diethyl ether diethyl ether diethyl ether, or simply ether, is an organic compound in the ether class with the formula (ch3ch2)2o or (c2h5)2o, sometimes abbreviated as et2o, where et stands for monovalent ethyl group ch3ch2 which is often written as c2h5 (see pseudoelement symbol). it is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. it is commonly used as 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 as halothane. it has been used as a recreational drug to cause intoxication. diethyl ether names 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 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/c1-3-5-4-2/h3-4h2,1-2h3 ykey: rtzkzfjdlaiyfh-uhfffaoysa-n yinchi=1/c4h10o/c1-3-5-4-2/h3-4h2,1-2h3key: rtzkzfjdlaiyfh-uhfffaoyab smiles ccocc properties chemical formula (ch3ch2)2o molar mass 74.123 g·mol−1 appearance colorless liquid odor dry, rum-like, sweetish odor 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 6.05 g/100 ml log p 0.98 vapor pressure 440 mmhg at 20 °c (58.66 kpa at 20 °c) magnetic susceptibility (χ) −55.1·10−6 cm3/mol refractive index (nd) 1.353 (20 °c) viscosity 0.224 cp (25 °c) structure dipole moment 1.15 d (gas) thermochemistry heat capacity (c) 172.5 j/(mol·k) std molarentropy (s⦵298) 253.5 j/(mol·k) std enthalpy offormation (δfh⦵298) (−271.2±1.9) kj/mol std enthalpy ofcombustion (δch⦵298) (−2732.1±1.9) kj/mol pharmacology atc code n01aa01 (who) hazards occupational safety and health (ohs/osh): main hazards extremely flammable, harmful to skin, decomposes to explosive peroxides in air and light ghs labelling: pictograms signal 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 1 flash point −45 °c (−49 °f; 228 k) autoignitiontemperature 160 °c (320 °f; 433 k) explosive limits 1.9–48.0% lethal dose or concentration (ld, lc): lc50 (median concentration) 73,000 ppm (rat, 2 hr)6500 ppm (mouse, 1.65 hr) lclo (lowest published) 106,000 ppm (rabbit)76,000 ppm (dog) niosh (us health exposure limits): pel (permissible) twa 400 ppm (1200 mg/m3) rel (recommended) no established rel idlh (immediate danger) 1900 ppm safety data sheet (sds) external msds related compounds related ethers dimethyl ethermethoxypropane related compounds diethyl sulfidebutanols (isomer) supplementary data page diethyl ether (data page) except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references 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. vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%. diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. 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+ → ch3ch2oh+2 + 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. ch3ch2oh+2 + 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 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. uses it is particularly important as a solvent in the production of cellulose plastics such as cellulose acetate. 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 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. chemistry 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 eb = 1.80 and cb = 1.63. diethyl ether is a common laboratory aprotic solvent. it has limited solubility in water (6.05 g/100 ml at 25 °c) and dissolves 1.5 g/100 g (1.0 g/100 ml) water at 25 °c. 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 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 sulfuric acid. anesthesia 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 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. british doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium. 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. diethyl ether does not depress the myocardium but rather it stimulates the sympathetic nervous system leading to hypertension and tachycardia. it is safely used in patients with shock as it preserves the baroreceptor reflex. 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. 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. 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 as isoflurane, desflurane, and sevoflurane, are halogenated ethers. diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. modern anesthetic agents reduce these side effects. prior to 2005 it was on the world health organization's list of essential medicines for use as an anesthetic. 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 "spirit of ether", hoffman's anodyne or hoffman's drops. in the united states this concoction was removed from the pharmacopeia at some point prior to june 1917, as a study published by william procter, jr. in the american journal of pharmacy as early as 1852 showed that there were differences in formulation to be found between commercial manufacturers, between international pharmacopoeia, and from hoffman's original recipe. it is also used to treat hiccups through instillation into nasal cavity. recreation