Diethyl Ether
   HOME

TheInfoList



OR:

Diethyl ether, or simply ether, is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...
, sometimes abbreviated as . It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely
flammable liquid A flammable liquid is a liquid which can be easily ignited in air at ambient temperatures, i.e. it has a flash point at or below nominal threshold temperatures defined by a number of national and international standards organisations. The Occup ...
. It belongs to the
ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R ...
class of organic compounds. It is a common
solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
and was formerly used as a general anesthetic.


Production

Most diethyl ether is produced as a byproduct of the vapor-phase hydration of
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...
to make
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
. This process uses solid-supported
phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, ...
catalysts Catalysis () is the increase in reaction rate, rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst ...
and can be adjusted to make more ether if the need arises: Vapor-phase
dehydration In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...
of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%. : Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.


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 In biochemistry, cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, and ...
.


Laboratory solvent

It is a common solvent for the Grignard reaction in addition to other reactions involving organometallic reagents. 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 chemistry, solubility is the ability of a chemical substance, substance, the solute, to form a solution (chemistry), solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form su ...
in
water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...
(6.05 g/(100 ml) at 25 °C) and dissolves 1.5 g/(100 g) (1.0 g/(100 ml)) water at 25 °C.


Fuel

Diethyl ether has a high cetane number of 85–96 and, in combination with petroleum distillates for gasoline and diesel engines, is used as a starting fluid because of its high volatility and low
flash point The flash point of a material is the "lowest liquid temperature at which, under certain standardized conditions, a liquid gives off vapours in a quantity such as to be capable of forming an ignitable vapour/air mixture". The flash point is somet ...
. 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: : Diethyl ether is a common laboratory aprotic solvent. It is susceptible to the formation of
hydroperoxide Hydroperoxides or peroxols are Chemical compound, compounds of the form ROOH, where R stands for any group, typically Organic compound, organic, which contain the hydroperoxy functional group (). Hydroperoxide also refers to the hydroperoxide anio ...
s.


Metabolism

A
cytochrome P450 Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...
enzyme is proposed to metabolize diethyl ether. Diethyl ether inhibits alcohol dehydrogenase, and thus slows the metabolism of
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
. It also inhibits metabolism of other drugs requiring oxidative metabolism. For example,
diazepam Diazepam, sold under the brand name Valium among others, is a medicine of the benzodiazepine family that acts as an anxiolytic. It is used to treat a range of conditions, including anxiety disorder, anxiety, seizures, alcohol withdrawal syndr ...
requires hepatic oxidization whereas its oxidized metabolite
oxazepam Oxazepam is a short-to-intermediate-acting benzodiazepine. Oxazepam is used for the treatment of anxiety, insomnia, and to control symptoms of alcohol withdrawal syndrome. It is a metabolite of diazepam, prazepam, and temazepam, and has moderate ...
does not.


Safety, stability, regulations

Diethyl ether is extremely flammable and may form explosive vapour/air mixtures. 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. 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 . The diffusion of diethyl ether in air is (298 K, 101.325 kPa). Ether is sensitive to light and air, tending to form explosive peroxides. Ether peroxides have a higher boiling point than ether and are contact explosives when dry. Commercial diethyl ether is typically supplied with trace amounts of the
antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...
butylated hydroxytoluene (BHT), which reduces the formation of peroxides. Storage over
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...
precipitates the intermediate ether hydroperoxides. Water and peroxides can be removed by either distillation from
sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...
and
benzophenone Benzophenone is a naturally occurring organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. It is a white solid with a low melting point and ros ...
, or by passing through a column of activated alumina. 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 Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
,
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...
and
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
.


History

The compound may have been synthesised by either Jābir ibn Hayyān in the 8th century or
Ramon Llull Ramon Llull (; ; – 1316), sometimes anglicized as ''Raymond Lully'', was a philosopher, theologian, poet, missionary, Christian apologist and former knight from the Kingdom of Majorca. He invented a philosophical system known as the ''Art ...
in 1275. 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 Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
and
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
(then known as oil of vitriol) – and noted some of its medicinal properties. At about the same time,
Paracelsus Paracelsus (; ; 1493 – 24 September 1541), born Theophrastus von Hohenheim (full name Philippus Aureolus Theophrastus Bombastus von Hohenheim), was a Swiss physician, alchemist, lay theologian, and philosopher of the German Renaissance. H ...
discovered the
analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...
properties of the molecule in dogs. The name ''ether'' was given to the substance in 1729 by August Sigmund Frobenius. It was considered to be a sulfur compound until the idea was disproved in about 1800. The synthesis of diethyl ether by a reaction between
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
and
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
has been known since the 13th century.


