The Structure of Vinyl Polymers. III.<sup>1</sup> The Polymer from α-Angelica Lactone

Marvel, C. S.; Levesque, Charles L.

doi:10.1021/ja01876a013

Cited by 26 publications

(19 citation statements)

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“…43 Angelica lactone. Distillation of levulinic acid (LevA) under reduced pressure 44 or intramolecular dehydration in the presence of an acid catalyst such as acetic anhydride 45 or phosphoric acid 46 yields a-Angelica lactone (AL) monomer 7 ( Fig. 6).…”

Section: Monomers Which Do Not Maintain the Original Sugar Structurementioning

confidence: 99%

Polymers from sugars: cyclic monomer synthesis, ring-opening polymerisation, material properties and applications

2017

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Plastics are ubiquitous in modern society. However, the reliance on fossil fuels and the environmental persistence of most polymers make them unsustainable. Scientists are facing the challenge of developing cost-effective and performance-competitive polymers from renewable resources. Carbohydrates are a renewable feedstock with tremendous potential: sugars are widely available, environmentally benign and are likely to impart biocompatibility and degradability properties to polymers due to their high oxygen content. Sugars are also a feedstock with great structurally diversity and functionalisation potential that can enable fine tuning of the resulting polymer properties. In recent years, Ring-Opening Polymerisation (ROP) has emerged as the method of choice for the controlled polymerisation of renewable cyclic monomers, in particular lactones and cyclic carbonates, to allow the precise synthesis of complex polymer architectures and address commodity and specialist applications. This feature article gives an overview of sugar-based polymers that can be made by ROP. In particular, recent advances in the synthetic routes towards monomers that preserve the original carbohydrate core structure are presented. The performances of various homogeneous catalysts and the properties of the resultant polymers are given, and future opportunities highlighted for the development of both the materials and catalysts.

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Section: Monomers Which Do Not Maintain the Original Sugar Structurementioning

confidence: 99%

Polymers from sugars: cyclic monomer synthesis, ring-opening polymerisation, material properties and applications

2017

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“…Large sample volumes, high temperature, high pressure, using ZnCl2 or Et3O(BF4) yielded no polymer or oligomer [16,18,50]. The ROP of αAL, βAL, αOHγBL and αAcγBL were also studied with very limited success, despite the use of Lewis acids based on Sn, B or Al [51][52][53][54][55][56][57].…”

Section: Lewis Acid-catalyzed Rop/rocp Of γ-Lactonesmentioning

confidence: 99%

Ring-opening polymerization of γ-lactones and copolymerization with other cyclic monomers

Song

Pascouau

Zhao

et al. 2020

Progress in Polymer Science

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Triggered by raised environmental awareness and the rising requirements for sustainable polymers such as degradable or recyclable polymers, studies on ring-opening (co)polymerization (ROP/ROCP) of (bio-based) cyclic monomers (e.g., cyclic esters, lactides, epoxides etc.) have been booming in recent years. Renewable five-membered γ-butyrolactone (γBL) and derivatives would thus be a desirable feedstock to produce poly(γ-butyrolactone) (PγBL) and different (bio-based) functional polyesters. Their copolymerization with other cyclic monomers could also afford an alternative to tune the properties of the resulting materials.Although γBL was traditionally regarded "non-polymerizable", some progresses were made recently concerning the ROP/ROCP of γBL and derivatives. More importantly, some polyesters could be totally depolymerized back to their monomers by thermal or chemical treatment. This review is specially focused on ROP of γ-lactones and their copolymerization with other cyclic monomers by different catalytic/initiating systems, including Lewis/Brønsted acids, organic bases and alkali metal compounds, organometallic compounds, and cooperative bicomponent catalytic systems. The depolymerization process of some obtained polyesters is also discussed.

