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Enzymatic Synthesis and Polymerization of Isosorbide-Based Monomethacrylates for High-Tg Plastics
- Source :
- ACS Sustainable Chemistry & Engineering. 6:17382-17390
- Publication Year :
- 2018
- Publisher :
- American Chemical Society (ACS), 2018.
-
Abstract
- Isosorbide is a stiff bicyclic diol derived from glycose-based polysaccharides, and is thus an attractive building block for novel rigid bioplastics. In the present work, a highly regioselective biocatalytic approach for the synthesis of isosorbide 5-methacrylate was developed. The Lipozyme RM IM (Rhizomucor miehei lipase)-catalyzed process is straightforward, easily scalable, and chromatography-free; a simple extractive workup afforded the monomer at >99% purity and in 87% yield. The developed strategy was applied for the synthesis of a series of monomethacrylated isosorbide derivatives. Radical polymerization of the monomers produced rigid polymethacrylates with a certain side group in either endo or exo configuration, exclusively, which generated materials with great diversity of properties. For example, the two regioisomeric polymers carrying hydroxyl groups reached a glass transition temperature at Tg = 167 °C. The polymer tethered with dodecanoate chains in exo position showed crystallinity with an ...
- Subjects :
- chemistry.chemical_classification
Isosorbide
Bicyclic molecule
Renewable Energy, Sustainability and the Environment
General Chemical Engineering
Diol
Radical polymerization
02 engineering and technology
General Chemistry
Polymer
010402 general chemistry
021001 nanoscience & nanotechnology
01 natural sciences
0104 chemical sciences
chemistry.chemical_compound
Monomer
chemistry
Polymerization
medicine
Environmental Chemistry
Organic chemistry
0210 nano-technology
Pendant group
medicine.drug
Subjects
Details
- ISSN :
- 21680485
- Volume :
- 6
- Database :
- OpenAIRE
- Journal :
- ACS Sustainable Chemistry & Engineering
- Accession number :
- edsair.doi...........5279e2f98292f6e4338081e91b9aac6d