Diethyl ether

Last updated
Diethyl ether
Diethyl-ether-2D-skeletal.svg
Diethyl-ether-3D-balls.png
Dietil eter.png
Names
Preferred IUPAC name
Ethoxyethane
Other names
  • 3-Oxapentane
  • Dether
  • Diethyl ether
  • Diethyl oxide
  • Ether
  • Ethyl ether
  • Ethyl oxide
  • Solvent ether
  • Sulfuric ether
  • Sulphuric ether
  • Sweet oil of vitriol
  • Vitriolic ether
Identifiers
3D model (JSmol)
1696894
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.425 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-467-2
25444
KEGG
PubChem CID
RTECS number
  • KI5775000
UNII
UN number 1155
  • InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 Yes check.svgY
    Key: RTZKZFJDLAIYFH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
    Key: RTZKZFJDLAIYFH-UHFFFAOYAB
  • CCOCC
Properties
C4H10O
Molar mass 74.123 g·mol−1
AppearanceColorless liquid
Odor Dry, Rum-like, sweetish odor [1]
Density 0.7134 g/cm3, liquid
Melting point −116.3 °C (−177.3 °F; 156.8 K)
Boiling point 34.6 °C (94.3 °F; 307.8 K) [2]
6.05 g/(100 mL) [3]
log P 0.98 [4]
Vapor pressure 440 mmHg (58.66 kPa) at 20 °C [1]
−55.1·10−6 cm3/mol
1.353 (20 °C)
Viscosity 0.224 cP (25 °C)
Structure
1.15 D (gas)
Thermochemistry
172.5 J/(mol·K)
Std molar
entropy (S⦵298)
253.5 J/(mol·K)
−271.2 ± 1.9 kJ/mol
−2732.1 ± 1.9 kJ/mol
Pharmacology
N01AA01 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Extremely flammable, harmful to skin, decomposes to explosive peroxides in air and light [1]
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H224, H302, H336
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P340, P312, P330, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
4
1
Flash point −45 °C (−49 °F; 228 K) [5]
160 °C (320 °F; 433 K) [5]
Explosive limits 1.9–48.0% [6]
Lethal dose or concentration (LD, LC):
73,000 ppm (rat, 2 hr)
6500 ppm (mouse, 1.65 hr) [7]
106,000 ppm (rabbit)
76,000 ppm (dog) [7]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 400 ppm (1200 mg/m3) [1]
REL (Recommended)
No established REL [1]
IDLH (Immediate danger)
1900 ppm [1]
Safety data sheet (SDS) External MSDS
Related compounds
Related ethers
Related compounds
Supplementary data page
Diethyl ether (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diethyl ether, or simply ether, is an organic compound with the chemical formula (CH3CH2)2O, sometimes abbreviated as Et2O. [lower-alpha 1] It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs to the ether class of organic compounds. It is a common solvent. It was formerly used as a general anesthetic. [8]

Contents

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: [9] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%. [10]

2 CH3CH2OH → (CH3CH2)2O + H2O

Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. [11]

Uses

The dominant use of diethyl ether is as a solvent. One particular application is in the production of cellulose plastics such as cellulose acetate. [9]

Laboratory solvent

It is a common solvent for the Grignard reaction in addition to other reactions involving organometallic reagents. [12] These uses exploit its basicity. Diethyl ether is a popular non-polar solvent in liquid-liquid extraction. As an extractant, it is immiscible with and less dense than water.

Although immiscible, it has significant solubility in water (6.05 g/(100 ml) at 25 °C [3] ) and dissolves 1.5 g/(100 g) (1.0 g/(100 ml)) water at 25 °C. [13]

Fuel

Diethyl ether has a high cetane number of 85–96 and, in combination with petroleum distillates for gasoline and diesel engines, [14] is used as a starting fluid because of its high volatility and low flash point. Ether starting fluid is sold and used in countries with cold climates, as it can help with cold starting an engine at sub-zero temperatures. For the same reason it is also used as a component of the fuel mixture for carbureted compression ignition model engines.

Chemical reactions

Triethyloxonium tetrafluoroborate is prepared from boron trifluoride, diethyl ether, and epichlorohydrin: [15]

4 Et2O·BF3 + 2 Et2O + 3 C2H3OCH2Cl → 3 [Et3O]+[BF4]− + B(OCH(CH2Cl)CH2OEt)3

Diethyl ether is a hard Lewis base that reacts with a variety of Lewis acids such as iodine, phenol, and trimethylaluminium, and its base parameters in the ECW model are EB = 1.80 and CB = 1.63. Diethyl ether is a common laboratory aprotic solvent.

Diethyl ether is susceptible to formation of hydroperoxides.

