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Diethyl ether, or simply ether, is an organic compound in the ether class with the formula (C
2H5)2O, sometimes abbreviated as E2O (see Pseudoelement symbols). It is a colorless, highly volatile, sweet-smelling (“Ethereal odour”), extremely flammable liquid
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Most diethyl ether is produced as a byproduct of the vapor-phase hydration of ethylene to make ethanol.
This process uses solid-supported phosphoric acid catalysts and can be adjusted to make more ether if the need arises.
Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%.9
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It is particularly important as a solvent in the production of cellulose plastics such as cellulose acetate.8
Fuel
Diethyl ether has a high cetane number of 85–96 and is used as a starting fluid,
in combination with petroleum distillates for gasoline and Diesel engines because of its high volatility and low flash point.
For the same reason it is also used as a component of the fuel mixture for carbureted compression ignition model engines.
In this way diethyl ether is very similar to one of its precursors, ethanol.
Anesthesia
William T. G. Morton participated in a public demonstration of ether anesthesia on October 16, 1846 at the Ether Dome in Boston, Massachusetts. However, Crawford Williamson Long is now known to have demonstrated its use privately as a general anesthetic in surgery to officials in Georgia, as early as March 30, 1842,
and Long publicly demonstrated ether’s use as a surgical anesthetic on six occasions before the Boston demonstration.
British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium.
Diethyl ether largely supplanted the use of chloroform as a general anesthetic due to ether’s more favorable therapeutic index, that is,
a greater difference between an effective dose and a potentially toxic dose.
Diethyl ether does not depress the myocardium but rather it stimulates the sympathetic nervous system leading to hypertension and tachycardia.
It is safely used in patients with shock as it preserves the baroreceptor reflex.
Its minimal effect myocardial depression, respiratory drive, low cost, and high therapeutic index allows it to see continued use in developing countries.
Diethyl ether could also be mixed with other anesthetic agents such as chloroform to make C.E. mixture, or chloroform and alcohol to make A.C.E. mixture.
Halothane was the first such anesthetic developed and other currently used inhaled anesthetics, such as isoflurane, desflurane, and sevoflurane, are halogenated ethers.
Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting.
Modern anesthetic agents reduce these side effects.
Prior to 2005 it was on the World Health Organization’s List of Essential Medicines for use as an anesthetic.
Medicine
Ether was once used in pharmaceutical formulations.
A mixture of alcohol and ether, one part of diethyl ether and three parts of ethanol, was known as “Spirit of ether”, Hoffman’s Anodyne or Hoffman’s Drops.
In the United States this concoction was removed from the Pharmacopeia at some point prior to June 1917,
as a study published by William Procter, Jr.
between international pharmacopoeia, and from Hoffman’s original recipe.
It’s also used to treat hiccups through instillation into nasal cavity.
Metabolism
A cytochrome P450 enzyme is proposed to metabolize diethyl ether.
Diethyl ether inhibits alcohol dehydrogenase, and thus slows the metabolism of ethanol.
It also inhibits metabolism of other drugs requiring oxidative metabolism.
For example, diazepam requires hepatic oxidization whereas its oxidized metabolite oxazepam does not.
Safety and stability
Diethyl ether is extremely flammable and may form explosive vapour/air mixtures.
Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources,
which does not need to be an open flame, but may be a hot plate, steam pipe, heater etc.
Vapour may be ignited by the static electricity which can build up when ether is being poured from one vessel into another.
The autoignition temperature of diethyl ether is 160 °C (320 °F). The diffusion of diethyl ether in air is 9.18 × 10−6 m2/s (298 K, 101.325 kPa).
Ether is sensitive to light and air, tending to form explosive peroxides.
Ether peroxides have a higher boiling point than ether and are contact explosives when dry.
Commercial diethyl ether is typically supplied with trace amounts of the antioxidant butylated hydroxytoluene (BHT), which reduces the formation of peroxides.
Storage over sodium hydroxide precipitates the intermediate ether hydroperoxides.
Water and peroxides can be removed by either distillation from sodium and benzophenone, or by passing through a column of activated alumina.
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