A New Method for the Synthesis of Perfluoro-Beta, Beta-Dimethylacrylonitrile

Abstract

The title compound was prepared in modest yield by treatment of perfluoroisobutylene (PFIB) in acetonitrile solvent with potassium cyanide in the presence of 18-crown-6 ether catalyst. Product formation in the time course of the reaction was observed to follow a Gaussian rather than a plateau profile; maximum concentration occurred between 60 and 70 min with incomplete conversion of the PFIB. A major by-product of the reaction was tentatively identified as a condensation product of the PFIB and title compound. Reaction mechanisms consistent with experimental results are proposed to explain product and by-product formation. Suggestions for further work are proposed. Keywords: Acetonitrile, Catalyst, Concentration profile, Crown ether, GLC analyses, NMR spectra, Fluorocyanoolefin, Potassium cyanide, Organofluorine compounds, Partition coefficient, Reaction mechanisms, Reaction optimization, Chemical warfare.

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Document Details

Document Type
Technical Report
Publication Date
May 01, 1988
Accession Number
ADA197985

Entities

People

  • Cliff R. King
  • James W. King
  • William R. Hydro

Organizations

  • Edgewood Chemical Biological Center

Tags

Communities of Interest

  • Biomedical

DTIC Thesaurus Topics

  • Acetonitrile
  • Alkenes
  • Boiling Point
  • Catalysts
  • Chemical Synthesis
  • Chemistry
  • Classification
  • Conversion
  • Crown Ethers
  • Cyanides
  • Materials
  • Nitriles
  • Organic Chemistry
  • Organic Compounds
  • Potassium
  • Potassium Cyanide
  • Reaction Mechanisms

Fields of Study

  • Chemistry

Readers

  • Analytical Chemistry
  • Combustion science or combustion engineering.
  • Materials Science and Engineering.