1220:
1037:. 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
1730:
1626:
1589:
1560:
1539:
1772:
1661:
46:
1709:
1644:
1054:
1679:
96:, 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
1226:
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
1448:, 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.
312:
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
1345:
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:
1227:
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:
173:
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
341:). 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
1467:
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
1858:
2003:
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".
913:
2108:
1003:
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.
1921:
Vojinović, Krunoslav; Losehand, Udo; Mitzel, Norbert W. (2004). "Dichlorosilane–Dimethyl Ether
Aggregation: A New Motif in Halosilane Adduct Formation".
3027:
1729:
1625:
1538:
3032:
1559:
923:
The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical
1588:
1526:
is similar to the
Williamson method except that the substrate is an aryl halide. Such reactions generally require a catalyst, such as copper.
1219:
2047:
1905:
162:. 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
1251:
The dehydration route often requires conditions incompatible with delicate molecules. Several milder methods exist to produce ethers.
1459:
can be used to replace the alcohol while maintaining the alkyl halide. Since phenols are acidic, they readily react with a strong
389:
group. The term "oxide" or other terms are used for high molar mass polymer when end-groups no longer affect polymer properties.
2101:
1167:
1429:(R–X). Although popular in textbooks, the method is usually impractical on scale because it cogenerates significant waste.
2931:
1816:
1355:
3065:
1030:
485:
946:
are unrepresentative classes of ethers and are discussed in separate articles. Important reactions are listed below.
3060:
2504:
2094:
1410:
452:
1388:
629:
1708:
1660:
2541:
1784:, an example with an ether on sn-1, an ester on sn-2, and an inorganic ether on sn-3 of the glyceryl scaffold.
912:
446:
1643:
3014:
1720:
1307:
605:
221:
39:
1319:
2914:
1315:
1311:
924:
917:
1678:
3021:
2909:
184:
Ethers can be symmetrical of the type ROR or unsymmetrical of the type ROR'. Examples of the former are
212:
Vinyl- and acetylenic ethers are far less common than alkyl or aryl ethers. Vinylethers, often called
2990:
2435:
1756:
1523:
1196:
1124:
513:
506:
1294:
is required for this reaction. Commericially important ethers prepared in this way are derived from
256:. If the ether is part of a more-complex molecule, it is described as an alkoxy substituent, so –OCH
2296:
1735:
1612:
1414:
1325:
1163:
550:
476:
163:
1422:
1023:
1000:
233:
155:
2039:
2032:
2980:
2950:
2708:
2330:
2043:
1981:
1934:
1901:
1128:
965:
647:
597:
217:
170:
61:
2685:
2179:
2117:
2072:
2012:
1959:
1926:
1893:
1872:
1771:
1464:
1460:
1418:
1306:. Using ethanol and methanol with these two alkenes, four fuel-grade ethers are produced:
1155:
1026:
996:
667:
601:
441:
365:(α-alkoxy ethers R–CH(–OR)–O–R) are another class of ethers with characteristic properties.
73:
69:
3055:
2904:
2663:
2658:
2641:
2624:
2425:
2174:
1839:
1806:
1746:
1666:
1631:
1159:
1058:
1042:
1038:
989:
961:
841:
557:
523:
201:
2063:
Frlan, Rok; Kikelj, Danijel (29 June 2006). "Recent
Progress in Diaryl Ether Synthesis".
2975:
2970:
2846:
2841:
2836:
2629:
2596:
2380:
2362:
2352:
1565:
1544:
1200:
955:
775:
489:
396:
193:
185:
151:
2016:
1182:
hydrogen atoms to form peroxides. Reaction with chlorine produces alpha-chloroethers.
3049:
2995:
2943:
2874:
2760:
2750:
2745:
2735:
2730:
2680:
2675:
2591:
2586:
2576:
2430:
2385:
2347:
2335:
2306:
2184:
1827:
1762:
1695:
1594:
1579:
1575:
1571:
1426:
1120:
969:
804:
729:
253:
189:
104:
31:
1868:
2926:
2813:
2808:
2785:
2536:
2375:
2301:
2238:
2233:
2211:
2167:
2152:
2142:
1831:
1811:
1445:
1392:
1007:
456:
131:
127:
1637:
A water miscible solvent often found in lithium batteries (b.p. 85 °C):
2985:
2938:
2899:
2780:
2668:
2653:
2648:
2636:
2201:
2196:
2162:
2157:
2147:
2125:
1976:
1863:
1801:
1781:
1714:
1608:
1604:
1377:
1303:
872:
862:
392:
101:
53:
1672:
A cyclic ether, one of the most polar simple ethers that is used as a solvent.
