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

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dc.contributor.authorLowry, Amy
dc.contributor.authorLynch, Rachel E.
dc.contributor.authorSzydło, Marcin
dc.contributor.authorMcGlacken, Gerard P.
dc.contributor.authorByrne, Peter A.
dc.contributor.funderUniversity College Cork, UCC
dc.contributor.funderSynthesis and Solid State Pharmaceutical Centre, SSPC, 15/RI/3221-12/RC/2275_P2
dc.date.accessioned2026-05-25T15:50:06Z
dc.date.available2026-05-25T15:50:06Z
dc.date.issued2026-04-23
dc.description.abstractCarboxylic 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.en
dc.description.sponsorshipThis publication has emanated from research conducted with the financial support of the Research Ireland (Grant numbers GOIPG/2018/169, GOIPG/2021/802, and 20 FFP-P-8865), and the SSPC (the Research Ireland Centre for Pharmaceuticals
dc.description.sponsorshipGrant number 12/RC/2275_P2). The work used equipment provided by Research Ireland though a research infrastructure award for process flow spectroscopy (ProSpect) (grant: 15/RI/3221). The authors wish to thank Dr. Denis Lynch and Dr. Lorraine Bateman from University College Cork, and Dr. Yannick Ortin and Dr. Patricia Fleming from University College Dublin for NMR spectroscopy support, and Dr. Jimmy Muldoon for mass spectrometry support. This publication has emanated from research conducted with the financial support of the Research Ireland (Grant numbers GOIPG/2018/169, GOIPG/2021/802, and 20 FFP‐P‐8865), and the SSPC (the Research Ireland Centre for Pharmaceuticals
dc.description.sponsorshipGrant number 12/RC/2275_P2). The work used equipment provided by Research Ireland though a research infrastructure award for process flow spectroscopy (ProSpect) (grant: 15/RI/3221). The authors wish to thank Dr. Denis Lynch and Dr. Lorraine Bateman from University College Cork, and Dr. Yannick Ortin and Dr. Patricia Fleming from University College Dublin for NMR spectroscopy support, and Dr. Jimmy Muldoon for mass spectrometry support.
dc.description.versionPublished Version
dc.format.mimetypeapplication/pdfen
dc.identifier.articleide202500119
dc.identifier.authororcidLowry, Amy
dc.identifier.authororcidLynch, Rachel E.
dc.identifier.authororcidSzydło, Marcin
dc.identifier.authororcidMcGlacken, Gerard P.§0000-0002-7821-0804
dc.identifier.authororcidByrne, Peter A.
dc.identifier.citationLowry, 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
dc.identifier.doi10.1002/cmtd.202500119
dc.identifier.issn2628-9725
dc.identifier.issued5
dc.identifier.journaltitleChemistry-Methods
dc.identifier.otherRIS: urn:DF5F7481DEB3172B3B4634F8833C8AC5
dc.identifier.otherORCID: /0000-0002-7821-0804/work/215732367
dc.identifier.urihttps://hdl.handle.net/10468/18872
dc.identifier.volume6
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.relation.urihttps://www.scopus.com/pages/publications/105037145560
dc.relation.urihttps://www.scopus.com/pages/publications/105037145560?origin=resultslist
dc.rights© 2026, the Author(s). Chemistry - Methods published by Chemistry Europe and Wiley-VCH GmbH.
dc.rights.accessrightsopen access
dc.rights.licensenameAttribution 4.0 International
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.statusPeer reviewed
dc.subject'Dry' [
dc.subjectCarboxylate salts
dc.subjectCarboxylation
dc.subjectCarboxylic acids
dc.subjectChromatographic analysis
dc.subjectChromatographic purification
dc.subjectColumn chromatography
dc.subjectDry column vacuum chromatography
dc.subjectFunctional groups
dc.subjectFunctionals
dc.subjectLiquid chromatography
dc.subjectNovel methodology
dc.subjectPharmaceutical industry
dc.subjectPotassium
dc.subjectProtonation
dc.subjectProtonations
dc.subjectPurification
dc.subjectUnsaturated carboxylic acids
dc.subjectWittig reactions
dc.subject[Chemistry]
dc.subjectpurification
dc.subjectcarboxylic acids
dc.subjectdry column vacuum chromatography
dc.subjectcarboxylation
dc.titlePurification of α,β-unsaturated carboxylic acids as their potassium carboxylate salts using dry column vacuum chromatographyen
dc.typeArticle (peer-reviewed)
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