Decarboxylation of Poly[<i>N</i>‐(acryloyloxy)phthalimide] as a Versatile Tool for Postpolymerization Modification

Frech, Stefan; Molle, Edgar; Hub, Cornelius; Mutlu, Hatice

doi:10.1002/marc.202200068

Cited by 11 publications

(5 citation statements)

References 28 publications

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“…Polyacrylates are regularly used in a number of applications including packaging, paints, coatings, adhesives, and sealants. − One of the most attractive features of polyacrylates is their durability, which arises from their chemical stability. However, the robust nature of polymers with all-carbon backbones often leads to the accumulation and persistence of post-consumer polyacrylate waste in landfills or oceans. − Accordingly, it is projected that 11 billion metric tons of plastic waste will amass in the environment by 2025 .…”

mentioning

confidence: 99%

Degradation of Polyacrylates by One-Pot Sequential Dehydrodecarboxylation and Ozonolysis

Korpusik,

Adili,

Bhatt

et al. 2023

J. Am. Chem. Soc.

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We establish a synthetically convenient method to degrade polyacrylate homopolymers. Carboxylic acids are installed along the polymer backbone by partial hydrolysis of the ester side chains, and then, in a one-pot sequential procedure, the carboxylic acids are converted into alkenes and oxidatively cleaved. This process enables the robustness and properties of polyacrylates to be maintained during their usable lifetime. The ability to tune the degree of degradation was demonstrated by varying the carboxylic acid content of the polymers. This method is compatible with a wide range of polymers prepared from vinyl monomers through copolymerization of acrylic acid with different monomers including acrylates, acrylamides, and styrenics.

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confidence: 99%

Degradation of Polyacrylates by One-Pot Sequential Dehydrodecarboxylation and Ozonolysis

Korpusik,

Adili,

Bhatt

et al. 2023

J. Am. Chem. Soc.

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“…19). 48 Using a ruthenium-based photocatalyst in combination with the Hantzsch ester as a reducing agent, this reaction generated radicals on the polymer backbone that could react with a methyl acrylate acceptor, or be intercepted by a stable nitroxyl radical to form the TEMPO adduct.…”

Section: Polymer Chemistry Reviewmentioning

confidence: 99%

Radical decarboxylation: an emerging tool in polymer synthesis

Anyaegbu,

Vidali,

Haridas

et al. 2024

Polym. Chem.

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“…For example, the inclusion of N -hydroxyphthalimide ester-containing monomers such as N -(methacryloxy)phthalimide (PhthMA) can lead to direct main chain scission of polymethacrylates . The PhthMA unit can accept an electron from a single electron donor, which induces a cascade reaction, liberating CO 2 and generating a backbone radical that can cleave the polymer backbone via β-scission. − …”

Section: Introductionmentioning

confidence: 99%

Bulk Depolymerization of Methacrylate Polymers via Pendent Group Activation

Hughes,

Lott,

Zastrow

et al. 2024

J. Am. Chem. Soc.

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In this study, we present an efficient approach for the depolymerization of poly(methyl methacrylate) (PMMA) copolymers synthesized via conventional radical polymerization. By incorporating low mol % phthalimide ester-containing monomers during the polymerization process, colorless and transparent polymers closely resembling unfunctionalized PMMA are obtained, which can achieve >95% reversion to methyl methacrylate (MMA). Notably, our catalyst-free bulk depolymerization method exhibits exceptional efficiency, even for high-molecular-weight polymers, including ultrahigh-molecular-weight (10 6 −10 7 g/mol) PMMA, where near-quantitative depolymerization is achieved. Moreover, this approach yields polymer byproducts of significantly lower molecular weight, distinguishing it from bulk depolymerization methods initiated from chain ends. Furthermore, we extend our investigation to polymethacrylate networks, demonstrating high extents of depolymerization. This innovative depolymerization strategy offers promising opportunities for the development of sustainable polymethacrylate materials, holding great potential for various applications in polymer science.

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Decarboxylation of Poly[N‐(acryloyloxy)phthalimide] as a Versatile Tool for Postpolymerization Modification

Cited by 11 publications

References 28 publications

Degradation of Polyacrylates by One-Pot Sequential Dehydrodecarboxylation and Ozonolysis

Degradation of Polyacrylates by One-Pot Sequential Dehydrodecarboxylation and Ozonolysis

Radical decarboxylation: an emerging tool in polymer synthesis

Bulk Depolymerization of Methacrylate Polymers via Pendent Group Activation

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