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Encyclopedia > Diethyl ether
Diethyl ether
Diethyl ether Diethyl ether
General
Systematic name ethoxyethane
3-oxapentane
Other names diethyl ether
ethyl ether
ethyl oxide
Molecular formula C4H10O
C2H5OC2H5
SMILES CCOCC
Molar mass 74.12 g/mol
Appearance clear, colorless liquid
CAS number [60-29-7]
Properties
Density and phase 0.7134 g/cm³, liquid
Solubility in water 6.9 g/100 ml (20 °C)
Melting point −116.3 °C (156.85 K)
Boiling point 34.6 °C (307.75 K)
Acidity (pKa)  ?
Basicity (pKb)  ?
Viscosity 0.224 cP at 25 °C
Structure
Molecular shape  ?
Dipole moment 1.15 D (gas)
Hazards
MSDS External MSDS
Main hazards Extremely Flammable (F+),
Irritant (Xi)
NFPA 704
4
2
1
 
Flash point -45 °C
Autoignition
temperature
170 °C
R/S statement R12 R19 R22 R66 R67
S9 S16 S29 S33
RTECS number KI5775000
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related Ethers Dimethyl ether
Methoxypropane
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references
This article is about the chemical compound. For other uses, see aether.

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. It is an isomer of butanol. Diethyl ether has the formula CH3-CH2-O-CH2-CH3. It is used as a common solvent and has been used as a general anesthetic. Ether is sparingly soluble in water (6.9 g/100 ml). Image File history File links Download high-resolution version (1100x318, 19 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Functional group Diethyl ether ... Image File history File links Size of this preview: 800 × 391 pixels Full resolution (1100 × 537 pixel, file size: 113 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Diethyl ether ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... Viscosity is a measure of the resistance of a fluid to deform under shear stress. ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation or hybridization (see also spelling differences) is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... This page provides supplementary chemical data on diethyl ether. ... This page provides supplementary chemical data on diethyl ether. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... This page provides supplementary chemical data on diethyl ether. ... This page provides supplementary chemical data on diethyl ether. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... It has been suggested that NMR Data Processing be merged into this article or section. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or informally, mass-spec and MS) is an analytical technique used to measure the mass-to-charge ratio of ions. ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... Dimethyl ether, also known as methoxymethane, oxybismethane, methyl ether, wood ether, and DME, is a colorless gaseous ether with an ethereal odor. ... Methoxypropane, or methyl propyl ether, is an ether once used as a general anaesthetic. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Look up aether, ether in Wiktionary, the free dictionary. ... Butanol or butyl alcohol (sometimes also called biobutanol when produced biologically), is an alcohol with a 4 carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Anesthesia (AE), also anaesthesia (BE), is the process of blocking the perception of pain and other sensations. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ...

Contents

History

Alchemist Raymundus Lullus is credited with discovering the compound in 1275 AD, although there is no contemporary evidence of this. It was first synthesized in 1540 by Valerius Cordus, who called it "oil of sweet vitriol" (oleum dulci vitrioli)—the name was due to the fact that it was originally discovered by distilling a mixture of ethanol and sulfuric acid (then known as oil of vitriol)—and noted some of its medicinal properties. At about the same time, Theophrastus Bombastus von Hohenheim, better known as Paracelsus, discovered ether's analgesic properties. The name ether was given to the substance in 1730 by A.S.Frobenius. This article or section includes a list of works cited or a list of external links, but its sources remain unclear because it lacks in-text citations. ... Ramon Llull. ... // April 22 - The first of the Statutes of Westminster are passed by the English parliament, establishing a series of laws in its 51 clauses, including equal treatment of rich and poor, free and fair elections, and definition of bailable and non-bailable offenses. ... Year 1540 was a leap year starting on Thursday (link will display the full calendar) of the Julian calendar. ... Valerius Cordus (18 February 1515 – 25 September 1544) was a German physician and botanist who authored one of the greatest pharmacopoeias and one of the most celebrated herbals in history. ... Grain alcohol redirects here. ... Sulfuric (or sulphuric) acid, H2SO4, is a strong mineral acid. ... Paracelsus (11 November or 17 December 1493 in Einsiedeln, Switzerland - 24 September 1541) was an alchemist, physician, astrologer, and general occultist. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... Events Pope Clement XII elected September 17 - Change of emperor of the Ottoman Empire from Ahmed III (1703-1730) to Mahmud I (1730-1754) Anna Ivanova (Anna I of Russia) became czarina Births April 16 - Henry Clinton, British general (d. ...


