Diethyl ether

This article is about the chemical compound.
Diethyl ether
Diethyl-ether-2D-skeletal.png Diethyl-ether-3D-balls.png
IUPAC name ethoxyethane
Other names diethyl ether
ethyl ether
ethyl oxide
3-oxapentane
Identifiers
CAS number [60-29-7]
RTECS number KI5775000
SMILES CCOCC
Properties
Molecular formula C4H10O
C2H5OC2H5
Molar mass 74.12 g/mol
Appearance clear, colorless liquid
Density 0.7134 g/cm³, liquid
Melting point

−116.3 °C (156.85 K)

Boiling point

34.6 °C (307.75 K)

Solubility in water 6.9 g/100 ml (20 °C)
Viscosity 0.224 cP at 25 °C
Structure
Dipole moment 1.15 D (gas)
Hazards
MSDS External MSDS
Main hazards Extremely Flammable (F+),
Harmful (Xn)
NFPA 704

NFPA 704.svg

4
2
0
 
R-phrases R12 R19 R22 R66 R67
S-phrases S9 S16 S29 S33
Flash point -45 °C
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)

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 was used in the past as a general anesthetic. It is sparingly soluble in water (6.9 g/100 mL). Given its high flammability and volatility, it should be kept away from open flames and electrically heated devices.

Contents

History

Alchemist Raymundus Lullus is credited with discovering the compound in 1275 C.E., 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 dulcis vitrioli). This name was chosen because 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.

Production

Diethyl ether is rarely prepared in laboratories because of the hazards involved and because it is easily available 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.[1] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95 percent.[2]

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 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

This reaction must be carried out at temperatures lower than 150°C in order to ensure that an elimination product (ethylene) is not 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.

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. 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 because of 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.[3] 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 higher therapeutic index, a larger difference between the recommended dosage and a toxic overdose. Ether is still the preferred anesthetic in some developing nations due to its low price and high therapeutic index (about 1.5-2.2).[4]

Based on its associations with Boston, the use of ether became known as the "Yankee Dodge."

Today, ether is rarely used for anesthesia. 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.[3]

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.

Ether, mixed with ethanol, was marketed in the nineteenth-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.[5] Ether tends to be difficult to consume alone, and thus was often mixed with drugs like ethanol for recreational use. Ether may also be used as an 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.[6]

Metabolism

A putative cytochrome P450 enzyme is believed to metabolize diethyl ether.[7]

Diethyl ether inhibits alcohol dehydrogenase, and thus slows down the metabolism of ethanol.[8] It also inhibits metabolism of other drugs requiring oxidative metabolism.[9]

Safety

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. The autoignition temperature of ether 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.

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. Water and peroxides can be removed by either distillation from sodium and benzophenone, or by passing through a column of activated alumina.[10]

See also

Notes

  1. 1.0 1.1 Lawrence Karas and W. J. Piel, Ethers, in Kirk‑Othmer Encyclopedia of Chemical Technology (John Wiley & Sons, Inc., 2004).
  2. Ethyl Ether, Chem. Economics Handbook (Menlo Park, CA: SRI International, 1991).
  3. 3.0 3.1 John W. Hill and Doris K. Kolb, Chemistry for Changing Times, 10th ed. (Upper Saddle River, NJ: Pearson Prentice Hall, 2004, ISBN 0536836841).
  4. F.A. Calderone, Studies on ether dosage after pre-anesthetic medication with narcotics, J. Pharmacology Experimental Therapeutics 55(1): 24-39. Retrieved November 24, 2008.
  5. Erowid, Hoffmann's Drops. Retrieved November 24, 2008.
  6. International Narcotics Control Board, List of Chemicals and Precursors Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control. Retrieved November 24, 2008.
  7. Matthew P. Brown and Gary A. Payne, 109. Aspergillus flavus mutant strain 241, blocked in aflatoxin biosynthesis, does not accumulate aflR transcript, North Carolina State University, Raleigh, NC 27695. Retrieved November 24, 2008.
  8. P.T. Normann, A. Ripel, and J. Morland, Diethyl Ether Inhibits Ethanol Metabolism in Vivo by Interaction with Alcohol Dehydrogenase, Alcoholism: Clinical and Experimental Research 11(2): 163–166. (doi = 10.1111/j.1530-0277.1987.tb01282.x).
  9. Larry K. Keefer, William A. Garland, Neil F. Oldfield, James E. Swagzdis, and Bruce A. Mico, 1985, Inhibition of N-Nitrosodimethylamine Metabolism in Rats by Ether Anesthesia, Cancer Research 45: 5457–60.
  10. W.L.F. Armarego and Christina Li Lin Chai, Purification of Laboratory Chemicals (Amsterdam: Butterworth-Heinemann, 2004, ISBN 978-0750675710).

References

  • Hill, John W., and Doris K. Kolb. 2004. Chemistry for Changing Times, 10th ed. Upper Saddle River, NJ: Pearson Prentice Hall. ISBN 0536836841.
  • McMurry, John. 2004. Organic Chemistry, 6th ed. Belmont, CA: Brooks/Cole. ISBN 0534420052.
  • Morrison, Robert T., and Robert N. Boyd. 1992. Organic Chemistry, 6th ed. Englewood Cliffs, NJ: Prentice Hall. ISBN 0136436692.
  • Solomons, T.W. Graham, and Craig B. Fryhle 2004. Organic Chemistry, 8th ed. Hoboken, NJ: John Wiley. ISBN 0471417998.

External links

All links retrieved October 23, 2017.


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