Scalable synthesis and polymerisation of a β-angelica lactone derived monomer

Dell'Acqua, Andrea; Stadler, Bernhard M.; Kirchhecker, Sarah; Tin, Sergey; Vries, Johannes G. de

doi:10.1039/d0gc00338g

Cited by 13 publications

(12 citation statements)

References 71 publications

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“…The majority of angelica lactone is produced as an intermediate or a by-product during the synthesis of γ-valerolactone, and thus the literature on angelica lactones is rather underdeveloped. However, there are examples of its use in polymer chemistry. , Furthermore, angelica lactone contains a double bond, which could enable its radical polymerization and thereby broaden the scope of this lactone in the field of polymer chemistry.…”

Section: Cyclic Monomersmentioning

confidence: 99%

“…However, obtaining pure β-angelica lactone can be challenging. 719 Norbornene can also be functionalized and subsequently polymerized to generate useful materials. Notable examples include the esterification of 5-norbornene-2-methanol with various fatty acids, followed by polymerization to generate polymers with glass transition temperatures that span a large temperature range, i.e., from −32 to +102 °C.…”

Section: Cyclic Olefins For Ring-opening Metathesis Polymerizationmentioning

confidence: 99%

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Polymers without Petrochemicals: Sustainable Routes to Conventional Monomers

et al. 2022

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Access to a wide range of plastic materials has been rationalized by the increased demand from growing populations and the development of high-throughput production systems. Plastic materials at low costs with reliable properties have been utilized in many everyday products. Multibillion-dollar companies are established around these plastic materials, and each polymer takes years to optimize, secure intellectual property, comply with the regulatory bodies such as the Registration, Evaluation, Authorisation and Restriction of Chemicals and the Environmental Protection Agency and develop consumer confidence. Therefore, developing a fully sustainable new plastic material with even a slightly different chemical structure is a costly and long process. Hence, the production of the common plastic materials with exactly the same chemical structures that does not require any new registration processes better reflects the reality of how to address the critical future of sustainable plastics. In this review, we have highlighted the very recent examples on the synthesis of common monomers using chemicals from sustainable feedstocks that can be used as a like-for-like substitute to prepare conventional petrochemical-free thermoplastics.

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Section: Cyclic Monomersmentioning

confidence: 99%

Section: Cyclic Olefins For Ring-opening Metathesis Polymerizationmentioning

confidence: 99%

Polymers without Petrochemicals: Sustainable Routes to Conventional Monomers

et al. 2022

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“…The GBL structure renders polymers complete recyclability, and therefore it is a considerable strategy to keep this core structure so that the special recyclability of materials could be preserved. Recently, novel GBL derivative monomers were reported, including angelica lactones, , N -substituted cis -4-thia- l -proline (thio)lactones, , penicillamine-derived β-thiolactones, and 2-thiabicyclo[2.2.1]heptan-3-one . Another direction is designing monomers with completely new structure, and more efforts should be devoted toward the monomer synthesis by using sustainable feedstock.…”

Section: Breakthrough From Nonpolymerizable To Efficient Polymerizationmentioning

confidence: 99%

Advances, Challenges, and Opportunities of Poly(γ-butyrolactone)-Based Recyclable Polymers

Liu

et al. 2021

ACS Macro Lett.

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The discovery and prosperous growth of synthetic polymers have presented both significant advantages and daunting challenges in the last century. To address the issues of environmental pollution and fossil consumption, recyclable, degradable, and/or biobased polymers have been given much attention in the polymer science community. This viewpoint focuses on the emerging fully chemical recyclable poly(γ-butyrolactone)-based polymers. The breakthrough from nonpolymerizable to efficient polymerization is highlighted by the benefits of the development of a series of catalysis for ring-opening polymerization of γ-butyrolactone. Subsequently, the design of γ-butyrolactone derivatives and synthesis of more recyclable polymers are summarized together with the discussions about the structure and property relationship. Finally, the remaining challenges and promising opportunities are suggested in order to provide insights into the further direction for sustainable polymers.

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“…Novel monomers have been proposed using AGL as a key biobased reagent. [138] The β-AGL has recently been transformed into gasoline-like hydrocarbon fuels and novel acrylic bioplastic using a Lewis-pair catalytic system. [139] AGL has been condensed with biomass-derived furanics, and the resulting oxygenates have been deoxygenated to hydrocarbon fuels by catalytic hydrogenation.…”

Section: La To Aglmentioning

confidence: 99%

“…Novel renewable polyesters can be prepared by the ring‐opening polymerization of AGL in the presence of a Lewis acid catalyst. Novel monomers have been proposed using AGL as a key biobased reagent [138] . The β‐AGL has recently been transformed into gasoline‐like hydrocarbon fuels and novel acrylic bioplastic using a Lewis‐pair catalytic system [139] .…”

Section: Chemical Modification Of Both Ketone and Carboxylic Acid Functionality In Lamentioning

confidence: 99%

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Dutta

Bhat

2021

ChemCatChem

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Levulinic acid (LA) is one of the most prominent biomass‐derived chemical building blocks that can be transformed into specialty chemicals like fuels, solvents, monomers for polymers, plasticizers, surfactants, agrochemicals, and pharmaceuticals. Over the past three decades, an enormous amount of research data have been acquired on the preparation and downstream value addition of LA, and these works have been reviewed. However, considering the astonishing number of publications appearing every year on LA derivatives, the periodical review of recent works focusing on unique aspects of chemistry must be undertaken to critically evaluate the achievements to date, reassess the challenges, and recognize new opportunities. This review discusses the chemical‐catalytic synthesis of various derivatives of LA by focusing on its functionalities and reactivity patterns. Recent literature on some crucial derivatives such as γ‐valerolactone, 4,4’‐diphenolic acid, and ethyl levulinate have been tabulated and discussed. The synthetic interconversion between various derivatives, mechanistic insights, critical analysis of the reaction parameters toward selective preparation of various derivatives, and their potential commercial applications have been elaborated using predominantly heterogeneous catalysts. A critical assessment of the relative advantages and shortcomings of the existing synthetic strategies for various derivatives of LA has been presented to enkindle fresh ideas.

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Scalable synthesis and polymerisation of a β-angelica lactone derived monomer

Abstract: A new bio-based norbornene polymer was prepared starting from β-angelica lactone, prepared in a sustainable and scalable manner from the platform chemical levulinic acid. The new material displays transparency comparable to petrochemical-derived polynorbornene.

Cited by 13 publications

References 71 publications

Polymers without Petrochemicals: Sustainable Routes to Conventional Monomers

Polymers without Petrochemicals: Sustainable Routes to Conventional Monomers

Advances, Challenges, and Opportunities of Poly(γ-butyrolactone)-Based Recyclable Polymers

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

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