An efficient heteropolyacid catalyzed acylation of pyruvate esters to alpha-acyloxyacrylate esters as potential candidate monomers for bio-based polymers

Wataru Ninomiya; Masahiro Sadakane; Shinji Matsuoka; Hiroki Nakamura; Hiroyuki Naitou; Wataru Ueda

doi:10.1039/b809940e

An efficient heteropolyacid catalyzed acylation of pyruvate esters to alpha-acyloxyacrylate esters as potential candidate monomers for bio-based polymers

Chem Commun (Camb). 2008 Nov 7:(41):5239-41. doi: 10.1039/b809940e. Epub 2008 Sep 12.

Authors

Wataru Ninomiya¹, Masahiro Sadakane, Shinji Matsuoka, Hiroki Nakamura, Hiroyuki Naitou, Wataru Ueda

Affiliation

¹ Mitsubishi Rayon Co., Ltd., Research and Development Administration Department, 6-41, Konan 1-chome, Minato-ku, Tokyo, 108-8506, Japan. ninomiya_wa@mrc.co.jp

PMID: 18956081
DOI: 10.1039/b809940e

Abstract

Alpha-acyloxyacrylate esters were efficiently synthesized from pyruvate esters and carboxylic anhydrides under mild conditions. These esters are potential candidate monomers for bio-based polymers with high durability and transparency. Tungsten-based Keggin type heteropolyacids, especially H(3)PW(12)O(40), worked more effectively as catalysts for this reaction than other typical acids.

MeSH terms

Acrylates / chemical synthesis
Acrylates / chemistry
Acylation
Catalysis
Esters / chemical synthesis
Esters / chemistry
Indicators and Reagents
Magnetic Resonance Spectroscopy
Polymers / chemical synthesis*
Polymethyl Methacrylate / chemistry
Pyruvates / chemistry*
Solvents
Tungsten

Substances

Acrylates
Esters
Indicators and Reagents
Polymers
Pyruvates
Solvents
Polymethyl Methacrylate
Tungsten