Anesthetic use

The American doctor Crawford Williamson Long, M.D., was the first surgeon to use it as a general anesthetic, on March 30, 1842.[1] William T.G. Morton was previously credited with the first public demonstration of ether anesthesia on October 16, 1846 at the Ether Dome in Boston, Massachusetts, although Dr. Crawford Long is now known to have demonstrated its use publicly to other officials in Georgia. Ether was sometimes used in place of Chloroform because it had a wider margin of error- that is, a larger difference between the recommended dosage and a toxic overdose. Crawford Williamson Long, November 1, 1815-June 16, 1878, was an American physician and pharmacist. ... A general anaesthetic drug is an anaesthetic (or anesthetic AE) drug that brings about a reversible loss of consciousness. ... William T.G. Morton William Thomas Green Morton (August 9, 1819 - July 15, 1868) was responsible for the first successful public demonstration of ether as an inhalation anesthetic. ... October 16 is the 289th day of the year (290th in leap years). ... 1846 was a common year starting on Thursday (see link for calendar). ... The Ether Dome was the operating room of the Bulfinch Building at Massachusetts General Hospital in Boston. ... Nickname: Location in Massachusetts, USA Coordinates: Country United States State Massachusetts County Suffolk County Government  - Mayor Thomas M. Menino (D) Area  - City  89. ... Crawford Long. ... For the song Chloroform by Spoon, see A Series of Sneaks Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with formula CHCl3. ...


Today, ether is rarely used. The use of flammable ether waned as nonflammable anesthetic agents such as halothane became available. Additionally, ether had many undesirable side effects, such as postanesthetic nausea and vomiting. Modern anesthetic agents, such as Methyl propyl ether (Neothyl) and methoxyflurane (Penthrane) reduce these side effects.[2] Halothane vapour is an inhalational general anaesthetic. ... Flash point < -20 Explosive limits 1. ... Methoxyflurane (C3H4Cl2F2O) is an inhalation anesthetic used in the 1960s, but withdrawn because of detrimental effects on the kidneys. ...


Because of its high volatility, low ignition point, and tendency to form explosive peroxides, diethyl ether must be used with care in laboratory settings. The ability of a liquid to evaporate quickly and at relatively low temperatures. ...


Ether may be used to anesthetize ticks before removing them from an animal or a person's body. The anesthesia relaxes the tick and prevents it from maintaining its mouthpart under the skin.[citation needed] Families Ixodidae - Hard ticks Argasidae - Soft ticks Nuttalliellidae Wikispecies has information related to: Ixodoidea Tick is the common name for the small arachnids that, along with other mites, constitute the order Acarina. ...


Recreational use

The anesthetic effects of ether have made it a recreational drug, although not a popular one. Diethyl ether is not as toxic as other solvents used as recreational drugs (see volatile substance abuse). Toxic redirects here, but this is also the name of a song by Britney Spears; see Toxic (song) Look up toxic and toxicity in Wiktionary, the free dictionary. ... Volatile substance abuse or solvent abuse (called huffing) is the practice of inhaling volatile substances for their psychoactive effects. ...


Ether, mixed with ethanol, was marketed in the 19th century as a cure-all and recreational drug, during one of Western society's temperance movements. At the time, it was considered improper for women to consume alcoholic beverages at social functions, and sometimes ether-containing drugs would be consumed instead. A cough medicine called Hoffmann's Drops was marketed at the time as one of these drugs, and contained both ether and alcohol in its capsules.[3] Ether tends to be difficult to consume alone, and thus was often mixed with drugs like ethanol for recreational use. Ethyl ether is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[4] Grain alcohol redirects here. ... A cartoon from Australia ca. ... United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances Opened for signature December 20, 1988[1] at Vienna Entered into force November 11, 1990[2] Conditions for entry into force 20 ratifications Parties 170[3] The 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and...


Due to its immiscibility with water and the fact that non-polar organic compounds are highly soluble in it, ether is also used in the production of freebase cocaine. Freebase refers to the standalone basic form of an alkaloid, as opposed to its water-soluble salt form. ...


Recreational use of Diethyl ether was portrayed in the film Fear and loathing in Las Vegas, based on the book of the same name by Hunter S. Thompson. Its effects are decribed in detail by the main character as the narrator - "It makes you behave like the village drunkard in some early Irish novel. Total loss of all basic motor function. Blurred vision, no balance, numb tongue. The mind recoils in horror, unable to communicate with the spinal column. Which is interesting because you can actually watch yourself behaving in this terrible way, but you can't control it". The hard cover version of the book. ... Hunter Stockton Thompson (July 18, 1937 – February 20, 2005) was an American journalist and author. ...


