Features of the acid-catalyzed hydrolysis of mono- and poly(ethylene glycol) methacrylates

[Display omitted] •The resistance of poly(ethylene glycol) methacrylates towards hydrolysis is independent of the ethoxylated chain length.•Nontrivial concentration dependences of the hydrolysis rate are associated with a change in acidity.•Pronounced self-acceleration of hydrolysis with increasing...

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Bibliographic Details
Published in:European polymer journal 2018-03, Vol.100, p.18-24
Main Authors: Orekhov, Dmitry V., Kazantsev, Oleg A., Sivokhin, Alexey P., Savinova, Maria V.
Format: Article
Language:English
Subjects:
2-Acrylamido-2-methylpropanesulfonic acid
2-Hydroxyethyl methacrylate
Acid-catalyzed hydrolysis
Concentration effect
Cyclotrons
Dilution
Esters
Hydrogen ions
Hydrolysis
Kinetics
Methacrylic acid
Organic chemistry
Poly(ethylene glycol) methacrylates
Polyethylene glycol
Structure of a solution
Sulfuric acid
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Summary:[Display omitted] •The resistance of poly(ethylene glycol) methacrylates towards hydrolysis is independent of the ethoxylated chain length.•Nontrivial concentration dependences of the hydrolysis rate are associated with a change in acidity.•Pronounced self-acceleration of hydrolysis with increasing conversion is observed when using methacrylic acid as a catalyst.•The hydrolysis kinetics is described by a second order equation. Hydrolysis of water-soluble industrially important mono- and poly(ethylene glycol) methacrylates catalyzed by sulfuric acid and organic monomeric acids (methacrylic and 2-acrylamido-2-methylpropanesulfonic acid) has been studied in aqueous solutions. Chemical stability of the methacrylates in dilute solutions was found to be independent of the length of ethoxylated fragments. Structurization of the studied solutions and the increase in concentration of hydrogen ions in concentrated solutions of the ethoxylated esters were shown to be the reason for the revealed unusual influence of the initial monomer concentration on the hydrolysis rate. The pronounced self-acceleration effect was observed for the methacrylic acid catalyzed reaction with increase in conversion.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2018.01.010