1209:
1026:. In addition to avoiding storage conditions likely to form peroxides, it is recommended, when an ether is used as a solvent, not to distill it to dryness, as any peroxides that may have formed, being less volatile than the original ether, will become concentrated in the last few drops of liquid. The presence of peroxide in old samples of ethers may be detected by shaking them with freshly prepared solution of a ferrous sulfate followed by addition of KSCN. Appearance of blood red color indicates presence of peroxides. The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like
1719:
1615:
1578:
1549:
1528:
1761:
1650:
35:
1698:
1633:
1043:
1668:
85:, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the
1215:
This direct nucleophilic substitution reaction requires elevated temperatures (about 125 °C). The reaction is catalyzed by acids, usually sulfuric acid. The method is effective for generating symmetrical ethers, but not unsymmetrical ethers, since either OH can be protonated, which would give a
1437:, see Ullmann condensation below). Likewise, this method only gives the best yields for primary halides. Secondary and tertiary halides are prone to undergo E2 elimination on exposure to the basic alkoxide anion used in the reaction due to steric hindrance from the large alkyl groups.
301:
IUPAC rules are often not followed for simple ethers. The trivial names for simple ethers (i.e., those with none or few other functional groups) are a composite of the two substituents followed by "ether". For example, ethyl methyl ether
1334:
are typically prepared by oxidation of alkenes. The most important epoxide in terms of industrial scale is ethylene oxide, which is produced by oxidation of ethylene with oxygen. Other epoxides are produced by one of two routes:
902:
1216:
mixture of products. Diethyl ether is produced from ethanol by this method. Cyclic ethers are readily generated by this approach. Elimination reactions compete with dehydration of the alcohol:
162:
than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in
330:). As for other organic compounds, very common ethers acquired names before rules for nomenclature were formalized. Diethyl ether is simply called ether, but was once called
1456:
to form phenoxide ions. The phenoxide ion will then substitute the –X group in the alkyl halide, forming an ether with an aryl group attached to it in a reaction with an
1992:
F.A.Cotton; S.A.Duraj; G.L.Powell; W.J.Roth (1986). "Comparative
Structural Studies of the First Row Early Transition Metal(III) Chloride Tetrahydrofuran Solvates".
1308:
992:
is used in some cases) to give the alkyl bromide. Depending on the substituents, some ethers can be cleaved with a variety of reagents, e.g. strong base.
1910:
Vojinović, Krunoslav; Losehand, Udo; Mitzel, Norbert W. (2004). "Dichlorosilane–Dimethyl Ether
Aggregation: A New Motif in Halosilane Adduct Formation".
1847:
912:
The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical
1515:
is similar to the
Williamson method except that the substrate is an aryl halide. Such reactions generally require a catalyst, such as copper.
151:. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of
2097:
1240:
The dehydration route often requires conditions incompatible with delicate molecules. Several milder methods exist to produce ethers.
3016:
1718:
1614:
1448:
can be used to replace the alcohol while maintaining the alkyl halide. Since phenols are acidic, they readily react with a strong
3021:
1527:
378:
group. The term "oxide" or other terms are used for high molar mass polymer when end-groups no longer affect polymer properties.
1548:
1577:
2036:
1894:
1418:(R–X). Although popular in textbooks, the method is usually impractical on scale because it cogenerates significant waste.
935:
are unrepresentative classes of ethers and are discussed in separate articles. Important reactions are listed below.
1208:
2090:
1773:, an example with an ether on sn-1, an ester on sn-2, and an inorganic ether on sn-3 of the glyceryl scaffold.
1156:
2920:
1805:
1344:
3054:
1019:
474:
173:
Ethers can be symmetrical of the type ROR or unsymmetrical of the type ROR'. Examples of the former are
3049:
2493:
2083:
1399:
441:
1697:
201:
Vinyl- and acetylenic ethers are far less common than alkyl or aryl ethers. Vinylethers, often called
1377:
618:
1649:
1632:
1283:
is required for this reaction. Commericially important ethers prepared in this way are derived from
245:. If the ether is part of a more-complex molecule, it is described as an alkoxy substituent, so –OCH
2530:
435:
3003:
1709:
1560:
1296:
594:
210:
28:
2028:
2021:
1667:
2903:
1304:
1300:
913:
906:
144:
3010:
2898:
1295:. Using ethanol and methanol with these two alkenes, four fuel-grade ethers are produced:
354:(α-alkoxy ethers R–CH(–OR)–O–R) are another class of ethers with characteristic properties.
2979:
2424:
1745:
1512:
1185:
1113:
901:
502:
495:
8:
2285:
2052:
Frlan, Rok; Kikelj, Danijel (29 June 2006). "Recent
Progress in Diaryl Ether Synthesis".
1724:
1601:
1403:
1314:
1152:
539:
465:
152:
1411:
1012:
989:
222:
2005:
1171:
hydrogen atoms to form peroxides. Reaction with chlorine produces alpha-chloroethers.
2969:
2939:
2697:
2319:
2032:
1970:
1923:
1890:
1117:
954:
636:
586:
206:
159:
50:
1857:
2674:
2168:
2106:
2061:
2001:
1948:
1915:
1882:
1861:
1852:
1453:
1449:
1407:
1144:
1015:
985:
656:
590:
430:
62:
58:
1626:
A water miscible solvent often found in lithium batteries (b.p. 85 °C):
3044:
2893:
2652:
2647:
2630:
2613:
2414:
2163:
1828:
1795:
1735:
1655:
1620:
1148:
1047:
1031:
1027:
978:
950:
830:
546:
512:
190:
1965:
2964:
2959:
2835:
2830:
2825:
2618:
2585:
2369:
2351:
2341:
1661:
A cyclic ether, one of the most polar simple ethers that is used as a solvent.
