119:
2627:
72:
104:
intermediate, which either reverts back to the starting material, or proceeds to the transesterified product (RCOOR). The various species exist in equilibrium, and the product distribution depends on the relative energies of the reactant and product. Depending on reaction conditions
248:. For example, a solid fat with mostly saturated fatty acids may be transesterified with a vegetable oil having high unsaturated acid contents, to produce a spreadable semisolid fat whose molecules have a mix both kinds of acids.
217:
methanol methodology, whereby high temperature, high-pressure vessels are used to physically catalyze the biolipid/methanol reaction into fatty-acid methyl esters.
599:
1290:
1280:
1275:
163:
The reverse reaction, methanolysis, is also an example of transesterification. This process has been used to recycle polyesters into individual monomers (see
1989:
1532:
1300:
1295:
1285:
1218:
1208:
1202:
1547:
1537:
1270:
1260:
1228:
1223:
1213:
1974:
1425:
1265:
1197:
1186:
1255:
2228:
1969:
1131:
2233:
2223:
1120:
497:
Yasushi Obora; Yasutaka Ishii (2012). "Discussion
Addendum: Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate".
408:
Wilhelm
Riemenschneider1 and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.
202:
transesterification may have been discovered much earlier. In the 1940s, researchers were looking for a method to more readily produce
575:
92:
can be made from methyl or ethyl esters in high purity by heating the mixture of ester, acid/base, and large alcohol.
2578:
2378:
541:
388:
2661:
2607:
210:
for World War II. Many of the methods used today by producers have their origin in the original 1940s research.
84:
If the alcohol produced by the reaction can be separated from the reactants by distillation this will drive the
101:
2473:
1567:
1510:
139:. In this application, diesters undergo transesterification with diols to form macromolecules. For example,
2656:
2521:
873:
745:
213:
Biolipid transesterification has also been recently shown by
Japanese researchers to be possible using a
2583:
1882:
813:
808:
148:
426:
2602:
2593:
2573:
803:
1927:
2458:
1824:
225:
100:
In the transesterification mechanism, the carbonyl carbon of the starting ester reacts to give a
2651:
2463:
848:
798:
793:
568:
140:
2498:
1887:
2588:
885:
858:
313:
85:
8:
1964:
1907:
1869:
1542:
1527:
1505:
853:
765:
665:
584:
318:
214:
60:. Bases catalyze the reaction by removing a proton from the alcohol, thus making it more
118:
2526:
2507:
2383:
1999:
1844:
1839:
1834:
1829:
1584:
1450:
916:
755:
647:
614:
328:
2630:
2561:
2482:
1994:
1597:
1576:
1552:
1500:
1495:
1398:
1378:
1368:
1358:
1353:
838:
770:
706:
639:
634:
561:
537:
446:
195:
164:
113:
will also occur, which results in some amount of free carboxylic acid being present.
2502:
2031:
1979:
1922:
1749:
1696:
1592:
1490:
1393:
1363:
1343:
1333:
1191:
843:
529:
506:
477:
463:
438:
409:
362:
106:
45:
25:
413:
2566:
2535:
2468:
2435:
2388:
2373:
2041:
1735:
1730:
1691:
1415:
1383:
1348:
898:
833:
828:
823:
818:
760:
725:
624:
323:
144:
2597:
2512:
2368:
1917:
1877:
1562:
1338:
1328:
1323:
1313:
1180:
1142:
1125:
1109:
1065:
1054:
1048:
893:
788:
678:
442:
300:
The reaction can be effected with high enantioselectivity when mediated with a
110:
64:. The reaction can also be accomplished with the help of enzymes, particularly
264:, which is cheaply available, undergoes transesterification, giving access to
2645:
2551:
2450:
2009:
1984:
1956:
1899:
1722:
1670:
1557:
1485:
1480:
1318:
1153:
1147:
1136:
1076:
1070:
1059:
750:
698:
673:
533:
510:
482:
466:"Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate"
465:
450:
261:
245:
229:
176:
135:
The largest scale application of transesterification is in the synthesis of
2440:
1816:
1475:
1043:
868:
333:
237:
184:
168:
89:
57:
427:"Variables affecting the in situ transesterification of microalgae lipids"
2556:
2530:
2420:
2267:
1859:
1854:
1849:
1640:
1114:
1037:
1031:
61:
366:
2517:
2430:
2425:
2330:
2131:
2061:
1937:
1759:
1660:
1470:
1465:
1435:
1430:
1388:
1103:
986:
976:
966:
921:
655:
629:
609:
380:
265:
233:
207:
71:
16:
Chemical reaction which exchanges the R groups of an alcohol and ester
2325:
2315:
2297:
2151:
1942:
1797:
1650:
1460:
1455:
1445:
1440:
1420:
1025:
997:
991:
981:
971:
926:
180:
172:
136:
2404:
2320:
2292:
2277:
2272:
2213:
2208:
2192:
2121:
2111:
2081:
2071:
2051:
1787:
1783:
1763:
1745:
1712:
1620:
956:
737:
711:
203:
199:
191:
152:
53:
37:
33:
2282:
2262:
2218:
2174:
2101:
2091:
1932:
1912:
1773:
1630:
961:
908:
863:
780:
686:
619:
464:
Tomotaka
Hirabayashi; Satoshi Sakaguchi; Yasutaka Ishii (2005).
