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Diethyl ether
Diethyl ether
Diethyl ether
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Diethyl ether
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Sample of diethyl ether
Sample of diethyl ether
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 Edit this at Wikidata
EC Number
  • 200-467-2
25444
KEGG
RTECS number
  • KI5775000
UNII
UN number 1155
  • InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 checkY
    Key: RTZKZFJDLAIYFH-UHFFFAOYSA-N checkY
  • 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
Appearance Colorless 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)[4]
6.05 g/(100 mL)[2]
log P 0.98[3]
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)
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, may cause dizziness in a less ventilated place or if ingested.[1]
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
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 four-colored diamondHealth 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)[7]
160 °C (320 °F; 433 K)[7]
Explosive limits 1.85–48.0%[5]
Lethal dose or concentration (LD, LC):
73,000 ppm (rat, 2 hr)
6500 ppm (mouse, 1.65 hr)[6]
106,000 ppm (rabbit)
76,000 ppm (dog)[6]
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).
checkY verify (what is checkY☒N ?)

Diethyl ether, or simply ether (abbreviated as eth.[8] or Et2O)[a][8] is an organic compound with the chemical formula (CH3CH2)2O, belonging to the ether class. It is a colourless, highly volatile, sweet-smelling (termed "ethereal odour"), extremely flammable liquid. It is a common solvent and was formerly used as a general anesthetic.[9]

Production

[edit]

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:[10] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%.[11]

2 CH3CH2OH → (CH3CH2)2O + H2O

Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.[12]

Uses

[edit]

The dominant use of diethyl ether is as a solvent. One particular application is in the production of cellulose plastics such as cellulose acetate.[10]

Laboratory solvent

[edit]

It is a common solvent for the Grignard reaction in addition to other reactions involving organometallic reagents.[13] 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[2]) and dissolves 1.5 g/(100 g) (1.0 g/(100 ml)) water at 25 °C.[14]

Fuel

[edit]

Diethyl ether has a high cetane number of 85–96 and, in combination with petroleum distillates for gasoline and diesel engines,[15] 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

[edit]

Triethyloxonium tetrafluoroborate is prepared from boron trifluoride, diethyl ether, and epichlorohydrin:[16]

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

Diethyl ether is a common laboratory aprotic solvent. It is susceptible to the formation of hydroperoxides.

Metabolism

[edit]

A cytochrome P450 enzyme is proposed to metabolize diethyl ether.[17]

Diethyl ether inhibits alcohol dehydrogenase, and thus slows the metabolism of ethanol.[18] It also inhibits metabolism of other drugs requiring oxidative metabolism. For example, diazepam requires hepatic oxidization whereas its oxidized metabolite oxazepam does not.[19]

Safety, stability, regulations

[edit]

Diethyl ether is extremely flammable and may form explosive vapour/air mixtures.[20]

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.[20] 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.[20] Ether peroxides have a higher boiling point than ether and are contact explosives when dry.[20] 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.[21]

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.[22]

History

[edit]

The compound may have been synthesised by either Jābir ibn Hayyān in the 8th century[23] or Ramon Llull in 1275.[23][24] 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.[23] At about the same time, Paracelsus discovered the analgesic properties of the molecule in dogs.[23] The name ether was given to the substance in 1729 by August Sigmund Frobenius.[25]

It was considered to be a sulfur compound until the idea was disproved in about 1800.[26]

The synthesis of diethyl ether by a reaction between ethanol and sulfuric acid has been known since the 13th century.[26]

Anesthesia

[edit]
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.

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").[27] 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.[28][29][30] British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium.[31] 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.[32]

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.[33] 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.[34] 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.[35] Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents reduce these side effects.[28]

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.[36][37]

Medicine

[edit]

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,[38] 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.[39] It is also used to treat hiccups through instillation into the nasal cavity.[40]

Recreational use

[edit]
See also: Ether addiction

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 them, nor memory that it had happened, demonstrating ether's anaesthetic effects.[41]

In the 19th and early 20th centuries, ether drinking was popular among Polish peasants.[42] It is a traditional and still relatively popular recreational drug among Lemkos.[43] 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.[44][medical citation needed]

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."[45]

See also

[edit]

Explanatory notes

[edit]

