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| Names | |
|---|---|
| IUPAC name
Ethoxyethane
|
|
| Other names
Diethyl ether; Dether; Ethyl ether; Ethyl oxide; 3-Oxapentane; Ethoxyethane; Diethyl oxide; Solvent ether
|
|
| Identifiers | |
| ATC code | N01AA01 |
|
CAS Registry Number
|
60-29-7 Y |
| ChEBI | CHEBI:35702 Y |
| ChEMBL | ChEMBL16264 Y |
| ChemSpider | 3168 Y |
|
InChI
|
|
| Jmol-3D images | Image |
| KEGG | D01772 Y |
| PubChem | 3283 |
| RTECS number | KI5775000 |
|
SMILES
|
|
| UNII | 0F5N573A2Y Y |
| Properties | |
|
Chemical formula
|
C4H10O |
| Molar mass | 74.12 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | pungent, 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) |
|
Solubility in water
|
69 g/L (20 °C) |
| Vapor pressure | 440 mmHg (20°C)[1] |
|
Refractive index (nD)
|
1.353 (20 °C) |
| Viscosity | 0.224 cP (25 °C) |
| Structure | |
|
Dipole moment
|
1.15 D (gas) |
| Thermochemistry | |
|
Specific
heat capacity (C) |
172.5 J/mol·K |
|
Std molar
entropy (S |
253.5 J/mol·K |
|
Std enthalpy of
formation (ΔfH |
-271.2 ± 1.9 kJ/mol |
|
Std enthalpy of
combustion (ΔcH |
-2732.1 ± 1.9 kJ/mol |
| Hazards | |
| Main hazards | Extremely Flammable, harmful to skin, decomposes to explosive peroxides in air and light[1] |
| Safety data sheet | See: data page External MSDS |
| R-phrases | R12 R19 R20/22 R66 R67 |
| S-phrases | S9 S16 S29 S33 |
| NFPA 704 |
4
2
1
|
| Flash point | −45 °C (−49 °F; 228 K) [3] |
|
Autoignition
temperature |
160 °C (320 °F; 433 K)[3] |
| Explosive limits | 1.9-48.0% [2] |
| US health exposure limits (NIOSH): | |
|
PEL (Permissible)
|
TWA 400 ppm (1200 mg/m3)[1] |
|
REL (Recommended)
|
No established REL[1] |
|
IDLH (Immediate danger)
|
1900 ppm[1] |
| Related compounds | |
|
Related Ethers
|
Dimethyl ether Methoxypropane |
|
Related compounds
|
Diethyl sulfide Butanols (isomer) |
| Supplementary data page | |
|
Structure and
properties |
Refractive index (n), Dielectric constant (εr), etc. |
|
Thermodynamic
data |
Phase behaviour solid–liquid–gas |
|
Spectral data
|
UV, IR, NMR, MS |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
| Y verify (what is: Y/N?) | |
| Infobox references | |
Diethyl ether, also known as ethoxyethane, ethyl ether, sulfuric ether, or simply ether, is an organic compound in the ether class with the formula (C
2H
5)
2O. It is a colorless, highly volatile flammable liquid. It is commonly used as a solvent and was once used as a general anesthetic. It has narcotic properties and has been known to cause temporary dependence, the only symptom of which is the will to consume more, sometimes referred to as etheromania[citation needed].
Contents
- 1 History
- 2 Applications
- 2.1 As a fuel
- 2.2 Laboratory uses
- 2.3 Anesthetic use
- 2.4 Medical use
- 2.5 Recreational use
- 3 Metabolism
- 4 Production
- 5 Safety and stability
- 6 References
- 7 External links
History
The compound may have been created by either Jābir ibn Hayyān in the 8th century[4] or Ramon Llull in 1275,[4][5] although there is no contemporary evidence of this. It was first synthesized 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.[4] At about the same time, Paracelsus discovered ether's analgesic properties in chickens.[4] The name ether was given to the substance in 1729 by August Sigmund Frobenius.[6]
Applications
It is particularly important as a solvent in the production of cellulose plastics such as cellulose acetate.[7]
As a fuel
Diethyl ether has a high cetane number of 85-96 and is used as a starting fluid, in combination with petroleum distillates for gasoline and diesel engines[8] because of its high volatility and low flash point. For the same reason it is also used as a component of the fuel mixture for carbureted compression ignition model engines. In this way diethyl ether is very similar to one of its precursors, ethanol.