1053:
2894:
2885:
2765:
2720:
2616:
2581:
2571:
2511:
2447:
2370:
2318:
1835:
1373:
1365:
1351:
1299:
1116:
703:
685:
625:
404:
400:
213:
45:
1963:
1867:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
666:). Such compounds are considered ethers as well. Examples of such ethers are
2861:
2775:
2740:
2725:
2713:
2556:
2531:
2340:
1876:
1742:
1616:
1452:
1441:
1295:
1291:
1151:
960:
Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and
655:
382:
178:
159:
1938:
547:
2076:
1897:
1451:
In a related reaction, alkyl halides undergo nucleophilic displacement by
17:
2869:
2823:
2790:
2486:
2392:
2266:
2221:
2206:
1821:
1396:
1107:
1097:
1077:
1067:
1034:
644:
620:
Many classes of compounds with C–O–C linkages are not considered ethers:
540:
386:
354:
35:
1954:
Wilhelm
Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Aliphatic" in
2831:
2755:
2606:
2601:
2566:
2551:
2546:
2516:
2499:
2323:
2250:
2216:
1684:
1649:
1600:
1550:
1456:
1437:
1342:
1337:
935:
928:
651:
584:
374:
350:
346:
263:
197:
174:
97:
81:
50:
2919:
2851:
2695:
2404:
2397:
2291:
2272:
2261:
2245:
2191:
1930:
1433:
1403:
1267:
1260:
1087:
1011:
943:
733:
636:
469:
378:
362:
135:
126:). Ethers are common in organic chemistry and even more prevalent in
77:
2086:
27:
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
1654:
A cyclic ether and high-boiling solvent (b.p. 101.1 °C).
2800:
2770:
2703:
2561:
2526:
2521:
2494:
2442:
2409:
2137:
1796:
1699:
1208:
1179:
1052:
1022:
When stored in the presence of air or oxygen, ethers tend to form
939:
767:
698:(the other name of this compound is disilyl ether, containing the
621:
381:
generally refers to polyether polyols with one or more functional
358:
269:
85:
1892:. PATAI'S Chemistry of Functional Groups. John Wiley & Sons.
2228:
1444:. This method usually does not work well for aryl halides (e.g.
1288:
663:
588:
89:
2090:
1468:
659:
1421:
to form the alkoxide, followed by addition of an appropriate
1033:. The reaction is accelerated by light, metal catalysts, and
1607:. Used as starting fluid for diesel engines. Also used as a
1455:. The R–X cannot be used to react with the alcohol. However
1218:
224:
is the most common example of this rare class of compounds.
1599:
A colourless liquid with sweet odour. A common low boiling
1045:(1,2-dimethoxyethane) are avoided in industrial processes.
968:
cleaves ethers only slowly. Methyl ethers typically afford
600:
polyethers containing aromatic cycles in their main chain:
49:
The general structure of an ether. R and R' represent most
1364:
By the base intramolecular nucleophilic substitution of a
1178:
This reactivity is similar to the tendency of ethers with
377:
containing ether linkages in their main chain. The term
1010:
processes are based on cleavage of ether bonds in the
519:
Polypropylene oxide (PPOX) or polyoxypropylene (POP)
2963:
2883:
2860:
2822:
2799:
2694:
2615:
2485:
2462:
2418:
2361:
2284:
2259:
2124:
236:system, ethers are named using the general formula
2031:
424:Name of the polymers with low to medium molar mass
30:For the substance whose common name is ether, see
482:Polyethylene oxide (PEO) or polyoxyethylene (POE)
395:are cyclic polyethers. Some toxins produced by
1956:Ullmann's Encyclopedia of Industrial Chemistry
556:Acid-catalyzed ring-opening polymerization of
2102:
1574:. A potential renewable alternative fuel for
1328:are typically used to promote this reaction.
1255:Electrophilic addition of alcohols to alkenes
8:
1302:, which protonate to give relatively stable
1259:Alcohols add to electrophilically activated
196:etc. Illustrative unsymmetrical ethers are
2482:
2281:
2109:
2095:
2087:
107:, commonly referred to simply as "ether" (
1950:
1948:
736:. Simple ethers are generally colorless.
596:The phenyl ether polymers are a class of
427:Name of the polymers with high molar mass
220:. Acetylenic ethers are especially rare.
1533:
1146:
1142:
1138:
1134:
1006:Despite these difficulties the chemical
995:Some ethers undergo rapid cleavage with
911:
738:
712:
708:
694:
690:
676:
672:
576:
572:
568:
564:
417:
122:
118:
114:
110:
44:
1975:J. F. W. McOmie and D. E. West (1973).
1851:
522:anionic ring-opening polymerization of
449:(POM) or polyacetal or polyformaldehyde
158:is 111° and C–O distances are 141
1603:(b.p. 34.6 °C) and an early
1384:Williamson and Ullmann ether syntheses
742:Selected data about some alkyl ethers
635:There are compounds which, instead of
407:are extremely large and are known as
349:, because it was originally found in
166:, the hybridization at oxygen is sp.
7:
1570:A colourless gas that is used as an
1432:Suitable leaving groups (X) include
2038:. Oxford University Press. p.
1719:Cyclic polyethers that are used as
1350:By the oxidation of alkenes with a
1864:Compendium of Chemical Terminology
1826:Chemical paper pulping processes:
1549:A cyclic ether. Also the simplest
1263:. The method is atom-economical:
732:similar to those of the analogous
272:radical is written in front, so CH
25:
2030:Clayden; Greeves; Warren (2001).
