Preparation of Allyl and Methallyl Methacrylates by the Thermal Decomposition of Allyl and Methallyl α-Acetoxyisobutyrates
1943
Rehberg, Chessie E. | Fisher, C.H. | Smith, Lee T.
1. Satisfactory methods were developed for preparing allyl and methallyl α-hydroxyisobutyrates from hydroxyisobutyric acid and the appropriate alcohol. 2. The hydroxy esters were converted into allyl and methallyl α-acetoxyisobutyrates by treatment with acetic anhydride. 3. Under milder conditions than those required for the thermal decomposition of the corresponding acetoxypropionates, allyl and methallyl acetoxyisobutyrates were transformed satisfactorily by pyrolysis into allyl and methallyl methacrylates. 4. These results and data previously reported indicate that (1) esters of α-acetoxyisobutyric acid yield unsaturated esters more readily when pyrolyzed than do corresponding lactic acid derivatives and (2) that esters prepared from allyl and methallyl alcohols are more stable than those prepared from n-butyl and β-phenoxyethyl alcohols but less stable than esters prepared from methyl, benzyl and ethyl alcohols. Allyl, methallyl and β-methoxyethyl esters appear to have approximately the same thermal stability.
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