Boiling Point Of Diethyl Ether

Organic chemical compound

Diethyl ether

Names
Preferred IUPAC proper noun 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
Identifiers
CAS Number	60-29-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1696894
ChEBI	CHEBI:35702 Y
ChEMBL	ChEMBL16264 Y
ChemSpider	3168 Y
ECHA InfoCard	100.000.425
EC Number	200-467-2
Gmelin Reference	25444
KEGG	D01772 Y
PubChem CID	3283
RTECS number	KI5775000
UNII	0F5N573A2Y Y
Un number	1155
CompTox Dashboard (EPA)	DTXSID3021720
InChI InChI=1S/C4H10O/c1-iii-v-4-2/h3-4H2,one-2H3 Y Key: RTZKZFJDLAIYFH-UHFFFAOYSA-N Y InChI=i/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 Primal: RTZKZFJDLAIYFH-UHFFFAOYAB
SMILES CCOCC
Properties
Chemic formula	C 4 H ten O
Molar mass	74.123 g·mol−1
Advent	Colorless liquid
Odor	Dry, Rum-like, sweetish olfactory property[1]
Density	0.7134 g/cm3, liquid
Melting bespeak	−116.3 °C (−177.3 °F; 156.eight K)
Boiling point	34.vi °C (94.3 °F; 307.8 K)[4]
Solubility in water	6.05 1000/100 mL[2]
log P	0.98[3]
Vapor pressure	440 mmHg at 20 °C (58.66 kPa at xx °C)[i]
Magnetic susceptibility (χ)	−55.1·10−six cm3/mol
Refractive index (n D)	one.353 (twenty °C)
Viscosity	0.224 cP (25 °C)
Structure
Dipole moment	1.xv D (gas)
Thermochemistry
Oestrus capacity (C)	172.v J/mol·K
Std molar entropy (S ⦵ 298)	253.five J/mol·One thousand
Std enthalpy of germination (Δf H ⦵ 298)	−271.2 ± one.9 kJ/mol
Std enthalpy of combustion (Δc H ⦵ 298)	−2732.one ± one.9 kJ/mol
Pharmacology
ATC code	N01AA01 (WHO)
Hazards
Occupational condom and wellness (OHS/OSH):
Main hazards	Extremely flammable, harmful to pare, decomposes to explosive peroxides in air and light[1]
GHS labelling:
Pictograms
Indicate word	Danger
Hazard statements	H224, H302, H336
Precautionary statements	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)	2 4 i
Flash point	−45 °C (−49 °F; 228 K)[7]
Autoignition temperature	160 °C (320 °F; 433 K)[seven]
Explosive limits	1.9–48.0%[v]
Lethal dose or concentration (LD, LC):
LC50 (median concentration)	73,000 ppm (rat, two hr) 6500 ppm (mouse, 1.65 hour)[half-dozen]
LCLo (lowest published)	106,000 ppm (rabbit) 76,000 ppm (canis familiaris)[6]
NIOSH (United states health exposure limits):
PEL (Permissible)	TWA 400 ppm (1200 mg/mthree)[1]
REL (Recommended)	No established REL[one]
IDLH (Firsthand danger)	1900 ppm[1]
Prophylactic data canvass (SDS)	External MSDS
Related compounds
Related ethers	Dimethyl ether Methoxypropane
Related compounds	Diethyl sulfide Butanols (isomer)
Supplementary data folio
Diethyl ether (data page)
Except where otherwise noted, data are given for materials in their standard country (at 25 °C [77 °F], 100 kPa). Yverify (what is Y N  ?) Infobox references

Chemical compound

Diethyl ether, or merely ether, is an organic chemical compound in the ether form with the formula (C
₂ H
_five )
_ii O, sometimes abbreviated equally Et
_two O (meet Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal olfactory property"), extremely combustible liquid. Information technology is ordinarily used every bit a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such every bit halothane. It has been used every bit a recreational drug to cause intoxication.

