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Green Chem., 2009, 11, 1666 - 1674, DOI: 10.1039/b914515j

An efficient synthesis of -acyloxyacrylate esters as candidate monomers for bio-based polymers by heteropolyacid-catalyzed acylation of pyruvate esters

Wataru Ninomiya, Masahiro Sadakane, Shinji Matsuoka, Hiroki Nakamura, Hiroyuki Naitou and Wataru Ueda

A series of -acyloxyacrylate esters are candidate monomers for bio-based polymers, converted from biomass feedstock. Polymers from these monomers are useful materials for bio-based plastics showing high heat resistance and transparency. In this paper, a new efficient method for -acyloxyacrylate ester synthesis with a strong inorganic acid, heteropolyacid, is presented. The reaction in the presence of the heteropolyacid catalyst was carried out in liquid phase under mild conditions and showed higher productivity than that of the conventional synthesis with a typical organic acid, p-toluenesulfonic acid. Among the various heteropolyacids examined, -Keggin-type tungsten-based phosphotungstic acid, H3PW12O40, showed the best performance, suggesting that the acid strength of the heteropolyacid is the crucial property for this reaction. We also found that pyruvate ester was consecutively converted into -acyloxyacrylate ester via 2,2-diacyloxypropionate ester.

Graphical abstract image for this article (ID: b914515j)