Laboratory uses
Diethyl ether is a common laboratory solvent. It has limited solubility in water (6.05 g/100 mL at 25 °C.) [9] and dissolves 1.5 g/100 mL water at 25 °C.[10] This, coupled with its high volatility, makes it ideal for use as the non-polar solvent in liquid-liquid extraction. When used with an aqueous solution, the diethyl ether layer is on top due to the fact that it has a lower density than the water. It is also a common solvent for the Grignard reaction in addition to other reactions involving organometallic reagents. 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 sulphuric acid.[11]
Anesthetic use
Panel from 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. However, Crawford Williamson Long, M.D., 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.[12][13][14] British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium.[15] Diethyl ether largely supplanted the use of 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.[16] Because of its associations with Boston, the use of ether became known as the "Yankee Dodge."
Diethyl ether depresses the myocardium and increases tracheobronchial secretions.[17]
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.
Today, 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.[18] Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents reduce these side effects.[12]
Medical use
It was once used in pharmaceuticals. A mixture of alcohol and ether was known as "Spirit of ether" or Hoffman's Drops. In the United States, it was removed from Pharmacopeia prior to June 1917.[19]
Recreational use
See also: Addiction to ether consumption
The anesthetic effects of ether have made it a recreational drug. Diethyl ether in anesthetic dosage is an inhalant which has a long history of recreational use. One disadvantage is the high flammability, especially in conjunction with oxygen. One advantage is a well-defined margin between therapeutic and toxic doses, which means one would lose consciousness before dangerous levels of dissolved ether in blood would be reached. With a strong, dense smell, ether causes irritation to respiratory mucosa and is uncomfortable to breathe, and in overdose triggering salivation, vomiting, coughing or spasms. In concentrations of 3-5% in air, an anesthetic effect can slowly be achieved in 15–20 minutes of breathing approximately 15-20ml of ether, depending on body weight and physical condition. Ether causes a very long excitation stage prior to blacking out.
In the 19th century and early 20th century ether drinking was popular among Polish peasants.[20] It is a traditional and still relatively popular recreational drug among Lemkos.[21] It is usually consumed in a small quantity (kropka, or "dot") poured over milk, water with sugar or orange juice in a shot glass.
Metabolism
A cytochrome P450 enzyme is proposed to metabolize diethyl ether.[22]
Diethyl ether inhibits alcohol dehydrogenase, and thus slows the metabolism of ethanol.[23] It also inhibits metabolism of other drugs requiring oxidative metabolism. For example diazepam requires hepatic oxidization whereas its oxidized metabolite oxazepam does not.[24]
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.[7] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%.[25]
Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.[26] Ethanol is mixed with a strong acid, typically sulfuric acid, H2SO4. The acid dissociates in the aqueous environment producing hydronium ions, H3O+. A hydrogen ion protonates the electronegative oxygen atom of the ethanol, giving the ethanol molecule a positive charge:
- CH3CH2OH + H3O+ → CH3CH2OH2+ + H2O
A nucleophilic oxygen atom of unprotonated ethanol displaces a water molecule from the protonated (electrophilic) ethanol molecule, producing water, a hydrogen ion and diethyl ether.
- CH3CH2OH2+ + CH3CH2OH → H2O + H+ + CH3CH2OCH2CH3
This reaction must be carried out at temperatures lower than 150 °C in order to ensure that an elimination product (ethylene) is not a product of the reaction. At higher temperatures, ethanol will dehydrate to form ethylene. The reaction to make diethyl ether is reversible, so eventually an equilibrium between reactants and products is achieved. Getting a good yield of ether requires that ether be distilled out of the reaction mixture before it reverts to ethanol, taking advantage of Le Chatelier's principle.
Another reaction that can be used for the preparation of ethers is the Williamson ether synthesis, in which an alkoxide (produced by dissolving an alkali metal in the alcohol to be used) performs a nucleophilic substitution upon an alkyl halide.
Safety and stability
Diethyl ether is extremely flammable and may be explosive.[27]
Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources, which need not be an open flame, but may be a hot plate, steam pipe, heater etc.[27] Vapour may 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). A common practice in chemical labs is to use steam (thus limiting the temperature to 100 °C (212 °F) ) when ether must be heated or distilled. The diffusion of diethyl ether in air is 0.918·10−5 m2/s (298K, 101.325 kPa).[citation needed]
Ether is sensitive to light and air, tending to form explosive peroxides.[27] Ether peroxides are higher boiling than ether and are contact explosives when dry.[27] 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.[28]
References
- ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0277". National Institute for Occupational Safety and Health (NIOSH).
