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Oxiranes, also referred to as epoxides, are organic compounds in which an oxygen atom is bonded to two adjacent carbon atoms, forming a 3-membered ring. The three-membered ring in oxirane is highly strained and readily opens under mild conditions. This property is extensively used in organic synthesis. For example, oxirane on treatment with reagents like water, methanol, hydrochloric acid, and base forms ethylene glycol, methyl cellosolve, 2-chloroethanol and polyethylene glycol, respectively. A unique behaviour of oxiranes is the trans-annular fission, which involves the cleavage of C-C and C-O bonds, which may occur with or without the accompanying hydrogen transfer to oxygen.
Oxiranes are critical in the manufacture of detergents, thickeners, solvents, and plastics. In the medical equipment industry, steam is replaced by oxirane to sterilize heat sensitive tools as it does not leave any residue. The prominent derivative of oxirane, ethylene glycol, can be converted into polyester fibers or polyethylene terephthalate (PET) resin. Polyester fibres are used in clothing, carpets, and upholstery; PET resin is a recyclable plastic used for packaging film and bottles.