1554:
1533:
1189:
944:
764:
478:
385:
182:
174:
140:
3038:
2984:
2932:
2863:
2749:
2739:
2734:
2724:
2719:
2669:
2664:
2580:
2575:
2565:
2419:
2374:
2336:
2324:
2295:
2173:
1952:
1856:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1816:
1760:
1751:
1684:
1583:
1568:
1564:
1415:
1109:
958:
793:
718:
655:). Such compounds are considered ethers as well. Examples of such ethers are
242:
178:
93:
20:
1865:
949:
Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and
2915:
2802:
2797:
2774:
2525:
2364:
2290:
2227:
2222:
2200:
2156:
2141:
2131:
1927:
1820:
1800:
1434:
1381:
996:
536:
445:
120:
116:
2065:
1886:
1440:
In a related reaction, alkyl halides undergo nucleophilic displacement by
2974:
2927:
2888:
2769:
2657:
2642:
2637:
2625:
2190:
2185:
2151:
2146:
2136:
2114:
1790:
1770:
1703:
1597:
1593:
1366:
1292:
861:
851:
609:
Many classes of compounds with C–O–C linkages are not considered ethers:
381:
90:
42:
1943:
Wilhelm
Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Aliphatic" in
2883:
2874:
2754:
2709:
2605:
2570:
2560:
2500:
2436:
2359:
2307:
1824:
1362:
1354:
1340:
1288:
1105:
692:
674:
614:
393:
389:
202:
2850:
2764:
2729:
2714:
2702:
2545:
2520:
2329:
1991:
1919:
1731:
1605:
1441:
1430:
1284:
1280:
1140:
644:
371:
167:
148:
115:). Ethers are common in organic chemistry and even more prevalent in
2075:
16:
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
2858:
2812:
2779:
2475:
2381:
2255:
2210:
2195:
1810:
1643:
A cyclic ether and high-boiling solvent (b.p. 101.1 °C).
1385:
1096:
1086:
1066:
1056:
1042:
1023:
633:
529:
375:
343:
24:
1011:
When stored in the presence of air or oxygen, ethers tend to form
687:(the other name of this compound is disilyl ether, containing the
370:
generally refers to polyether polyols with one or more functional
34:
2820:
2744:
2595:
2590:
2555:
2540:
2535:
2505:
2488:
2312:
2239:
2205:
1881:. PATAI'S Chemistry of Functional Groups. John Wiley & Sons.
1673:
1638:
1589:
1539:
1445:
1426:
1331:
1326:
924:
917:
640:
573:
363:
339:
335:
252:
186:
163:
86:
70:
39:
1433:. This method usually does not work well for aryl halides (e.g.
1243:
2908:
2840:
2684:
2393:
2386:
2280:
2261:
2250:
2234:
2180:
1422:
1392:
1256:
1249:
1076:
1000:
932:
722:
625:
458:
367:
351:
124:
66:
1963:
2789:
2759:
2692:
2550:
2515:
2510:
2483:
2431:
2398:
2126:
1785:
1688:
1410:
to form the alkoxide, followed by addition of an appropriate
1197:
1168:
1022:. The reaction is accelerated by light, metal catalysts, and
928:
756:
610:
347:
258:
74:
1596:. Used as starting fluid for diesel engines. Also used as a
1444:. The R–X cannot be used to react with the alcohol. However
213:
is the most common example of this rare class of compounds.
2217:
1588:
A colourless liquid with sweet odour. A common low boiling
1277:
1034:(1,2-dimethoxyethane) are avoided in industrial processes.
957:
cleaves ethers only slowly. Methyl ethers typically afford
652:
589:
polyethers containing aromatic cycles in their main chain:
577:
78:
38:
The general structure of an ether. R and R' represent most
1353:
By the base intramolecular nucleophilic substitution of a
1167:
This reactivity is similar to the tendency of ethers with
1457:
1372:
648:
366:
containing ether linkages in their main chain. The term
1909:
999:
processes are based on cleavage of ether bonds in the
2018:
508:
Polypropylene oxide (PPOX) or polyoxypropylene (POP)
225:system, ethers are named using the general formula
2020:
413:Name of the polymers with low to medium molar mass
19:For the substance whose common name is ether, see
471:Polyethylene oxide (PEO) or polyoxyethylene (POE)
3036:
384:are cyclic polyethers. Some toxins produced by
196:
1945:Ullmann's Encyclopedia of Industrial Chemistry
545:Acid-catalyzed ring-opening polymerization of
2091:
1563:. A potential renewable alternative fuel for
1317:are typically used to promote this reaction.
1244:Electrophilic addition of alcohols to alkenes
1291:, which protonate to give relatively stable
1248:Alcohols add to electrophilically activated
2051:
185:etc. Illustrative unsymmetrical ethers are
2098:
2084:
1876:
1179:
96:, commonly referred to simply as "ether" (
1939:
1937:
725:. Simple ethers are generally colorless.
585:The phenyl ether polymers are a class of
416:Name of the polymers with high molar mass
209:. Acetylenic ethers are especially rare.
1041:
995:Despite these difficulties the chemical
984:Some ethers undergo rapid cleavage with
900:
130:
33:
1964:J. F. W. McOmie and D. E. West (1973).