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Diethyl ether

View on Grokipedia
from Grokipedia
Diethyl ether, also known simply as , is a colorless, with the (C₂H₅)₂O, consisting of an oxygen atom bonded to two ethyl groups. It appears as a clear with a characteristic sweet, and is highly flammable, with a low of 34.6°C and a of -45°C. Historically, it served as the first widely used general in , revolutionizing medical practice in the , though its medical role has largely diminished due to safer alternatives. Today, it is primarily employed as a in , laboratory extractions, and industrial applications such as starting fluids for engines. The synthesis of diethyl ether dates back to the 16th century, when German botanist Valerius Cordus first prepared it by reacting with , naming it "sweet oil of vitriol." Earlier references suggest possible preparation as far back as 1275 by Raymond Lully, but Cordus's method laid the groundwork for its production. Its anesthetic properties were demonstrated publicly on October 16, 1846, by American dentist during a surgery at , marking the birth of modern and earning the event the moniker "Ether Day." By the mid-19th century, diethyl ether had become a standard surgical anesthetic, prized for its ability to induce unconsciousness and provide postoperative analgesia, though it was later supplanted in the 1960s by non-flammable halogenated compounds like . In terms of physical properties, diethyl ether has a density of 0.7134 g/mL at 20°C, a melting point of -116.3°C, and is slightly soluble in water (approximately 6.9 g/100 mL at 20°C) but miscible with most organic solvents. Chemically, it is relatively inert but can form explosive peroxides upon prolonged exposure to air and light, necessitating stabilizers like BHT in commercial preparations and careful storage to mitigate hazards. Beyond its historical medical significance, current applications include its use as a reaction medium in pharmaceutical manufacturing, in the production of cellulose plastics, and as an extractant in food processing, though its flammability and peroxide risk require stringent safety protocols. Despite declining medical use in developed countries, diethyl ether remains a cost-effective anesthetic option in resource-limited settings, where it cost about $0.01 per milliliter as of 2015 and supports analgesia without needing advanced equipment.

Molecular structure and properties

Chemical structure

Diethyl ether has the molecular formula C₄H₁₀O, commonly represented as (CH₃CH₂)₂O. Its IUPAC name is ethoxyethane, though it is more widely known by its common name, diethyl ether. The molecular structure features a central oxygen atom bonded to two identical ethyl groups (–CH₂CH₃) via two sigma bonds, resulting in a bent C–O–C arrangement characteristic of ethers. This configuration classifies diethyl ether as a symmetrical dialkyl ether, where the alkyl substituents on either side of the oxygen are the same. The C–O–C bond angle is approximately 110°, influenced by the sp³ hybridization of the oxygen atom and repulsions./18%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/18.01%3A_Names_and_Properties_of_Ethers) For structural context, diethyl ether can be compared to related ethers such as ((CH₃)₂O), which has shorter methyl groups and a slightly larger C–O–C angle of about 112°, or ethyl methyl ether (CH₃CH₂OCH₃), an unsymmetrical dialkyl ether with differing alkyl chains on each side of the oxygen./Ethers/Properties_of_Ethers/Physical_Properties_of_Ether) Spectroscopic techniques confirm this structure. In (IR) spectroscopy, the C–O stretching vibration appears as a strong absorption band at approximately 1100 cm⁻¹. (¹H NMR) spectroscopy shows the methyl (CH₃) protons as a triplet at around 1.2 ppm and the methylene (CH₂) protons adjacent to oxygen as a quartet at about 3.5 ppm, reflecting their distinct chemical environments due to the ether linkage./18%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/18.08%3A_Spectroscopy_of_Ethers)

Physical properties

Diethyl ether is a colorless, volatile liquid with a characteristic sweet, pungent . The low of diethyl ether arises from weak intermolecular forces, as the oxygen cannot participate in hydrogen bonding to the same extent as in alcohols. Key physical constants for diethyl ether under standard conditions are summarized in the following table:
PropertyValueConditions
Molar mass74.12 g/mol-
Melting point-116.3 °C-
Boiling point34.6 °C760 mmHg
Density0.7134 g/cm³20 °C
Refractive index1.352620 °C (D line)
Diethyl ether is miscible with most organic solvents, including ethanol, acetone, benzene, and chloroform. Its solubility in water is limited at 6.9 g/100 mL at 20 °C. The vapor pressure is 58.9 kPa at 20 °C. Thermodynamic data include a heat of vaporization of 26.5 kJ/mol at the boiling point. The flash point is -45 °C, and the autoignition temperature is 160 °C. Due to its high volatility, diethyl ether evaporates rapidly at .