1761:A linear polyether, e.g. used in
1741:A linear polyether, e.g. used in
1413:, involves treatment of a parent
1150:). Ethers also coordinate to the
216:, are important intermediates in
130:, as they are common linkages in
92:). They have the general formula
1770:
1728:
1707:
1677:
1659:
1642:
1624:
1587:
1558:
1537:
1131:, i.e. borane diethyl etherate (
1694:and a major constituent of the
1380:, are produced from epoxides.
1043:ethylene glycol dimethyl ether
927:, they are more reactive than
1:
2017:10.1016/S0020-1693(00)86863-2
1817:History of general anesthesia
34:. For the digital asset, see
988:These reactions proceed via
208:Vinyl- and acetylenic ethers
1958:Wiley-VCH, Weinheim, 2002.
1777:Platelet-activating factor
1166:ethers. It forms with many
1031:diethyl ether hydroperoxide
934:Specialized ethers such as
916:Structure of the polymeric
486:Ring-opening polymerization
3082:
1991:, vol. 5, p. 412
1611:and in the manufacture of
1411:Williamson ether synthesis
1402:R–ONa + R′–X → R–O–R′ + Na
1335:
953:
759:Solubility in 1 liter of H
630:carboxylic acid anhydrides
453:Step-growth polymerisation
29:
3004:
1977:"3,3′-Dihydroxylbiphenyl"
1389:Nucleophilic displacement
741:
643:linkage, contain heavier
373:Polyethers are generally
345:. Methyl phenyl ether is
1964:10.1002/14356007.a10_023
1888:Saul Patai, ed. (1967).
1838:pulping process and the
1721:phase transfer catalysts
1572:aerosol spray propellant
992:intermediates, i.e. Br.
436:Examples of trade names
3015:chemical classification
1877:10.1351/goldbook.E02221
1308:methyl tert-butyl ether
1191:Dehydration of alcohols
222:Di-tert-butoxyacetylene
40:Aether (disambiguation)
1316:ethyl tert-butyl ether
1312:methyl tert-amyl ether
1223:
1112:
920:
918:diethyl ether peroxide
260:would be considered a
72:that contain an ether
57:
38:. For other uses, see
3022:chemical nomenclature
2077:10.1055/s-2006-942440
1898:10.1002/9780470771075
1320:ethyl tert-amyl ether
1222:
1056:
915:
419:Aliphatic polyethers
200:(methoxybenzene) and
142:Structure and bonding
48:
1757:Polypropylene glycol
1615:, along with use in
1524:Ullmann condensation
1326:Solid acid catalysts
632:(RC(=O)–O–C(=O)R′).
514:Polypropylene glycol
343:sweet oil of vitriol
146:Ethers feature bent
3066:Impression material
2478:not C, H or O)
1736:Polyethylene glycol
1613:smokeless gunpowder
1425:bearing a suitable
1409:This reaction, the
1215:at high temperature
1162:is more basic than
724:Physical properties
551:Polytetrahydrofuran
477:Polyethylene glycol
420:
325:), diphenylether (C
268:group. The simpler
164:valence bond theory
80:atom bonded to two
2920:Hypervalent iodine
1582:as high as 56–57.
1423:aliphatic compound
1224:
1174:Alpha-halogenation
1113:
1057:Structure of VCl3(
1018:Peroxide formation
1001:aluminium chloride
921:
628:(R–CH(–OH)–O–R′),
418:
284:would be given as
234:IUPAC Nomenclature
58:
3061:Functional groups
3043:
3042:
2981:Sulfenyl chloride
2959:
2958:
2458:
2457:
2277:(only C, H and O)
2118:Functional groups
2071:(14): 2271–2285.
2049:978-0-19-850346-0
2034:Organic chemistry
2005:Inorg. Chim. Acta
1989:Collected Volumes
1982:Organic Syntheses
1925:(16): 2578–2581.
