Diethyl ether
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Names | |||
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Preferred IUPAC name
Ethoxyethane | |||
Other names
Diethyl ether; Dether; Ethyl ether; Ethyl oxide; 3-Oxapentane; Ethoxyethane; Diethyl oxide; Solvent ether; Sulfuric ether; Vitriolic ether; Sweet oil of vitriol
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Identifiers | |||
3D model (
JSmol ) |
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1696894 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.000.425 | ||
EC Number |
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25444 | |||
KEGG | |||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1155 | ||
CompTox Dashboard (EPA)
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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 at 20 °C (58.66 kPa at 20 °C)[1] | ||
−55.1·10−6 cm3/mol | |||
Refractive index (nD)
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1.353 (20 °C) | ||
Viscosity | 0.224 cP (25 °C) | ||
Structure | |||
1.15 D (gas) | |||
Thermochemistry | |||
Heat capacity (C)
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172.5 J/(mol·K) | ||
Std molar
entropy (S⦵298) |
253.5 J/(mol·K) | ||
Std enthalpy of (ΔfH⦵298)formation |
(−271.2±1.9) kJ/mol | ||
Std enthalpy of (ΔcH⦵298)combustion |
(−2732.1±1.9) kJ/mol | ||
Pharmacology | |||
N01AA01 (WHO) | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Extremely flammable, harmful to skin, decomposes to explosive peroxides in air and light[1] | ||
GHS labelling: | |||
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) | |||
Flash point | −45 °C (−49 °F; 228 K)[7] | ||
160 °C (320 °F; 433 K)[7] | |||
Explosive limits
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1.9–48.0%[5] | ||
Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration)
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73,000 ppm (rat, 2 hr) 6500 ppm (mouse, 1.65 hr)[6] | ||
LCLo (lowest published)
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106,000 ppm (rabbit) 76,000 ppm (dog)[6] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 400 ppm (1200 mg/m3)[1] | ||
REL (Recommended)
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No established REL[1] | ||
IDLH (Immediate danger) |
1900 ppm[1] | ||
Safety data sheet (SDS) | External MSDS | ||
Related compounds | |||
Related ethers
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Dimethyl ether Methoxypropane | ||
Related compounds
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Diethyl sulfide Butanols (isomer) | ||
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).
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Diethyl ether, or simply ether, is an
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.[8] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%.[9]
Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.[10] Ethanol is mixed with a strong acid, typically sulfuric acid, H2SO4. The acid dissociates in the aqueous environment producing hydronium ions, [H3O]+. A hydronium ion protonates the electronegative oxygen atom of the ethanol, giving the ethanol molecule a positive charge:
- CH3CH2OH + [H3O]+ → [CH3CH2OH2]+ + H2O
A
- [CH3CH2OH2]+ + CH3CH2OH → [H3O]+ + 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 to decrease reverse reaction rate, taking advantage of Le Chatelier's principle.[citation needed]
Another reaction that can be used for the preparation of ethers is the
Uses
It is particularly important as a solvent in the production of cellulose plastics such as cellulose acetate.[8]
Fuel
Diethyl ether has a high cetane number of 85–96 and, in combination with petroleum distillates for gasoline and diesel engines,[11] 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. In this way diethyl ether is very similar to one of its precursors, ethanol.[citation needed]
Chemistry
Diethyl ether is a
Anesthesia
Diethyl ether does not depress the
Prior to 2005, it was on the
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
Recreation
The anesthetic and intoxicating 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 15–20 ml of ether, depending on body weight and physical condition. Ether causes a very long excitation stage prior to blacking out.[citation needed]
The recreational use of ether also took place at organised parties in the 19th century called ether frolics, where guests were encouraged to inhale therapeutic amounts of diethyl ether or nitrous oxide, producing a state of excitation. Long, as well as fellow dentists Horace Wells, William Edward Clarke and William T. G. Morton observed that during these gatherings, people would often experience minor injuries but appear to show no reaction to the injury, nor memory that it had happened, demonstrating ether's anaesthetic effects.[28]
In the 19th century and early 20th century ether drinking was popular among Polish peasants.
