in the air. The formation of gaseous acetaldehyde makes the isolation of TPA from the reaction mixture facile and industrially favorable, especially since solvents are unnecessary. The present methodology is also extended to the deconstruction of other frequently used polyester plastics, polybutylene terephthalate (PBT), polyethylene naphthalate (PEN), and polyethylene furanoate (PEF), and operates equally well with post-consumer waste products. Notably, this process is also compatible with plastic mixtures of polyesters with polyolefins, polyamides, and polycarbonates, leading to the selective conversion of each polyester to the corresponding monomer, leaving the residual polymer unchanged and polyester-free.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

DOE OSTI2020

Performance of Vehicle Fuel System Elastomers and Plastics with Test Fuels Representing Gasoline Blended with 10% Ethanol (E10) and 16% Isobutanol (iBu16)

The compatibilities of fuel system elastomers and plastics were evaluated for test fuels containing 16 vol.% isobutanol (iBu16) and 10 vol.% ethanol (E10). Elastomers included two fluorocarbons, four acrylonitrile butadiene rubbers (NBRs), and one type of fluorosilicone, neoprene, and epichlorohydrin/ethylene oxide. Plastic materials included four nylon grades, three polyamides, polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), ethylene tetrafluoroethylene (ETFE), polyphenylene sulfide (PPS), high-density polyethylene (HDPE), polybutylene terephthalate (PBT), polyoxymethylene (POM), flexible polyvinylchloride (PVC), polyetherimide (PEI), polyetheretherketone (PEEK), and a phenol formaldehyde reinforced with glass fiber (GFPF). For each polymer material, the volume, mass, and hardness were measured before and after drying. Dynamic mechanical analysis (DMA) measurements were also performed on the dried specimens.For the elastomer materials the measured properties were similar for both fuels. The fluorocarbons and fluorosilicone swelled the least (~20%), while more moderate (20-45%) expansion occurred for the two NBR hose grades and (ECO). HNBR, neoprene, and silicone exhibited high swelling and softening, which likely precludes their use in many fuel systems. For the plastic materials, the observed swell was low; Nylon 11 swelled around 15%, but otherwise, their measured swell was <10%. Many of the plastics also showed sensitivity to alcohol type, as the E10 test fuel often imparted appreciably higher swell than iBu16. In general, the plastic materials showed good compatibility with the iBu16 and E10 test fuels. Here, the sole exception was the PVC material, which was structurally degraded from exposure to either fuel type. Compositional analysis showed high fuel retention in Nylon 12 and PVC. PVC also experienced a significant reduction in plasticizer compounds following exposure, which resulted in embrittlement and an increase in the glass-to-rubber transition temperature.

33 ADVANCED PROPULSION SYSTEMS↗

DOE OSTI2022

Impact of Biodiesel, Renewable Diesel, 1-Octanol, Dibutoxymethane, n-Undecane, Hexyl hexanoate and 2-Nonanone with Infrastructure Plastics as Blends with Diesel

In this work the volume and hardness were measured for thermoplastics and thermosetting resins with diesel containing up to 30% of the following blend stocks: biodiesel, renewable diesel, n-undecane, dibutoxymethane, 1-octanol, hexyl hexanoate, and 2-nonanone. Thermoplastics included polyphenylene sulfide (PPS), polyethylene terephthalate (PET), polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), polyoxymethylene (POM), polybutylene terephthalate (PBT), polypropylene (PP), high density polyethylene (HDPE), nylons, acetals, polyetherimide (PEI), polyetheretherketone (PEEK), a PET co-polymer, polyphthalamides (PPAs), polyarylamide (PARA) and ethylene tetrafluoroethylene (ETFE). Three thermosetting resins were also evaluated. The material specimens were exposed to the test fuels under ambient conditions for 16 weeks. In general, the volume and hardness of the specimens were relatively unaffected following exposure to the test fuels; however, n-undecane produced significant swelling in polypropylene and may not be suitable for use with this material. N-undecane, along with hexyl hexanoate and 2-nonanone also caused low levels of swelling in nylon, which was not significant enough to preclude the use of nylons in sealing applications with these fuels.

09 BIOMASS FUELS↗

NASA NTRS1982

A new brominated polymeric additive for flame retardant glass-filled polybutylene terephthalate

Attention is called to the undesirable effects (poor ultraviolet light stability and blooming) sometimes introduced by brominated flame retarders. A brominated polymeric additive (BPA) with little or none of these undesirable side effects is compared with decabromobiphenyl oxide (DBBPO). The additive bears the product name F-2300. It is found to be more easily dispersed than DBBPO. The F-2300 is as effective as the DBBPO in the oxygen index test. The improved efficiency of the F-2300 may be explained by its better dispersion in polybutylene terephthalate (PBT). Glass-filled PBT containing F-2300 is found to be more resistant to UV degradation than DBBPO-containing formulas. Formulations with F-2300 therefore have a longer useful outdoor life. F-2300 is a diglycidyl-type polymer containing 50 percent aromatically bound bromine. Its melting point is 112 C, and it is stable up to 372 C. It is pointed out that since its melts at a relatively low temperature, it can be introduced into the formulation as a large agglomerate and still be dispersed evenly throughout the polymer.

Nir, Z.↗