Anesthesia

William T. G. Morton participated in a public demonstration of ether anesthesia on October 16, 1846, at the Ether Dome in
Boston, Massachusetts Boston is the capital and most populous city in the Commonwealth (U.S. state), Commonwealth of Massachusetts in the United States. The city serves as the cultural and Financial centre, financial center of New England, a region of the Northeas ...
. Morton had called his ether preparation, with aromatic oils to conceal its smell, "''Letheon''" after the Lethe River (Λήθη, meaning "forgetfulness, oblivion"). 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.Hill, John W. and Kolb, Doris K. ''Chemistry for Changing Times: 10th Edition''. p. 257. Pearson: Prentice Hall. Upper Saddle River, New Jersey. 2004. British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium. Diethyl ether was preferred by some practitioners over
chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...
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. Diethyl ether does not depress the
myocardium Cardiac muscle (also called heart muscle or myocardium) is one of three types of vertebrate muscle tissues, the others being skeletal muscle and smooth muscle. It is an involuntary, striated muscle that constitutes the main tissue of the wall o ...
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. 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. Diethyl ether could also be mixed with other anesthetic agents such as
chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...
to make C.E. mixture, or chloroform and
alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...
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 Halothane, sold under the brand name Fluothane among others, is a general anaesthetic. It can be used to induce or maintain anaesthesia. One of its benefits is that it does not increase the production of saliva, which can be particularly useful ...
was the first such anesthetic developed and other currently used inhaled anesthetics, such as isoflurane, desflurane, and sevoflurane, are halogenated ethers.Morgan, G. Edward, Jr. et al. (2002). ''Clinical Anesthesiology'' 3rd Ed. New York: McGraw-Hill. p. 3. Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents reduce these side effects. Prior to 2005, it was on the World Health Organization's List of Essential Medicines for use as an anesthetic.


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 A pharmacopoeia, pharmacopeia, or pharmacopoea (or the typographically obsolete rendering, ''pharmacopœia''), meaning "drug-making", in its modern technical sense, is a reference work containing directions for the identification of compound med ...
at some point prior to June 1917, 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 A pharmacopoeia, pharmacopeia, or pharmacopoea (or the typographically obsolete rendering, ''pharmacopœia''), meaning "drug-making", in its modern technical sense, is a reference work containing directions for the identification of compound med ...
, and from Hoffman's original recipe. It is also used to treat hiccups through instillation into the nasal cavity.


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 Nitrous oxide (dinitrogen oxide or dinitrogen monoxide), commonly known as laughing gas, nitrous, or factitious air, among others, is a chemical compound, an Nitrogen oxide, oxide of nitrogen with the Chemical formula, formula . At room te ...
, 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 them, nor memory that it had happened, demonstrating ether's anaesthetic effects. In the 19th and early 20th centuries, ether drinking was popular among Polish peasants. It is a traditional and still relatively popular recreational drug among Lemkos. 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. Ether intoxication is referenced in Hunter S. Thompson's '' Fear and Loathing in Las Vegas'', where in one of the book's most famous quotes, protagonist Raoul Duke declares that "There is nothing in the world more helpless and irresponsible and depraved than a man in the depths of an ether binge."


See also

* ''The Great Moment'' – film about William T.G. Morton and ether * Flurothyl – fluorinated derivative


Explanatory notes


References


External links


Michael Faraday's announcement of ether as an anesthetic in 1818
* Calculation o
vapor pressureliquid densitydynamic liquid viscositysurface tension
of diethyl ether, ddbonline.ddbst.de

{{DEFAULTSORT:Diethyl Ether Dialkyl ethers General anesthetics Dissociative drugs Euphoriants Fuels Ether solvents GABAA receptor positive allosteric modulators NMDA receptor antagonists Glycine receptor agonists Symmetrical ethers Sweet-smelling chemicals