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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Date
2024-05-30
Authors
Jašek, Vojtěch
Fučík, Jan
Melčová, Veronika
Přikryl, Radek
Figalla, Silvestr
0000-0002-8020-4948Advisor
Referee
Mark
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AMER CHEMICAL SOC
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Abstract
The 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-bas
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en