Metabolism

A cytochrome P450 enzyme is proposed to metabolize diethyl ether. [16]

Diethyl ether inhibits alcohol dehydrogenase, and thus slows the metabolism of ethanol. [17] It also inhibits metabolism of other drugs requiring oxidative metabolism. For example, diazepam requires hepatic oxidization whereas its oxidized metabolite oxazepam does not. [18]

Safety, stability, regulations

Diethyl ether is extremely flammable and may form explosive vapour/air mixtures. [19]

Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources. Ether will ignite if exposed to an open flame, though due to its high flammability, an open flame is not required for ignition. Other possible ignition sources include – but are not limited to – hot plates, steam pipes, heaters, and electrical arcs created by switches or outlets. [19] Vapour may also be ignited by the static electricity which can build up when ether is being poured from one vessel into another. The autoignition temperature of diethyl ether is 160 °C (320 °F). The diffusion of diethyl ether in air is 9.18 × 10−6 m2/s (298 K, 101.325 kPa).[ citation needed ]

Ether is sensitive to light and air, tending to form explosive peroxides. [19] Ether peroxides have a higher boiling point than ether and are contact explosives when dry. [19] Commercial 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. [20]

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 as well as substances such as acetone, toluene and sulfuric acid. [21]

History

The compound may have been synthesised by either Jābir ibn Hayyān in the 8th century [22] or Ramon Llull in 1275. [22] [23] It was synthesised 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. [22] At about the same time, Paracelsus discovered the analgesic properties of the molecule in dogs. [22] The name ether was given to the substance in 1729 by August Sigmund Frobenius. [24]

It was considered to be a sulfur compound until the idea was disproved in about 1800. [25]

The synthesis of diethyl ether by a reaction between ethanol and sulfuric acid has been known since the 13th century. [25]

Anesthesia

The first use of ether in dental surgery, by Ernest Board. The first use of ether in dental surgery, 1846. Ernest Board. Wellcome V0018140.jpg
The first use of ether in dental surgery, by Ernest Board.
Panel from Ether Monument in Boston commemorating Morton's demonstration of ether's anesthetic use. Ether monument-Boston.JPG
Panel from Ether 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. Morton had called his ether preparation, with aromatic oils to conceal its smell, "Letheon" after the Lethe River (Λήθη, meaning "forgetfulness, oblivion"). [26] However, Crawford Williamson Long 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 six occasions before the Boston demonstration. [27] [28] [29] British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium. [30] Diethyl ether was preferred by some practitioners over chloroform as a general anesthetic due to ether's more favorable therapeutic index, that is, a greater difference between an effective dose and a potentially toxic dose. [31]

Diethyl ether does not depress the myocardium but rather it stimulates the sympathetic nervous system leading to hypertension and tachycardia. It is safely used in patients with shock as it preserves the baroreceptor reflex. [32] Its minimal effect on myocardial depression and respiratory drive, as well as its low cost and high therapeutic index allows it to see continued use in developing countries. [33] 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. In the 21st century, ether is rarely used. The use of flammable ether was displaced by nonflammable fluorinated hydrocarbon anesthetics. Halothane was the first such anesthetic developed and other currently used inhaled anesthetics, such as isoflurane, desflurane, and sevoflurane, are halogenated ethers. [34] Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents reduce these side effects. [27]

An illustration depicting ether's effects, 1840s-1870s Ether Dreams.jpg
An illustration depicting ether's effects, 1840s–1870s

Prior to 2005, it was on the World Health Organization's List of Essential Medicines for use as an anesthetic. [35] [36]

Medicine

Ether was once used in pharmaceutical formulations. A mixture of alcohol and ether, one part of diethyl ether and three parts of ethanol, was known as "Spirit of ether", Hoffman's Anodyne or Hoffman's Drops. In the United States this concoction was removed from the Pharmacopeia at some point prior to June 1917, [37] as a study published by William Procter, Jr. in the American Journal of Pharmacy as early as 1852 showed that there were differences in formulation to be found between commercial manufacturers, between international pharmacopoeia, and from Hoffman's original recipe. [38] It is also used to treat hiccups through instillation into the nasal cavity. [39]

Recreational abuse

The recreational use of ether also took place at organised parties in the 19th century called ether frolics, where guests were encouraged to inhale therapeutic amounts of diethyl ether or nitrous oxide, producing a state of excitation. Long, as well as fellow dentists Horace Wells, William Edward Clarke and William T. G. Morton observed that during these gatherings, people would often experience minor injuries but appear to show no reaction to the injury, nor memory that it had happened, demonstrating ether's anaesthetic effects. [40]

In the 19th century and early 20th century ether drinking was popular among Polish peasants. [41] It is a traditional and still relatively popular recreational drug among Lemkos. [42] It is usually consumed in a small quantity ( kropka , or "dot") poured over milk, sugar water, or orange juice in a shot glass. As a drug, it has been known to cause psychological dependence, sometimes referred to as etheromania. [43] [ medical citation needed ]

See also

Explanatory notes

  1. ↑ Et stands for monovalent ethyl group CH3CH2 which is often written as C2H5 (see pseudoelement symbol)

Related Research Articles

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom bonded to two organyl groups. They have the general formula R−O−R′, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Ethanol</span> Organic compound (CH₃CH₂OH)

Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. In nature, grape-sugar breaks up by the action of fermentation into alcohol or carbonic acid, without anything being added. As a psychoactive depressant, it is the active ingredient in alcoholic drinks, and the second most consumed drug globally behind caffeine.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

<span class="mw-page-title-main">Azeotrope</span> Mixture of two or more liquids whose proportions do not change when the mixture is distilled

An azeotrope or a constant heating point mixture is a mixture of two or more components in fluidic states whose proportions cannot be altered or changed by simple distillation. This happens because when an azeotrope is boiled, the vapour has the same proportions of constituents as the unboiled mixture. Azeotropic mixture behavior is important for fluid separation processes.