2348:
2141:
1373:
301:
183:) was used to power heavy-duty vehicles in South Africa before
65:
49:
29:
2287:
425:
Ehimen, E. A.; Sun, Z. F.; Carrington, C. G. (1 March 2010).
175:. This conversion was one of the first uses. Transesterified
260:
derivatives, which are difficult to prepare by other means.
553:
496:
257:
48:
catalyst. Strong acids catalyze the reaction by donating a
41:
241:
158:
88:
toward the products. This means that esters with larger
79:: alcohol + ester → different alcohol + different ester
155:, which is evaporated to drive the reaction forward.
424:
353:Otera, Junzo. (June 1993). "Transesterification".
2643:
526:Encyclopedia of Reagents for Organic Synthesis
569:
524:Manchand, Percy S. (2001). "Vinyl Acetate".
576:
562:
256:Transesterification is used to synthesize
481:
381:"ENZYME – 3.1.1.3 Triacylglycerol lipase"
68:(one example is the lipase E.C.3.1.1.3).
24:is the process of exchanging the organic
523:
70:
130:
2644:
402:
557:
389:SIB Swiss Institute of Bioinformatics
352:
159:Methanolysis and biodiesel production
1723:Polyhydric alcohols (sugar alcohols)
490:
167:). It is also used to convert fats (
56:group, thus making it a more potent
13:
14:
2673:
2379:2-Methyl-2-propyl-1,3-propanediol
220:
2626:
2625:
117:
32:with the organic group R' of an
2608:Nucleophilic conjugate addition
125:
517:
457:
418:
373:
346:
1:
2579:Fischer–Speier esterification
1511:Propylene glycol methyl ether
414:10.1002/14356007.a09_565.pub2
339:
583:
251:
206:, which was used to produce
95:
36:. These reactions are often
7:
746:4-Methylcyclohexanemethanol
307:
10:
2678:
2584:Williamson ether synthesis
1883:2,4-Dichlorobenzyl alcohol
814:2-(2-Methoxyethoxy)ethanol
809:2-(2-Methoxyethoxy)ethanol
443:10.1016/j.fuel.2009.10.011
194:in the US in the 1950s by
149:polyethylene terephthalate
2621:
2603:Friedel-Crafts alkylation
2594:Nucleophilic substitution
2574:Nucleophilic substitution
2544:
2491:
2449:
2413:
2397:
2361:
2339:
2306:
2253:
2246:
2201:
2183:
2165:
2017:
2008:
1951:
1896:
1868:
1815:
1721:
1705:
1684:
1613:
1606:
1518:
1407:
1237:
1162:
1085:
1007:
938:
907:
804:2-(2-Ethoxyethoxy)ethanol
779:
736:
724:
697:
664:
598:
591:
1825:2,2-Dimethylpropan-1-ol
881:-Diisopropylaminoethanol
534:10.1002/047084289X.rv008
511:10.15227/orgsyn.089.0307
483:10.15227/orgsyn.082.0055
2459:1,3-Difluoro-2-propanol
226:Fat interesterification
2662:Substitution reactions
2464:2,2,2-Trifluoroethanol
849:Aminoethylethanolamine
799:2,2,2-Trifluoroethanol
794:2,2,2-Trichloroethanol
141:dimethyl terephthalate
81:
40:by the addition of an