Production [edit]

Most diethyl ether is produced as a byproduct of the vapor-phase hydration of ethylene to make ethanol. This procedure uses solid-supported phosphoric acid catalysts and tin be adapted to brand more than ether if the need arises.^[8] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%.^[ix]

Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.^[x] Ethanol is mixed with a potent acid, typically sulfuric acrid, H_iiAnd so₄. The acrid 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⁺ → CH_threeCH₂OH + ii + H₂O

A nucleophilic oxygen atom of unprotonated ethanol displaces a water molecule from the protonated (electrophilic) ethanol molecule, reforming the hydronium ion and yielding diethyl ether.

CH₃CH_twoOH + 2 + CH_iiiCH₂OH → H₃O⁺ + CH_iiiCH₂OCH_twoCH_three

This reaction must be carried out at temperatures lower than 150 °C in gild 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 earlier it reverts to ethanol, taking advantage of Le Chatelier's principle.^{[ citation needed ]}

Some other reaction that tin can be used for the preparation of ethers is the Williamson ether synthesis, in which an alkoxide (produced past dissolving an alkali metallic in the booze to be used) performs a nucleophilic substitution upon an alkyl halide.^{[ commendation needed ]}

Uses [edit]

It is specially important every bit a solvent in the production of cellulose plastics such as cellulose acetate.^[8]

Fuel [edit]

Diethyl ether has a loftier cetane number of 85–96 and is used every bit a starting fluid, in combination with petroleum distillates for gasoline and diesel engines^[11] because of its loftier volatility and depression flash point. Ether starting fluid is sold and used in countries with cold climates, as information technology can aid with cold starting an engine at sub-zero temperatures. For the same reason information technology is also used equally a component of the fuel mixture for carbureted pinch ignition model engines. In this way diethyl ether is very like to one of its precursors, ethanol.^{[ citation needed ]}

Chemical science [edit]

Diethyl ether is a hard Lewis base that reacts with a variety of Lewis acids such as iodine, phenol, and trimethylaluminium, and its base parameters in the ECW model are Due east_B = one.80 and C_B = 1.63. Diethyl ether is a common laboratory aprotic solvent. Information technology has limited solubility in water (6.05 g/100 ml at 25 °C^[2]) and dissolves one.5 m/100 thousand (1.0 thousand/100 ml) water at 25 °C.^[12] 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 as information technology has a lower density than the h2o. It is besides 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 every bit well as substances such as acetone, toluene and sulfuric acid.^[13]

Anesthesia [edit]

Console from monument in Boston commemorating Morton's demonstration of ether's anesthetic utilise.

William T. 1000. Morton participated in a public demonstration of ether anesthesia on October sixteen, 1846, at the Ether Dome in Boston, Massachusetts. All the same, Crawford Williamson Long is now known to have demonstrated its use privately every bit a general coldhearted in surgery to officials in Georgia, as early on as March 30, 1842, and Long publicly demonstrated ether's use as a surgical anesthetic on vi occasions before the Boston demonstration.^{[14] [15] [xvi]} British doctors were enlightened of the coldhearted backdrop of ether as early as 1840 where it was widely prescribed in conjunction with opium.^[17] Diethyl ether largely supplanted the employ of chloroform as a full general anesthetic due to ether's more favorable therapeutic index, that is, a greater difference between an constructive dose and a potentially toxic dose.^[18]

Diethyl ether does not depress the myocardium but rather information technology stimulates the sympathetic nervous system leading to hypertension and tachycardia. It is safely used in patients with shock as it preserves the baroreceptor reflex.^[xix] Its minimal outcome on myocardial depression and respiratory drive, as well as its low cost and high therapeutic index allows it to run into connected use in developing countries.^[xx] Diethyl ether could also be mixed with other coldhearted agents such as chloroform to brand 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 offset such anesthetic developed and other currently used inhaled anesthetics, such as isoflurane, desflurane, and sevoflurane, are halogenated ethers.^[21] Diethyl ether was found to accept undesirable side effects, such every bit mail-anesthetic nausea and airsickness. Modern anesthetic agents reduce these side furnishings.^[14]