1907:978-0-470-77107-5
1890:The Ether Linkage
1788:
1787:
1687:(methoxybenzene)
1207:2 R–OH → R–O–R +
1156:Grignard reagents
1129:boron trifluoride
966:Hydrogen chloride
905:
904:
668:silyl enol ethers
648:chemical elements
616:Related compounds
610:-phenylene oxide)
594:
593:
587:and PolyTHF from
218:organic synthesis
62:organic chemistry
16:(Redirected from
3073:
3010:
2915:Trifluoromethoxy
2483:
2479:
2282:
2278:
2131:
2111:
2104:
2097:
2088:
2081:
2080:
2060:
2054:
2053:
2037:
2027:
2021:
2020:
2000:
1994:
1992:
1985:
1972:
1966:
1952:
1943:
1942:
1931:10.1039/b405684a
1918:
1912:
1911:
1885:
1879:
1856:
1774:
1732:
1711:
1681:
1663:
1646:
1628:
1591:
1562:
1541:
1534:
1530:Important ethers
1465:sodium hydroxide
1203:affords ethers:
1149:
1119:. For instance,
1115:Ethers serve as
1105:
1095:
1085:
1075:
1065:
997:boron tribromide
739:
719:
716:(containing the
715:
701:
697:
683:
680:(containing the
679:
642:
624:(R–C(=O)–O–R′),
602:polyphenyl ether
580:
447:Polyoxymethylene
442:Paraformaldehyde
421:
240:, for example CH
149:
125:
95:
21:
3081:
3080:
3076:
3075:
3074:
3072:
3071:
3070:
3046:
3045:
3044:
3039:
3008:
3000:
2955:
2910:Trichloromethyl
2905:Trifluoromethyl
2879:
2856:
2818:
2795:
2690:
2659:Phosphine oxide
2611:
2477:
2475:
2474:
2472:
2470:
2468:
2466:
2464:
2454:
2414:
2357:
2276:
2275:
2270:
2265:
2255:
2129:
2128:
2120:
2115:
2085:
2084:
2062:
2061:
2057:
2050:
2029:
2028:
2024:
2002:
2001:
1997:
1987:
1974:
1973:
1969:
1953:
1946:
1920:
1919:
1915:
1908:
1887:
1886:
1882:
1857:
1853:
1848:
1840:Sulfite process
1807:Ether addiction
1793:
1747:pharmaceuticals
1667:Tetrahydrofuran
1632:Dimethoxyethane
1532:
1517:
1513:
1509:
1505:
1498:
1494:
1490:
1486:
1482:
1472:
1386:
1340:
1334:
1284:
1280:
1275:
1271:
1257:
1246:
1242:
1238:
1234:
1212:
1193:
1188:
1176:
1160:Tetrahydrofuran
1148:
1144:
1140:
1136:
1132:
1111:
1103:
1101:
1093:
1091:
1083:
1081:
1073:
1071:
1063:
1051:
1039:tetrahydrofuran
1020:
983:
979:
962:hydroiodic acid
958:
952:
910:
888:
884:
880:
853:
849:
842:Tetrahydrofuran
824:
820:
816:
812:
787:
783:
766:Dipole moment (
762:
726:
717:
714:
710:
706:
699:
696:
692:
688:
681:
678:
674:
670:
640:
618:
583:Terathane from
578:
574:
570:
566:
562:
558:tetrahydrofuran
535:
531:
524:propylene oxide
501:
497:
464:
397:dinoflagellates
371:
357:ethers include
340:
336:
332:
328:
324:
320:
316:
310:
303:
299:
291:
283:
279:
275:
259:
251:
247:
243:
230:
210:
202:dimethoxyethane
171:electronegative
169:Oxygen is more
147:
144:
124:
120:
116:
112:
108:
93:
68:are a class of
43:
28:
23:
22:
15:
12:
11:
5:
3079:
3077:
3069:
3068:
3063:
3058:
3048:
3047:
3041:
3040:
3038:
3037:
3036:
3035:
3030:
3018:
3011:
3005:
3002:
3001:
2999:
2998:
2996:Sulfinylamines
2993:
2988:
2983:
2978:
2976:Phosphoramides
2973:
2971:Isothiocyanate
2967:
2965:
2961:
2960:
2957:
2956:
2954:
2953:
2948:
2947:
2946:
2936:
2935:
2934:
2924:
2923:
2922:
2917:
2912:
2907:
2902:
2891:
2889:
2881:
2880:
2878:
2877:
2872:
2866:
2864:
2858:
2857:
2855:
2854:
2849:
2847:Selenenic acid
2844:
2842:Seleninic acid
2839:
2837:Selenonic acid
2834:
2828:
2826:
2820:
2819:
2817:
2816:
2811:
2805:
2803:
2797:
2796:
2794:
2793:
2788:
2783:
2778:
2773:
2768:
2763:
2758:
2753:
2748:
2743:
2738:
2733:
2728:
2723:
2718:
2717:
2716:
2706:
2700:
2698:
2692:
2691:
2689:
2688:
2683:
2678:
2673:
2672:
2671:
2661:
2656:
2651:
2646:
2645:
2644:
2634:
2633:
2632:
2630:Phosphodiester
2621:
2619:
2613:
2612:
2610:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2508:
2507:
2502:
2491:
2489:
2480:
2476:(one element,
2460:
2459:
2456:
2455:
2453:
2452:
2451:
2450:
2440:
2439:
2438:
2433:
2422:
2420:
2416:
2415:
2413:
2412:
2407:
2402:
2401:
2400:
2390:
2389:
2388:
2383:
2378:
2367:
2365:
2359:
2358:
2356:
2355:
2353:Methylenedioxy
2350:
2345:
2344:
2343:
2338:
2328:
2327:
2326:
2321:
2311:
2310:
2309:
2299:
2294:
2288:
2286:
2279:
2257:
2256:
2254:
2253:
2248:
2243:
2242:
2241:
2236:
2226:
2225:
2224:
2219:
2214:
2209:
2204:
2199:
2189:
2188:
2187:
2182:
2172:
2171:
2170:
2165:
2160:
2155:
2150:
2145:
2134:
2132:
2130:(only C and H)
2122:
2121:
2116:
2114:
2113:
2106:
2099:
2091:
2083:
2082:
2055:
2048:
2022:
1995:
1967:
1944:
1913:
1906:
1880:
1850:
1849:
1847:
1844:
1843:
1842:
1824:
1819:
1814:
1809:
1804:
1799:
1792:
1789:
1786:
1785:
1778:
1775:
1767:
1766:
1759:
1754:
1751:
1750:
1739:
1733:
1725:
1724:
1717:
1712:
1704:
1703:
1688:
1682:
1674:
1673:
1670:
1664:
1656:
1655:
1652:
1647:
1639:
1638:
1635:
1629:
1621:
1620:
1597:
1592:
1584:
1583:
1576:diesel engines
1568:
1566:Dimethyl ether
1563:
1555:
1554:
1547:
1545:Ethylene oxide
1542:
1531:
1528:
1520:
1519:
1515:
1511:
1507:
1503:
1500:
1496:
1492:
1488:
1484:
1480:
1470:
1417:with a strong
1407:
1406:
1385:
1382:
1370:
1369:
1362:
1336:Main article:
1333:
1330:
1286:
1285:
1282:
1278:
1273:
1269:
1256:
1253:
1249:
1248:
1244:
1240:
1239:(OH) → R–CH=CH
1236:
1232:
1217:
1216:
1210:
1192:
1189:
1187:
1184:
1175:
1172:
1102:
1092:
1082:
1072:
1062:
1050:
1047:
1019:
1016:
986:
985:
981:
977:
970:methyl halides
956:Ether cleavage
951:
948:
909:
906:
903:
902:
899:
896:
893:
890:
886:
882:
878:
875:
869:
868:
865:
860:
857:
854:
851:
847:
844:
838:
837:
834:
831:
828:
825:
822:
818:
814:
810:
807:
801:
800:
797:
794:
791:
788:
785:
781:
778:
776:Dimethyl ether
772:
771:
764:
760:
757:
754:
751:
748:
744:
743:
730:boiling points
725:
722:
617:
614:
592:
591:
581:
560:
554:
548:
544:
543:
537:
533:
529:
526:
520:
517:
510:
509:
505:Carbowax from
503:
499:
495:
492:
490:ethylene oxide
483:
480:
473:
472:
466:
462:
459:
450:
444:
438:
437:
434:
433:Repeating unit
431:
428:
425:
370:
367:
338:
334:
330:
326:
322:
318:
314:
309:
306:
301:
297:
289:
281:
277:
273:
257:
249:
245:
241:
238:"alkoxyalkane"
229:
226:
209:
206:
194:dipropyl ether
186:dimethyl ether
152:dimethyl ether
143:
140:
84:groups (e.g.,
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3078:
3067:
3064:
3062:
3059:
3057:
3054:
3053:
3051:
3034:
3031:
3029:
3026:
3025:
3024:
3023:
3019:
3017:
3016:
3012:
3007:
3006:
3003:
2997:
2994:
2992:
2989:
2987:
2984:
2982:
2979:
2977:
2974:
2972:
2969:
2968:
2966:
2962:
2952:
2949:
2945:
2942:
2941:
2940:
2937:
2933:
2930:
2929:
2928:
2925:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2897:
2896:
2893:
2892:
2890:
2888:
2887:
2882:
2876:
2875:Telluroketone
2873:
2871:
2868:
2867:
2865:
2863:
2859:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2833:
2830:
2829:
2827:
2825:
2821:
2815:
2812:
2810:
2807:
2806:
2804:
2802:
2798:
2792:
2789:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2762:
2761:Sulfonic acid
2759:
2757:
2754:
2752:
2751:Sulfinic acid
2749:
2747:
2746:Thiosulfonate
2744:
2742:
2739:
2737:
2736:Thiosulfinate
2734:
2732:
2731:Sulfenic acid
2729:
2727:
2724:
2722:
2719:
2715:
2712:
2711:
2710:
2707:
2705:
2702:
2701:
2699:
2697:
2693:
2687:
2686:Phosphaallene
2684:
2682:
2681:Phosphaalkyne
2679:
2677:
2676:Phosphaalkene
2674:
2670:
2667:
2666:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2643:
2640:
2639:
2638:
2635:
2631:
2628:
2627:
2626:
2623:
2622:
2620:
2618:
2614:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2506:
2503:
2501:
2498:
2497:
2496:
2493:
2492:
2490:
2488:
2484:
2481:
2461:
2449:
2446:
2445:
2444:
2441:
2437:
2434:
2432:
2429:
2428:
2427:
2424:
2423:
2421:
2417:
2411:
2408:
2406:
2403:
2399:
2396:
2395:
2394:
2391:
2387:
2384:
2382:
2379:
2377:
2374:
2373:
2372:
2369:
2368:
2366:
2364:
2360:
2354:
2351:
2349:
2348:Ethylenedioxy
2346:
2342:
2339:
2337:
2334:
2333:
2332:
2329:
2325:
2322:
2320:
2317:
2316:
2315:
2312:
2308:
2305:
2304:
2303:
2300:
2298:
2295:
2293:
2290:
2289:
2287:
2283:
2280:
2274:
2268:
2263:
2258:
2252:
2249:
2247:
2244:
2240:
2237:
2235:
2232:
2231:
2230:
2227:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2198:
2195:
2194:
2193:
2190:
2186:
2183:
2181:
2178:
2177:
2176:
2173:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2140:
2139:
2136:
2135:
2133:
2127:
2123:
2119:
2112:
2107:
2105:
2100:
2098:
2093:
2092:
2089:
2078:
2074:
2070:
2066:
2059:
2056:
2051:
2045:
2041:
2036:
2035:
2026:
2023:
2018:
2014:
2010:
2006:
1999:
1996:
1990:
1984:
1983:
1978:
1971:
1968:
1965:
1961:
1957:
1951:
1949:
1945:
1940:
1936:
1932:
1928:
1924:
1923:Dalton Trans.