511:anionic ring-opening polymerization of
438:(POM) or polyacetal or polyformaldehyde
147:is 111° and C–O distances are 141
3037:
1934:
1592:(b.p. 34.6 °C) and an early
1373:Williamson and Ullmann ether syntheses
731:Selected data about some alkyl ethers
712:
624:There are compounds which, instead of
2105:
2079:
1162:
1006:
396:are extremely large and are known as
338:, because it was originally found in
155:, the hybridization at oxygen is sp.
1559:A colourless gas that is used as an
1421:Suitable leaving groups (X) include
604:
2027:. Oxford University Press. p.
1708:Cyclic polyethers that are used as
1518:
1339:By the oxidation of alkenes with a
13:
1853:Compendium of Chemical Terminology
1815:Chemical paper pulping processes:
1538:A cyclic ether. Also the simplest
1252:. The method is atom-economical:
1207:
721:similar to those of the analogous
261:radical is written in front, so CH
14:
3066:
2019:Clayden; Greeves; Warren (2001).
1750:A linear polyether, e.g. used in
1730:A linear polyether, e.g. used in
1402:, involves treatment of a parent
1139:). Ethers also coordinate to the
205:, are important intermediates in
119:, as they are common linkages in
81:). They have the general formula
1759:
1717:
1696:
1666:
1648:
1631:
1613:
1576:
1547:
1526:
1120:, i.e. borane diethyl etherate (
1683:and a major constituent of the
296:
216:
2045:
2012:
1985:
1957:
1903:
1870:
1841:
1369:, are produced from epoxides.
1037:
1032:ethylene glycol dimethyl ether
916:, they are more reactive than
1:
2006:10.1016/S0020-1693(00)86863-2
1834:
1806:History of general anesthesia
357:
23:. For the digital asset, see
1174:
977:These reactions proceed via
896:
197:Vinyl- and acetylenic ethers
7:
1947:Wiley-VCH, Weinheim, 2002.
1779:
1766:Platelet-activating factor
1320:
1155:ethers. It forms with many
1020:diethyl ether hydroperoxide
938:
923:Specialized ethers such as
905:Structure of the polymeric
475:Ring-opening polymerization
10:
3071:
1980:, vol. 5, p. 412
1600:and in the manufacture of
1400:Williamson ether synthesis
1391:R–ONa + R′–X → R–O–R′ + Na
1324:
942:
748:Solubility in 1 liter of H
619:carboxylic acid anhydrides
442:Step-growth polymerisation
18:
2993:
2952:
2872:
2849:
2811:
2788:
2683:
2604:
2474:
2451:
2407:
2350:
2273:
2248:
2113:
1966:"3,3′-Dihydroxylbiphenyl"
1378:Nucleophilic displacement
730:
632:linkage, contain heavier
362:Polyethers are generally
334:. Methyl phenyl ether is
1953:10.1002/14356007.a10_023
1877:Saul Patai, ed. (1967).
1827:pulping process and the
1710:phase transfer catalysts
1561:aerosol spray propellant
981:intermediates, i.e. Br.
425:Examples of trade names
3004:chemical classification
1866:10.1351/goldbook.E02221
1297:methyl tert-butyl ether
1180:Dehydration of alcohols
211:Di-tert-butoxyacetylene
29:Aether (disambiguation)
1305:ethyl tert-butyl ether
1301:methyl tert-amyl ether
1212:
1101:
909:
907:diethyl ether peroxide
249:would be considered a
61:that contain an ether
46:
27:. For other uses, see
3011:chemical nomenclature
2066:10.1055/s-2006-942440
1887:10.1002/9780470771075
1309:ethyl tert-amyl ether
1211:
1045:
904:
408:Aliphatic polyethers
189:(methoxybenzene) and
131:Structure and bonding
37:
1746:Polypropylene glycol
1604:, along with use in
1513:Ullmann condensation
1315:Solid acid catalysts
621:(RC(=O)–O–C(=O)R′).
503:Polypropylene glycol
332:sweet oil of vitriol
135:Ethers feature bent
3055:Impression material
2467:not C, H or O)
1725:Polyethylene glycol
1602:smokeless gunpowder
1414:bearing a suitable
1398:This reaction, the
1204:at high temperature
1151:is more basic than
713:Physical properties
540:Polytetrahydrofuran
466:Polyethylene glycol
409:
314:), diphenylether (C
257:group. The simpler
153:valence bond theory
69:atom bonded to two
2909:Hypervalent iodine
1571:as high as 56–57.
1412:aliphatic compound
1213:
1163:Alpha-halogenation
1102:
1046:Structure of VCl3(
1007:Peroxide formation
990:aluminium chloride
910:
617:(R–CH(–OH)–O–R′),
407:
273:would be given as
223:IUPAC Nomenclature
47:
3050:Functional groups
3032:
3031:
2970:Sulfenyl chloride
2948:
2947:
2447:
2446:
2266:(only C, H and O)
2107:Functional groups
2060:(14): 2271–2285.
2038:978-0-19-850346-0
2023:Organic chemistry
1994:Inorg. Chim. Acta
1978:Collected Volumes
1971:Organic Syntheses
1914:(16): 2578–2581.