Metabolism
A cytochrome P450 enzyme is proposed to metabolize diethyl ether.[32]
Diethyl ether inhibits
Safety and stability
Diethyl ether is extremely flammable and may form explosive vapour/air mixtures.[35]
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.[35] 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.[35] Ether peroxides have a higher boiling point than ether and are contact explosives when dry.[35] 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.[36]
History
The compound may have been synthesised by either
It was considered to be a sulfur compound until the idea was disproved in about 1800.[40]
The synthesis of diethyl ether by a reaction between ethanol and sulfuric acid has been known since the 13th century.[40]
See also
- The Great Moment – film about William T.G. Morton and ether
Explanatory notes
- pseudoelement symbol)
References
- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0277". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b Merck Index, 10th Edition, Martha Windholz, editor, Merck & Co., Inc, Rahway, NJ, 1983, page 551
- ^ "Diethyl ether_msds".
- ^ "Diethyl ether". ChemSpider. Retrieved 19 January 2017.
- ^ Carl L. Yaws, Chemical Properties Handbook, McGraw-Hill, New York, 1999, page 567
- ^ a b "Ethyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Ethyl Ether MSDS". J.T. Baker. Archived from the original on 2012-03-28. Retrieved 2010-06-24.
- ^ a b "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2004.
- ^ 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.
the structure of ethyl alcohol cohen julius diethyl ether.
- ^ "Extra Strength Starting Fluid: How it Works". Valvovine. Archived from the original on 2007-09-27. Retrieved 2007-09-05.
- .
- ^ Microsoft Word – RedListE2007.doc Archived February 27, 2008, at the Wayback Machine
- ISBN 978-0-7614-7767-9.
- ^ a b Hill, John W. and Kolb, Doris K. Chemistry for Changing Times: 10th Edition. p. 257. Pearson: Prentice Hall. Upper Saddle River, New Jersey. 2004.
- ^ Madden, M. Leslie (May 14, 2004). "Crawford Long (1815–1878)". New Georgia Encyclopedia. University of Georgia Press. Retrieved February 13, 2015.
- ^ "Crawford W. Long". Doctors' Day. Southern Medical Association. Archived from the original on February 13, 2015. 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). "Studies on Ether Dosage After Pre-Anesthetic Medication with Narcotics (Barbiturates, Magnesium Sulphate and Morphine)" (PDF). Journal of Pharmacology and Experimental Therapeutics. 55 (1): 24–39.
- ^ "Ether effects". 31 October 2010.
- ^ "Ether and its effects in Anesthesia". Anesthesia General. 2010-10-31.
- ^ Morgan, G. Edward, Jr. et al. (2002). Clinical Anesthesiology 3rd Ed. New York: Mc Graw-Hill. p. 3.
- ^ "Essential Medicines WHO Model List (revised April 2003)" (PDF). apps.who.int (13th ed.). Geneva, Switzerland: World Health Organization. April 2003. Retrieved 6 September 2017.
- ^ "Essential Medicines WHO Model List (revised March 2005)" (PDF). apps.who.int (14th ed.). Geneva, Switzerland: World Health Organization. March 2005. Archived from the original (PDF) on 5 August 2005. Retrieved 6 September 2017.
- ^ The National druggist, Volume 47, June 1917, pp.220
- ^ Procter, William Jr. (1852). "On Hoffman's Anodyne Liquor". American Journal of Pharmacy. 28.
- ^ ncbi, Treatment of hiccups with instillation of ether into the nasal cavity.
- ^ "How Ether Went From a Recreational 'Frolic' Drug to the First Surgery Anesthetic". Smithsonian Magazine. Retrieved 2020-10-11.
- 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".
- PMID 12873252.
- ^ 109. Aspergillus flavus mutant strain 241, blocked in aflatoxin biosynthesis, does not accumulate aflR transcript. Archived 2017-09-17 at the Wayback Machine Matthew P. Brown and Gary A. Payne, North Carolina State University, Raleigh, NC 27695 fgsc.net
- PMID 3296835.
- PMID 4053020.
- ^ a b c d "Archived copy" (PDF). Archived from the original (PDF) on 2014-11-13. Retrieved 2014-02-15.
{{cite web}}
: CS1 maint: archived copy as title (link) - ISBN 978-0-7506-7571-0.
- ^ )
- ISBN 978-0-07-160045-3. Retrieved 2011-05-25.
- S2CID 186207852.
- ^ a b Chisholm, Hugh, ed. (1911). . Encyclopædia Britannica. Vol. 9 (11th ed.). Cambridge University Press. p. 806.
External links
- Michael Faraday's announcement of ether as an anesthetic in 1818 Archived 2011-05-22 at the Wayback Machine
- Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of diethyl ether, ddbonline.ddbst.de
- CDC – NIOSH Pocket Guide to Chemical Hazards