Production

Industrial methods

The primary industrial method for producing diethyl ether involves the catalytic dehydration of , typically using or supported as catalysts at temperatures around 140°C. This process follows the reversible equilibrium reaction: 2\ceCH3CH2OH⇌(CH3CH2)2O+H2O2 \ce{CH3CH2OH ⇌ (CH3CH2)2O + H2O} The reaction is carried out in a reactor where ethanol vapor is passed over the catalyst bed, with yields optimized by removing to shift the equilibrium toward ether formation. acts as a strong proton donor to facilitate the formation of an intermediate, while , often impregnated on carriers like alumina, provides a alternative that reduces corrosion and simplifies handling. A significant portion of diethyl ether is obtained as a side product, typically in yields of 5-10%, during the industrial production of via the vapor-phase hydration of . In this process, reacts with water over a solid at (around 70 bar) and (300°C), where minor side reactions lead to diethyl ether formation alongside the main product. The ether is then separated from the reaction for recovery. Historically, diethyl ether production shifted from the , which involved reacting alkyl halides with sodium alkoxides and was more suited to laboratory-scale unsymmetrical ether preparation, to modern catalytic dehydration methods in the early for efficient large-scale output. This transition enabled cost-effective commercialization, with global annual production reaching approximately 300,000 metric tons as of 2020, driven by demand in solvents and pharmaceuticals. Following synthesis, diethyl ether is purified primarily through to achieve greater than 99% purity, effectively removing residual and azeotropes. The crude product is fed into a distillation column where lower-boiling ether (boiling point 34.6°C) is collected as overhead, while (78.4°C) and (100°C) are separated in subsequent stages or side streams; additional treatments like caustic washing may address trace acids. Economically, diethyl ether production benefits from the abundance and low cost of feedstock, particularly from bioethanol sources, keeping expenses below 50% of total costs in many facilities. However, the process is energy-intensive due to the high-temperature step and requires periodic catalyst regeneration—such as reconcentration of diluted —to maintain efficiency and minimize downtime.

Laboratory synthesis

Diethyl ether was first synthesized in the laboratory by the German botanist and pharmacist Valerius Cordus in 1540 through the distillation of a mixture of ethanol and sulfuric acid, a method he termed the preparation of "sweet oil of vitriol." This historical procedure laid the foundation for subsequent laboratory preparations and involved heating the reactants in an alembic still to collect the volatile ether distillate. In contemporary laboratory settings, the preferred method for preparing diethyl ether on a small scale is the sulfuric acid-catalyzed dehydration of , conducted at temperatures of 130–140 °C to favor ether formation over elimination to ethene, which predominates above 150 °C. The reaction proceeds via of one , followed by nucleophilic attack from a second in an SN2 manner, displacing water to yield the protonated , which is then deprotonated. Typically, concentrated is added to excess in a equipped with a condenser and a setup; the mixture is heated gently while the low-boiling (b.p. 34.6 °C) is continuously distilled and collected in a receiver cooled with ice. The crude product is then dried over and redistilled to purify it, achieving typical yields of 50–70% based on the consumed. An alternative classic approach is the , involving the reaction of (prepared from and sodium metal or a strong base like NaH) with an ethyl halide such as ethyl bromide or iodide in an SN2 displacement. This method, while effective for symmetrical ethers like diethyl ether, is rarely employed in laboratories due to the toxicity and handling hazards of ethyl halides, which can cause severe and systemic upon or skin contact. Regardless of the synthesis route, freshly prepared diethyl ether must be stored under an inert atmosphere, such as nitrogen, to prevent autoxidation and the formation of explosive peroxides during prolonged exposure to air and light.

Applications

Solvent applications

Diethyl ether serves as a primary non-polar aprotic solvent in organic synthesis, particularly for reactions involving highly reactive organometallic reagents such as Grignard (RMgX) and organolithium compounds, where its ability to dissolve non-polar substances without donating protons prevents unwanted side reactions. Its Lewis basic oxygen atom coordinates with magnesium or lithium centers, stabilizing these reagents in solution. In liquid-liquid extractions, diethyl ether facilitates the separation of organic compounds from aqueous phases due to its low of 0.71 g/cm³ and immiscibility with , allowing the organic layer to form on top for easy isolation. This property makes it ideal for partitioning non-polar solutes, enhancing recovery yields in purification workflows. Within the , diethyl ether is employed for extracting natural products like alkaloids from plant materials, as seen in the isolation of from aqueous solutions, and as a reaction medium in the synthesis of active pharmaceutical ingredients. Its solvating power supports scalable processes while minimizing interference with drug precursors. Historically, diethyl ether has been a staple in settings for recrystallization of organic solids and as a mobile phase in techniques like thin-layer and column methods, where it effectively elutes non-polar compounds. Compared to alternatives like (THF), it offers advantages in moisture-sensitive applications due to lower hygroscopicity, requiring less rigorous drying. In modern applications, diethyl ether finds niche use in the extraction of perfumes and essential oils, where it dissolves aromatic and waxes from plant matter without altering volatile profiles. A significant portion of global diethyl ether production supports demands across these chemical and extraction processes. Due to its high flammability, careful handling is essential in all applications.

