Diethyl ether

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  8. Ethers
  9. General anesthetics
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  11. Ether solvents


{{#if:Colorless liquid0.7134 g/cm3, liquid−116.3 °C, 156.9 K, −177.3 °F34.6 °C, 307.8 K, 94.3 °F69 g/L (20 °C)1.353 (20 °C)0.224 cP (25 °C)1041|! style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Diethyl ether
Skeletal formula
Ball-and-stick model
IUPAC name

Ethoxyethane

Other names

Diethyl ether; Ethyl ether; Ethyl oxide; 3-Oxapentane; Ethoxyethane

Identifiers
CAS number 60-29-7 7pxY
PubChem 3283
ChemSpider 3168 7pxY
UNII 0F5N573A2Y 7pxY
KEGG D01772 7pxY
ChEBI CHEBI:35702 7pxY
ChEMBL CHEMBL16264 7pxY
RTECS number KI5775000
ATC code N01AA01
Jmol-3D images Image 1
Molecular formula C4H10O
Molar mass 74.12 g mol−1
Structure
Dipole moment 1.15 D (gas)
Hazards
MSDS External MSDS




R-phrases R12 R19 R20 R22 R66 R67
S-phrases S9 S16 S29 S33
Main hazards Extremely Flammable (F+),
Harmful (Xn)
NFPA 704
4
2
1
Flash point −45 °C[1]
Autoignition
temperature 		160 °C[1]
Explosive limits 1.9-48.0% [2]
Related compounds
Related Ethers Dimethyl ether
Methoxypropane
Related compounds Diethyl sulfide
Butanols (isomer)
 14pxY (verify) (what is: 10pxY/10pxN?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula (C2H5)2O. It is a colorless, highly volatile flammable liquid with a characteristic odor. It is commonly used as a solvent and was once used as a general anesthetic.

History

The compound may have been created by either Jābir ibn Hayyān in the 8th century[3] or Raymundus Lullus in 1275,[3][4] 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 dulce vitrioli)—the name reflects the fact that it is obtained by distilling a mixture of ethanol and sulfuric acid (then known as oil of vitriol)—and noted some of its medicinal properties.[3] At about the same time, Theophrastus Bombastus von Hohenheim, better known as Paracelsus, discovered ether's analgesic properties in chickens.[3] The name ether was given to the substance in 1730 by August Sigmund Frobenius.

Applications

It is particularly important as a solvent in the production of cellulose plastics such as cellulose acetate.[5]

As a 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[6] 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.

Laboratory uses

Diethyl ether is a common laboratory solvent. It has limited solubility in water (6.05 g/100 mL at 25 °C.) [7] and dissolves 1.5 g/100 mL water at 25 °C.[8] Therefore, it is commonly used for liquid-liquid extraction. When used with an aqueous solution, the organic layer is on top as the diethyl ether has a lower density than the water. It is also a common solvent for the Grignard reaction in addition to other reactions involving organometallic reagents. Due to its application in the manufacturing of illicit substances, it is listed in the Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[9]

Anesthetic use

File:Ether monument-Boston.JPG
Panel from monument in Boston commemorating Morton's demonstration of ether's anesthetic use.

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, M.D., 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 numerous occasions before 1846.[10] British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium.[11] The story of the discovery of the anesthetic use of ether has been portrayed in a play [12]

Diethyl ether was formerly sometimes used in place of chloroform because it had a higher therapeutic index, a larger difference between the recommended dosage and a toxic overdose.[13] Because of its associations with Boston, the use of ether became known as the "Yankee Dodge."

Diethyl ether depresses the myocardium and also increases tracheobronchial secretions.[14]

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.

Today, ether is rarely used. The use of flammable ether was displaced by nonflammable anesthetics such as halothane. Diethyl ether was found to have many undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents, such as methyl propyl ether (Neothyl) and methoxyflurane (Penthrane) reduce these side effects.[10]

Medical use

It was once used in pharmaceuticals. A formulation of alcohol and mixture was known as "Spirit of ether" or Hoffman's drop. In the United States, it was removed from Pharmacopeia prior to June 1917.[15]

Recreational use

See also: Addiction to ether consumption

The anesthetic effects of ether have made it a recreational drug.

Ether, mixed with ethanol, was marketed in the 19th century as a cure-all and recreational drug[citation needed], 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.[citation needed]

In the 19th century and early 20th century ether drinking was popular among Polish peasants.[16] It is a traditional and still relatively popular recreational drug among Lemkos.[17] It is usually consumed in a small quantity (kropka, or "dot") poured over milk, water with sugar or orange juice in a shot glass.

