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Related Concept Videos

Types of Step-Growth Polymers: Polyesters01:20

Types of Step-Growth Polymers: Polyesters

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The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Acid Halides to Esters: Alcoholysis01:12

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Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
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Esters to Carboxylic Acids: Saponification01:25

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Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
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Enhanced Polyester Degradation through Transesterification with Salicylates.

Hee Joong Kim, Marc A Hillmyer, Christopher J Ellison

    Journal of the American Chemical Society
    |September 16, 2021
    PubMed
    Summary
    This summary is machine-generated.

    Researchers developed a scalable method to create degradable polyesters by incorporating salicylate units. These modified polyesters, like polylactide, maintain performance while offering enhanced hydrolytic degradation, paving the way for sustainable plastics.

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    Area of Science:

    • Polymer Science
    • Materials Science
    • Sustainable Chemistry

    Background:

    • Conventional polyesters dominate the global plastic market but lack biodegradability.
    • Existing degradable polyester alternatives face challenges in practical application and scalability.
    • There is a critical need for high-performance, sustainable, and degradable polyester materials.

    Purpose of the Study:

    • To develop a scalable method for creating degradable polyesters by modifying commercial polyester backbones.
    • To investigate the impact of incorporating salicylate units on the properties and degradability of polyesters.
    • To assess the potential of this approach for creating sustainable alternatives to conventional plastics.

    Main Methods:

    • Utilized transesterification, including in situ polymerization-transesterification, to incorporate salicylate units into commercial polyesters.
    • Employed melt-processing techniques like compounding and extrusion for scalable polymer synthesis.
    • Evaluated hydrolytic degradation in various aqueous environments (buffer, seawater, alkaline solutions).

    Main Results:

    • Successfully synthesized high molar mass polyesters with incorporated salicylate moieties.
    • Modified polylactide demonstrated enhanced hydrolytic degradability without compromising thermal, mechanical, or oxygen barrier properties.
    • Incorporation of salicylate units into polycaprolactone and a poly(ethylene terephthalate) derivative also yielded facile alkaline degradation.

    Conclusions:

    • The developed transesterification strategy offers a scalable and practical route to engineer degradable polyesters.
    • Salicylate-modified polyesters present a promising class of materials with tunable degradability and retained performance.
    • This research provides a foundation for developing next-generation sustainable and high-performance polyester materials.