Fuel and industrial uses

Diethyl ether serves as an additive in diesel fuels, typically blended at concentrations up to 30% to enhance properties. Its high , ranging from 85 to 96, significantly shortens ignition delay compared to conventional diesel, facilitating smoother starts and reducing unburned emissions during operation. This additive effect is particularly beneficial for cold starts in low-temperature environments, where diethyl ether's low and oxygen content promote premixed , improving fuel and overall engine performance without requiring engine modifications. In rocketry, diethyl ether has historical applications as a propellant in early experimental engines, notably tested by Harry W. Bull at in 1932 with gaseous oxygen to evaluate its viability alongside other hydrocarbons like and . Its role extended to ignition enhancement in (LOX)-based systems, where it functioned as a starting to initiate in hydrocarbon-fueled motors, such as those developed by . The compound's high contributes to effective atomization during injection, aiding mixing and generation in these hybrid or bipropellant setups, though it was largely supplanted by more reliable hypergolic alternatives in subsequent designs. Industrially, diethyl ether is a key component in engine starting fluids, comprising 30-50% of formulations used to aid ignition in diesel and engines during cold weather. Its volatility and low ignition provide rapid in the intake manifold, compensating for poor atomization in sub-zero conditions and preventing battery drain from prolonged cranking. Additionally, diethyl ether finds minor application in manufacturing processes, where it influences chain growth in free-radical polymerizations, though its use remains limited compared to dedicated transfer agents. As a biofuel, diethyl ether holds potential for renewable production through the dehydration of bioethanol over heteropolyacid catalysts like tungstophosphoric acid, yielding up to 75% selectivity at 140-180°C and offering a sustainable pathway from biomass-derived feedstocks. This process aligns with environmental goals by reducing reliance on fossil oxygenates, providing lower lifecycle and compatibility with existing diesel infrastructure. Bio-based diethyl ether variants may support renewable fuel targets by enhancing diesel blend oxygen content without increasing particulate matter. Global production of diethyl ether allocates a notable portion to applications, including diesel additives and starting fluids, though its incorporation into blends has been discontinued in regions like the due to regulatory restrictions on volatile oxygenates aimed at curbing evaporative emissions. As of 2024, market analyses project steady growth in fuel-related demand through 2030, driven by integration, but constrained by safety handling requirements.

Chemical reactivity

Acid-base reactions

Diethyl ether exhibits Lewis base character due to the lone pairs on its oxygen atom, which can coordinate to Lewis acids to form stable complexes. For instance, it readily forms a 1:1 with , known as boron trifluoride diethyl etherate ((CH₃CH₂)₂O·BF₃), where the oxygen donates to the electron-deficient boron center. This complex is widely used as a convenient source of BF₃ in synthetic applications, highlighting the moderate basicity of diethyl ether compared to stronger donors like amines. In coordination chemistry, diethyl ether can further react with strong alkylating agents to generate trialkyloxonium salts, such as (Et₃O⁺ BF₄⁻), typically prepared by treating diethyl ether with ethyl fluoroborate or via Meerwein's method involving BF₃ etherate and . These oxonium ions are highly reactive electrophiles employed in the ethylation of nucleophiles, including the synthesis of other ethers through of alcohols or under mild conditions. Diethyl ether undergoes acid-catalyzed cleavage with strong acids like HBr, proceeding via of the oxygen to form an oxonium intermediate, followed by nucleophilic attack by bromide on one of the ethyl groups. The reaction yields ethyl bromide and : (\ceCH3CH2)2\ceO+\ceHBr→\ceCH3CH2Br+\ceCH3CH2OH(\ce{CH3CH2})2\ce{O} + \ce{HBr} \rightarrow \ce{CH3CH2Br} + \ce{CH3CH2OH} This cleavage requires forcing conditions, such as concentrated aqueous HBr at elevated temperatures (typically above 100°C), as the reaction is rare at due to the high stability of the C-O bond and the need for to activate the . Diethyl ether is generally inert toward dilute acids and bases at ambient conditions, reflecting its low reactivity as a neutral , but it protonates readily in concentrated to form a dialkyloxonium . At high temperatures (around 140-160°C), this leads to via cleavage, producing and potentially further products under pressure. In inorganic chemistry, diethyl etherates serve analytical purposes, such as forming soluble complexes with gases like hydrogen chloride (HCl·OEt₂) to facilitate drying and purification by distillation, or as solvents for metal salts where the ether coordinates to cations like Li⁺ or Mg²⁺, enhancing solubility in non-aqueous media.

