Issue 6, 2015

Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

Abstract

We present an alternative synthetic route to acrylic acid, starting from the platform chemical lactic acid and using heterogeneous catalysis. To improve selectivity, we designed an indirect dehydration reaction that proceeds via acetoxylation of lactic acid to 2-acetoxypropionic acid. This intermediate can then be pyrolized to acrylic acid. Acetic acid is used both as a reagent and a solvent in the first step, and may be recovered in the subsequent pyrolysis step. We tested a range of solid acid catalysts for the acetoxylation step (Y zeolites, sulfated zirconia, ion-exchange resins, sulfonated graphene, and various sulfonated silica gels and mixed oxides). Recycling studies were carried out for the most active catalysts. To enable quantitative analysis using gas chromatography we also developed a reliable silylation derivatization method, which is also reported. These results open opportunities for improving the biorenewable production of acrylic acid.

Graphical abstract: Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

Supplementary files

Article information

Article type
Paper
Submitted
19 Oct 2014
Accepted
20 Nov 2014
First published
20 Nov 2014

RSC Adv., 2015,5, 4103-4108

Author version available

Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

R. Beerthuis, M. Granollers, D. R. Brown, H. J. Salavagione, G. Rothenberg and N. R. Shiju, RSC Adv., 2015, 5, 4103 DOI: 10.1039/C4RA12695E

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