1888:3-Nitrobenzyl alcohol
74:
2589:Elimination reaction
1291:1-Heptatetracontanol
1281:1-Pentatetracontanol
1276:1-Tetratetracontanol
1183:(melissyl / myricyl)
1150:(cluytyl / montanyl)
859:Dimethylethanolamine
314:Biodiesel production
131:Polyester production
2657:Reactions of esters
2613:Transesterification
1990:Palmitoleyl alcohol
1965:3-Methyl-3-pentanol
1908:Cetostearyl alcohol
1845:3-Methylbutan-2-ol
1840:3-Methylbutan-1-ol
1835:2-Methylbutan-2-ol
1830:2-Methylbutan-1-ol
1614:Monohydric alcohols
1543:3-Methyl-3-pentanol
1533:2-Methylheptan-2-ol
1528:2-Methyl-2-pentanol
1301:1-Nonatetracontanol
1296:1-Octatetracontanol
1286:1-Hexatetracontanol
1219:1-Heptatriacontanol
1209:1-Pentatriacontanol
1203:1-Tetratriacontanol
889:-Methylethanolamine
854:Diethylethanolamine
766:Methylazoxymethanol
683:Methanol poisoning
367:10.1021/cr00020a004
77:Transesterification
22:Transesterification
2508:Carbonyl reduction
2384:Diethylpropanediol
2000:tert-Butyl alcohol
1706:Trihydric alcohols
1548:3-Methyloctan-3-ol
1538:2-Methylhexan-2-ol
1451:3-Methyl-2-butanol
1271:1-Tritetracontanol
1261:1-Hentetracontanol
1229:1-Nonatriacontanol
1224:1-Octatriacontanol
1214:1-Hexatriacontanol
1062:(cetyl / palmityl)
917:2-Methyl-1-butanol
756:Cyclohexylmethanol
615:2-Methyl-1-butanol
329:Transamidification
82:
2639:
2638:
2562:Alcohol oxidation
2483:Trifluoromethanol
2357:
2356:
2242:
2241:
1995:tert-Amyl alcohol
1975:Linolenyl alcohol
1870:Aromatic alcohols
1811:
1810:
1685:Dihydric alcohols
1598:Triphenylmethanol
1553:Diacetone alcohol
1501:Pinacolyl alcohol
1426:2-Deoxyerythritol
1399:Veratrole alcohol
1379:Propargyl alcohol
1369:Phenethyl alcohol
1359:Nicotinyl alcohol
1354:Neopentyl alcohol
1309:
1308:
1266:1-Dotetracontanol
1198:1-Tritriacontanol
1187:1-Hentriacontanol
839:2-Mercaptoethanol
771:Trifluoromethanol
720:
719:
707:Isopropyl alcohol
635:Phenethyl alcohol
600:Alcohols found in
385:enzyme.expasy.org
232:to rearrange the
165:plastic recycling
2669:
2629:
2628:
2251:
2250:
2247:Terpene alcohols
2032:Methylene glycol
2015:
2014:
1980:Linoleyl alcohol
1923:Myristyl alcohol
1750:Propylene glycol
1697:Propylene glycol
1611:
1610:
1593:Triphenylethanol
1506:Pirkle's alcohol
1491:Diphenylmethanol
1394:Vanillyl alcohol
1364:Perillyl alcohol
1344:Furfuryl alcohol
1334:Cinnamyl alcohol
1192:1-Dotriacontanol
844:2-Methoxyethanol
734:
733:
602:alcoholic drinks
596:
595:
578:
571:
564:
555:
554:
548:
547:
521:
515:
514:
494:
488:
487:
485:
461:
455:
454:
422:
416:
406:
400:
399:
397:
395:
377:
371:
370:
361:(4): 1449–1470.