Prior to 2005 it was on the World Health Organization'south List of Essential Medicines for employ every bit an anesthetic.^{[22] [23]}

Medicine [edit]

Ether was once used in pharmaceutical formulations. A mixture of alcohol and ether, ane part of diethyl ether and three parts of ethanol, was known every bit "Spirit of ether", Hoffman'due south Anodyne or Hoffman'south Drops. In the Us this concoction was removed from the Pharmacopeia at some bespeak prior to June 1917,^[24] equally a study published by William Procter, Jr. in the American Journal of Chemist's shop as early on as 1852 showed that in that location were differences in conception to be found between commercial manufacturers, between international pharmacopoeia, and from Hoffman's original recipe.^[25] It is besides used to treat hiccups through instillation into nasal cavity.^[26]

Recreation [edit]

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. I disadvantage is the high flammability, particularly in conjunction with oxygen. One advantage is a well-defined margin between therapeutic and toxic doses, which ways 1 would lose consciousness before unsafe levels of dissolved ether in blood would be reached. With a strong, dense aroma, ether causes irritation to respiratory mucosa and is uncomfortable to breathe, and in overdose triggering salivation, vomiting, cough or spasms. In concentrations of 3–v% in air, an anesthetic upshot can slowly be achieved in 15–twenty minutes of breathing approximately fifteen–20 ml of ether, depending on trunk weight and concrete condition. Ether causes a very long excitation phase prior to blacking out.^{[ citation needed ]}

The recreational apply of ether as well 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 young man dentists Horace Wells, William Edward Clarke and William T. K. 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.^[27]

In the 19th century and early 20th century ether drinking was popular amidst Polish peasants.^[28] It is a traditional and still relatively pop recreational drug amongst Lemkos.^[29] It is usually consumed in a small quantity (kropka, or "dot") poured over milk, sugar water, or orangish juice in a shot glass. Every bit a drug, information technology has been known to cause psychological dependence, sometimes referred to equally etheromania.^{[30] [ medical citation needed ]}

Metabolism [edit]

A cytochrome P450 enzyme is proposed to metabolize diethyl ether.^[31]

Diethyl ether inhibits booze dehydrogenase, and thus slows the metabolism of ethanol.^[32] It also inhibits metabolism of other drugs requiring oxidative metabolism. For instance, diazepam requires hepatic oxidization whereas its oxidized metabolite oxazepam does non.^[33]

Safety and stability [edit]

Diethyl ether is extremely flammable and may form explosive vapour/air mixtures.^[34]

Since ether is heavier than air it tin collect low to the ground and the vapour may travel considerable distances to ignition sources. Ether will ignite if exposed to an open up flame, though due its loftier flammability, an open flame is non required for ignition. Other possible ignition sources include - only are not express to - hot plates, steam pipes, heaters, and electrical arcs created by switches or outlets.^[34] Vapour may also be ignited by the static electricity which tin build upwardly when ether is being poured from one vessel into another. The autoignition temperature of diethyl ether is 160 °C (320 °F). The improvidence of diethyl ether in air is 9.18 × 10^{−half-dozen} k^two/due south (298 K, 101.325 kPa).^{[ citation needed ]}

Ether is sensitive to light and air, tending to form explosive peroxides.^[34] Ether peroxides take a college boiling point than ether and are contact explosives when dry.^[34] 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. H2o and peroxides can be removed by either distillation from sodium and benzophenone, or by passing through a column of activated alumina.^[35]

History [edit]

The compound may take been synthesised by either Jābir ibn Hayyān in the 8th century^[36] or Ramon Llull in 1275.^{[36] [37]} It was synthesised in 1540 by Valerius Cordus, who called it "sweet oil of vitriol" (oleum dulce vitrioli)—the proper noun reflects the fact that it is obtained past distilling a mixture of ethanol and sulfuric acrid (then known as oil of vitriol)—and noted some of its medicinal properties.^[36] At nearly the same time, Paracelsus discovered the analgesic backdrop of the molecule in dogs.^[36] The proper name ether was given to the substance in 1729 by Baronial Sigmund Frobenius.^[38]

