DIETHYL ETHER

Diethyl ether
Diethyl ether Diethyl ether
General
Systematic name	ethoxyethane 3-oxapentane
Other names	diethyl ether ethyl ether ethyl oxide
Molecular formula	C4H10O C2H5OC2H5
SMILES	CCOCC
Molar mass	74.12 g/mol
Appearance	clear, colorless liquid
CAS number	[60-29-7]
Properties
Density and phase	0.7134 g/cm³, liquid
Solubility in water	6.9 g/100 ml (20 °C)
Melting point	−116.3 °C (156.85 K)
Boiling point	34.6 °C (307.75 K)
Acidity (p''K''a)	?
Basicity (p''K''b)	?
Viscosity	0.224 cP at 25 °C
Structure
Molecular shape	?
Dipole moment	1.15 D (gas)
Hazards
MSDS	External MSDS
Main hazards	Extremely Flammable (F+), Harmful (Xn)
NFPA 704
Flash point	-45 °C
Autoignition temperature	170 °C
R/S statement
RTECS number	KI5775000
Supplementary data page
Structure and properties	''n'', εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related Ethers	Dimethyl ether Methoxypropane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

:''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 boiling point and a characteristic smell. It is the most common member of a class of chemical compounds known generically as ethers. It is an isomer of butanol. Diethyl ether has the formula CH₃-CH₂-O-CH₂-CH₃. It is used as a common solvent and has been used as a general anesthetic. Ether is sparingly soluble in water (6.9 g/100 ml).

Contents

History

Applications

Anesthetic use

Recreational use

Cultural references

Synthesis

Chemistry

References

External links

History

Alchemist Raymundus Lullus is credited with discovering the compound in 1275 AD, although there is no contemporary evidence of this. It was first synthesized in 1540 by Valerius Cordus, who called it "'oil of sweet 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 oil of 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 August Siegmund Frobenius.

Applications

Diethyl ether is a common laboratory solvent. It has limited solubility in water, thus it is commonly used for liquid-liquid extraction. Being less dense than water, the ether layer is usually on top. Its counterpart is dichloromethane, which is similarly insoluble in water, and is also used for liquid-liquid extraction (dichloromethane is usually the lower phase). Diethyl ether is a common solvent for the Grignard reaction, and for many other reactions involving organometallic reagents. It is particularly important as a solvent in the production of cellulose plastics such as cellulose acetate.^[1] Diethyl ether has a high cetane number of 85 - 96 and is used as a starting fluid for diesel and gasoline engines ^[2] because ot its high volatility and low autoignition temperature.

Anesthetic use

The American doctor Crawford Williamson Long, M.D., was the first surgeon to use it as a general anesthetic, on March 30, 1842.Hill, John W. and Kolb, Doris K. ''Chemistry for changing times: 10th edition''. Page 257. Pearson: Prentice Hall. Upper saddle river, New Jersey. 2004. William T.G. Morton was previously credited with the first public demonstration of ether anesthesia on October 16, 1846 at the Ether Dome in Boston, Massachusetts, although Dr. Crawford Long is now known to have demonstrated its use publicly to other officials in Georgia. Ether was sometimes used in place of 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 halothane became available. Additionally, ether had many undesirable side effects, such as postanesthetic nausea and vomiting. Modern anesthetic agents, such as methyl propyl ether (Neothyl) and methoxyflurane (Penthrane) reduce these side effects.
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.

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 (see volatile substance abuse).
Ether, mixed with ethanol, was marketed in the 19th century as a cure-all and recreational drug, during one of Western society's temperance movements. At the time, it was considered improper for women to consume alcoholic beverages at social functions, and sometimes ether-containing drugs would be consumed instead. A cough medicine called Hoffmann's Drops was marketed at the time as one of these drugs, and contained both ether and alcohol in its capsules.^[3] Ether tends to be difficult to consume alone, and thus was often mixed with drugs like ethanol for recreational use.
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.^[4]

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. Its effects are described in detail by the main character as the narrator - "It makes you behave like the village drunkard in some early Irish novel. Total loss of all basic motor function. Blurred vision, no balance, numb tongue. The mind recoils in horror, unable to communicate with the spinal column. Which is interesting because you can actually watch yourself behaving in this terrible way, but you can't control it." He also says that "there is nothing more helpless and irresponsible than a man in the depths of an ether binge."
Recreational use of ether was portrayed in the novel The Cider House Rules by John Irving and in the film adaptation of the same name.
Mr. Burns, evil billionaire of The Simpsons, uses ether recreationally.

Synthesis

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 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%^[5] .
Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Ethanol is mixed with a strong dehydrating acid, typically sulfuric acid, H₂SO₄. The acid dissociates producing hydrogen ions, H⁺. A hydrogen ion protonates the electronegative oxygen atom of the ethanol, giving the ethanol molecule a positive charge:
CH₃CH₂OH + H⁺ → CH₃CH₂OH₂⁺
A nucleophilic oxygen atom of unprotonated ethanol displaces a water molecule from the protonated (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 equilibrium between reactants and products is achieved. Getting a good yield of ether requires that ether be distilled out of the reaction mixture before it reverts to ethanol, taking advantage of Le Chatelier's principle.
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.
Water and peroxides can be removed by either distillation from sodium and benzophenone, or by passing through a column of activated alumina.^[6]

Chemistry

Diethyl ether is prone to peroxide formation, and can form explosive diethyl ether peroxide. Ether peroxides are higher boiling and are contact explosives when dry. Diethyl ether is typically supplied with trace amounts of the antioxidant BHT (2,6-di-tert-butyl-4-methylphenol), which reduces the formation of peroxides. Storage over NaOH precipitates the intermediate ether hydroperoxides.

References

1.
2. Extra Strength Starting Fluid: How it Works
3. http://www.erowid.org/chemicals/ether/ether_info1.shtml
4. http://www.incb.org/pdf/e/list/red.pdf
5. Ethyl Ether, Chem. Economics Handbook, , , , SRI International, 1991,
6. Purification of laboratory chemicals, W. L. F. Armarego and C. L. L. Chai, , , Butterworth-Heinemann, 2003,

External links

★ Erowid

★ The unusual history of ether as an anesthetic

★ Etheromania