Studies on the Kinetics of the Addition of Acetic Acid to Isobutene

Author: Showell, John Sheldon

Year: 1949

Degree: Master's thesis

Advisor: Lucas, Howard J.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/5kmx-0d09

Abstract

The kinetics of the addition of acetic acid to isobutene with anhydrous and water-containing acetic acid as the solvent were studied. The rate was determined by following the changing unsaturation with bromine. The reaction was found to be sensitive to the presence of water, tertiary butyl alcohol being the principal product, when water was present and no polymerization was observed. Under anhydrous conditions the tertiary butyl acetate was formed and the isobutene was observed to polymerize. The kinetics of the anhydrous reaction were theoretically treated quantitatively and the rate step was shown to be the addition of the proton to the isobutene. The water containing conditions were studied, but could not be quantitatively interpreted due to the complex equilibrium system set up, the results were however interpreted qualitatively. The concept of the carbonium ion intermediate of Whitmore was shown to be consistent with the esterification and t he polymerization reaction.

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