Purification of α,β-unsaturated carboxylic acids as their potassium carboxylate salts using dry column vacuum chromatography

Lowry, Amy; Lynch, Rachel E.; Szydło, Marcin; McGlacken, Gerard P.; Byrne, Peter A.

Purification of α,β-unsaturated carboxylic acids as their potassium carboxylate salts using dry column vacuum chromatography

Files

Chemistry_Methods_-_2026_-_Lowry_-_Purification_of_Unsaturated_Carboxylic_Acids_as_Their_Potassium_Carboxylate_Salts.pdf(657.88 KB)

Date

2026-04-23

Authors

Lowry, Amy

Lynch, Rachel E.

Szydło, Marcin

McGlacken, Gerard P.

Byrne, Peter A.

Publisher

Wiley-VCH Verlag

Published Version

10.1002/cmtd.202500119

Abstract

Carboxylic acids are ubiquitous functional groups and are used widely in the bulk chemistry and fine pharmaceutical industries. During the development of novel methodology for the synthesis of α,β-unsaturated carboxylic acids, it was found that established methods for the purification of the product carboxylic acids led to unsatisfactory outcomes. However, chromatographic purification of the products of these reactions as their potassium carboxylate salts proved highly successful. Unlike their parent carboxylic acids, the carboxylate salts could be separated readily from the other constituents of the reaction mixture using dry column vacuum chromatography (DCVC). The yields of the carboxylic acid products obtained by subsequent protonation of the carboxylate salts were found to depend strongly on the identity of the acid used to effect the protonation, with methanesulfonic acid and (+)-camphorsulfonic acid resulting in the highest recoveries of pure products. The combined DCVC and acidification protocols developed were shown to be effective for the purification of numerous functionalised α,β-unsaturated carboxylic acids. © 2026 The Author(s). Chemistry - Methods published by Chemistry Europe and Wiley-VCH GmbH.

Keywords

'Dry' [ , Carboxylate salts , Carboxylation , Carboxylic acids , Chromatographic analysis , Chromatographic purification , Column chromatography , Dry column vacuum chromatography , Functional groups , Functionals , Liquid chromatography , Novel methodology , Pharmaceutical industry , Potassium , Protonation , Protonations , Purification , Unsaturated carboxylic acids , Wittig reactions , [Chemistry]

Citation

Lowry, A, Lynch, R E, Szydło, M, McGlacken, G P & Byrne, P A 2026, 'Purification of α,β-unsaturated carboxylic acids as their potassium carboxylate salts using dry column vacuum chromatography', Chemistry-Methods, vol. 6, no. 5, e202500119. https://doi.org/10.1002/cmtd.202500119