1896:978-0-470-77107-5
1879:The Ether Linkage
1777:
1776:
1676:(methoxybenzene)
1196:2 R–OH → R–O–R +
1145:Grignard reagents
1118:boron trifluoride
955:Hydrogen chloride
894:
893:
657:silyl enol ethers
637:chemical elements
605:Related compounds
599:-phenylene oxide)
583:
582:
576:and PolyTHF from
207:organic synthesis
51:organic chemistry
3062:
2999:
2904:Trifluoromethoxy
2472:
2471:
2468:
2271:
2270:
2267:
2120:
2100:
2093:
2086:
2077:
2076:
2070:
2069:
2049:
2043:
2042:
2026:
2016:
2010:
2009:
1989:
1983:
1981:
1974:
1961:
1955:
1941:
1932:
1931:
1920:10.1039/b405684a
1907:
1901:
1900:
1874:
1868:
1845:
1763:
1721:
1700:
1670:
1652:
1635:
1617:
1580:
1551:
1530:
1523:
1522:
1519:Important ethers
1454:sodium hydroxide
1192:affords ethers:
1138:
1108:. For instance,
1104:Ethers serve as
1094:
1084:
1074:
1064:
1054:
986:boron tribromide
728:
727:
708:
705:(containing the
704:
690:
686:
672:
669:(containing the
668:
631:
613:(R–C(=O)–O–R′),
591:polyphenyl ether
569:
436:Polyoxymethylene
431:Paraformaldehyde
410:
406:
229:, for example CH
138:
114:
84:
3070:
3069:
3065:
3064:
3063:
3061:
3060:
3059:
3035:
3034:
3033:
3028:
2997:
2989:
2944:
2899:Trichloromethyl
2894:Trifluoromethyl
2868:
2845:
2807:
2784:
2679:
2648:Phosphine oxide
2600:
2466:
2464:
2463:
2461:
2459:
2457:
2455:
2453:
2443:
2403:
2346:
2265:
2264:
2259:
2254:
2244:
2118:
2117:
2109:
2104:
2074:
2073:
2050:
2046:
2039:
2017:
2013:
1990:
1986:
1976:
1962:
1958:
1942:
1935:
1908:
1904:
1897:
1875:
1871:
1846:
1842:
1837:
1829:Sulfite process
1796:Ether addiction
1782:
1736:pharmaceuticals
1656:Tetrahydrofuran
1621:Dimethoxyethane
1521:
1506:
1502:
1498:
1494:
1487:
1483:
1479:
1475:
1471:
1461:
1375:
1329:
1323:
1273:
1269:
1264:
1260:
1246:
1235:
1231:
1227:
1223:
1201:
1182:
1177:
1165:
1149:Tetrahydrofuran
1137:
1133:
1129:
1125:
1121:
1100:
1092:
1090:
1082:
1080:
1072:
1070:
1062:
1060:
1052:
1040:
1028:tetrahydrofuran
1009:
972:
968:
951:hydroiodic acid
947:
941:
899:
877:
873:
869:
842:
838:
831:Tetrahydrofuran
813:
809:
805:
801:
776:
772:
755:Dipole moment (
751:
715:
706:
703:
699:
695:
688:
685:
681:
677:
670:
667:
663:
659:
629:
607:
572:Terathane from
567:
563:
559:
555:
551:
547:tetrahydrofuran
524:
520:
513:propylene oxide
490:
486:
453:
386:dinoflagellates
360:
346:ethers include
329:
325:
321:
317:
313:
309:
305:
299:
292:
288:
280:
272:
268:
264:
248:
240:
236:
232:
219:
199:
191:dimethoxyethane
160:electronegative
158:Oxygen is more
136:
133:
113:
109:
105:
101:
97:
82:
57:are a class of
32:
17:
12:
11:
5:
3068:
3058:
3057:
3052:
3047:
3030:
3029:
3027:
3026:
3025:
3024:
3019:
3007:
3000:
2994:
2991:
2990:
2988:
2987:
2985:Sulfinylamines
2982:
2977:
2972:
2967:
2965:Phosphoramides
2962:
2960:Isothiocyanate
2956:
2954:
2950:
2949:
2946:
2945:
2943:
2942:
2937:
2936:
2935:
2925:
2924:
2923:
2913:
2912:
2911:
2906:
2901:
2896:
2891:
2880:
2878:
2870:
2869:
2867:
2866:
2861:
2855:
2853:
2847:
2846:
2844:
2843:
2838:
2836:Selenenic acid
2833:
2831:Seleninic acid
2828:
2826:Selenonic acid
2823:
2817:
2815:
2809:
2808:
2806:
2805:
2800:
2794:
2792:
2786:
2785:
2783:
2782:
2777:
2772:
2767:
2762:
2757:
2752:
2747:
2742:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2706:
2705:
2695:
2689:
2687:
2681:
2680:
2678:
2677:
2672:
2667:
2662:
2661:
2660:
2650:
2645:
2640:
2635:
2634:
2633:
2623:
2622:
2621:
2619:Phosphodiester
2610:
2608:
2602:
2601:
2599:
2598:
2593:
2588:
2583:
2578:
2573:
2568:
2563:
2558:
2553:
2548:
2543:
2538:
2533:
2528:
2523:
2518:
2513:
2508:
2503:
2498:
2497:
2496:
2491:
2480:
2478:
2469:
2465:(one element,
2449:
2448:
2445:
2444:
2442:
2441:
2440:
2439:
2429:
2428:
2427:
2422:
2411:
2409:
2405:
2404:
2402:
2401:
2396:
2391:
2390:
2389:
2379:
2378:
2377:
2372:
2367:
2356:
2354:
2348:
2347:
2345:
2344:
2342:Methylenedioxy
2339:
2334:
2333:
2332:
2327:
2317:
2316:
2315:
2310:
2300:
2299:
2298:
2288:
2283:
2277:
2275:
2268:
2246:
2245:
2243:
2242:
2237:
2232:
2231:
2230:
2225:
2215:
2214:
2213:
2208:
2203:
2198:
2193:
2188:
2178:
2177:
2176:
2171:
2161:
2160:
2159:
2154:
2149:
2144:
2139:
2134:
2123:
2121:
2119:(only C and H)
2111:
2110:
2103:
2102:
2095:
2088:
2080:
2072:
2071:
2044:
2037:
2011:
1984:
1956:
1933:
1902:
1895:
1869:
1839:
1838:
1836:
1833:
1832:
1831:
1813:
1808:
1803:
1798:
1793:
1788:
1781:
1778:
1775:
1774:
1767:
1764:
1756:
1755:
1748:
1743:
1740:
1739:
1728:
1722:
1714:
1713:
1706:
1701:
1693:
1692:
1677:
1671:
1663:
1662:
1659:
1653:
1645:
1644:
1641:
1636:
1628:
1627:
1624:
1618:
1610:
1609:
1586:
1581:
1573:
1572:
1565:diesel engines
1557:
1555:Dimethyl ether
1552:
1544:
1543:
1536:
1534:Ethylene oxide
1531:
1520:
1517:
1509:
1508:
1504:
1500:
1496:
1492:
1489:
1485:
1481:
1477:
1473:
1469:
1459:
1406:with a strong
1396:
1395:
1374:
1371:
1359:
1358:
1351:
1325:Main article:
1322:
1319:
1275:
1274:
1271:
1267:
1262:
1258:
1245:
1242:
1238:
1237:
1233:
1229:
1228:(OH) → R–CH=CH
1225:
1221:
1206:
1205:
1199:
1181:
1178:
1176:
1173:
1164:
1161:
1135:
1131:
1127:
1123:
1091:
1081:
1071:
1061:
1051:
1039:
1036:
1008:
1005:
975:
974:
970:
966:
959:methyl halides
945:Ether cleavage
940:
937:
898:
895:
892:
891:
888:
885:
882:
879:
875:
871:
867:
864:
858:
857:
854:
849:
846:
843:
840:
836:
833:
827:
826:
823:
820:
817:
814:
811:
807:
803:
799:
796:
790:
789:
786:
783:
780:
777:
774:
770:
767:
765:Dimethyl ether
761:
760:
753:
749:
746:
743:
740:
737:
733:
732:
719:boiling points
714:
711:
701:
697:
683:
679:
665:
661:
606:
603:
581:
580:
570:
565:
561:
557:
553:
549:
543:
537:
533:
532:
526:
522:
518:
515:
509:
506:
499:
498:
494:Carbowax from
492:
488:
484:
481:
479:ethylene oxide
472:
469:
462:
461:
455:
451:
448:
439:
433:
427:
426:
423:
422:Repeating unit
420:
417:
414:
359:
356:
327:
323:
319:
315:
311:
307:
303:
298:
295:
290:
286:
278:
270:
266:
262:
246:
238:
234:
230:
227:"alkoxyalkane"
218:
215:
198:
195:
183:dipropyl ether
175:dimethyl ether
141:dimethyl ether
132:
129:
111:
107:
103:
99:
73:groups (e.g.,
15:
9:
6:
4:
3:
2:
3067:
3056:
3053:
3051:
3048:
3046:
3043:
3042:
3040:
3023:
3020:
3018:
3015:
3014:
3013:
3012:
3008:
3006:
3005:
3001:
2996:
2995:
2992:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2957:
2955:
2951:
2941:
2938:
2934:
2931:
2930:
2929:
2926:
2922:
2919:
2918:
2917:
2914:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2886:
2885:
2882:
2881:
2879:
2877:
2876:
2871:
2865:
2864:Telluroketone
2862:
2860:
2857:
2856:
2854:
2852:
2848:
2842:
2839:
2837:
2834:
2832:
2829:
2827:
2824:
2822:
2819:
2818:
2816:
2814:
2810:
2804:
2801:
2799:
2796:
2795:
2793:
2791:
2787:
2781:
2778:
2776:
2773:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2753:
2751:
2750:Sulfonic acid
2748:
2746:
2743:
2741:
2740:Sulfinic acid
2738:
2736:
2735:Thiosulfonate
2733:
2731:
2728:
2726:
2725:Thiosulfinate
2723:
2721:
2720:Sulfenic acid
2718:
2716:
2713:
2711:
2708:
2704:
2701:
2700:
2699:
2696:
2694:
2691:
2690:
2688:
2686:
2682:
2676:
2675:Phosphaallene
2673:
2671:
2670:Phosphaalkyne
2668:
2666:
2665:Phosphaalkene
2663:
2659:
2656:
2655:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2632:
2629:
2628:
2627:
2624:
2620:
2617:
2616:
2615:
2612:
2611:
2609:
2607:
2603:
2597:
2594:
2592:
2589:
2587:
2584:
2582:
2579:
2577:
2574:
2572:
2569:
2567:
2564:
2562:
2559:
2557:
2554:
2552:
2549:
2547:
2544:
2542:
2539:
2537:
2534:
2532:
2529:
2527:
2524:
2522:
2519:
2517:
2514:
2512:
2509:
2507:
2504:
2502:
2499:
2495:
2492:
2490:
2487:
2486:
2485:
2482:
2481:
2479:
2477:
2473:
2470:
2450:
2438:
2435:
2434:
2433:
2430:
2426:
2423:
2421:
2418:
2417:
2416:
2413:
2412:
2410:
2406:
2400:
2397:
2395:
2392:
2388:
2385:
2384:
2383:
2380:
2376:
2373:
2371:
2368:
2366:
2363:
2362:
2361:
2358:
2357:
2355:
2353:
2349:
2343:
2340:
2338:
2337:Ethylenedioxy
2335:
2331:
2328:
2326:
2323:
2322:
2321:
2318:
2314:
2311:
2309:
2306:
2305:
2304:
2301:
2297:
2294:
2293:
2292:
2289:
2287:
2284:
2282:
2279:
2278:
2276:
2272:
2269:
2263:
2257:
2252:
2247:
2241:
2238:
2236:
2233:
2229:
2226:
2224:
2221:
2220:
2219:
2216:
2212:
2209:
2207:
2204:
2202:
2199:
2197:
2194:
2192:
2189:
2187:
2184:
2183:
2182:
2179:
2175:
2172:
2170:
2167:
2166:
2165:
2162:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2129:
2128:
2125:
2124:
2122:
2116:
2112:
2108:
2101:
2096:
2094:
2089:
2087:
2082:
2081:
2078:
2067:
2063:
2059:
2055:
2048:
2040:
2034:
2030:
2025:
2024:
2015:
2007:
2003:
1999:
1995:
1988:
1979:
1973:
1972:
1967:
1960:
1954:
1950:
1946:
1940:
1938:
1929:
1925:
1921:
1917:
1913:
1912:Dalton Trans.
