Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 6, Issue 12, Pages 17382-17390Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.8b05074
Keywords
Lipase-catalyzed regioselective methacrylation; Vinyl methacrylate; Methacrylic anhydride; Isosorbide; Polymethacrylate; Renewable; Rhizomucor miehei lipase; Biobased plastics
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Funding
- European Regional Development Fund [MOBTT21, TK134]
- Estonian State Forest Management Centre [LLTTI16016, LEP 1-18/53]
- Estonian Environmental Investment Centre [SLTTI16038]
- European Union's Seventh Framework Programme for research, technological development, and demonstration [621364]
- Estonian Ministry of Education and Research [IUT23-7]
- Swedish Research Council Formas [2016-00468]
- Swedish Foundation for Strategic Research [RBP14-0046]
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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 T-g = 167 degrees C. The polymer tethered with dodecanoate chains in exo position showed crystallinity with an unexpectedly high melting point at T-m = 83 degrees C. In contrast, the corresponding sample with dodecanoate chains in endo positions was fully amorphous with T-g = 54 degrees C. Efficient biocatalytic synthesis combined with attractive polymer properties opens possibilities for production of these biobased polymers on an industrial scale.
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