1917:
1914:
1909:
1903:
1899:
1895:
1891:
1884:
1881:
1878:
1874:
1870:
1866:
1865:
1860:
1855:
1852:
1845:
1841:
1837:
1833:
1829:
1828:Kraft process
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1794:
1790:
1783:
1779:
1776:
1773:
1769:
1768:
1764:
1763:polyurethanes
1760:
1758:
1755:
1753:
1752:
1748:
1744:
1740:
1737:
1734:
1731:
1727:
1726:
1722:
1718:
1716:
1713:
1710:
1706:
1705:
1701:
1697:
1696:essential oil
1693:
1689:
1686:
1683:
1680:
1676:
1675:
1671:
1668:
1665:
1662:
1658:
1657:
1653:
1651:
1648:
1645:
1641:
1640:
1636:
1633:
1630:
1627:
1623:
1622:
1618:
1614:
1610:
1606:
1602:
1598:
1596:
1595:Diethyl ether
1593:
1590:
1586:
1585:
1581:
1580:cetane rating
1577:
1573:
1569:
1567:
1564:
1561:
1557:
1556:
1552:
1548:
1546:
1543:
1540:
1536:
1535:
1529:
1527:
1525:
1501:
1478:
1477:
1476:
1474:
1466:
1462:
1458:
1454:
1449:
1447:
1443:
1439:
1435:
1430:
1428:
1427:leaving group
1424:
1420:
1416:
1412:
1405:
1401:
1400:
1399:
1398:
1394:
1393:alkyl halides
1390:
1383:
1381:
1379:
1375:
1372:Many ethers,
1367:
1363:
1360:
1358:
1353:
1349:
1348:
1347:
1344:
1339:
1331:
1329:
1327:
1323:
1321:
1317:
1313:
1309:
1305:
1301:
1297:
1293:
1290:
1276:
1266:
1265:
1264:
1262:
1254:
1252:
1230:
1229:
1228:
1221:
1214:
1206:
1205:
1204:
1202:
1198:
1190:
1185:
1183:
1181:
1173:
1171:
1169:
1165:
1161:
1157:
1153:
1130:
1126:
1122:
1121:diethyl ether
1118:
1109:
1099:
1089:
1079:
1069:
1060:
1055:
1048:
1046:
1044:
1040:
1036:
1032:
1028:
1025:
1017:
1015:
1013:
1009:
1008:paper pulping
1004:
1002:
998:
993:
991:
975:
974:
973:
971:
967:
963:
957:
949:
947:
945:
941:
937:
932:
930:
926:
919:
914:
907:
900:
897:
894:
891:
876:
874:
871:
870:
866:
864:
861:
858:
855:
845:
843:
840:
839:
835:
832:
829:
826:
808:
806:
805:Diethyl ether
803:
802:
798:
795:
792:
789:
779:
777:
774:
773:
769:
765:
758:
755:
752:
749:
746:
745:
740:
737:
735:
731:
723:
721:
705:
702:linkage) and
687:
669:
665:
661:
657:
653:
649:
646:
638:
633:
631:
627:
623:
615:
613:
611:
609:
603:
599:
590:
586:
582:
561:
559:
555:
552:
549:
546:
545:
542:
538:
527:
525:
521:
518:
515:
512:
511:
508:
504:
493:
491:
487:
484:
481:
478:
475:
474:
471:
467:
460:
458:
454:
451:
448:
445:
443:
440:
439:
435:
432:
429:
426:
423:
422:
416:
414:
410:
406:
402:
398:
394:
390:
388:
384:
380:
376:
368:
366:
364:
360:
356:
352:
348:
344:
307:
305:
295:
287:
271:
267:
265:
255:
254:methoxyethane
239:
235:
227:
225:
223:
219:
215:
207:
205:
203:
199:
195:
191:
190:diethyl ether
187:
182:
180:
176:
172:
167:
165:
161:
157:
153:
150:linkages. In
141:
139:
137:
133:
132:carbohydrates
129:
106:
105:diethyl ether
103:
99:
91:
87:
83:
79:
75:
71:
67:
63:
55:
52:
47:
41:
37:
33:
32:Diethyl ether
19:
3020:
3013:
2927:Vinyl halide
2884:
2814:Borinic acid
2809:Boronic acid
2786:Thioxanthate
2313:
2126:Hydrocarbons
2068:
2064:
2058:
2033:
2025:
2008:
2004:
1998:
1988:
1980:
1970:
1955:
1922:
1916:
1889:
1883:
1862:
1854:
1832:Soda pulping
1812:Ether (song)
1715:Crown ethers
1691:
1521:
1510:–O + R–X → C
1450:
1446:bromobenzene
1431:
1408:
1387:
1378:crown ethers
1371:
1356:
1341:
1324:
1318:(ETBE), and
1304:carbocations
1287:
1281:CH–C(–O–R)–R
1258:
1250:
1225:
1194:
1177:
1114:
1021:
1005:
994:
987:
959:
933:
922:
728:Ethers have
727:
634:
619:
607:
595:
468:Delrin from
457:formaldehyde
415:polyethers.
