Synthesis of D (+)-l-Phenylethyl Acrylate in Organic Solvents Catalyzed by Lipase and Its Polymer

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Lipase-catalyzed transesterification of vinyl acrylate (VA) with D, L-1-phenylethanol was carried out to synthesize D (+)-1-phenylethyl acrylate (PEA) in organic solvents, Lipase OF was the most appropriate enzyme for the synthesis of PEA among four kinds of lipases studied. The conversion to PEA increased with increasing lipase OF concentration. Isooctane was the most appropriate solvent among three kinds of solvents studied. While PEA was synthesized when VA was used as an acylating agent, it was hardly synthesized with acrylic acid or ethyl acrylate. The conversion to 1-phenylethyl methacrylate using vinyl methacrylate or methacrylic anhydride as an acylating agent was much lower than that of PEA. The formation of PEA was confirmed by ¹H-NMR spectrum. The optical purity of PEA was 100%. Optically active polymer having molecular weight of about 30, 000 was obtained by a solution polymerization method.