It was considered to be a sulfur compound until the thought was disproved in about 1800. ^[39]

References [edit]

1. ^ ^{a b c d e f} NIOSH Pocket Guide to Chemic Hazards. "#0277". National Institute for Occupational Safe and Wellness (NIOSH).
2. ^ ^{a b} Merck Index, 10th Edition, Martha Windholz, editor, Merck & Co., Inc, Rahway, NJ, 1983, folio 551
3. ^ "Diethyl ether_msds".
4. ^ "Diethyl ether". ChemSpider. Retrieved nineteen January 2017.
5. ^ Carl Fifty. Yaws, Chemical Backdrop Handbook, McGraw-Hill, New York, 1999, page 567
6. ^ ^{a b} "Ethyl ether". Immediately Unsafe to Life or Health Concentrations (IDLH). National Institute for Occupational Safe and Health (NIOSH).
7. ^ ^{a b} "Ethyl Ether MSDS". J.T. Baker. Archived from the original on 2012-03-28. Retrieved 2010-06-24 .
8. ^ ^{a b} "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Engineering. John Wiley & Sons, Inc. 2004.
9. ^ Ethyl Ether, Chem. Economics Handbook. Menlo Park, Calif: SRI International. 1991.
10. ^ Cohen, Julius Berend (1920). A Class-book of Organic Chemistry, Volume i. London: Macmillan and Co. p. 39. the construction of ethyl alcohol cohen julius diethyl ether.
11. ^ "Actress Force Starting Fluid: How it Works". Valvovine. Archived from the original on 2007-09-27. Retrieved 2007-09-05 .
12. ^ H. H. Rowley; Wm. R. Reed (1951). "Solubility of H2o in Diethyl Ether at 25 °". J. Am. Chem. Soc. 73 (six): 2960. doi:10.1021/ja01150a531.
13. ^ Microsoft Word – RedListE2007.doc Archived February 27, 2008, at the Wayback Car
14. ^ ^{a b} Hill, John Westward. and Kolb, Doris Thou. Chemistry for Changing Times: 10th Edition. p. 257. Pearson: Prentice Hall. Upper Saddle River, New Jersey. 2004.
15. ^ Madden, M. Leslie (May 14, 2004). "Crawford Long (1815–1878)". New Georgia Encyclopedia. Academy of Georgia Press. Retrieved February xiii, 2015.
16. ^ "Crawford W. Long". Doctors' Twenty-four hours. Southern Medical Association. Archived from the original on February thirteen, 2015. Retrieved February 13, 2015.
17. ^ Grattan, North. "Treatment of Uterine Bleeding". Provincial Medicine and Surgical Journal. Vol. 1, No. half-dozen (November. 7, 1840), p. 107.
18. ^ 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.
19. ^ "Ether effects". 31 October 2010.
20. ^ "Ether and its effects in Anesthesia". 2010-10-31.
21. ^ Morgan, One thousand. Edward, Jr. et al. (2002). Clinical Anesthesiology tertiary Ed. New York: Mc Graw-Loma. p. 3.
22. ^ "Essential Medicines WHO Model Listing (revised April 2003)" (PDF). apps.who.int (13th ed.). Geneva, Switzerland: Globe Health Organization. April 2003. Retrieved 6 September 2017.
23. ^ "Essential Medicines WHO Model List (revised March 2005)" (PDF). apps.who.int (14th ed.). Geneva, Switzerland: World Wellness Organization. March 2005. Archived from the original (PDF) on 5 Baronial 2005. Retrieved vi September 2017.
24. ^ The National druggist, Volume 47, June 1917, pp.220
25. ^ Procter, William Jr. (1852). "On Hoffman's Anodyne Liquor". American Journal of Pharmacy. 28.
26. ^ ncbi, Treatment of hiccups with instillation of ether into the nasal cavity.