1906:
1898:
1892:
1888:
1884:
1880:
1873:
1867:
1863:
1859:
1855:
1854:
1849:
1844:
1840:
1830:
1826:
1822:
1818:
1817:Kraft process
1814:
1812:
1809:
1807:
1804:
1802:
1799:
1797:
1794:
1792:
1789:
1787:
1784:
1783:
1772:
1768:
1765:
1762:
1758:
1757:
1753:
1752:polyurethanes
1749:
1747:
1744:
1742:
1741:
1737:
1733:
1729:
1726:
1723:
1720:
1716:
1715:
1711:
1707:
1705:
1702:
1699:
1695:
1694:
1690:
1686:
1685:essential oil
1682:
1678:
1675:
1672:
1669:
1665:
1664:
1660:
1657:
1654:
1651:
1647:
1646:
1642:
1640:
1637:
1634:
1630:
1629:
1625:
1622:
1619:
1616:
1612:
1611:
1607:
1603:
1599:
1595:
1591:
1587:
1585:
1584:Diethyl ether
1582:
1579:
1575:
1574:
1570:
1569:cetane rating
1566:
1562:
1558:
1556:
1553:
1550:
1546:
1545:
1541:
1537:
1535:
1532:
1529:
1525:
1524:
1516:
1514:
1490:
1467:
1466:
1465:
1463:
1455:
1451:
1447:
1443:
1438:
1436:
1432:
1428:
1424:
1419:
1417:
1416:leaving group
1413:
1409:
1405:
1401:
1394:
1390:
1389:
1388:
1387:
1383:
1382:alkyl halides
1379:
1370:
1368:
1364:
1361:Many ethers,
1356:
1352:
1349:
1347:
1342:
1338:
1337:
1336:
1333:
1328:
1318:
1316:
1312:
1310:
1306:
1302:
1298:
1294:
1290:
1286:
1282:
1279:
1265:
1255:
1254:
1253:
1251:
1241:
1219:
1218:
1217:
1210:
1203:
1195:
1194:
1193:
1191:
1187:
1172:
1170:
1160:
1158:
1154:
1150:
1146:
1142:
1119:
1115:
1111:
1110:diethyl ether
1107:
1098:
1088:
1078:
1068:
1058:
1049:
1044:
1035:
1033:
1029:
1025:
1021:
1017:
1014:
1004:
1002:
998:
997:paper pulping
993:
991:
987:
982:
980:
964:
963:
962:
960:
956:
952:
946:
936:
934:
930:
926:
921:
919:
915:
908:
903:
889:
886:
883:
880:
865:
863:
860:
859:
855:
853:
850:
847:
844:
834:
832:
829:
828:
824:
821:
818:
815:
797:
795:
794:Diethyl ether
792:
791:
787:
784:
781:
778:
768:
766:
763:
762:
758:
754:
747:
744:
741:
738:
735:
734:
729:
726:
724:
720:
710:
694:
691:linkage) and
676:
658:
654:
650:
646:
642:
638:
635:
627:
622:
620:
616:
612:
602:
600:
598:
592:
588:
579:
575:
571:
550:
548:
544:
541:
538:
535:
534:
531:
527:
516:
514:
510:
507:
504:
501:
500:
497:
493:
482:
480:
476:
473:
470:
467:
464:
463:
460:
456:
449:
447:
443:
440:
437:
434:
432:
429:
428:
424:
421:
418:
415:
412:
411:
405:
403:
399:
395:
391:
387:
383:
379:
377:
373:
369:
365:
355:
353:
349:
345:
341:
337:
333:
294:
284:
276:
260:
256:
254:
244:
243:methoxyethane
228:
224:
214:
212:
208:
204:
194:
192:
188:
184:
180:
179:diethyl ether
176:
171:
169:
165:
161:
156:
154:
150:
146:
142:
139:linkages. In
128:
126:
122:
121:carbohydrates
118:
95:
94:diethyl ether
92:
88:
80:
76:
72:
68:
64:
60:
56:
52:
44:
41:
36:
30:
26:
22:
21:Diethyl ether
3009:
3002:
2916:Vinyl halide
2873:
2803:Borinic acid
2798:Boronic acid
2775:Thioxanthate
2302:
2115:Hydrocarbons
2057:
2053:
2047:
2022:
2014:
1997:
1993:
1987:
1977:
1969:
1959:
1944:
1911:
1905:
1878:
1872:
1851:
1843:
1821:Soda pulping
1801:Ether (song)
1704:Crown ethers
1680:
1510:
1499:–O + R–X → C
1439:
1435:bromobenzene
1420:
1397:
1376:
1367:crown ethers
1360:
1345:
1330:
1313:
1307:(ETBE), and
1293:carbocations
1276:
1270:CH–C(–O–R)–R
1247:
1239:
1214:
1183:
1166:
1103:
1010:
994:
983:
976:
948:
922:
911:
717:Ethers have
716:
623:
608:
596:
584:
457:Delrin from
446:formaldehyde
404:polyethers.
