Detoxification of bisphenol A <i>via</i> sulfur-mediated carbon–carbon σ-bond scission

Thiounn, Timmy; Karunarathna, Menisha S.; Lauer, Moira K.; Tennyson, Andrew G.; Smith, Rhett C.

doi:10.1039/d2su00138a

Cited by 8 publications

(1 citation statement)

References 90 publications

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“…HSMs prepared by these CS bond‐forming processes have found promise for a panoply of diverse applications including transparent lenses for thermal imaging, 40 absorbents, 41–45 electrode materials, 46–55 and fertilizers 56,57 . We recently reported additional uses of elemental sulfur in processes to recycle/upcycle waste plastic 58–60 . One of these applications involved the chemical recycling of poly(ethylene terephthalate) (PET) via sequential glycolysis, esterification with oleoyl chloride, and inverse vulcanization with elemental sulfur (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Composites produced from waste plastic with agricultural and energy sector by‐products

Lopez,

Smith

2023

J of Applied Polymer Sci

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A three‐stage route to chemically upcycle post‐consumer poly(ethylene terephthalate) (PET) to produce high compressive strength composites is reported. This procedure involves initial glycolysis with diethylene glycol to produce a mixture (GPET) comprising oligomers of 2–7 terephthalate units followed by trans/esterification of GPET with fatty acid chains supplied by brown grease, an agricultural by‐product of animal fat of relatively low nutritional or fuel value. This process yields PGB comprising a mixture of mono‐terephthalate ester derivatives. The olefin units provided by unsaturated fatty acid chains in brown grease were crosslinked by an inverse vulcanization reaction with elemental sulfur to give composites GBSx (x = wt% S, varied from 80%–90%). The compressive strengths of GBS80 (27.5 ± 2.6 MPa) and GBS90 (19.2 ± 0.8 MPa) exceed the compressive strength required of ordinary Portland cement (17 MPa) for its use in residential building foundations. The current route represents a way to repurpose waste plastic, energy sector by‐product sulfur, and agricultural by‐product brown grease to give high strength composites with mechanical properties suggesting their possible use to replace less sustainably sourced legacy structural materials.

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Section: Introductionmentioning

confidence: 99%

Composites produced from waste plastic with agricultural and energy sector by‐products

Lopez,

Smith

2023

J of Applied Polymer Sci

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Reactivity of Biomass‐Derived Olefins with Elemental Sulfur: Mechanistic Insight

Kapuge Dona,

Maladeniya,

Smith

2024

Eur J Org Chem

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Lignocellulosic biomass remains underutilized despite its annual production in gigaton quantities. Sulfur is another vastly underutilized waste product of fossil fuel refining. New mechanistic insight into the reactions of sulfur unveiled since 2020 suggest a rich and hitherto unexplored chemistry between biomass‐derived olefins and elemental sulfur. In this study, four biomass‐derived olefins (eugenol (1), 4‐allyl‐2,6‐dimethoxy phenol (2), o‐eugenol (3), and 2‐allyl‐6‐methylphenol (4)) were reacted with elemental sulfur to elucidate the S–C bond‐forming and other reactivity of these compounds. Each of the compounds was reacted with elemental sulfur in three sulfur : organic reactant ratios (2:1, 4:1 and 9:1) and at two temperatures (180 °C or 230 °C). Product mixtures were characterized using 1H NMR spectrometry and GC‐MS analysis. Products resulting from a range of mechanisms were unveiled, including inverse vulcanization, S–Callylic/benzylic bond formation, S–Caryl bond formation, intramolecular cyclization, C–C s‐bond scission, and C–O s‐bond scission. It is anticipated that the insights from this study will support further synergy between the critical sustainability goals of biomass and sulfur utilization.

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Transesterification‐vulcanization route to durable composites from post‐consumer poly(ethylene terephthalate), terpenoids, and industrial waste sulfur

Derr,

Lopez,

Maladeniya

et al. 2023

Journal of Polymer Science

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Despite improvements in chemical recycling, most post‐consumer plastics are still deposited in landfills where they pose a significant threat to ecological health. Herein we report a two‐stage method for chemically recycling poly(ethylene terephthalate) (PET) using terpenoids and waste sulfur to yield composites. In this method, post‐consumer PET (from beverage bottles) undergoes transesterification with a terpenoid alcohol (citronellol or geraniol) to yield low‐molecular PET oligomers. The terpene‐derived alkenes in these PET oligomer derivatives then served as reaction sites for inverse vulcanization with 90 wt% elemental sulfur to form composite CPS (using citronellol) or GPS (using geraniol). Composition, mechanical, thermal, and morphological properties were characterized by NMR spectroscopy, MALDI, FT‐IR spectroscopy, compressive and flexural strength analysis, TGA, DSC, elemental analysis, and SEM/EDX. The composites CPS (compressive strength = 5.20 MPa, flexural strength = 3.10 MPa) and GPS (compressive strength = 5.8 MPa, flexural strength = 2.77 MPa) showed mechanical strengths comparable to those of commercial bricks (classification C62 for general building). The approach delineated herein thus represents a method to chemically recycle waste plastic with industrial waste sulfur and plant‐derived terpenoids to yield composites having favorable properties comparable to existing building materials.

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Detoxification of bisphenol A via sulfur-mediated carbon–carbon σ-bond scission

Abstract: Environmental contamination with bisphenol A (BPA), produced via degradation of plastic waste, can be disintegrated to monoaryls by its reaction with elemental sulfur.

Cited by 8 publications

References 90 publications

Composites produced from waste plastic with agricultural and energy sector by‐products

Composites produced from waste plastic with agricultural and energy sector by‐products

Reactivity of Biomass‐Derived Olefins with Elemental Sulfur: Mechanistic Insight

Transesterification‐vulcanization route to durable composites from post‐consumer poly(ethylene terephthalate), terpenoids, and industrial waste sulfur

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