Chloroform, or trichloromethane, is an organochloride with the formula CHCl3 and a common solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to refrigerants and PTFE. Chloroform is a trihalomethane that serves as a powerful general anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested; for this reason, Chloroform was used as an inhalational anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

<span class="mw-page-title-main">Trichloroethylene</span> C2HCl3, widely used industrial solvent

Trichloroethylene (TCE) is a halocarbon with the formula C2HCl3, commonly used as an industrial degreasing solvent. It is a clear, colourless, non-flammable, volatile liquid with a chloroform-like pleasant mild smell and sweet taste. Its IUPAC name is trichloroethene. Trichloroethylene has been sold under a variety of trade names. Industrial abbreviations include TCE, trichlor, Trike, Tricky and tri. Under the trade names Trimar and Trilene, it was used as a volatile anesthetic and as an inhaled obstetrical analgesic. It should not be confused with the similar 1,1,1-trichloroethane, which is commonly known as chlorothene.

<span class="mw-page-title-main">Ethanethiol</span> Chemical compound

Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. It is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with sulfur in place of oxygen. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic in high concentrations. It occurs naturally as a minor component of petroleum, and may be added to otherwise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">Halogenated ether</span> Subcategory of ether used in anesthesiology

A halogenated ether is a subcategory of a larger group of chemicals known as ethers. An ether is an organic chemical that contains an ether group—an oxygen atom connected to two (substituted) alkyl groups. A good example of an ether is the solvent diethyl ether. What differentiates a halogenated ether from other types of ethers is the substitution (halogenation) of one or more hydrogen atoms with a halogen atom. Halogen atoms include fluorine, chlorine, bromine, and iodine.

Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance.

<span class="mw-page-title-main">Ethyl sulfate</span> Chemical compound

Ethyl sulfate, also known as sulfovinic acid, is an organic chemical compound used as an intermediate in the production of ethanol from ethylene. It is the ethyl ester of sulfuric acid.

<span class="mw-page-title-main">Enol ether</span> Class of chemical compounds

In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers include the reagent 3,4-dihydropyran and the monomers methyl vinyl ether and ethyl vinyl ether.

<span class="mw-page-title-main">Dimethoxymethane</span> Chemical compound

Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.

Divinyl ether is the organic compound with the formula O(CH=CH2)2. It is a colorless, volatile liquid that has mainly been of interest as an inhalation anesthetic. It is prepared by treating bis(chloroethyl) ether with base.

<span class="mw-page-title-main">Fire accelerant</span> Substance that speeds the development of fire

In fire protection, an accelerant is any substance or mixture that accelerates or speeds the development and escalation of fire. Accelerants are often used to commit arson, and some accelerants may cause an explosion. Some fire investigators use the term "accelerant" to mean any substance that initiates and promotes a fire without implying intent or malice. The accelerant works by burning rapidly. As such, the accelerant itself is consumed in the process, and should not be considered as a catalyst. In Arson investigation, the significance of accelerant is to detect the presence of a such substance in order to proved that the fire is classified as an arson.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor.

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  6. ↑ Carl L. Yaws, Chemical Properties Handbook, McGraw-Hill, New York, 1999, p. 567
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  12. ↑ Moyer, W. W.; Marveltitle=Triethyl Carbinol, C. S. (1931). Organic Syntheses. 11: 98. doi:10.15227/orgsyn.011.0098.{{cite journal}}: Missing or empty |title= (help)
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  21. ↑ Microsoft Word – RedListE2007.doc Archived February 27, 2008, at the Wayback Machine
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  37. ↑ The National Druggist, Volume 47, June 1917, pp. 220
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  39. ↑ ncbi, Treatment of hiccups with instillation of ether into the nasal cavity.
  40. ↑ "How Ether Went From a Recreational 'Frolic' Drug to the First Surgery Anesthetic". Smithsonian Magazine. Retrieved 2020-10-11.
  41. ↑ Zandberg, Adrian (2010). "Short Article "Villages … Reek of Ether Vapours": Ether Drinking in Silesia before 1939". Medical History. 54 (3): 387–396. doi:10.1017/s002572730000466x. PMC   2890321 . PMID   20592886.
  42. ↑ Kaszycki, Nestor (2006-08-30). "Łemkowska Watra w Żdyni 2006 – pilnowanie ognia pamięci". Histmag.org – historia od podszewki (in Polish). Kraków, Poland: i-Press. 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".
  43. ↑ Krenz, Sonia; Zimmermann, Grégoire; Kolly, Stéphane; Zullino, Daniele Fabio (August 2003). "Ether: a forgotten addiction". Addiction. 98 (8): 1167–1168. doi:10.1046/j.1360-0443.2003.00439.x. PMID   12873252.
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