401:
397:
382:Crown ethers
380:
361:
331:
300:
297:Trivial name
282:
274:
250:
226:
220:
217:Nomenclature
200:
172:
170:), however.
157:
134:
117:biochemistry
54:
48:
43:substituents
2980:Thiocyanate
2975:Sulfonamide
2940:Perchlorate
2928:Acyl halide
2889:Fluoroethyl
2770:Thionoester
2658:Phosphonium
2643:Phosphinate
2638:Phosphonous
2626:Phosphonate
2325:Hydroperoxy
2147:Cyclopropyl
1791:Ether lipid
1771:ether lipid
1598:refrigerant
1594:anaesthetic
1476:OH + OH → C
1464:mechanism.
1363:ethoxylates
1186:dehydration
1106:Lewis bases
1038:Lewis bases
693:stannoxanes
615:hemiacetals
528:Arcol from
419:Preparation
203:enol ethers
91:anaesthetic
3039:Categories
2884:Haloalkane
2755:Thioketone
2710:Persulfide
2606:Phosphorus
2571:Isocyanate
2561:Isonitrile
2462:or oxygen
2460:hydrogen,
2456:not being
2437:Orthoester
2330:Dioxiranes
2308:Enol ether
2196:1-Propenyl
1835:References
1825:Organosolv
1681:aryl ether
1442:phenoxides
1431:sulfonates
1355:halohydrin
1341:peroxyacid
1289:isoamylene
1266:+ R–OH → R
1143:center in
1126:·O(CH
1018:, such as
969:+ HBr → CH
943:See also:
914:reactivity
745:b.p. (°C)
742:m.p. (°C)
739:Structure
709:linkage).
675:disiloxane
673:linkage),
664:Si−O−CR=CR
593:(PPE) and
394:ciguatoxin
390:brevetoxin
374:such as a
372:end-groups
358:Polyethers
145:bond angle
3017:inorganic
2851:Tellurium
2765:Thioester
2730:Sulfoxide
2715:Disulfide
2703:Sulfonium
2653:Phosphine
2631:Phosphite
2614:Phosphate
2546:Carbamate
2521:Hydrazone
2454:element,
2452:Only one
2425:Anhydride
2164:Methylene
2054:Synthesis
1732:cosmetics
1606:perfumery
1386:alkoxides
1285:isobutene
1281:catalysis
1175:Synthesis
1157:complexes
1030:(THF) or
1024:aldehydes
1016:peroxides
1013:explosive
897:Reactions
822:69 g
785:70 g
168:aldehydes
59:compounds
2998:See also
2933:Chloride
2859:Tellurol
2813:Selenium
2780:Xanthate
2494:Ammonium
2476:Nitrogen
2458:carbon,
2415:Carboxyl
2382:Aldehyde
2370:Acryloyl
2352:carbonyl
2256:hydrogen
2211:Cumulene
1928:15303175
1811:Inhalant
1780:See also
1343:such as
1332:Epoxides
1321:Epoxides
1311:(TAEE).
1303:(TAME),
1299:(MTBE),
1190:alcohols
1112:forms a
1097:Nitrogen
1087:Hydrogen
1067:Chlorine
1057:Vanadium
973:Br + ROH
939:Cleavage
925:epoxides
887:Miscible
852:Miscible
700:Sn−O−SnR
682:Si−O−SiH
634:group 14
587:aromatic
530:Covestro
388:such as
376:hydroxyl
364:polymers
344:aromatic
25:Ethereum
3022:organic
2821:Selenol
2745:Sulfone
2698:Sulfide
2596:NONOate
2591:Nitroso
2581:Nitrite
2576:Nitrate
2566:Cyanate
2556:Nitrile
2541:Amidine
2536:Imidate
2506:Nitrene
2501:Hydrazo
2489:Enamine
2420:Acetoxy
2408:carboxy
2375:Benzoyl
2313:Epoxide
2296:Methoxy
2286:Alcohol
2240:Carbene
2174:Methine
1674:Anisole
1639:Dioxane
1590:solvent
1567:with a
1540:epoxide
1446:phenols
1427:bromide
1404:alcohol
1327:epoxide
1250:alkenes
1153:acyclic
1114:complex
933:acetals
918:alkanes
862:Dioxane
723:alkanes
707:Sn−O−Sn
689:Si−O−Si
639:(e.g.,
628:in the
601:(PPO).
