Ethyl sulfate process in which ethylene is reacted with sulfuric acid to produce ethyl sulfate followed by hydrolysis, but this method has been mostly replaced by direct hydration of ethylene. Ethyl sulfate can be produced in a laboratory setting by reacting ethanol with sulfuric acid under a gentle boil, while keeping the reaction below 140 °C. The sulfuric acid must be added dropwise or the reaction must be actively cooled because the reaction itself is highly exothermic. If the temperature exceeds 140 °C, the ethyl sulfate product tends to react with residual ethanol starting material, producing diethyl ether. If the temperature exceeds
Ethyl acetoacetate acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol. Ethyl acetoacetate is subject to keto-enol tautomerism. In the neat liquid at 33 °C, the enol consists of 15% of the total. Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are acidic, and the resulting carbanion can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible. Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as