Extremely flammable, harmful to skin, decomposes to explosiveperoxides inair andlight, may cause dizziness in a less ventilated place or if ingested.[1]
Most diethyl ether is produced as a byproduct of the vapor-phasehydration ofethylene to makeethanol. This process uses solid-supportedphosphoric acidcatalysts and can be adjusted to make more ether if the need arises:[10] Vapor-phasedehydration of ethanol over somealumina 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]
It is a common solvent for theGrignard reaction in addition to other reactions involving organometallic reagents.[13] These uses exploit its basicity. Diethyl ether is a popular non-polar solvent inliquid-liquid extraction. As an extractant, it is immiscible with and lessdense than water.
Although immiscible, it has significantsolubility inwater (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]
Diethyl ether has a highcetane number of 85–96 and, in combination with petroleum distillates for gasoline and diesel engines,[15] is used as astarting fluid because of its high volatility and lowflash 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 forcarbureted compression ignition model engines.
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 is9.18 × 10−6 m2/s (298 K, 101.325 kPa).[citation needed]
Ether is sensitive to light and air, tending to form explosiveperoxides.[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 theantioxidantbutylated hydroxytoluene (BHT), which reduces the formation of peroxides. Storage oversodium hydroxide precipitates the intermediate ether hydroperoxides. Water and peroxides can be removed by either distillation fromsodium andbenzophenone, or by passing through a column ofactivated alumina.[21]
The first use of ether in dental surgery, byErnest Board.Panel fromEther 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 theEther Dome inBoston, Massachusetts. Morton had called his ether preparation, with aromatic oils to conceal its smell, "Letheon" after theLethe River (Λήθη, meaning "forgetfulness, oblivion").[27] However,Crawford Williamson Long is now known to have demonstrated its use privately as ageneral 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 overchloroform as a general anesthetic due to ether's more favorabletherapeutic index, that is, a greater difference between an effective dose and a potentially toxic dose.[32]
Diethyl ether does not depress themyocardium but rather it stimulates the sympathetic nervous system leading to hypertension and tachycardia. It is safely used in patients with shock as it preserves thebaroreceptor 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 aschloroform to makeC.E. mixture, or chloroform andalcohol to makeA.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 asisoflurane,desflurane, andsevoflurane, 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
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'sAnodyne or Hoffman's Drops. In the United States this concoction was removed from thePharmacopeia at some point prior to June 1917,[38] as a study published byWilliam Procter, Jr. in theAmerican Journal of Pharmacy as early as 1852 showed that there were differences in formulation to be found between commercial manufacturers, between internationalpharmacopoeia, and from Hoffman's original recipe.[39] It is also used to treathiccups through instillation into the nasal cavity.[40]
The recreational use of ether also took place at organised parties in the 19th century calledether frolics, where guests were encouraged to inhale therapeutic amounts of diethyl ether ornitrous oxide, producing a state of excitation. Long, as well as fellow dentistsHorace Wells, William Edward Clarke, andWilliam 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 amongLemkos.[43] It is usually consumed in a small quantity (kropka, or "dot") poured over milk, sugar water, or orange juice in ashot glass. As a drug, it has been known to causepsychological dependence, sometimes referred to asetheromania.[44][medical citation needed]
Ether intoxication is referenced inHunter S. Thompson'sFear 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]
^abcdToski, 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 (4th ed.). Lippincott Williams & Wilkins. p. 3.ISBN978-0-7817-2268-1.
^Hademenos, George J.; Murphree, Shaun; Zahler, Kathy; Warner, Jennifer M. (2008).McGraw-Hill's PCAT. McGraw-Hill. p. 39.ISBN978-0-07-160045-3. Retrieved2011-05-25.
^"VIII. An account of a spiritus vini æthereus, together with several experiments tried therewith".Philosophical Transactions of the Royal Society of London.36 (413):283–289. 1730.doi:10.1098/rstl.1729.0045.S2CID186207852.
^Kaszycki, Nestor (2006-08-30)."Łemkowska Watra w Żdyni 2006 – pilnowanie ognia pamięci".Histmag.org – historia od podszewki (in Polish). Kraków, Poland: i-Press. Retrieved2009-11-25.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".
