Detail publikace

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

JAŠEK, V. FUČÍK, J. IVANOVÁ, L. VESELÝ, D. FIGALLA, S. MRAVCOVÁ, L. SEDLÁČEK, P. KRAJČOVIČ, J. PŘIKRYL, R.

Originální název

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

Typ

článek v časopise ve Web of Science, Jimp

Jazyk

angličtina

Originální abstrakt

The 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 min−1 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 min−1 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.

Klíčová slova

poly(lactic acid); poly(3-hydroxybutyrate); depolymerization; alcoholysis; methacrylation; polymerizable monomers; kinetics

Autoři

JAŠEK, V.; FUČÍK, J.; IVANOVÁ, L.; VESELÝ, D.; FIGALLA, S.; MRAVCOVÁ, L.; SEDLÁČEK, P.; KRAJČOVIČ, J.; PŘIKRYL, R.

Vydáno

1. 12. 2022

Nakladatel

MDPI

Místo

Switzerland

ISSN

2073-4360

Periodikum

Polymers

Ročník

14

Číslo

23

Stát

Švýcarská konfederace

Strany od

1

Strany do

18

Strany počet

18

URL

https://www.mdpi.com/2073-4360/14/23/5236

Plný text v Digitální knihovně

http://hdl.handle.net/11012/208729

BibTex

@article{BUT180377,
  author="Vojtěch {Jašek} and Jan {Fučík} and Lucia {Ivanová} and Dominik {Veselý} and Silvestr {Figalla} and Ludmila {Mravcová} and Petr {Sedláček} and Jozef {Krajčovič} and Radek {Přikryl}",
  title="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",
  journal="Polymers",
  year="2022",
  volume="14",
  number="23",
  pages="1--18",
  doi="10.3390/polym14235236",
  issn="2073-4360",
  url="https://www.mdpi.com/2073-4360/14/23/5236"
}