355:Chemical Reviews
350:
319:Otera's catalyst
295:
294:
293:
283:
282:
281:
121:
107:ester hydrolysis
26:functional group
2677:
2676:
2672:
2671:
2670:
2668:
2667:
2666:
2642:
2641:
2640:
2635:
2617:
2567:Glycol cleavage
2540:
2536:Ziegler process
2487:
2469:2-Fluoroethanol
2445:
2409:
2393:
2389:Ethylene glycol
2374:1,5-Pentanediol
2353:
2341:
2335:
2308:
2302:
2255:
2238:
2202:Glycylglycitols
2197:
2185:
2179:
2167:
2161:
2157:
2147:
2137:
2127:
2117:
2107:
2097:
2087:
2077:
2067:
2057:
2047:
2042:Ethylene glycol
2037:
2025:
2021:
2004:
1955:
1953:
1947:
1898:
1892:
1864:
1807:
1803:
1793:
1779:
1769:
1755:
1741:
1736:Ethylene glycol
1731:Pentaerythritol
1717:
1701:
1692:Ethylene glycol
1680:
1676:
1666:
1656:
1646:
1636:
1626:
1607:Hydric alcohols
1602:
1520:
1514:
1416:1-Phenylethanol
1409:
1403:
1384:Salicyl alcohol
1349:Isoamyl alcohol
1305:
1256:1-Tetracontanol
1249:
1245:
1241:
1239:
1233:
1174:
1170:
1166:
1164:
1158:
1097:
1093:
1089:
1087:
1081:
1019:
1015:
1011:
1009:
1003:
950:
946:
942:
940:
934:
903:
899:Tribromoethanol
834:2-Fluoroethanol
829:2-Ethoxyethanol
824:2-Chloroethanol
819:2-Butoxyethanol
775:
761:Methoxymethanol
727:
716:
693:
666:Medical alcohol
660:
625:Isoamyl alcohol
601:
587:
582:
552:
551:
544:
522:
518:
495:
491:
462:
458:
423:
419:
407:
403:
393:
391:
379:
378:
374:
351:
347:
342:
324:Transalkylation
310:
292:
289:
288:
287:
285:
280:
277:
276:
275:
273:
254:
228:is used in the
223:
161:
145:ethylene glycol
133:
128:
98:
80:
17:
12:
11:
5:
2675:
2665:
2664:
2659:
2654:
2637:
2636:
2634:
2633:
2622:
2619:
2618:
2616:
2615:
2610:
2605:
2600:
2598:carbonyl group
2591:
2586:
2581:
2576:
2571:
2570:
2569:
2559:
2554:
2548:
2546:
2542:
2541:
2539:
2538:
2533:
2524:
2515:
2513:Ether cleavage
2510:
2505:
2495:
2493:
2489:
2488:
2486:
2485:
2480:
2478:-butyl alcohol
2471:
2466:
2461:
2455:
2453:
2451:Fluoroalcohols
2447:
2446:
2444:
2443:
2438:
2433:
2428:
2423:
2417:
2415:
2411:
2410:
2408:
2407:
2401:
2399:
2395:
2394:
2392:
2391:
2386:
2381:
2376:
2371:
2369:1,4-Butanediol
2365:
2363:
2359:
2358:
2355:
2354:
2352:
2351:
2345:
2343:
2337:
2336:
2334:
2333:
2328:
2323:
2318:
2312:
2310:
2304:
2303:
2301:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2259:
2257:
2248:
2244:
2243:
2240:
2239:
2237:
2236:
2231:
2229:Maltotetraitol
2226:
2221:
2216:
2211:
2205:
2203:
2199:
2198:
2196:
2195:
2189:
2187:
2181:
2180:
2178:
2177:
2171:
2169:
2163:
2162:
2160:
2159:
2155:
2149:
2145:
2139:
2135:
2129:
2125:
2119:
2115:
2109:
2105:
2099:
2095:
2089:
2085:
2079:
2075:
2069:
2065:
2059:
2055:
2049:
2045:
2039:
2035:
2028:
2026:
2023:
2019:
2012:
2010:Sugar alcohols
2006:
2005:
2003:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1970:Erucyl alcohol
1967:
1961:
1959:
1957:fatty alcohols
1949:
1948:
1946:
1945:
1940:
1935:
1930:
1925:
1920:
1918:Lauryl alcohol
1915:
1910:
1904:
1902:
1900:fatty alcohols
1894:
1893:
1891:
1890:
1885:
1880:
1878:Benzyl alcohol
1874:
1872:
1866:
1865:
1863:
1862:
1857:
1852:
1847:
1842:
1837:
1832:
1827:
1821:
1819:
1813:
1812:
1809:
1808:
1806:
1805:
1801:
1795:
1791:
1781:
1777:
1771:
1767:
1757:
1753:
1743:
1739:
1733:
1727:
1725:
1719:
1718:
1716:
1715:
1709:
1707:
1703:
1702:
1700:
1699:
1694:
1688:
1686:
1682:
1681:
1679:
1678:
1674:
1668:
1664:
1658:
1654:
1648:
1644:
1638:
1634:
1628:
1624:
1617:
1615:
1608:
1604:
1603:
1601:
1600:
1595:
1590:
1588:-Butyl alcohol
1582:
1574:
1572:-butyl alcohol
1565:
1563:Methylpentynol
1560:
1555:
1550:
1545:
1540:
1535:
1530:
1524:
1522:
1516:
1515:
1513:
1508:
1503:
1498:
1493:
1488:
1483:
1478:
1473:
1468:
1463:
1458:
1453:
1448:
1443:
1438:
1433:
1428:
1423:
1418:
1413:
1411:
1405:
1404:
1402:
1401:
1396:
1391:
1386:
1381:
1376:
1371:
1366:
1361:
1356:
1351:
1346:
1341:
1339:Crotyl alcohol
1336:
1331:
1329:Benzyl alcohol
1326:
1324:Anisyl alcohol
1321:
1316:
1314:2-Ethylhexanol
1310:
1307:
1306:
1304:
1303:
1298:
1293:
1288:
1283:
1278:
1273:
1268:
1263:
1258:
1252:
1250:
1247:
1243:
1238:Straight-chain
1235:
1234:
1232:
1231:
1226:
1221:
1216:
1211:
1206:
1200:
1195:
1189:
1184:
1181:1-Triacontanol
1177:
1175:
1172:
1168:
1163:Straight-chain
1160:
1159:
1157:
1156:
1151:
1145:
1143:1-Heptacosanol
1140:
1134:
1132:1-Pentacosanol
1129:
1126:1-Tetracosanol
1123:
1118:
1112:
1110:1-Heneicosanol
1107:
1100:
1098:
1095:
1091:
1086:Straight-chain
1083:
1082:
1080:
1079:
1074:
1068:
1066:1-Heptadecanol
1063:
1057:
1055:1-Pentadecanol
1052:
1049:1-Tetradecanol
1046:
1041:
1035:
1029:
1022:
1020:
1017:
1013:
1008:Straight-chain
1005:
1004:
1002:
1001:
995:
989:
984:
979:
974:
969:
964:
959:
953:
951:
948:
944:
939:Straight-chain
936:
935:
933:
932:
924:
919:
913:
911:
905:
904:
902:
901:
896:
894:Phenoxyethanol
891:
883:
871:
866:
861:
856:
851:
846:
841:
836:
831:
826:
821:
816:
811:
806:
801:
796:
791:
789:1-Aminoethanol
785:
783:
777:
776:
774:
773:
768:
763:
758:
753:
748:
742:
740:
731:
722:
721:
718:
717:
715:
714:
709:
703:
701:
699:Toxic alcohols
695:
694:
692:
691:
690:
689:
681:
679:Methylpentynol
676:
670:
668:
662:
661:
659:
658:
653:
651:-Butyl alcohol
645:
637:
632:
627:
622:
617:
612:
606:
604:
593:
592:By consumption
589:
588:
581:
580:
573:
566:
558:
550:
549:
542:
516:
489:
456:
437:(3): 677–684.
