History
Ethylene oxide was first reported in 1859 by the French chemist Charles-Adolphe Wurtz, who prepared it by treating 2-chloroethanol with potassium hydroxide:
- Cl–CH2CH2–OH + KOH → (CH2CH2)O + KCl + H2O
Wurtz measured the boiling point of ethylene oxide as 13.5 °C, slightly higher than the present value, and discovered the ability of ethylene oxide to react with acids and salts of metals. Wurtz mistakenly assumed that ethylene oxide has the properties of an organic base. This misconception persisted until 1896 when Georg Bredig found that ethylene oxide is not an electrolyte. Its distinct difference with ethers, in particular, its propensity to join the addition reactions typical of unsaturated compounds, had long been a matter of debate. Only in 1893, the heterocyclic triangular structure of ethylene oxide had been proposed.
The first synthesis method had long remained the only, despite numerous attempts of scientists, including Wurtz himself, to produce ethylene oxide directly from ethylene. Only in 1931, French chemist Theodore Lefort developed a method of direct oxidation of ethylene in the presence of silver catalyst. Since 1940, almost all industrial production of ethylene oxide has used this process. Sterilization by ethylene oxide for the preservation of spices was patented in 1938 by the American chemist Lloyd Hall. Ethylene oxide achieved industrial importance during World War I as a precursor to both the coolant ethylene glycol and the chemical weapon mustard gas.
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