Oxidation and peroxide formation

Diethyl ether is highly susceptible to auto-oxidation in the presence of atmospheric oxygen, a radical chain process that generates hazardous peroxides. The mechanism begins with initiation via abstraction of an alpha hydrogen atom, forming an alkyl radical that reacts with O₂ to produce a peroxy radical (e.g., DEEOO•). Propagation involves hydrogen abstraction by the peroxy radical, leading to hydroperoxides such as 1-ethoxyethyl hydroperoxide (CH₃CH(OOH)OCH₂CH₃) as primary products, with possible secondary formation of dialkyl peroxides, alongside other oxygenated species. This proceeds slowly at under , often exhibiting a long induction period of several months, but is significantly accelerated by exposure to light, heat, or trace metals. The resulting are unstable and potentially at concentrations above 100 ppm (0.01%) by weight, capable of violent triggered by shock, friction, or heat, especially when concentrated by or ; notably, they are odorless and thus undetectable by smell alone, unlike diethyl itself. To mitigate this risk, commercial diethyl ether is typically stabilized with antioxidants such as (BHT), which interrupts the radical chain by scavenging reactive species. accumulation enhances the overall flammability of ether, contributing to severe fire hazards if ignited. Detection of peroxides relies on sensitive colorimetric assays, such as the / test, where a blue-black color develops upon reaction with hydroperoxides in an acidic medium. Prevention involves inert storage under gas or in contact with wire, which acts as a radical , along with regular testing and avoidance of prolonged air exposure; should not be stored for more than 6-12 months without verification. of peroxide-contaminated is particularly dangerous, as evaporation concentrates the peroxides in the residue or distillate, potentially leading to . Safe handling thresholds are set below 100 ppm peroxide content to prevent . Historical laboratory incidents underscore these risks, including a 2006 explosion at UC Berkeley that injured a researcher when peroxides in aged THF (mixed with diethyl ether) detonated during manipulation, highlighting the consequences of inadequate testing on old stock. Similar accidents have been reported in academic settings due to overlooked peroxide buildup in stored ether. Compared to (THF), diethyl ether forms s more slowly owing to steric hindrance at the alpha positions, despite sharing weak C-H bonds vulnerable to radical abstraction; however, both require vigilant management.

Biological interactions

Metabolism

Diethyl ether undergoes hepatic metabolism primarily through the cytochrome P450 2E1 () enzyme, which catalyzes oxidative dealkylation to produce and . This pathway is supported by studies using liver microsomes, where CYP2E1 demonstrates high activity toward diethyl ether as a substrate, with kinetic parameters indicating efficient turnover (Km ≈ 13.4 µM, Vmax ≈ 8.2 nmol/min/nmol P-450 in acetone-induced preparations). The metabolic reaction can be represented as: (\ceCH3CH2)2\ceO→\ceCH3CHO+\ceCH3CH2OH(\ce{CH3CH2})2\ce{O} \rightarrow \ce{CH3CHO} + \ce{CH3CH2OH} Isolated rat hepatocytes exposed to anesthetic concentrations of diethyl ether exhibit dose-dependent production of these metabolites, with enhanced rates in cells from phenobarbital-pretreated animals, confirming involvement of an inducible microsomal system akin to CYP2E1. In humans, diethyl ether anesthesia similarly results in detectable blood acetaldehyde levels (average ≈ 21 µM), comparable to those observed after moderate ethanol consumption, though ethanol production is less emphasized in clinical contexts. Approximately 90% of absorbed diethyl ether is eliminated unchanged via through the lungs, reflecting its high volatility and low in aqueous media, which limits extensive tissue retention. Blood concentrations decline rapidly, with a of approximately 10–15 minutes, facilitating quick recovery from exposure. Only 1–2% is excreted in urine, primarily as unchanged compound or minor metabolites. Diethyl ether interacts with alcohol-metabolizing enzymes by inhibiting (ADH) in a mixed noncompetitive/uncompetitive manner, as demonstrated in kinetic assays with equine liver ADH (Ki ≈ 20 mM). This inhibition reduces oxidation to , potentially causing acetaldehyde accumulation and disulfiram-like effects if diethyl ether is co-ingested with . Metabolic rates differ across species; in rats, diethyl ether induces activity (1.5–2-fold increase), accelerating clearance compared to humans, where baseline expression yields slower metabolism without significant induction under typical exposure. No substantial conjugation of diethyl ether with occurs, distinguishing it from many xenobiotics that undergo phase II detoxification via this pathway. Toxicokinetics of diethyl ether involve rapid absorption primarily through (alveolar uptake proportional to inspired concentration) or (), followed by distribution favoring lipid-rich tissues such as the and liver due to its high blood-gas (≈12).