417:
401:
372:
344:
343:
341:
338:
337:
336:
331:
326:
321:
316:
309:
306:
298:
297:
290:
278:
253:
250:
246:vegetable oils
222:
221:Fat processing
219:
160:
157:
147:react to form
132:
129:
127:
124:
123:
122:
111:esterification
97:
94:
75:
15:
9:
6:
4:
3:
2:
2674:
2663:
2660:
2658:
2655:
2653:
2652:Lipid methods
2650:
2649:
2647:
2632:
2624:
2623:
2620:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2568:
2565:
2564:
2563:
2560:
2558:
2555:
2553:
2552:Deprotonation
2550:
2549:
2547:
2543:
2537:
2534:
2532:
2528:
2525:
2523:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2500:
2497:
2496:
2494:
2490:
2484:
2481:
2479:
2477:
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2456:
2454:
2452:
2448:
2442:
2439:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2419:
2418:
2416:
2412:
2406:
2403:
2402:
2400:
2396:
2390:
2387:
2385:
2382:
2380:
2377:
2375:
2372:
2370:
2367:
2366:
2364:
2360:
2350:
2347:
2346:
2344:
2338:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2313:
2311:
2307:Sesquiterpene
2305:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2264:
2261:
2260:
2258:
2252:
2249:
2245:
2235:
2232:
2230:
2227:
2225:
2222:
2220:
2217:
2215:
2212:
2210:
2207:
2206:
2204:
2200:
2194:
2191:
2190:
2188:
2182:
2176:
2173:
2172:
2170:
2164:
2153:
2150:
2143:
2140:
2133:
2130:
2123:
2120:
2113:
2110:
2103:
2100:
2093:
2090:
2083:
2080:
2073:
2070:
2063:
2060:
2053:
2050:
2043:
2040:
2033:
2030:
2029:
2027:
2016:
2013:
2011:
2007:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1985:Oleyl alcohol
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1963:
1962:
1960:
1958:
1950:
1944:
1941:
1939:
1936:
1934:
1931:
1929:
1926:
1924:
1921:
1919:
1916:
1914:
1911:
1909:
1906:
1905:
1903:
1901:
1895:
1889:
1886:
1884:
1881:
1879:
1876:
1875:
1873:
1871:
1867:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1822:
1820:
1818:
1817:Amyl alcohols
1814:
1799:
1796:
1789:
1785:
1782:
1775:
1772:
1765:
1761:
1758:
1751:
1747:
1744:
1737:
1734:
1732:
1729:
1728:
1726:
1724:
1720:
1714:
1711:
1710:
1708:
1704:
1698:
1695:
1693:
1690:
1689:
1687:
1683:
1672:
1671:Cetyl alcohol
1669:
1662:
1659:
1652:
1649:
1642:
1639:
1632:
1629:
1622:
1619:
1618:
1616:
1612:
1609:
1605:
1599:
1596:
1594:
1591:
1589:
1587:
1583:
1581:
1580:-Amyl alcohol
1579:
1575:
1573:
1571:
1566:
1564:
1561:
1559:
1558:Ethchlorvynol
1556:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1525:
1523:
1521:alcohols (3°)
1517:
1512:
1509:
1507:
1504:
1502:
1499:
1497:
1494:
1492:
1489:
1487:
1486:Cyclopropanol
1484:
1482:
1481:Cyclopentanol
1479:
1477:
1474:
1472:
1469:
1467:
1464:
1462:
1459:
1457:
1454:
1452:
1449:
1447:
1444:
1442:
1439:
1437:
1434:
1432:
1429:
1427:
1424:
1422:
1419:
1417:
1414:
1412:
1410:alcohols (2°)
1406:
1400:
1397:
1395:
1392:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1372:
1370:
1367:
1365:
1362:
1360:
1357:
1355:
1352:
1350:
1347:
1345:
1342:
1340:
1337:
1335:
1332:
1330:
1327:
1325:
1322:
1320:
1319:Allyl alcohol
1317:
1315:
1312:
1311:
1302:
1299:
1297:
1294:
1292:
1289:
1287:
1284:
1282:
1279:
1277:
1274:
1272:
1269:
1267:
1264:
1262:
1259:
1257:
1254:
1253:
1251:
1236:
1230:
1227:
1225:
1222:
1220:
1217:
1215:
1212:
1210:
1207:
1204:
1201:
1199:
1196:
1193:
1190:
1188:
1185:
1182:
1179:
1178:
1176:
1161:
1155:
1154:1-Nonacosanol
1152:
1149:
1148:1-Octacosanol
1146:
1144:
1141:
1138:
1137:1-Hexacosanol
1135:
1133:
1130:
1127:
1124:
1122:
1119:
1116:
1113:
1111:
1108:
1105:
1102:
1101:
1099:
1084:
1078:
1077:1-Nonadecanol
1075:
1072:
1071:1-Octadecanol
1069:
1067:
1064:
1061:
1060:1-Hexadecanol
1058:
1056:
1053:
1050:
1047:
1045:
1042:
1039:
1036:
1033:
1030:
1027:
1024:
1023:
1021:
1006:
999:
996:
993:
990:
988:
985:
983:
980:
978:
975:
973:
970:
968:
965:
963:
960:
958:
955:
954:
952:
937:
931:
929:
925:
923:
920:
918:
915:
914:
912:
910:
906:
900:
897:
895:
892:
890:
888:
884:
882:
880:
876:
872:
870:
867:
865:
862:
860:
857:
855:
852:
850:
847:
845:
842:
840:
837:
835:
832:
830:
827:
825:
822:
820:
817:
815:
812:
810:
807:
805:
802:
800:
797:
795:
792:
790:
787:
786:
784:
782:
778:
772:
769:
767:
764:
762:
759:
757:
754:
752:
751:Aminomethanol
749:
747:
744:
743:
741:
739:
735:
732:
729:
723:
713:
710:
708:
705:
704:
702:
700:
696:
688:
685:
684:
682:
680:
677:
675:
674:Ethchlorvynol
672:
671:
669:
667:
663:
657:
654:
652:
650:
646:
644:
643:-Amyl alcohol
642:
638:
636:
633:
631:
628:
626:
623:
621:
618:
616:
613:
611:
608:
607:
605:
603:
597:
594:
590:
586:
579:
574:
572:
567:
565:
560:
559:
556:
545:
543:0-471-93623-5
539:
535:
531:
527:
520:
512:
508:
504:
500:
493:
484:
479:
475:
471:
467:
460:
452:
448:
444:
440:
436:
432:
428:
421:
415:
411:
405:
390:
386:
382:
376:
368:
364:
360:
356:
349:
345:
335:
332:
330:
327:
325:
322:
320:
317:
315:
312:
311:
305:
303:
271:
270:
269:
267:
263:
262:Vinyl acetate
259:
249:
247:
243:
239:
238:triglycerides
235:
231:
230:food industry
227:
218:
216:
215:supercritical
211:
209:
205:
201:
197:
193:
188:
186:
182:
178:
177:vegetable oil
174:
170:
169:triglycerides
166:
156:
154:
150:
146:
142:
138:
120:
116:
115:
114:
112:
108:
103:
93:
91:
90:alkoxy groups
87:
78:
73:
69:
67:
63:
59:
55:
51:
47:
43:
39:
35:
31:
27:
23:
19:
2612:
2499:Substitution
2492:Preparations
2475:
2441:Stigmasterol
2436:β-Sitosterol
2234:Polyglycitol
2224:Maltotriitol
2184:Cyclic sugar
1952:Branched and
1860:Pentan-3-ol
1855:Pentan-2-ol
1850:Pentan-1-ol
1585:
1577:
1569:
1476:Cyclohexanol
1128:(lignoceryl)
1121:1-Tricosanol
1044:1-Tridecanol
1000:(pelargonic)
927:
886:
878:
874:
869:Ethanolamine
648:
640:
525:
519:
502:
498:
492:
473:
469:
459:
434:
430:
420:
404:
392:. Retrieved
384:
375:
358:
354:
348:
334:Cocaethylene
299:
266:vinyl ethers
255:
224:
212:
189:
185:World War II
162:
134:
126:Applications
99:
83:
76:
62:nucleophilic