Metabolism

A cytochrome P450 enzyme is proposed to metabolize diethyl ether.[18]

Diethyl ether inhibits alcohol dehydrogenase, and thus slows the metabolism of ethanol.[19] It also inhibits metabolism of other drugs requiring oxidative metabolism.[20]

Production

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.[5] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%.[21]

Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Ethanol is mixed with a strong acid, typically sulfuric acid, H2SO4. The acid dissociates in the aqueous environment producing hydronium ions, H3O+. A hydrogen ion protonates the electronegative oxygen atom of the ethanol, giving the ethanol molecule a positive charge:

CH3CH2OH + H3O+ → CH3CH2OH2+ + H2O

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

This reaction must be carried out at temperatures lower than 150 °C in order to ensure that an elimination product (ethylene) is not a product of the reaction. At higher temperatures, ethanol will dehydrate to form ethylene. 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.

Another reaction that can be used for the preparation of ethers is the Williamson ether synthesis, in which an alkoxide (produced by dissolving an alkali metal in the alcohol to be used) performs a nucleophilic substitution upon an alkyl halide.

Safety

Diethyl ether is susceptible 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 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.[22]

Diethyl ether is extremely flammable. The autoignition temperature of diethyl ether is 160 °C (320 °F), therefore it can be ignited by a hot surface without a flame or spark. A 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). The diffusion of diethyl ether in air is 0.918·10−5 m2/s (298K, 101.325 kPa)[citation needed].

References

  1. ↑ 1.0 1.1 "Ethyl Ether MSDS". J.T. Baker. http://hazard.com/msds/mf/baker/baker/files/e2340.htm. Retrieved 2010-06-24.
  2. ↑ Carl L. Yaws, Chemical Properties Handbook, McGraw-Hill, New York, 1999, page 567
  3. ↑ 3.0 3.1 3.2 3.3 Script error
  4. ↑ Script error
  5. ↑ 5.0 5.1 Script error
  6. ↑ "Extra Strength Starting Fluid: How it Works". Valvovine. Archived from the original on 2007-09-27. http://web.archive.org/web/20070927222427/http://www.valvoline.com/pages/products/product_detail.asp?product=38&section=402. Retrieved 2007-09-05.
  7. ↑ The Merck Index, 10th Edition, Martha Windholz, editor, Merck & Co., Inc, Rahway, NJ, 1983, page 551
  8. ↑ Script error
  9. ↑ Microsoft Word - RedListE2007.doc
  10. ↑ 10.0 10.1 Hill, John W. and Kolb, Doris K. Chemistry for changing times: 10th edition. Page 257. Pearson: Prentice Hall. Upper saddle river, New Jersey. 2004.
  11. ↑ Grattan, N. Treatment of Uterine Haemorrhage. Provincial Medicine and Surgical Journal. Vol. 1, No. 6 (Nov. 7, 1840), p. 107.
  12. ↑ "Ether Dome". Alley Theater. http://www.alleytheatre.org/Alley/Ether_Dome_EN.asp. Retrieved June 12, 2012.
  13. ↑ Script error
  14. ↑ Script error
  15. ↑ The National druggist, Volume 47, June 1917, pp.220
  16. ↑ Script error
  17. ↑ Kaszycki, Nestor (2006-08-30). "Łemkowska Watra w Żdyni 2006 – pilnowanie ognia pamięci" (in Polish). Histmag.org – historia od podszewki. Kraków, Poland: i-Press. http://histmag.org/?id=349. Retrieved 2009-11-25. "Dawniej eteru używało się w lecznictwie do narkozy, ponieważ ma właściwości halucynogenne, a już kilka kropel inhalacji wystarczyło do silnego znieczulenia pacjenta. Jednak eter, jak każda ciecz, może teoretycznie być napojem. Łemkowie tę teorię praktykują. Mimo to, nazywanie skroplonego eteru – „kropki” – ich „napojem narodowym” byłoby przesadą. Chociaż stanowi to pewną część mitu „bycia Łemkiem”."
  18. ↑ 109. Aspergillus flavus mutant strain 241, blocked in aflatoxin biosynthesis, does not accumulate aflR transcript. Matthew P. Brown and Gary A. Payne, North Carolina State University, Raleigh, NC 27695 fgsc.net
  19. ↑ Script error
  20. ↑ Script error
  21. ↑ Script error
  22. ↑ Script error

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