Pharmacological effects

Diethyl ether functions as a () , exerting its effects primarily through potentiation of inhibitory GABA_A receptors and receptors, as well as inhibition of excitatory NMDA receptors. These molecular interactions enhance influx in neurons, leading to hyperpolarization and reduced excitability, while NMDA diminishes glutamate-mediated excitation. The agent's potency is characterized by a () of 1.92 vol%, representing the alveolar concentration required to prevent movement in 50% of subjects in response to . The pharmacological effects of diethyl ether include induction of unconsciousness, analgesia, and skeletal muscle relaxation, facilitating surgical procedures. Anesthesia progresses through distinct stages originally described for ether: an initial stage of analgesia with preserved consciousness, followed by a stage of excitement or delirium marked by irregular breathing and potential involuntary movements, then the surgical stage of controlled unconsciousness with regular respiration, and finally an overdose stage risking respiratory depression. Common side effects encompass postoperative nausea and vomiting, headache, and coughing or laryngospasm due to its irritant properties on the respiratory tract. For clinical administration, diethyl ether is delivered via , with induction typically requiring concentrations of 10-15% v/v in oxygen or air to achieve rapid onset. Maintenance occurs at lower levels around the MAC, and recovery is comparatively swift—often within minutes to hours—attributable to its moderate of 12, which limits tissue accumulation, alongside efficient metabolic clearance primarily via hepatic oxidation. In contemporary practice, diethyl ether has been largely supplanted in human surgery by less irritant halogenated agents but persists in for certain and in resource-limited settings lacking vaporizers or , where its simplicity and properties prove advantageous. It interacts additively with other inhalational agents like , potentiating CNS depression and requiring careful dose adjustment to avoid excessive respiratory inhibition. Recreational inhalation of small volumes of diethyl ether, such as 30-50 mL, can elicit transient and at sub-anesthetic doses, mimicking mild intoxication. However, this practice poses significant risks, including hypoxia from oxygen displacement during inhalation and potential for acute or hazards. While not highly addictive in the manner of opioids, chronic abuse can lead to dependence known as etheromania, with withdrawal symptoms resembling those of alcohol cessation.

Safety and environmental considerations

Health and fire hazards

Diethyl ether poses significant risks primarily through and . It acts as an irritant to the , with a (TLV) of 400 ppm for occupational exposure to prevent irritation and effects. of concentrations exceeding 5% (approximately 50,000 ppm) can induce narcosis, leading to , , , and potentially . Oral exposure has an LD50 of 1,215 mg/kg in rats, indicating moderate , with symptoms including , , and . Chronic exposure to diethyl ether may result in effects, including potential . It is classified as GHS Category 2 for , suspected of damaging fertility or the unborn child. Diethyl ether presents severe hazards due to its extreme flammability, with a of -45°C and explosive limits ranging from 1.9% to 36% in air, allowing ignition from sparks or . Its vapors are heavier than air, capable of traveling considerable distances to ignition sources and forming mixtures. The (NFPA) rates it 4 for flammability, signifying a severe requiring stringent controls like explosion-proof equipment. A critical fire-related risk is the formation of peroxides upon exposure to air, light, or heat, particularly in old or distilled samples where concentrates the peroxides. These shock-sensitive compounds can detonate spontaneously or upon disturbance, leading to incidents such as explosions during or storage. To mitigate this, diethyl ether should be stored with peroxide inhibitors like BHT, dated upon receipt, and tested periodically using iodide-starch for peroxide presence; containers showing peroxides must be disposed of as without . Historical lab accidents, including explosions in university settings during the , underscore the need for vigilant peroxide management protocols. In cases of exposure, focuses on supportive measures, as no specific exists. For inhalation, move the affected person to with adequate ventilation and monitor for respiratory distress, providing oxygen if needed. requires immediate flushing with for at least 15 minutes while lifting eyelids; seek medical evaluation for . exposure should be washed promptly with and to prevent defatting and . necessitates seeking immediate medical attention, avoiding induction of , and providing supportive care for symptoms.

