Synthesis of a new monomer for sulfonated poly(arylene ether sulfones)

Begunov, R. S.; Valyaeva, A. N.; Фахрутдинов, Артем Н.; Pirogova, S. A.

doi:10.1007/s11172-017-1769-9

Cited by 2 publications

(1 citation statement)

References 21 publications

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“…PSU is composed of diphenylsulfone and bisphenol A. Since thiolate anions can cleave aryl-SO 2 bonds 70 – 74 , we were concerned that the present catalytic method may cleave the aryl-SO 2 bond in the diphenylsulfone unit as well as the target C–O main chain. However, we found that polysulfone (PSU) pellets 7 (purchased from Sigma-Aldrich) and 7’ (purchased from Acros Organics) with different M w ( M w 35000 and M w 60000) in each of the catalog specifications underwent the decomposition with 2a via selective C–O bond cleavage 38 to furnish the corresponding 4,4’-dialkylthiobenzosulfone ( 8a ) and bisphenol A ( 9 ) in high yields (Table 2 , Entries 1 and 2).…”

Section: Resultsmentioning

confidence: 99%

Catalytic thiolation-depolymerization-like decomposition of oxyphenylene-type super engineering plastics via selective carbon–oxygen main chain cleavages

Minami,

Imamura,

Matsuyama

et al. 2024

Commun Chem

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As the effective use of carbon resources has become a pressing societal issue, the importance of chemical recycling of plastics has increased. The catalytic chemical decomposition for plastics is a promising approach for creating valuable products under efficient and mild conditions. Although several commodity and engineering plastics have been applied, the decompositions of stable resins composed of strong main chains such as polyamides, thermoset resins, and super engineering plastics are underdeveloped. Especially, super engineering plastics that have high heat resistance, chemical resistance, and low solubility are nearly unexplored. In addition, many super engineering plastics are composed of robust aromatic ethers, which are difficult to cleave. Herein, we report the catalytic depolymerization-like chemical decomposition of oxyphenylene-based super engineering plastics such as polyetheretherketone and polysulfone using thiols via selective carbon–oxygen main chain cleavage to form electron-deficient arenes with sulfur functional groups and bisphenols. The catalyst combination of a bulky phosphazene base P4-tBu with inorganic bases such as tripotassium phosphate enabled smooth decomposition. This method could be utilized with carbon- or glass fiber-enforced polyetheretherketone materials and a consumer resin. The sulfur functional groups in one product could be transformed to amino and sulfonium groups and fluorine by using suitable catalysts.

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Section: Resultsmentioning

confidence: 99%

Catalytic thiolation-depolymerization-like decomposition of oxyphenylene-type super engineering plastics via selective carbon–oxygen main chain cleavages

Minami,

Imamura,

Matsuyama

et al. 2024

Commun Chem

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show abstract

Catalytic thiolation-depolymerization of oxyphenylene type super engineering plastics via selective carbon-oxygen main chain cleavages

Minami,

Imamura,

Matsuyama

et al. 2023

Preprint

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As the effective use of carbon resources has become a pressing societal issue, the importance of chemical recycling of plastics has increased. The catalytic depolymerization method for plastics is a promising approach for creating valuable products under efficient and mild conditions. Although depolymerization methods for various commodity plastics and several engineering plastics have been developed, the degradation of robust super engineering plastics that have very high heat resistance, chemical resistance, and low solubility is nearly unexplored. Herein, we report the catalytic depolymerization of oxyphenylene-based super engineering plastics such as polyetheretherketone, polysulfone, and polyetherimide using thiols via selective carbon–oxygen main chain cleavage to form monomer-type molecules, electron-deficient arenes with sulfur functional groups and bisphenols. The catalyst combination of a bulky phosphazene base P4-tBu with inorganic bases such as tripotassium phosphate or cesium carbonate enabled smooth depolymerization by activating the thiols to form reactive thiolates. This depolymerization method could be utilized with carbon- or glass fiber-enforced polyetheretherketone materials and a consumer resin. The sulfur functional groups in one product could be transformed to amino and sulfonium groups and fluorine by using suitable catalysts. Notably these fluorinated products are the monomers of the parent super engineering plastics.

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Synthesis of a new monomer for sulfonated poly(arylene ether sulfones)

Cited by 2 publications

References 21 publications

Catalytic thiolation-depolymerization-like decomposition of oxyphenylene-type super engineering plastics via selective carbon–oxygen main chain cleavages

Catalytic thiolation-depolymerization-like decomposition of oxyphenylene-type super engineering plastics via selective carbon–oxygen main chain cleavages

Catalytic thiolation-depolymerization of oxyphenylene type super engineering plastics via selective carbon-oxygen main chain cleavages

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