- ^ Carl L. Yaws, Chemical Properties Handbook, McGraw-Hill, New York, 1999, page 567
- ^ a b "Ethyl Ether MSDS". J.T. Baker. Retrieved 2010-06-24.
- ^ a b c d Toski, Judith A; Bacon, Douglas R; Calverley, Rod K (2001). The history of Anesthesiology. In: Barash, Paul G; Cullen, Bruce F; Stoelting, Robert K. Clinical Anesthesia (4 ed.) (Lippincott Williams & Wilkins). p. 3. ISBN 978-0-7817-2268-1.
- ^ Hademenos, George J.; Murphree, Shaun; Zahler, Kathy; Warner, Jennifer M. (2008-11-12). McGraw-Hill's PCAT. McGraw-Hill. p. 39. ISBN 978-0-07-160045-3. Retrieved 2011-05-25.
- ^ Dr. Frobenius (1729) "An account of a spiritus vini æthereus, together with several experiments tried therewith," Philosophical Transactions of the Royal Society (London), 36 : 283-289.
- ^ a b "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2004.
- ^ "Extra Strength Starting Fluid: How it Works". Valvovine. Archived from the original on 2007-09-27. Retrieved 2007-09-05.
- ^ The Merck Index, 10th Edition, Martha Windholz, editor, Merck & Co., Inc, Rahway, NJ, 1983, page 551
- ^ H. H. Rowley, Wm. R. Reed (1951). "Solubility of Water in Diethyl Ether at 25 °". J. Am. Chem. Soc. 73 (6): 2960–2960. doi:10.1021/ja01150a531.
- ^ Microsoft Word - RedListE2007.doc
- ^ a b Hill, John W. and Kolb, Doris K. Chemistry for changing times: 10th edition. Page 257. Pearson: Prentice Hall. Upper saddle river, New Jersey. 2004.
- ^ Madden, M. Leslie (May 14, 2004). "Crawford Long (1815-1878)". New Georgia Encylcopedia. University of Georgia Press. Retrieved February 13, 2015.
- ^ "Crawford W. Long". Doctors' Day. Southern Medical Association. Retrieved February 13, 2015.
- ^ Grattan, N. Treatment of Uterine Haemorrhage. Provincial Medicine and Surgical Journal. Vol. 1, No. 6 (Nov. 7, 1840), p. 107.
- ^ Calderone, F.A. (1935). J. Pharmacology Experimental Therapeutics (PDF) 55 (1): 24–39 Jpet.aspetjournals.org http://jpet.aspetjournals.org/cgi/reprint/55/1/24.pdf Jpet.aspetjournals.org. Missing or empty
|title=(help) - ^ "Ether and its effects in Anesthesia".
- ^ Morgan, G. Edward, Jr. et al. "Clinical Anesthesiology" 3rd Ed, p. 3. New York: Mc Graw-Hill. 2002
- ^ The National druggist, Volume 47, June 1917, pp.220
- ^ 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.
- ^ 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”.
- ^ 109. Aspergillus flavus mutant strain 241, blocked in aflatoxin biosynthesis, does not accumulate aflR transcript. Matthew P. Brown and Gary A. Payne, North Carolina State University, Raleigh, NC 27695 fgsc.net
- ^ P. T. Normann, A. Ripel and J. Morland (1987). "Diethyl Ether Inhibits Ethanol Metabolism in Vivo by Interaction with Alcohol Dehydrogenase". Alcoholism: Clinical and Experimental Research 11 (2): 163–166. doi:10.1111/j.1530-0277.1987.tb01282.x. PMID 3296835.
- ^ Larry K. Keefer, William A. Garland, Neil F. Oldfield, James E. Swagzdis, and Bruce A. Mico (1985). "Inhibition of N-Nitrosodimethylamine Metabolism in Rats by Ether Anesthesia" (PDF). Cancer Research 45 (11 Pt 1): 5457–60. PMID 4053020.
- ^ Ethyl Ether, Chem. Economics Handbook. Menlo Park, Calif: SRI International. 1991.
- ^ Cohen, Julius Berend (1920). A Class-book of Organic Chemistry, Volume 1. London: Macmillan and Co. p. 39.