Environmental impact and regulations

Diethyl ether is classified as a (VOC) due to its high and tendency to evaporate rapidly into the atmosphere upon release. In environmental media, it exhibits low persistence; it volatilizes quickly from and surfaces, with estimated half-lives of approximately 3.1 hours in rivers and 3.6 days in lakes, driven by its low Henry's Law constant and . Its high mobility in (Koc value of 73) facilitates transport, but bioconcentration in aquatic organisms is minimal (BCF range: 0.9–9.1). Aerobic biodegradation occurs primarily to and via microbial action, though rates are slow in standard screening tests (0–2.5% BOD over 5 days with sewage inocula); specialized consortia, such as sp., can enhance degradation under aerobic conditions. As a VOC, diethyl ether contributes to tropospheric smog formation through photo-oxidation reactions initiated by hydroxyl radicals, producing intermediates like that participate in generation in urban environments. Its atmospheric lifetime is short (about 1.2 days with OH radicals, 5.8 days with radicals), limiting long-range transport but enabling local air quality impacts. is negligible, as it lacks atoms required for stratospheric and is not regulated under the . Aquatic toxicity is low, with LC50 values exceeding 1000 mg/L for fish species such as fathead minnows (2560 mg/L at 96 hours) and guppies (2134 mg/L at 14 days), indicating minimal hazard to aquatic ecosystems at typical exposure levels. Regulatory frameworks address diethyl ether's risks primarily through occupational and precursor controls. In the United States, it is designated a List I chemical by the (DEA) as a precursor for illicit synthesis, subjecting it to tracking and reporting requirements under 21 CFR 1310.02. The (OSHA) sets a (PEL) of 400 ppm (1200 mg/m³) as an 8-hour time-weighted average to mitigate hazards in workplaces. In the , diethyl ether is registered under the REACH regulation (EC 1907/2006), with ongoing assessments for safe use in industrial applications. Recent 2025 developments include evaluations of diethyl ether in biofuel blends, such as with , which demonstrate emission reductions in diesel engines. Waste management prioritizes at controlled facilities to destroy diethyl ether efficiently, minimizing VOC emissions through high-temperature (above 800°C). via is feasible for high-purity industrial streams, recovering up to 95% of the solvent while reducing disposal volumes. Global regulations have restricted diethyl ether in consumer aerosol products since the 1970s due to flammability and VOC concerns, with bans enforced under frameworks like the U.S. Clean Air Act and VOC directives to curb atmospheric releases. Emerging research highlights gaps in understanding diethyl ether's atmospheric reactivity, particularly its role as an ether VOC in urban air pollution; 2024 studies on reactive organic gases (ROGs) from volatile chemical products emphasize contributions to secondary aerosol formation in cities, underscoring needs for refined emission inventories.

History

Early discovery

Earlier accounts suggest a possible preparation of diethyl ether as far back as 1275 by the alchemist Raymond Lully, who described a reaction producing a "sweet oil of vitriol," though evidence for this attribution is debated and not definitively confirmed. The earliest observations of diethyl ether's effects are attributed to the Swiss physician and alchemist Paracelsus in the 1520s to 1540s, who noted its intoxicating properties when administered to animals, referring to it as an early form of "sweet vitriol" derived from the distillation of ethanol with sulfuric acid. This compound, later identified as diethyl ether, was first systematically synthesized in 1540 by the German botanist and physician Valerius Cordus through the distillation of ethanol (referred to as "spirit of wine") with sulfuric acid (known as "oil of vitriol"), which he named "sweet oil of vitriol" (oleum dulce vitrioli) due to its pleasant aroma compared to the harsh original acid. Cordus's method marked the initial recognition of diethyl ether as a distinct chemical entity, though its publication occurred posthumously in 1561 by Conrad Gesner. In the 17th and 18th centuries, chemists further isolated and refined the compound, with Johann Rudolph Glauber contributing to its production around 1648 by improving the distillation process using his method for generating sulfuric acid, leading to more consistent yields of the substance then called "sulfuric ether" in reference to its preparation involving sulfuric acid. The name "ether" itself was coined in 1729 by German chemist August Sigmund Frobenius, who provided the first detailed description of its properties, including its volatility and solubility, in a paper presented to the Royal Society. During this period, diethyl ether gained attention beyond pure chemistry; in the 18th century, it was incorporated into medicinal tonics such as "Hoffmann's drops," a mixture of ether and ethanol promoted by Friedrich Hoffmann as an analgesic and restorative for ailments like colic and hysteria, though its intoxicating effects were also noted anecdotally. Chemical characterization advanced in the early through vapor density studies that confirmed diethyl 's molecular formula. In 1815, determined that the vapor density of one volume of corresponded to the combined densities of two volumes of (olefiant gas) and one volume of , supporting an consistent with C4H10O. This was further refined in 1828 by and Eugène-Melchior Péligot (sometimes associated with Henry Boullay's related work), whose measurements linked the vapor densities of , diethyl , and , solidifying the understanding of as (C2H5)2O and dispelling earlier misconceptions about its composition. These investigations established diethyl 's place in prior to its broader applications.