27. ^ "How Ether Went From a Recreational 'Frolic' Drug to the Commencement Surgery Anesthetic". Smithsonian Mag . Retrieved 2020-10-11 .
28. ^ Zandberg, Adrian (2010). "Short Article "Villages … Reek of Ether Vapours": Ether Drinking in Silesia before 1939". Medical History. 54 (three): 387–396. doi:10.1017/s002572730000466x. PMC2890321. PMID 20592886.
29. ^ 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 exercise narkozy, ponieważ ma właściwości halucynogenne, a już kilka kropel inhalacji wystarczyło practise 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".
30. ^ Krenz, Sonia; Zimmermann, Grégoire; Kolly, Stéphane; Zullino, Daniele Fabio (Baronial 2003). "Ether: a forgotten addiction". Addiction. 98 (eight): 1167–1168. doi:10.1046/j.1360-0443.2003.00439.x. PMID 12873252.
31. ^ 109. Aspergillus flavus mutant strain 241, blocked in aflatoxin biosynthesis, does not accumulate aflR transcript. Matthew P. Brown and Gary A. Payne, Due north Carolina Land University, Raleigh, NC 27695 fgsc.net
32. ^ P. T. Normann; A. Ripel; J. Morland (1987). "Diethyl Ether Inhibits Ethanol Metabolism in Vivo by Interaction with Alcohol Dehydrogenase". Alcoholism: Clinical and Experimental Inquiry. 11 (ii): 163–166. doi:ten.1111/j.1530-0277.1987.tb01282.x. PMID 3296835.
33. ^ Larry Yard. Keefer; William A. Garland; Neil F. Oldfield; James E. Swagzdis; Bruce A. Mico (1985). "Inhibition of N-Nitrosodimethylamine Metabolism in Rats by Ether Anesthesia" (PDF). Cancer Research. 45 (11 Pt one): 5457–sixty. PMID 4053020.
34. ^ ^{a b c d} "Archived re-create" (PDF). Archived from the original (PDF) on 2014-11-thirteen. Retrieved 2014-02-15 . {{cite web}}: CS1 maint: archived copy as championship (link)
35. ^ West. L. F. Armarego; C. Fifty. L. Chai (2003). Purification of laboratory chemicals. Boston: Butterworth-Heinemann. ISBN978-0-7506-7571-0.
36. ^ ^{a b c d} Toski, Judith A; Salary, Douglas R; Calverley, Rod G (2001). The history of Anesthesiology. In: Barash, Paul G; Cullen, Bruce F; Stoelting, Robert K. Clinical Anesthesia (iv ed.). Lippincott Williams & Wilkins. p. 3. ISBN978-0-7817-2268-1.
37. ^ Hademenos, George J.; Murphree, Shaun; Zahler, Kathy; Warner, Jennifer Grand. (2008-eleven-12). McGraw-Colina'south PCAT. McGraw-Hill. p. 39. ISBN978-0-07-160045-3 . Retrieved 2011-05-25 .
38. ^ "VIII. An account of a spiritus vini æthereus, together with several experiments tried therewith". Philosophical Transactions of the Purple Society of London. 36 (413): 283–289. 1730. doi:10.1098/rstl.1729.0045. S2CID 186207852.
39. ^ Chisholm, Hugh, ed. (1911). "Ether". Encyclopædia Britannica. Vol. 9 (11th ed.). Cambridge University Printing. p. 806.

External links [edit]

• Michael Faraday's announcement of ether equally an anesthetic in 1818 Archived 2011-05-22 at the Wayback Machine
• Adding of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of diethyl ether, ddbonline.ddbst.de
• CDC – NIOSH Pocket Guide to Chemical Hazards

Boiling Point Of Diethyl Ether,

Source: https://en.wikipedia.org/wiki/Diethyl_ether

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