- ^ a b c d http://www.chem.purdue.edu/chemsafety/safetyclass/SDS/GHS-Et2O.pdf
- ^ W. L. F. Armarego and C. L. L. Chai (2003). Purification of laboratory chemicals. Boston: Butterworth-Heinemann. ISBN 978-0-7506-7571-0.
External links
| Wikimedia Commons has media related to Diethyl ether. |
- Michael Faraday's announcement of ether as an anesthetic in 1818
- Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of diethyl ether, ddbonline.ddbst.de
- CDC - NIOSH Pocket Guide to Chemical Hazards
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English Journal
- Alkali metal salts of ditopic carbanionic carbenes as reagents for the synthesis of novel complexes of group 12 and 14 metals.
- Waters JB1, Goicoechea JM.
- Dalton transactions (Cambridge, England : 2003).Dalton Trans.2014 May 15. [Epub ahead of print]
- Reaction of the lithiated N-heterocyclic carbene [:C[N(2,6-iPr2C6H3)]2(CH)CLi]n () with KOtBu in diethylether (Et2O) afforded the novel organo-potassium compound [:C[N(2,6-iPr2C6H3)]2(CH)CK(THF)2] (·2THF). Both and can be interpreted as ditopic carbanionic carbenes (or alkali metal salts of anionic
- PMID 24827736
- Preparation of layered double hydroxide/chlorophyll a hybrid nano-antennae: a key step.
- Sommer Márquez AE1, Lerner DA, Fetter G, Bosch P, Tichit D, Palomares E.
- Dalton transactions (Cambridge, England : 2003).Dalton Trans.2014 Mar 28. [Epub ahead of print]
- In the first step to obtain an efficient nano-antenna in a bottom-up approach, new hybrid materials were synthesized using a set of layered double hydroxides (LDHs) with basic properties and pure chlorophyll a (Chl a). The stability of the adsorbed monolayer of Chl a was shown to be dependent on the
- PMID 24676400
- Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials.
- Oliveira E1, Baptista RM, Costa SP, Raposo MM, Lodeiro C.
- Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.Photochem Photobiol Sci.2014 Mar;13(3):492-8. doi: 10.1039/c3pp50352f. Epub 2013 Dec 9.
- The demand for dyes with solvatochromic properties has increased in the last few years, mainly due to their wide range of applications in the analytical and industrial fields, such as in the textile industry. The phenomenon of solvatochromism is associated with the differential solvation of the grou
- PMID 24317329
Japanese Journal
- Reminiscence of phospholipase B in Penicillium notatum
- SAITO Kunihiko
- Proceedings of the Japan Academy, Series B 90(9), 333-346, 2014
- … PLB activity is influenced by various substances, e.g. detergents, deoxycholate, diethylether, Fe3+, and endogenous protease. …
- NAID 130004704865
- Characterization of Volatile Components and Odor-active Compounds in the Oil of Edible Mushroom Boletopsis leucomelas
- Nosaka Sota,Miyazawa Mitsuo
- Journal of Oleo Science 63(6), 577-583, 2014
- … The volatile oil from Boletopsis leucomelas (Pers.) Fayod was extracted by hydrodistillation with diethylether, and the volatile components of the oil were analyzed by gas chromatography-mass spectrometry. …
- NAID 130004436140
- ナフトキノン骨格を有するチオエーテル化合物のポリモルフィズム特性
- 絹田 貴史,原田 拓典,田嶋 暢夫,佐藤 友宏,黒田 玲子,松原 凱男,今井 喜胤
- 基礎有機化学討論会要旨集（基礎有機化学連合討論会予稿集） 2010(0), 2P28-2P28, 2011
- … Dichloromethaneとdiethylether溶媒で結晶化を行った場合、色調の異なる単結晶、それぞれ橙色結晶と赤褐色結晶が得られた。 …
- NAID 130004729166
Related Links
- [Diethyl Ether] [60-29-7] | 価格や在庫、物性値などの詳細情報ページです。 ... 別名 (英名) Ether Anhydrous (stabilized with BHT) 別名 (英名) Ethyl Ether Anhydrous (stabilized with BHT) 和名 ジエチルエーテル (無水)
- diethyl ether di·eth·yl ether (dī-ěth'əl) n. A pungent, volatile, highly flammable liquid derived from the distillation of ethyl alcohol with sulfuric acid and widely used as an inhalation anesthetic. Also called ethyl ether, ethyl oxide, sulfuric ...
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