Ring-opening metathesis polymerization of 2,3-dihydrofuran
Abstract/Contents
- Abstract
- Plastics are critical to every modern industry, but the chemical stability of common polymers causes them persist for decades. As a result, plastics are accumulating in the environment at an alarming rate. To address the growing plastic pollution crisis, new end-of-life strategies must be developed. One important approach is the development of new polymers that can be broken down on demand. These degradable polymers may be converted back into monomers or into building blocks for second-generation materials. This thesis introduces the surprising ring-opening metathesis polymerization (ROMP) of 2,3-dihydrofuran (DHF), a commercial cyclic enol ether. Enol ethers have historically been used as quenching agents in ROMP, reacting rapidly with Grubbs catalysts to form thermodynamically stable electron-rich Fischer carbenes. However, these Fischer carbenes remain competent metathesis catalysts. Using Grubbs catalysts, DHF can be both homopolymerized and copolymerized with common norbornene ROMP monomers. Furthermore, rapid acid-catalyzed hydrolysis enables degradation of enol ether-containing materials. Chapter 1 introduces the challenge of polymer recycling for both thermoplastics and thermosets. Special attention is paid to modern approaches and recently commercialized recycling technologies. The foundation for the discovery of DHF ROMP is also described. Chapter 2 summarizes the synthesis of degradable and depolymerizable polyDHF. Chapter 3 explores copolymerization of DHF with common norbornene monomers. Finally, Chapter 4 describes the use of DHF in ROMP of dicyclopentadiene. In addition to enabling hydrolysis of polydicyclopentadiene thermosets, the unique reactivity of Ru Fischer carbenes suppresses crosslinking in these materials.
Description
| Type of resource | text |
|---|---|
| Form | electronic resource; remote; computer; online resource |
| Extent | 1 online resource. |
| Place | California |
| Place | [Stanford, California] |
| Publisher | [Stanford University] |
| Copyright date | 2023; ©2023 |
| Publication date | 2023; 2023 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Feist, John David |
|---|---|
| Degree supervisor | Xia, Yan, 1980- |
| Thesis advisor | Xia, Yan, 1980- |
| Thesis advisor | Moore, Jeffrey |
| Thesis advisor | Waymouth, Robert M |
| Degree committee member | Moore, Jeffrey |
| Degree committee member | Waymouth, Robert M |
| Associated with | Stanford University, School of Humanities and Sciences |
| Associated with | Stanford University, Department of Chemistry |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | John David Feist. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2023. |
| Location | https://purl.stanford.edu/dr452ry9295 |
Access conditions
- Copyright
- © 2023 by John David Feist
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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