412:
408:
393:Crown ethers
391:
372:
342:
311:
308:Trivial name
293:
285:
261:
237:
231:
228:Nomenclature
211:
183:
181:), however.
168:
145:
128:biochemistry
65:
59:
54:substituents
2991:Thiocyanate
2986:Sulfonamide
2951:Perchlorate
2939:Acyl halide
2900:Fluoroethyl
2781:Thionoester
2669:Phosphonium
2654:Phosphinate
2649:Phosphonous
2637:Phosphonate
2336:Hydroperoxy
2158:Cyclopropyl
1802:Ether lipid
1782:ether lipid
1609:refrigerant
1605:anaesthetic
1487:OH + OH → C
1475:mechanism.
1374:ethoxylates
1197:dehydration
1117:Lewis bases
1049:Lewis bases
704:stannoxanes
626:hemiacetals
539:Arcol from
430:Preparation
214:enol ethers
102:anaesthetic
3050:Categories
2895:Haloalkane
2766:Thioketone
2721:Persulfide
2617:Phosphorus
2582:Isocyanate
2572:Isonitrile
2473:or oxygen
2471:hydrogen,
2467:not being
2448:Orthoester
2341:Dioxiranes
2319:Enol ether
2207:1-Propenyl
1846:References
1836:Organosolv
1692:aryl ether
1453:phenoxides
1442:sulfonates
1366:halohydrin
1352:peroxyacid
1300:isoamylene
1277:+ R–OH → R
1154:center in
1137:·O(CH
1029:, such as
980:+ HBr → CH
954:See also:
925:reactivity
756:b.p. (°C)
753:m.p. (°C)
750:Structure
720:linkage).
686:disiloxane
684:linkage),
675:Si−O−CR=CR
604:(PPE) and
405:ciguatoxin
401:brevetoxin
385:such as a
383:end-groups
369:Polyethers
156:bond angle
18:Ether bond
3028:inorganic
2862:Tellurium
2776:Thioester
2741:Sulfoxide
2726:Disulfide
2714:Sulfonium
2664:Phosphine
2642:Phosphite
2625:Phosphate
2557:Carbamate
2532:Hydrazone
2465:element,
2463:Only one
2436:Anhydride
2175:Methylene
2065:Synthesis
1743:cosmetics
1617:perfumery
1397:alkoxides
1296:isobutene
1292:catalysis
1186:Synthesis
1168:complexes
1041:(THF) or
1035:aldehydes
1027:peroxides
1024:explosive
908:Reactions
833:69 g
796:70 g
179:aldehydes
70:compounds
3009:See also
2944:Chloride
2870:Tellurol
2824:Selenium
2791:Xanthate
2505:Ammonium
2487:Nitrogen
2469:carbon,
2426:Carboxyl
2393:Aldehyde
2381:Acryloyl
2363:carbonyl
2267:hydrogen
2222:Cumulene
1939:15303175
1822:Inhalant
1791:See also
1354:such as
1343:Epoxides
1332:Epoxides
1322:(TAEE).
1314:(TAME),
1310:(MTBE),
1201:alcohols
1123:forms a
1108:Nitrogen
1098:Hydrogen
1078:Chlorine
1068:Vanadium
984:Br + ROH
950:Cleavage
936:epoxides
898:Miscible
863:Miscible
711:Sn−O−SnR
693:Si−O−SiH
645:group 14
598:aromatic
541:Covestro
399:such as
387:hydroxyl
375:polymers
355:aromatic
36:Ethereum
3033:organic
2832:Selenol
2756:Sulfone
2709:Sulfide
2607:NONOate
2602:Nitroso
2592:Nitrite
2587:Nitrate
2577:Cyanate
2567:Nitrile
2552:Amidine
2547:Imidate
2517:Nitrene
2512:Hydrazo
2500:Enamine
2431:Acetoxy
2419:carboxy
2386:Benzoyl
2324:Epoxide
2307:Methoxy
2297:Alcohol
2251:Carbene
2185:Methine
1685:Anisole
1650:Dioxane
1601:solvent
1578:with a
1551:epoxide
1457:phenols
1438:bromide
1415:alcohol
1338:epoxide
1261:alkenes
1164:acyclic
1125:complex
944:acetals
929:alkanes
873:Dioxane
734:alkanes
718:Sn−O−Sn
700:Si−O−Si
650:(e.g.,
639:in the
612:(PPO).
