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Kinetics and Mechanism of the Hydrolysis and Alcoholysis of Alkoxysilanes
Journal of Adhesion Science and Technology
  • David J. Oostendorp
  • Gary L. Bertrand, Missouri University of Science and Technology
  • James O. Stoffer, Missouri University of Science and Technology
Abstract

As Part of Our Work with the Use of Silane Coupling Agents, We Have Been Investigating the Transformations of Alkoxysilancs into Siloxanes. the Influence of a Para-Substituted Phenyl Group Attached to the Silicon Was Investigated and the Rates of Acid Catalyzed Hydrolysis and Alcoholysis of These Para-Substituted Phenylalkoxysilanes Have Been Determined. the Kinetics and Mechanism of the Reactions Are Presented. These Reactions Are of Interest Because of their Role in the Use of Silane Coupling Agents as Adhesion Promoters, in the Preparation of Zinc-Rich Silicate Coatings, in the Sol-Gel Process and in the Preparation of Silicones in General. the Hydrolysis Reaction Was Found to Be First Order in Acid, Zero Order in Water and to Have a Hammett Ρ of -1.42 When Catalyzed by Sulfuric Acid. These Results Are Consistent with Current Opinion that the Reaction Mechanism is SN1, and Involves a Positive Intermediate, Possibly a Siliconium Intermediate. the Alcoholysis Reaction Was Found to Be First Order in Both the Silane and the Catalysts, and of Intermediate Order in the Alcohol, When Catalyzed by Carboxylic Acids. When Catalyzed by Dichloro- Acetic Acid, the Reaction Has a Hammet Ρ Value of +0.43. This is Consistent with a Concerted Displacement Reaction between the Alkoxysilane and the Complex Involving the Alcohol and the Carboxylate Anion. the Intermediate is a Negatively Charged Intermediate, Probably a Penta- Substituted Silicon Species. © vs.P 1992.

Department(s)
Chemistry
Keywords and Phrases
  • Alcoholysis,
  • Alkoxysilanes,
  • Coupling agents,
  • Hydrolysis,
  • Siliconium
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2023 Taylor and Francis Group; Taylor and Francis, All rights reserved.
Publication Date
1-1-1992
Publication Date
01 Jan 1992
Disciplines
Citation Information
David J. Oostendorp, Gary L. Bertrand and James O. Stoffer. "Kinetics and Mechanism of the Hydrolysis and Alcoholysis of Alkoxysilanes" Journal of Adhesion Science and Technology Vol. 6 Iss. 1 (1992) p. 171 - 191 ISSN: 1568-5616; 0169-4243
Available at: http://works.bepress.com/gary-bertrand/65/