Diethyl Ether

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diethyl ether

(organic chemistry)
C4H10O A colorless liquid, slightly soluble in water; used as a reagent and solvent. Also known as ethyl ether; ethyl oxide; ethylic ether.
McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.
The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Diethyl Ether


(also ether), (C2H5)2O, the most important ether.

Diethyl ether takes the form of a colorless, mobile liquid with a characteristic odor. It has a melting point of – 116.2°C, a boiling point of 34.6°C, and a density of 0.713 g/cm3 at 20°C. Miscible in all proportions with alcohol and many other organic solvents, it is only 6.6-percent soluble in water at 20°C. It readily dissolves fats. Diethyl ether forms an azeotropic mixture with water; the mixture is 98.74-percent diethyl ether, and it has a boiling point of 34.25°C. Diethyl ether is highly flammable, and it forms explosive mixtures with air in concentrations of 1.71–48.0 percent by volume. Upon storage, it is slowly oxidized by atmospheric oxygen to form explosive peroxide compounds.

Diethyl ether is produced from ethyl alcohol at a temperature of 130°–140°C by the action of sulfuric acid—hence, its trivial name in Russian, sernyi efir (sulfuric ether). It may also be produced at 200°–250°C by the vapor-phase dehydration of ethyl alcohol over aluminum oxide (Al2O3) or potassium alums. Diethyl ether is used in industry as a solvent and extracting agent—for example, in the production of powders, motion-picture film, and photographic film. It also has various laboratory uses (seeGRIGNARD REACTION).

In medicine, two grades of diethyl ether are used—medicinal and highly purified. The former is usually applied externally or used for the preparation of tinctures and extracts; it is occasionally taken internally for vomiting. The latter is inhaled as an anesthetic before surgery or sometimes taken as an enema in the form of an oil to reduce pain during childbirth.

The maximum permissible concentration of diethyl ether vapor in the air is 0.3 mg per liter.

The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.
References in periodicals archive ?
The benzene was removed in vacuo and the solid was partitioned between H2O (40 mL) and Et2O (3A-50 mL).
Rf: 0.44 (Et2O), IR (Imax, cm-1): 1699 2.03-2.08 (2H, m, H4(Alpha) , 5(Beta)), 2.37-2.41 (5H, m, H4(Beta), H8, H9), 2.67 (2H, t, J = 6.3 Hz, H10), 5.79 ( 1H, d, J = 1.8 Hz, H2); 13C-NMR (75 MHz, CDCl3, o in ppm): 23.3 (t, C9), 23.6 (q, Me at C6), 30.0 (t, C5), 32.1, 34.0 (t, C4, C8), 38.0 (t, C10), 51.0 (s, C6), 126.1 (d, C2), 166.4 (s, C1), 198.8 (s, C3), 211.5 (s, C7); LREIMS (m/z): 178 [M+.] (31%), 150 [M+.- CO]+.
The reaction mixture was stirred for 3 hours and the resulting white precipitate was filtered and washed with Et2O (50 mL) under suction.
Column chromatography of crude over silica gel (13.5 cm in height) in a column (6.4 cm diameter) afforded WMK 18 (18.840 g, 62%) as greenish yellow oil in 11th-17th fraction (250 mL each) by elution with n-hexane, 30, 40, 50 and 60% Et2O in n-hexane (4A-0.8, 2.4 L).
Rf: 0.58 (CH2Cl2 / Et2O 1:3), d (g/mL): 1.067; IR (Imax, cm-1): 2875 (C=C-H), 1693 (C=O, isolated), 1667 (C=O, conjugated), UV: Imax (216 nm), log Iu (2.526); [(Alpha) ]20D: +1.7 (c = 1.07, CHCl3); 1H-NMR oH: 1.14 (3H, s, Me at C1), 1.28
NH4Cl solution (30 mL), diluted with H2O (50 mL), extracted with Et2O (3A-100 mL), dried the combined organic layer over anhydrous MgSO4 and concentrated under reduced pressure to afford greenish yellow crude oil (4.340 g).
Evaporation of MeOH in vacuo followed by the partitioning between H2O and Et2O (3A-50 mL), dryness over anhydrous MgSO4 and concentration under reduced pressure afforded crude yellow oil (4.962 g).