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Poly(isoprenecarboxylates) from Glucose via Anhydromevalonolactone
Nicolas R Ball-Jones1, Grant W Fahnhorst1, Thomas R Hoye1
1Department of Chemistry, 207 Pleasant St., SE, University of Minnesota, Minneapolis, MN 55455.
ACS Macro Letters
|December 10, 2016
Summary
Researchers developed a sustainable synthesis for isoprenecarboxylic acid esters (ICAEs) and polymers. These glucose-derived materials offer a promising alternative to conventional poly(acrylates) in various applications.
Area of Science:
- Polymer Chemistry
- Organic Synthesis
- Sustainable Materials
Background:
- Poly(acrylates) are widely used but derived from non-renewable resources.
- There is a growing need for sustainable alternatives in polymer science.
- Glucose-derived monomers offer a renewable feedstock for novel polymers.
Purpose of the Study:
- To develop an efficient synthesis of isoprenecarboxylic acid esters (ICAEs).
- To synthesize high molecular weight poly(isoprenecarboxylates) using controlled polymerization techniques.
- To characterize the thermal and physical properties of the resulting polymers.
Main Methods:
- Base-catalyzed eliminative ring-opening of anhydromevalonolactone to yield isoprenecarboxylic acid.
- Esterification to produce various ICAEs.
- Reversible Addition-Fragmentation chain-Transfer (RAFT) polymerization for polymer synthesis.
Main Results:
- Successful synthesis of ICAEs and high molecular weight poly(isoprenecarboxylates) (Đ ≈ 1.5).
- Characterization of glass transition temperatures (Tg) and entanglement molecular weights (Me).
- Polymer properties showed trends similar to analogous poly(acrylate esters).
Conclusions:
- A short and efficient synthetic route to ICAEs and their polymers was established.
- Glucose-derived poly(isoprenecarboxylates) present tunable properties comparable to poly(acrylates).
- These novel polymers represent a sustainable alternative for materials applications.
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