Novel synthesis of macrocyclic disulfides from poly(phenylene sulfide) by depolymerization reaction

Wang, Shuanjin; Bian, Shi; Yan, Hua; Xiao, Min; Ye, Meng

doi:10.1002/app.29010

Cited by 6 publications

(7 citation statements)

References 14 publications

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“…In addition to alkyl halides, an acid chloride was applicable in this sequence to form a corresponding monomer product, 20 in 81% yield. Further treatment with hydrogen chloride after depolymerization afforded 4,4'-dimercaptobenzophenone (21). This one-pot depolymerization/functionalization method was applicable in the three-step sequence.…”

Section: Resultsmentioning

confidence: 95%

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Depolymerization of robust polyetheretherketone to regenerate monomer units using sulfur reagents

Minami

Matsuyama

Takeichi

et al. 2022

Preprint

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Super engineering plastics, high-performance thermoplastic resins such as polyetheretherketone (PEEK), and polyphenylene sulfide (PPS) have been utilized in industries, owing to their high thermal stability and mechanical strength. However, their robustness hinders their depolymerization to produce monomers and low-weight molecules. Presently, chemical recycling for most super engineering plastics remains relatively unexplored. Herein, we report the depolymerization of insoluble PEEK using sulfur nucleophiles via carbon–oxygen bond cleavages to form benzophenone dithiolate and hydroquinone. Treatment with organic halides converted only the former products to afford various dithiofunctionalized benzophenones. The depolymerization proceeded as a solid–liquid reaction in the initial phase. Therefore, this method was not affected by the shape of PEEK, e.g., pellets or films. Moreover, this depolymerization method was applicable to carbon- or glass fiber-enforced PEEK material. The depolymerized product, dithiofunctionalized benzophenones, could be converted into diiodobenzophenone which is an active form of aromatic substitution reactions.

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Section: Resultsmentioning

confidence: 95%

“…Currently, the existing depolymerization studies involve only PPS and PESU (Fig. 1b), [20][21][22][23][24][25] indicating that there are no generic depolymerization methods for these resins. This will constitute a significant environmental burden in the future.…”

mentioning

confidence: 99%

Depolymerization of robust polyetheretherketone to regenerate monomer units using sulfur reagents

Minami

Matsuyama

Takeichi

et al. 2022

Preprint

View full text Add to dashboard Cite

show abstract

“…We also examined the polymerization using molecules obtained by the present depolymerization (see Supplementary pages S22-S24). The reaction of 4,4′-dimercaptobenzophenone (21) with nonanedioyl dichloride (28) underwent in chloroform under reflux 73 to form a polythioester 29 with M w = 49,641 and PDI = 2.04 in 94% yield (Fig. 6c).…”

Section: Resultsmentioning

confidence: 99%

“…Currently, the existing depolymerization studies involve only PPS and PESU (Fig. 1b) [27][28][29][30][31][32] , indicating that there are no generic depolymerization methods for these resins. This will constitute a significant environmental burden in the future.…”

mentioning

confidence: 99%

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Depolymerization of robust polyetheretherketone to regenerate monomer units using sulfur reagents

et al. 2023

View full text Add to dashboard Cite

Super engineering plastics, high-performance thermoplastic resins such as polyetheretherketone, and polyphenylene sulfide have been utilized in industries, owing to their high thermal stability and mechanical strength. However, their robustness hinders their depolymerization to produce monomers and low-weight molecules. Presently, chemical recycling for most super engineering plastics remains relatively unexplored. Herein, we report the depolymerization of insoluble polyetheretherketone using sulfur nucleophiles via carbon–oxygen bond cleavages to form benzophenone dithiolate and hydroquinone. Treatment with organic halides converted only the former products to afford various dithiofunctionalized benzophenones. The depolymerization proceeded as a solid–liquid reaction in the initial phase. Therefore, this method was not affected by the shape of polyetheretherketone, e.g., pellets or films. Moreover, this depolymerization method was applicable to carbon- or glass fiber-enforced polyetheretherketone material. The depolymerized product, dithiofunctionalized benzophenones, could be converted into diiodobenzophenone, which was applicable to the polymerization.

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Hydroxylation-Depolymerization of Oxyphenylene-Based Super Engineering Plastics To Regenerate Arenols

Minami,

Inagaki,

Tsuyuki

et al. 2023

JACS Au

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Super engineering plastics, high-performance thermoplastic resins, show high thermal stability and mechanical strength as well as chemical resistance. On the other hand, chemical recycling for these plastics has not been developed due to their stability. This study describes depolymerization of oxyphenylene super engineering plastics via carbon–oxygen main chain cleaving hydroxylation reaction with an alkali hydroxide nucleophile. This method is conducted with cesium hydroxide as a hydroxy source and calcium hydride as a dehydration agent in 1,3-dimethyl-2-imidazolidinone, which provides hydroxylated monomers effectively. In the case of polysulfone, both 4,4′-sulfonyldiphenol (bisphenol S) and 4,4′-(propane-2,2-diyl)diphenol (bisphenol A) were obtained in high yields. Other super engineering plastics such as polyethersulfone, polyphenylsulfone, and polyetheretherketone were also applicable to this depolymerization.

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Novel synthesis of macrocyclic disulfides from poly(phenylene sulfide) by depolymerization reaction

Abstract: A new effective method is presented for the easier preparation of macrocyclics from poly(phenyl sulfide)by two steps: (1) depolymerization reaction of poly(phenyl sulfide) with Na 2 S in the presence of weak base, and (2) oxidation reaction of depolymerization products.

Cited by 6 publications

References 14 publications

Depolymerization of robust polyetheretherketone to regenerate monomer units using sulfur reagents

Depolymerization of robust polyetheretherketone to regenerate monomer units using sulfur reagents

Depolymerization of robust polyetheretherketone to regenerate monomer units using sulfur reagents

Hydroxylation-Depolymerization of Oxyphenylene-Based Super Engineering Plastics To Regenerate Arenols

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