Nucleophile-Assisted Hydrolysis of Mustard
Abstract
The hydrolysis rate of 0.1-0.2M mustard (typical field decontamination concentrations) is inhibited by two processes: (1) the recombination of the chloride ion with the ethylenesulfonium ion to form mustard, known as the return step; and (2) the formation of stable and unreactive dimeric sulfonium chloride salts (reaction between thiodiglycol and ethylenesulfonium ions). The above inhibitions can be completely eliminated by adding a large amount of a competitive nucleophile to the reaction mixture. The hydrolysis rate can thus be increased to a first-order rate that is controlled by the solvent polarity only. In this study, the nucleophile-assisted hydrolysis rates were measured by nuclear magnetic resonance techniques in a 50 vol % acetone solution and in a microemulsion system. The competition rates of nucleophiles and chloride ion with water for reaction with the ethylenesulfonium ion are also discussed. (js)
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 01, 1990
- Accession Number
- ADA229663
Entities
People
- J. R. Ward
- Linda L. Szafraniec
- William T. Beaudry
- Yu-chu Yang
Organizations
- Edgewood Chemical Biological Center