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“…Acetic anhydride or phosphoric acid were found to be suitable for this purpose. 90,91 Finally, diphenolic acid (DPA) can easily be obtained thanks to the reaction of one mole of LA with two moles of phenol at 100°C under acidic conditions. 84,92 Another pathway, using ionic liquids was also reported in 2013.…”

Section: B Levulinic Acid-based Polymers 1 Accessible Monomers From Levulinic Acidmentioning

confidence: 99%

Bio-Sourced Polymers: Recent Advances

Cramail

Bizet

Lamarzelle

et al. 2020

Series on Chemistry, Energy and the Environment

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Synthetic polymers are of major interest in the chemical industry, with a world production superior to 350Mt in 2016. They find applications in all the branches of industry, from packaging films to the stateof-the-art materials for sports and leisure activities, construction and aerospace industry or medical applications. Half of the amount of molecules produced by the petrochemical industry thus finds itself incorporated in the elaboration of polymer materials. With a production of 160Mt / year, ethylene can be considered as the major example of petroleum-based monomers. Green Chemistry introduced in 1998 by Anastase et al. (refer to Chapter 1 of this book), aims at providing solutions to reduce environmental impacts of our society. More precisely, this pursue of a more sustainable chemistry consists in using a source of renewable carbon to both reduce the dependence on fossil resources and thus stabilize greenhouse gas emissions (in particular CO 2 ) at the end of life. The use of renewable resources is of major interest in the elaboration of bio-sourced polymers. By using them, it is possible to mimick the fossil-based polymers -drop-in structures such as biopolyethylene-or to design new chemical structures, such as poly(lactic acid), PLA. Nowadays, the vegetal-based chemistry (renewable resources) mobilizes less than 0.5 % of arable land in the world. Some reminders of the definitions of the terms biomass, biopolymer, biodegradable polymer, bio-sourced polymer, bioplastic, biorefinery may be necessary: Biomass: material of biological origin (elaborated by alive bodies) with the exception of the materials of geological or fossil formation.Biopolymer: polymer developed by alive bodies, extracted from the biomass. Examples: polysaccharides, proteins, bacterial polymers.Biodegradable polymer: polymer the main degradation mechanism of which can be biotic, by enzymatic way. Under the action of micro-organisms and in the presence of oxygen (aerobic conditions), the organic compound decomposes totally within few months into carbon dioxide, water and mineral salts, with the appearance of a new biomass; in the absence of oxygen (anaerobic conditions), the organic compound decomposes totally within few months into carbon dioxide, methane, mineral salts and creation of a new biomass.Bio-sourced (or bio-based) polymer: synthetic polymer partially (generally > 20 %) or totally obtained from by-products stemming from the biomass. The bio-sourced character of a polymer can be determined in particular from its content in C14, according to the standard ASTM D6866. For the materials of totally fossil origin, the content in C14 is null.Bioplastic: term of popularization which indicates a 'biobased plastic' (restricted definition) and/or biodegradable (wider definition).Biorefinery: by analogy with a classic refinery, which works from fossil resources, a bio-refinery handles biomasses to produce, according to the cases, energy, fuels, materials, chemical and polymer products and/or animal and human feed. Today, two biopolymers ac...

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The Structure of Vinyl Polymers. III.¹ The Polymer from α-Angelica Lactone

Cited by 26 publications

References 0 publications

Polymers from sugars: cyclic monomer synthesis, ring-opening polymerisation, material properties and applications

Polymers from sugars: cyclic monomer synthesis, ring-opening polymerisation, material properties and applications

Ring-opening polymerization of γ-lactones and copolymerization with other cyclic monomers

Bio-Sourced Polymers: Recent Advances

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The Structure of Vinyl Polymers. III.1 The Polymer from α-Angelica Lactone

Cited by 26 publications

References 0 publications

Polymers from sugars: cyclic monomer synthesis, ring-opening polymerisation, material properties and applications

Polymers from sugars: cyclic monomer synthesis, ring-opening polymerisation, material properties and applications

Ring-opening polymerization of γ-lactones and copolymerization with other cyclic monomers

Bio-Sourced Polymers: Recent Advances

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The Structure of Vinyl Polymers. III.¹ The Polymer from α-Angelica Lactone