585:Invista
363:Acetals
351:aniseed
347:anisole
286:methoxy
264:methoxy
232:In the
198:anisole
175:ketones
98:solvent
82:organyl
51:organyl
3056:Ethers
2932:Iodide
2852:Selone
2696:Sulfur
2405:Ketone
2398:Ketene
2376:Acetyl
2331:Peroxy
2302:Alkoxy
2292:Acetal
2273:oxygen
2262:carbon
2246:Alkyne
2239:Benzyl
2234:Phenyl
2217:Allene
2212:Crotyl
2192:Alkene
2180:Bridge
2168:Pentyl
2153:Propyl
2143:Methyl
2046:
2011:: 81.
1937:
1904:
1869:ethers
1738:(PEG)
1702:seed.
1669:(THF)
1634:(DME)
1495:–O + H
1434:iodide
1106:
1104:
1096:
1094:
1088:Carbon
1086:
1084:
1076:
1074:
1066:
1064:
1012:lignin
999:(even
942:, and
940:ketals
856:−108.4
827:−116.3
790:−138.5
747:Ether
682:Si−O−C
622:Esters
553:(PTHF)
470:DuPont
413:ladder
409:cyclic
379:polyol
359:furans
353:. The
294:ethane
154:, the
136:lignin
94:R−O−R′
78:oxygen
66:ethers
2964:Other
2801:Boron
2771:Thial
2704:Thiol
2597:Nitro
2562:Imide
2542:Amide
2527:Oxime
2522:Imine
2495:Amine
2443:Ester
2410:Ynone
2314:Ether
2285:R-O-R
2260:Only
2202:Allyl
2197:Vinyl
2163:Butyl
2148:Ethyl
2138:Alkyl
1859:IUPAC
1830:(and
1797:Ester
1700:anise
1463:like
1440:, or
1359:-CPBA
1180:alpha
1127:with
990:onium
901:0.45
895:101.3
867:1.74
836:1.14
817:–O–CH
799:1.30
793:−23.0
784:–O–CH
641:C−O−C
606:poly(
532:CH(CH
516:(PPG)
479:(PEG)
276:–O–CH
270:alkyl
248:–O–CH
148:C−O−C
117:−O−CH
86:alkyl
74:group
2886:Halo
2371:Acyl
2271:and
2229:Aryl
2069:2006
2044:ISBN
1935:PMID
1902:ISBN
1745:and
1522:The
1461:base
1419:base
1376:and
1289:Acid
1272:C=CR
1231:R–CH
1195:The
1080:, Cl
976:ROCH
892:11.8
859:66.0
846:O(CH
830:34.4
589:BASF
403:and
134:and
100:and
90:aryl
76:—an
2537:Azo
2073:doi
2040:129
2013:doi
2009:113
1960:doi
1927:doi
1894:doi
1873:doi
1871:".
1834:),
1780:An
1698:of
1690:An
1395:by
1391:of
1298:or
1243:+ H
1235:–CH
1199:of
1110:, N
1100:, H
1090:, C
1070:, V
1061:)3.
1059:thf
931:.
877:O(C
563:−CH
536:)O–
528:–CH
507:Dow
494:–CH
488:of
461:–CH
455:of
411:or
313:(CH
304:).
296:(CH
288:(CH
252:is
244:–CH
177:or
121:−CH
113:−CH
88:or
60:In
3052::
2269:,
2264:,
2067:.
2042:.
2007:.
1986:;
1979:.
1947:^
1933:.
1900:.
1861:,
1765:.
1749:.
1723:.
1619:.
1553:.
1518:OR
1436:,
1170:.
1158:.
1152:Mg
1141:CH
1133:BF
1014:.
972::
964:.
938:,
821:CH
813:CH
809:CH
780:CH
770:)
763:O
664:Pb
662:,
660:Sn
658:,
656:Ge
654:,
652:Si
579:O−
575:CH
571:CH
567:CH
502:O–
498:CH
465:O–
361:.
333:OC
317:OC
300:CH
292:O)
280:CH
266:-"
204:.
192:,
188:,
160:pm
138:.
109:CH
64:,
2110:e
2103:t
2096:v
2079:.
2075::
2052:.
2019:.
2015::
1993:.
1962::
1941:.
1929::
1910:.
1896::
1875::
1516:5
1514:H
1512:6
1508:5
1506:H
1504:6
1502:C
1499:O
1497:2
1493:5
1491:H
1489:6
1485:5
1483:H
1481:6
1479:C
1473:2
1471:N
1469:S
1404:X
1368:.
1361:.
1357:m
1283:2
1279:2
1274:2
1270:2
1268:R
1247:O
1245:2
1241:2
1237:2
1233:2
1213:O
1211:2
1209:H
1147:2
1145:)
1143:3
1139:2
1135:3
982:3
978:3
889:O
887:2
885:)
883:4
881:H
879:2
852:4
850:)
848:2
823:3
819:2
815:2
811:3
786:3
782:3
768:D
761:2
713:3
709:3
707:R
695:3
691:3
689:H
677:2
673:3
671:R
637:C
608:p
577:2
573:2
569:2
565:2
534:3
530:2
500:2
496:2
463:2
339:5
337:H
335:6
331:5
329:H
327:6
323:5
321:H
319:2
315:3
302:3
298:2
290:3
282:3
278:2
274:3
262:"
258:3
250:3
246:2
242:3
123:3
119:2
115:2
111:3
56:.
42:.
20:)
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