Diethyl sulfate ( DES) is an organosulfur compound with the Chemical formula (C2H5)2SO4.
Structure and properties
Although the formula for diethyl sulfate is typically written (C2H5)2SO4, a more descriptive formula would be (C2H5O)2SO2. It is a diester of sulfuric acid. Sulfur is tetrahedral.
Diethyl sulfate hydrolyzes readily, forming ethanol and ethyl sulfate. Eventually sulfuric acid is formed with excess water.
Reactions
Diethyl sulfate is used to an alkylating agent to prepare ethyl ethers, ethyl amines[
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Both dimethyl sulfate and diethyl sulfate react with inorganic nucleophiles as well. For example, potassium iodide gives ethyl iodide.
Preparation
Diethyl sulfate cannot be prepared efficiently analogously to the method used for dimethyl sulfate. The reaction of oleum with diethyl ether results in excessive oxidation of the ethyl groups. Instead, diethyl sulfate is prepared in two steps starting from chlorosulfuric acid:
The resulting ethyl sulfate is then heated with sodium sulfate, leading to a redistribution reaction:
Safety
Like other strong and especially dimethyl sulfate, diethyl sulfate is toxic
Neutralization
Dialkyl sulfates can be rendered nontoxic by treatment with aqueous ammonia.[
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Further reading
External links