574:Invista
352:Acetals
340:aniseed
336:anisole
275:methoxy
253:methoxy
221:In the
187:anisole
164:ketones
87:solvent
71:organyl
40:organyl
3045:Ethers
2921:Iodide
2841:Selone
2685:Sulfur
2394:Ketone
2387:Ketene
2365:Acetyl
2320:Peroxy
2291:Alkoxy
2281:Acetal
2262:oxygen
2251:carbon
2235:Alkyne
2228:Benzyl
2223:Phenyl
2206:Allene
2201:Crotyl
2181:Alkene
2169:Bridge
2157:Pentyl
2142:Propyl
2132:Methyl
2035:
2000:: 81.
1926:
1893:
1858:ethers
1727:(PEG)
1691:seed.
1658:(THF)
1623:(DME)
1484:–O + H
1423:iodide
1095:
1093:
1085:
1083:
1077:Carbon
1075:
1073:
1065:
1063:
1055:
1053:
1001:lignin
988:(even
931:, and
929:ketals
845:−108.4
816:−116.3
779:−138.5
736:Ether
671:Si−O−C
611:Esters
542:(PTHF)
459:DuPont
402:ladder
398:cyclic
368:polyol
348:furans
342:. The
283:ethane
143:, the
125:lignin
83:R−O−R′
67:oxygen
55:ethers
2953:Other
2790:Boron
2760:Thial
2693:Thiol
2586:Nitro
2551:Imide
2531:Amide
2516:Oxime
2511:Imine
2484:Amine
2432:Ester
2399:Ynone
2303:Ether
2274:R-O-R
2249:Only
2191:Allyl
2186:Vinyl
2152:Butyl
2137:Ethyl
2127:Alkyl
1848:IUPAC
1819:(and
1786:Ester
1689:anise
1452:like
1429:, or
1348:-CPBA
1169:alpha
1116:with
979:onium
890:0.45
884:101.3
856:1.74
825:1.14
806:–O–CH
788:1.30
782:−23.0
773:–O–CH
630:C−O−C
595:poly(
521:CH(CH
505:(PPG)
468:(PEG)
265:–O–CH
259:alkyl
237:–O–CH
137:C−O−C
106:−O−CH
75:alkyl
63:group
2875:Halo
2360:Acyl
2260:and
2218:Aryl
2058:2006
2033:ISBN
1924:PMID
1891:ISBN
1734:and
1511:The
1450:base
1408:base
1365:and
1278:Acid
1261:C=CR
1220:R–CH
1184:The
1069:, Cl
965:ROCH
881:11.8
848:66.0
835:O(CH
819:34.4
578:BASF
392:and
123:and
89:and
79:aryl
65:—an
2526:Azo
2062:doi
2029:129
2002:doi
1998:113
1949:doi
1916:doi
1883:doi
1862:doi
1860:".
1823:),
1769:An
1687:of
1679:An
1384:by
1380:of
1287:or
1232:+ H
1224:–CH
1188:of
1099:, N
1089:, H
1079:, C
1059:, V
1050:)3.
1048:thf
920:.
866:O(C
552:−CH
525:)O–
517:–CH
496:Dow
483:–CH
477:of
450:–CH
444:of
400:or
302:(CH
293:).
285:(CH
277:(CH
241:is
233:–CH
166:or
110:−CH
102:−CH
77:or
49:In
3041::
2258:,
2253:,
2056:.
2031:.
1996:.
1975:;
1968:.
1936:^
1922:.
1889:.
1850:,
1754:.
1738:.
1712:.
1608:.
1542:.
1507:OR
1425:,
1159:.
1147:.
1141:Mg
1130:CH
1122:BF
1003:.
961::
953:.
927:,
810:CH
802:CH
798:CH
769:CH
759:)
752:O
653:Pb
651:,
649:Sn
647:,
645:Ge
643:,
641:Si
568:O−
564:CH
560:CH
556:CH
491:O–
487:CH
454:O–
350:.
322:OC
306:OC
289:CH
281:O)
269:CH
255:-"
193:.
181:,
177:,
149:pm
127:.
98:CH
53:,
2099:e
2092:t
2085:v
2068:.
2064::
2041:.
2008:.
2004::
1982:.
1951::
1930:.
1918::
1899:.
1885::
1864::
1505:5
1503:H
1501:6
1497:5
1495:H
1493:6
1491:C
1488:O
1486:2
1482:5
1480:H
1478:6
1474:5
1472:H
1470:6
1468:C
1462:2
1460:N
1458:S
1393:X
1357:.
1350:.
1346:m
1272:2
1268:2
1263:2
1259:2
1257:R
1236:O
1234:2
1230:2
1226:2
1222:2
1202:O
1200:2
1198:H
1136:2
1134:)
1132:3
1128:2
1124:3
971:3
967:3
878:O
876:2
874:)
872:4
870:H
868:2
841:4
839:)
837:2
812:3
808:2
804:2
800:3
775:3
771:3
757:D
750:2
702:3
698:3
696:R
684:3
680:3
678:H
666:2
662:3
660:R
626:C
597:p
566:2
562:2
558:2
554:2
523:3
519:2
489:2
485:2
452:2
328:5
326:H
324:6
320:5
318:H
316:6
312:5
310:H
308:2
304:3
291:3
287:2
279:3
271:3
267:2
263:3
251:"
247:3
239:3
235:2
231:3
112:3
108:2
104:2
100:3
45:.
31:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
.svg)