Diethyl ether

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Diethyl ether
Chemical nameEthoxyethane, diethyl ether
Chemical formulaC4H10O
Molecular mass74.12 g/mol
Melting point-116.3 C
Boiling point34.6 C
Density0.7134 g/cm3
Flash point-40 C
CAS number60-29-7
SMILESCCOCC
Chemical structure of diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a typical smell. Diethyl ether has the formula CH3-CH2-O-CH2-CH3. It is used as a common solvent and has been used as a general anaesthetic. Diethyl ether has a high cetane number of 85 - 96 and is used as a starting fluid for diesel and gasoline engines. Ether is sparingly soluble in water (7 g/100 ml).

Contents

History

Alchemist Raymundus Lullus is credited with discovering the compound in 1275, although there is no contemporary evidence of this. It was first synthesized in 1540 by Valerius Cordus, who called it "sweet oil of vitriol" (oleum dulci vitrioli, the name was due to the fact that it was originally discovered by distilling a mixture of ethanol and sulfuric acid, then known as vitriol), and noted some of its medicinal properties. At about the same time, Theophrastus Bombastus von Hohenheim, better known as Paracelsus, discovered ether's analgesic properties. The name ether was given to the substance in 1730 by A.S.Frobenius.

Anaesthetic use

The American doctor Crawford Williamson Long, M.D., was the first surgeon to use it as an general anesthetic, on March 30, 1842. Its first use is normally associated with the Etherdome in Boston, Massachusetts. Ether is no longer used as an anesthetic when other, safer substances are available; ether is flammable, and is an irritant to some patients.

Due to this and the high volatility and the low ignition point of diethyl ether, diethyl ether is one of the risk factors in laboratories.

Ether may be used to anesthesiate ticks before removing them from an animal or a person's body. The anesthesia relaxes the tick and prevents it from maintaining its mouthpart under the skin.

Drug use

The anaesthetic effects of ether have made it a recreational drug, although not a popular one. Diethyl ether is not as toxic as other solvents used as recreational drugs (see volatile substance abuse).

Ether was sold in the late 1800s as a 'medicinal' for women. It was not considered proper for women to drink alcohol, especially during the temperance movement, and so they instead took extremely potent 'medicines' when the men did their drinking. One product was called Hoffmann's Drops, which was 3 parts ethanol to 1 part diethyl ether.

Ether, taken straight, will burn the mouth and be very unpleasant, but when mixed with alcohol it is possible to ingest orally. In the English translation of the book Phantastica by Louis Lewin (originally published in Germany in 1924), the translator calls it "Liquor Hoffmanni" and says "A large number of 'abstainers', especially women, employ this spirit of ether as a remedy against states of depression from which they frequently suffer. They would protest at being called alcoholists or etheromaniacs. Nevertheless they are to a certain degree slaves to the habit, which often becomes a mania. I know a court case where a woman was said to have consumed within four years thirty thousand marks' worth of this liquid. Attention should be paid to drinkers of these drops."

Ethyl ether is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[1] (http://www.incb.org/pdf/e/list/red.pdf).

Precautions

Diethyl ether is highly flammable. Its vapors are denser than air and will accumulate if proper ventilation is not present. Simple static electricity will ignite ether vapors. Diethyl ether vapors ignite explosively, and should only be used inside a fume hood.

Additionally, diethyl ether is prone to peroxide formation. Ether peroxides are higher boiling and are contact explosives when dry. Never distill ether to dryness, as the risk of explosion increases dramatically. Diethyl ether is typically supplied with BHT (2,6-di-tert-butyl-4-methylphenol), which reduces the formation of peroxides. Bottles older than 3 months should be routinely tested for peroxides.

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