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Related Concept Videos

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.0K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.2K
Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
2.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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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...
2.3K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Related Experiment Video

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Chemically Recyclable Dithioacetal Polymers via Reversible Entropy-Driven Ring-Opening Polymerization.

Lasith S Kariyawasam1, Julian F. Highmoore1, Ying Yang1

  • 1Department of Chemistry, University of Nevada, Reno, Reno, NV 89557, USA.

Angewandte Chemie (International Ed. in English)
|March 29, 2023
PubMed
Summary
This summary is machine-generated.

Polymers called polydithioacetals (PDTAs) can be chemically recycled into monomers and reformed into polymers. This efficient monomer-polymer recycling demonstrates a new platform for sustainable, recyclable materials.

Keywords:
Chemical Recycling to MonomerEntropy-Driven Ring-Opening PolymerizationMacrocyclesPolydithioacetalTransthioacetalization

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Sustainable Chemistry

Background:

  • The development of polymers for a sustainable circular economy is crucial.
  • Chemical recyclability of polymers into monomers is highly desirable for sustainability.
  • Polymers capable of efficient monomer-polymer recycling are needed.

Purpose of the Study:

  • To report an efficient monomer-polymer recycling process for polydithioacetals (PDTAs).
  • To demonstrate PDTA as a new molecular platform for designing recyclable polymers.
  • To highlight the advantages of entropy-driven ring-opening polymerization (ED-ROP) for recyclable polymers.

Main Methods:

  • Synthesis of pristine polydithioacetals (PDTAs) from 3,4,5-trimethoxybenzaldehyde and alkyl dithiols.
  • Depolymerization of PDTAs via ring-closing depolymerization into macrocycles.
  • Entropy-driven ring-opening polymerization (ED-ROP) to reform virgin polymers.
  • Investigation of thermal reprocessability of crosslinked PDTA networks via acid-catalyzed dithioacetal exchange.
  • Assessment of recyclability of crosslinked networks into macrocyclic monomers.

Main Results:

  • PDTAs were readily synthesized and exhibited efficient depolymerizability into macrocyclic monomers.
  • High conversions were achieved in both the forward (polymerization) and reverse (depolymerization) reactions.
  • Crosslinked PDTA networks showed thermal reprocessability and recyclability into monomers.
  • The regenerated macrocyclic monomers could repolymerize to reform the crosslinked network.

Conclusions:

  • Polydithioacetals (PDTAs) represent a novel molecular platform for creating recyclable polymers.
  • The study showcases the effectiveness of entropy-driven ring-opening polymerization (ED-ROP) for polymer recycling.
  • ED-ROP is favored at higher temperatures, offering advantages for recyclable polymer design.