Hydrolysis of 2-chloroethyl ethyl sulfide in aqueous ethanol-water and acetone-water mixtures. Technical report, October 1983-December 1984
The rate of hydrolysis of 2,2-dichlorodiethyl sulfide (mustard) was investigated at 25 C in water in the presence of 5% by volume acetone. The results led to a proposed SN1 mechanism using a sulfonium ion intermediate. The hydrolysis of a less-toxic and commonly used mustard simulant, 2-chloroethyl ethyl sulfide (CEES), however, was never investigated. This study measures the rates of hydrolysis of CEES over a wide range of temperatures in binary aqueous mixtures of ethanol-water and acetone-water. The presence of the organic-solvent component was necessary because the rate of dissolution of CEES in pure water was too slow for accurate reaction rate measurements. It was also expected that an investigation in the activation parameters and their variation with solvent composition should provide further evidence of the reaction mechanism. These variations are expected to follow similar patterns as that of t-butyl chloride (TBC), a frequently used model for SN1 hydrolysis. Therefore, rate constants of TBC hydrolysis in the same solvent mixtures were also measured for comparison with CEES and for comparison with earlier work.
- Research Organization:
- Chemical Research, Development and Engineering Center, Aberdeen Proving Ground, MD (USA)
- OSTI ID:
- 7170349
- Report Number(s):
- AD-A-173177/7/XAB; CRDEC-TR-86048
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALKYL RADICALS
BUTYL RADICALS
CHEMICAL REACTIONS
CHEMICAL WARFARE AGENTS
CHLORIDES
CHLORINE COMPOUNDS
DECOMPOSITION
DISPERSIONS
ENERGY
ENTHALPY
ETHYL RADICALS
FLUIDS
FREE ENERGY
HALIDES
HALOGEN COMPOUNDS
HYDROGEN COMPOUNDS
HYDROLYSIS
KINETICS
LIQUIDS
LYSIS
MIXTURES
ORGANIC SOLVENTS
OXYGEN COMPOUNDS
PHYSICAL PROPERTIES
RADICALS
REACTION KINETICS
SIMULATION
SOLVENTS
SOLVOLYSIS
THERMODYNAMIC PROPERTIES
WATER
WEAPONS