Improvements in the Production of Isosorbide Monomethacrylate Using a Biobased Catalyst and Liquid-Liquid Extraction Isolation for Modifications of Oil-Based Resins

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dc.contributor.authorJašek, Vojtěchcs
dc.contributor.authorFučík, Jancs
dc.contributor.authorMelčová, Veronikacs
dc.contributor.authorPřikryl, Radekcs
dc.contributor.authorFigalla, Silvestrcs
dc.coverage.issue23cs
dc.coverage.volume9cs
dc.date.accessioned2024-07-23T10:46:07Z
dc.date.available2024-07-23T10:46:07Z
dc.date.issued2024-05-30cs
dc.description.abstractThe improved production of a polar curable monomer, isosorbide monomethacrylate (MISD), with methacrylic anhydride (MAAH) as an acyl donor, was performed. A sustainable and cheap catalyst, potassium acetate (CH3COOK), was used for a solvent-free synthesis, requiring only the equimolar amount of reagents (no excess). The production included the quantitative separation of the secondary product, methacrylic acid (MAA), preventing the reaction batch from the purification process (neutralization of MAA), and gaining a usable reagent. The synthesis resulted in a sufficient yield of MISD (61.8%) obtained by the liquid-liquid extraction process (LLE), which is a significant improvement in the process, avoiding the flash chromatography step in the isolation of MISD. The purity of synthesized and isolated MISD via the LLE was confirmed by H-1 NMR, MS, and FTIR analyses. The thermal analyses, namely, DSC and TGA, were used to characterize the curability and thermal stability of MISD. The activation energy of MISD's curing was calculated (E-a = 94.6 kJ/mol) along with the heat-resistant index (T-s = 136.8). The polar character of isosorbide monomethacrylate was investigated in a mixture with epoxidized acrylated soybean oil (EASO). It was found that MISD is entirely soluble in EASO and can modify the rheological behavior and surface energy of EASO-based resins. The apparent viscosity of EASO at 30 degrees C (eta(app) = 3413 mPa<middle dot>s) decreased with the 50% content of MISD significantly (eta(app) = 500 mPa<middle dot>s), and the free surface energy value of EASO (gamma(S) = 42.2 mJ/m(2)) also increased with the 50% content of MISD (gamma(S) = 48.7 mJ/m(2)). The produced MISD can be successfully used as a diluent and the polarity modifier of curable oil-basen
dc.formattextcs
dc.format.extent11cs
dc.format.mimetypeapplication/pdfcs
dc.identifier.citationACS OMEGA. 2024, vol. 9, issue 23, 11 p.en
dc.identifier.doi10.1021/acsomega.4c01275cs
dc.identifier.issn2470-1343cs
dc.identifier.orcid0000-0002-8020-4948cs
dc.identifier.orcid0000-0002-3408-4383cs
dc.identifier.orcid0000-0002-2124-6953cs
dc.identifier.orcid0000-0002-7811-9840cs
dc.identifier.orcid0000-0003-2392-8031cs
dc.identifier.other188795cs
dc.identifier.researcheridABD-4360-2020cs
dc.identifier.researcheridE-8210-2010cs
dc.identifier.scopus57204110910cs
dc.identifier.urihttps://hdl.handle.net/11012/249346
dc.language.isoencs
dc.publisherAMER CHEMICAL SOCcs
dc.relation.ispartofACS OMEGAcs
dc.relation.urihttps://pubs.acs.org/doi/full/10.1021/acsomega.4c01275cs
dc.rightsCreative Commons Attribution 4.0 Internationalcs
dc.rights.accessopenAccesscs
dc.rights.sherpahttp://www.sherpa.ac.uk/romeo/issn/2470-1343/cs
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/cs
dc.subjectMixturesen
dc.subjectOrganic compoundsen
dc.subjectOrganic polymersen
dc.subjectSurface energyen
dc.subjectViscosityen
dc.titleImprovements in the Production of Isosorbide Monomethacrylate Using a Biobased Catalyst and Liquid-Liquid Extraction Isolation for Modifications of Oil-Based Resinsen
dc.type.driverarticleen
dc.type.statusPeer-revieweden
dc.type.versionpublishedVersionen
sync.item.dbidVAV-188795en
sync.item.dbtypeVAVen
sync.item.insts2024.07.23 12:46:07en
sync.item.modts2024.07.23 12:13:44en
thesis.grantorVysoké učení technické v Brně. Fakulta chemická. Ústav chemie materiálůcs
thesis.grantorVysoké učení technické v Brně. Fakulta chemická. Ústav chemie a technologie ochrany životního prostředícs
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