Diethyl ether

This article is about the chemical compound. For other uses, see aether.

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low water (6.9 g/100 ml).

History

ether was given to the substance in 1730 by August Siegmund Frobenius.

Metabolism

A putative cytochrome P450 enzyme is believed to metabolize diethyl ether.^[1]

Diethyl ether inhibits oxidative metabolism ^[3]

Applications

Diethyl ether is a common laboratory autoignition temperature.

Anesthetic use

The American doctor Crawford Williamson Long, M.D., was the first surgeon to use it as a chloroform because it had a wider margin of therapeutic index, a larger difference between the recommended dosage and a toxic overdose.

Today, ether is rarely used. The use of flammable ether waned as nonflammable anesthetic agents such as methoxyflurane (Penthrane) reduce these side effects.^[6]

Ether may be used to anesthetize 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.^{[citation needed]}

Recreational use

The anesthetic 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.

Ether, mixed with inhalant.

Due to its immiscibility with water and the fact that non-polar organic compounds are highly soluble in it, ether is also used in the production of freebase cocaine, and is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.^[8]

Production

Diethyl ether is rarely prepared in laboratories because of the hazards involved and the easy availability to legitimate labs. Most diethyl ether is produced as a byproduct of the vapor-phase alumina catalysts can give diethyl ether yields of up to 95%^[9] .

Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. electronegative oxygen atom of the ethanol, giving the ethanol molecule a positive charge:

CH₃CH₂OH + H⁺ → CH₃CH₂OH₂⁺

A electrophilic) ethanol molecule, producing water, a hydrogen ion and diethyl ether.

CH₃CH₂OH₂⁺ + CH₃CH₂OH → H₂O + H⁺ + CH₃CH₂OCH₂CH₃

The reaction to make diethyl ether is reversible, so eventually an Le Chatelier's principle.

Safety

Diethyl ether is prone to activated alumina.^[10]

Ether is an extremely flammable material. Open flames and even electrically heated devices should be avoided when using ether since it is easily ignited by a flame or spark. Ether's autoignition temperature is only 170°C (338°F), so it can be ignited by a hot surface without a flame or spark. The most common practice in chemical labs is to use steam (thus limiting the temperature to 100°C (212°F)) when ether must be heated or distilled.

Cultural references

Recreational use of diethyl ether was portrayed in the film Fear and Loathing in Las Vegas, based on the book of the same name by Hunter S. Thompson, and portrayed in the novel The Cider House Rules by John Irving and in the film adaptation of the same name. An example of ether being used as a drug in the 19th century is to be found in Italo Svevo's novel Senilità (1898). One of the main characters, Amalia, a reticent spinster in her early thirties, has become addicted to ether, falls into delirium and dies.

References