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Olefin Metathesis Polymerization: Overview

Olefin Metathesis Polymerization: Overview

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 of a...

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...

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 polymer...

Free-Radical Chain Reaction and Polymerization of Alkenes

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.

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

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

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...

Radical Chain-Growth Polymerization: Chain Branching

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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Aliphatic long-chain C20 polyesters from olefin metathesis.

Justyna Trzaskowski¹, Dorothee Quinzler, Christian Bährle

¹Chair of Chemical Materials Science, Department of Chemistry Universitätsstrasse 10, 78457 Konstanz, Germany.

Macromolecular Rapid Communications

|July 14, 2011

Summary

This study synthesized pure 1,20-eicosanedioic acid via self-metathesis and hydrogenation. Subsequent polycondensation yielded polyester 20,20, offering a controlled alternative to irregular polyesters from ADMET polymerization.

Keywords:

dispersions metathesis polyesters thermal properties thermoplastics

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Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

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Published on: November 27, 2015

Area of Science:

Polymer Chemistry
Organic Synthesis
Materials Science

Background:

Ring-opening metathesis polymerization (ROMP) is a common method for synthesizing polyesters.
Alternative methods are needed to control polymer structure and properties.

Purpose of the Study:

To develop a new method for synthesizing long-chain aliphatic polyesters with controlled structures.
To compare the properties of polyesters synthesized via self-metathesis with those from ADMET polymerization.

Main Methods:

Self-metathesis of undecenoic acid using a ruthenium catalyst.
Hydrogenation of the resulting diacid to yield 1,20-eicosanedioic acid.
Polycondensation of 1,20-eicosanedioic acid with eicosane-1,20-diol.
Comparison with ADMET polymerization of undec-10-enyl undec-10-enoate.

Main Results:

Pure 1,20-eicosanedioic acid was obtained with >99% purity.
Polyester 20,20 was synthesized with a melting point (Tm) of 108°C.
ADMET polymerization yielded a polyester with irregular ester linkages and Tm of 103°C.
Aqueous dispersions of the polyester were successfully prepared.

Conclusions:

Self-metathesis followed by polycondensation offers a route to well-defined long-chain aliphatic polyesters.
This method provides better control over polymer structure compared to ADMET polymerization.
The synthesized polyesters exhibit distinct thermal properties based on their structural regularity.