High-Pressure Depolymerization of Poly(lactic acid) (PLA) and Poly(3-hydroxybutyrate) (PHB) Using Bio-Based Solvents: A Way to Produce Alkyl Esters Which Can Be Modified to Polymerizable Monomers

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dc.contributor.authorJašek, Vojtěchcs
dc.contributor.authorFučík, Jancs
dc.contributor.authorIvanová, Luciacs
dc.contributor.authorVeselý, Dominikcs
dc.contributor.authorFigalla, Silvestrcs
dc.contributor.authorMravcová, Ludmilacs
dc.contributor.authorSedláček, Petrcs
dc.contributor.authorKrajčovič, Jozefcs
dc.contributor.authorPřikryl, Radekcs
dc.coverage.issue23cs
dc.coverage.volume14cs
dc.date.accessioned2023-01-03T15:56:51Z
dc.date.available2023-01-03T15:56:51Z
dc.date.issued2022-12-01cs
dc.description.abstractThe polyesters poly(lactic acid) (PLA) and poly(3-hydroxybutyrate) (PHB) used in various applications such as food packaging or 3D printing were depolymerized by biobased aliphatic alcohols—methanol and ethanol with the presence of para-toluenesulphonic acid (p-TSA) as a catalyst at a temperature of 151 °C. It was found that the fastest depolymerization is reached using methanol as anucleophile for the reaction with PLA, resulting in the value of reaction rate constant (k) of 0.0425 min1 and the yield of methyl lactate of 93.8% after 120 min. On the other hand, the value of constant k for the depolymerization of PHB in the presence of ethanol reached 0.0064 min1 and the yield of ethyl 3-hydroxybutyrate was of 76.0% after 240 min. A kinetics study of depolymerization was performed via LC–MS analysis of alkyl esters of lactic acid and 3-hydroxybutanoic acid. The structure confirmation of the products was performed via FT-IR, MS, 1H NMR, and 13C NMR. Synthesized alkyl lactates and 3-hydroxybutyrates were modified into polymerizable molecules using methacrylic anhydride as a reactant and potassium 2-ethylhexanoate as a catalyst at a temperature of 80 °C. All alkyl esters were methacrylated for 24 h, guaranteeing the quantitative yield (which in all cases reached values equal to or of more than 98%). The methacrylation rate constants (k) were calculated to compare the reaction kinetics of each alkyl ester. It was found that lactates reach afaster rate of reaction than 3-hydroxybutyrates. The value of k for themethacrylated methyl lactate reached 0.0885 dm3/(mol·min). Opposite to this result, methacrylated ethyl 3-hydroxybutyrate’s constant k was 0.0075 dm3/(mol·min). The reaction rate study was conducted by the GC-FID method and the structures were confirmed via FT-IR, MS, 1H NMR, and 13C NMR.en
dc.formattextcs
dc.format.extent1-18cs
dc.format.mimetypeapplication/pdfcs
dc.identifier.citationPolymers. 2022, vol. 14, issue 23, p. 1-18.en
dc.identifier.doi10.3390/polym14235236cs
dc.identifier.issn2073-4360cs
dc.identifier.other180377cs
dc.identifier.urihttp://hdl.handle.net/11012/208729
dc.language.isoencs
dc.publisherMDPIcs
dc.relation.ispartofPolymerscs
dc.relation.urihttps://www.mdpi.com/2073-4360/14/23/5236cs
dc.rightsCreative Commons Attribution 4.0 Internationalcs
dc.rights.accessopenAccesscs
dc.rights.sherpahttp://www.sherpa.ac.uk/romeo/issn/2073-4360/cs
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/cs
dc.subjectpoly(lactic acid)en
dc.subjectpoly(3-hydroxybutyrate)en
dc.subjectdepolymerizationen
dc.subjectalcoholysisen
dc.subjectmethacrylationen
dc.subjectpolymerizable monomersen
dc.subjectkineticsen
dc.titleHigh-Pressure Depolymerization of Poly(lactic acid) (PLA) and Poly(3-hydroxybutyrate) (PHB) Using Bio-Based Solvents: A Way to Produce Alkyl Esters Which Can Be Modified to Polymerizable Monomersen
dc.type.driverarticleen
dc.type.statusPeer-revieweden
dc.type.versionpublishedVersionen
sync.item.dbidVAV-180377en
sync.item.dbtypeVAVen
sync.item.insts2023.02.20 16:50:37en
sync.item.modts2023.02.20 16:13:26en
thesis.grantorVysoké učení technické v Brně. Fakulta chemická. Centrum materiálového výzkumucs
thesis.grantorVysoké učení technické v Brně. Fakulta chemická. Ústav chemie a technologie ochrany životního prostředícs
thesis.grantorVysoké učení technické v Brně. Fakulta chemická. Ústav chemie materiálůcs
thesis.grantorVysoké učení technické v Brně. Fakulta chemická. Ústav fyzikální a spotřební chemiecs
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