The one group of cyclic ethers that behaves differently from open-chain ethers are the three-membered-ring compounds called epoxides, or oxiranes, which we saw in Section 8.7. The strain of the three-membered ring gives epoxides unique chemical reactivity. Ethylene oxide, the simplest epoxide, is an intermediate in the manufacture of both ethylene glycol, used for automobile antifreeze, and polyester polymers. Approximately 18 million metric tons of ethylene oxide is produced worldwide each year, most of it by air oxidation of ethylene over a silver oxide catalyst at 300 °C. This process is not useful for other epoxides, however, and is of little value in the laboratory. Note that the name ethylene oxide is not a systematic one because the -ene ending implies the presence of a double bond in the molecule. The name is frequently used, however, because ethylene oxide is derived from ethylene by addition of an oxygen atom. Other simple epoxides are named similarly. The systematic name for ethylene oxide is 1,2-epoxyethane.
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