Anesthetic development

The development of diethyl ether as a surgical anesthetic began in the United States in the early 1840s. On March 30, 1842, Crawford Williamson Long, a physician in Jefferson, Georgia, administered ether to his patient James Venable to facilitate the painless removal of a neck tumor, marking the first documented use of ether for surgical anesthesia. Long continued to employ ether in subsequent procedures, including a toe amputation in July 1842, but he did not publish his findings until 1849, limiting the immediate dissemination of his discovery. The public recognition of ether's anesthetic potential came four years later through William T. G. Morton, a Boston dentist. On October 16, 1846, Morton successfully demonstrated ether inhalation during a surgery at Massachusetts General Hospital's surgical amphitheater, now known as the Ether Dome, where surgeon John Collins Warren removed a vascular tumor from patient Edward Abbott without eliciting pain. This event, dubbed "Ether Day," propelled ether into widespread medical use, as Morton had developed and patented an inhaler device to control ether vapor delivery, which he licensed as "Letheon" to protect his invention. Ether's adoption accelerated rapidly following Morton's demonstration, spreading internationally within months and supplanting earlier pain-relief methods like mesmerism, a form of that had been inconsistently applied in . In the , dentist James Robinson performed the first ether anesthetic there on December 19, 1846, extracting a from a patient at Francis Boott's home, leading to its quick integration into British surgical practice by early 1847. By the 1850s, ether had achieved global dissemination, with reports of its use in surgeries across , , and beyond, often via simple open-drop techniques on cloth masks. Advancements included the development of cone-shaped masks in the late for more efficient vapor delivery and early vaporizers, such as John Snow's 1847 design, which allowed precise control of ether concentration. During the 1850s, ether was frequently combined with —introduced in 1847—to balance induction speed and safety, as in mixtures administered for procedures like those on royalty. Ether remained the dominant general anesthetic through the mid-20th century, including its prominent role in field surgeries where its simplicity and reliability suited resource-limited environments, often via open-drop methods. However, concerns over its flammability, prolonged recovery times, and postoperative complications led to its gradual replacement by safer halogenated agents like , introduced in 1956, with ether largely phased out of routine use by the 1960s.

Other historical applications

In the 19th century, was employed in medicinal preparations known as "Spirit of ether," a solution typically consisting of approximately one part to three parts , used internally to alleviate respiratory ailments such as asthmatic coughs and spasms associated with . This remedy was also prescribed for hiccups and other minor complaints like coughs, often combined with syrups for , though its volatile nature and potential for irritation led to discontinuation of such internal uses by the late 19th century due to associated health risks including flammability and toxicity. Recreational consumption of diethyl ether emerged in the 1830s, particularly in the , where social gatherings called "ether frolics" became popular among students and young professionals seeking euphoric effects from inhaling or sipping the substance at parties. Similar practices spread to the during the , with ether imbibed neat or mixed to induce brief, intoxicating highs, often at informal events mimicking the "laughing gas" parties of the prior decade. In , particularly among Polish peasants in regions like during the late 19th and early 20th centuries, ether drinking developed as an affordable alternative to alcohol, consumed orally in small doses for its rapid inebriating properties despite leading to widespread in some communities. Industrially, diethyl ether served as a key in the late for dissolving to produce lacquers and early plastics, enabling the creation of flexible coatings and films through evaporation of ether-ethanol mixtures. This application stemmed from its ability to form stable solutions with nitrated , facilitating innovations in materials like for and protective varnishes. During , diethyl ether was utilized as a in the production of explosives, particularly in double-base propellants where it dissolved and alongside to form gelatinous mixtures for and rockets. Culturally, diethyl ether appeared in 19th-century as a symbol of altered consciousness and , referenced in works exploring visionary states, though its recreational and medicinal contexts often highlighted risks of dependency. By the early , concerns over abuse prompted prohibitions; in Ireland, ether was reclassified as a in 1891, drastically reducing consumption after annual intake peaked at thousands of gallons among the , while in , sales for non-medical use were banned in 1923 and it was deemed a by 1928 to curb and rural epidemics.

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