Synthesis

Diethyl ether is typically prepared both in laboratories and on an industrial scale by the acid ether synthesis. Ethyl alcohol is mixed with a strong dehydrating acid, typically sulfuric acid, H2SO4. The acid releases hydrogen ions into solution at very high concentrations. Some of these ions, as H+, will seek out the relatively electronegative oxygen atoms on the ethyl alcohol molecules, creating a form of protonated ethanol with a positive charge:


CH3-CH2-OH + H+ --> CH3-CH2-OH2+


This species is highly electron-deficient (electrophillic) and positively charged, so it will attract non-protonated ethanol molecules, which contain the nucleophilic hydroxyl group. The resulting attack will result in the production of diethyl ether and water:


CH3-CH2-OH2+ + CH3-CH2-OH --> H2O + H+ + CH3-CH2-O-CH2-CH3


Because the alcohol group is not a terribly good nucleophile (being uncharged), this reaction goes to equilibrium. In order to produce significant amounts of diethyl ether, distillation must be used to remove the low-boiling ether and drive the reaction forward. When performing this synthesis, it is advisable to use electric heating rather than an open-flame burner, as this will reduce (but by no means eliminate) the risk of fire. Also, note that the addition of sulfuric acid to the ethyl alcohol will release a great deal of heat, especially if the ethyl alcohol contains traces of water. Performing this addition carefully in an ice bath will prevent ether from boiling out prematurely.


Precautions

Diethyl ether is highly flammable. Its vapors are denser than air and will accumulate if proper ventilation is not present. Simple static electricity will ignite ether vapors. Diethyl ether vapors ignite explosively, and should only be used inside a fume hood. Static electricity is a class of phenomena involving the net charge present on an object; typically referring to charged object with voltages of sufficient magnitude to produce visible attraction, repulsion, and sparks. ... A common modern fume hood. ...


Additionally, diethyl ether is prone to peroxide formation, and can form explosive diethyl ether peroxide. Ether peroxides are higher boiling and are contact explosives when dry. Ether should never be distilled to dryness, as the risk of explosion increases dramatically. Diethyl ether is typically supplied with BHT (2,6-di-tert-butyl-4-methylphenol), which reduces the formation of peroxides. Bottles older than 3 months should be routinely tested for peroxides. An iron wire, releasing Fe(III) ions catalyzing the peroxide decomposition, was often added to bottles with diethyl ether as a preventive measure, however, Fe(III) ions also strongly enhance peroxide formation. Storage over NaOH precipitates the intermediate ether hydroperoxides. The general structure of an organic peroxide. ... Diethyl ether peroxides are a class of organic peroxides that slowly form in diethyl ether upon storage under air, light, or in the presence of metal by autoxidation. ... Flash point 127 °C R/S statement R: 22-36 37 38 S: 26-36 RTECS number GO7875000 Related compounds Related compounds butylated hydroxyanisole Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references BHT is the common...


As Diethyl ether is also an anesthetic, inhalation of significant quantities of fumes can also cause severe side effects and in large doses, unconsciousness.


In the words of gonzo journalist Hunter S. Thompson: Hunter Stockton Thompson (July 18, 1937 – February 20, 2005) was an American journalist and author. ...

"There is nothing in the world more helpless and irresponsible and depraved than a man in the depths of an ether binge."

References

  1. ^ Hill, John W. and Kolb, Doris K. Chemistry for changing times: 10th edition. Page 257. Pearson: Prentice Hall. Upper saddle river, New Jersey. 2004.
  2. ^ Hill, John W. and Kolb, Doris K. Chemistry for changing times: 10th edition. Page 257. Pearson: Prentice Hall. Upper saddle river, New Jersey. 2004.
  3. ^ http://www.erowid.org/chemicals/ether/ether_info1.shtml
  4. ^ http://www.incb.org/pdf/e/list/red.pdf

External links


  Results from FactBites:
 
Diethyl ether Summary (0 words)
Diethyl ether has the formula CH It is used as a common solvent and has been used as a general anesthetic.
Diethyl ether has a high cetane number of 85 - 96 and is used as a starting fluid for diesel and gasoline engines.
Ether, mixed with ethanol, was marketed in the 19th century as a cure-all and recreational drug, during one of Western society's temperance movements.
Chlorophyll a, diethyl ether (0 words)
The chemical structure of Chlorophyll a, diethyl ether is shown at the right.
This is a graph of the molar extinction coefficient of Chlorophyll a dissolved in diethyl ether.
This is the fluorescence emission spectrum of Chlorophyll a dissolved in diethyl ether.
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