Synthesis of Methylene Butyrolactone Polymers from Itaconic Acid
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2017 Wiley Periodicals, Inc. Herein, we report the transformation of -monomethyl itaconate, an inexpensive and biorenewable alternative to petroleum feedstocks, to the high-value monomer -methylene-,-dimethyl--butyrolactone (Me2MBL) through a selective addition strategy. This strategy is also applied to the synthesis of -methylene--butyrolactone (MBL, tulipalin A), a monomer that can be polymerized to give materials with desirable properties (high decomposition temperature, glass transition temperature, and refractive index). Subsequent polymerization of both Me2MBL and MBL through reversible addition-fragmentation chain-transfer polymerization generates well-defined poly(Me2MBL) and poly(MBL) (PMBL). Physical characterization of poly(Me2MBL) shows good physical properties comparable with known PMBL materials. 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 27302737.