58:electrophile
21:
20:
18:
2557:Protonation
2474:Nonafluoro-
2421:Cholesterol
2398:Trialcohols
2268:Citronellol
2254:Monoterpene
2166:Deoxy sugar
1954:unsaturated
1641:Isopropanol
1568:Nonafluoro-
1496:Isopropanol
1115:1-Docosanol
1106:(arachidyl)
1038:1-Dodecanol
1032:1-Undecanol
394:17 February
234:fatty acids
102:tetrahedral
86:equilibrium
2646:Categories
2518:Hydrolysis
2503:haloalkane
2431:Lanosterol
2426:Ergosterol
2362:Dialcohols
2331:Patchoulol
2132:Galactitol
2062:Erythritol
1938:Tridecanol
1760:Erythritol
1661:1-Pentanol
1471:3-Pentanol
1466:2-Pentanol
1436:3-Heptanol
1431:2-Heptanol
1389:Tryptophol
1194:(lacceryl)
1104:1-Icosanol
1051:(myristyl)
1034:(hendecyl)
987:1-Heptanol
977:1-Pentanol
967:1-Propanol
922:Isobutanol
656:Tryptophol
630:Isobutanol
610:1-Propanol
499:Org. Synth
470:Org. Synth
340:References
240:in edible
208:explosives
137:polyesters
2545:Reactions
2527:Hydration
2340:Diterpene
2326:Nerolidol
2316:Bisabolol
2298:Terpineol
2152:Volemitol
1943:Undecanol
1897:Saturated
1798:Volemitol
1651:1-Butanol
1461:2-Octanol
1456:2-Nonanol
1446:3-Hexanol
1441:2-Hexanol
1421:2-Butanol
1408:Secondary
1240:saturated
1165:saturated
1117:(behenyl)
1088:saturated
1073:(stearyl)
1026:1-Decanol
1010:saturated
998:1-Nonanol
992:1-Octanol
982:1-Hexanol
972:1-Butanol
941:saturated
451:0016-2361
252:Synthesis
198:, though
181:biodiesel
173:biodiesel
96:Mechanism
38:catalyzed
28:R″ of an
2631:Category
2405:Glycerol
2342:alcohols
2321:Farnesol
2309:alcohols
2293:Rhodinol
2278:Linalool
2273:Geraniol
2256:alcohols
2214:Lactitol
2209:Maltitol
2193:Inositol
2186:alcohols
2168:alcohols
2122:Sorbitol
2112:Mannitol
2082:Arabitol
2072:Threitol
2052:Glycerol
1788:Sorbitol
1784:Mannitol
1764:Threitol
1746:Glycerol
1713:Glycerol
1621:Methanol
1519:Tertiary
1205:(geddyl)
1040:(lauryl)
1028:(capric)
994:(capryl)
957:Methanol
930:-Butanol
738:Methanol
728:alcohols
712:Methanol
585:Alcohols
308:See also
274:AcOCH=CH
204:glycerol
200:biolipid
192:patented
153:methanol
54:carbonyl
2522:epoxide
2414:Sterols
2283:Menthol
2263:Borneol
2219:Isomalt
2175:Fucitol
2102:Xylitol
2092:Ribitol
1933:Octanol
1928:Nonanol
1913:Decanol
1774:Xylitol
1631:Ethanol
1139:(ceryl)
962:Ethanol
909:Butanol
864:Ethanol
781:Ethanol
726:Primary
687:Ethanol
620:Ethanol
505:: 307.
286:ROCH=CH
196:Colgate
190:It was
171:) into
109:and/or
66:lipases
52:to the
34:alcohol
2531:alkene
2349:Phytol
2142:Iditol
1374:Prenol
540:
476:: 55.
449:
302:lipase
296:+ AcOH
272:ROH +
50:proton
2288:Nerol
30:ester
2476:tert
1586:tert
1578:tert
1570:tert
730:(1°)
649:tert
641:tert
538:ISBN
447:ISSN
431:Fuel
396:2021
258:enol
244:and
242:fats
151:and
143:and
46:base
42:acid
2596:of
2529:of
2520:of
2501:of
2022:— C
1246:— C
1171:— C
1094:— C
1016:— C
947:— C
530:doi
507:doi
478:doi
439:doi
410:doi
363:doi
236:of
44:or
2648::
2154:(C
2144:(C
2134:(C
2124:(C
2114:(C
2104:(C
2094:(C
2084:(C
2074:(C
2064:(C
2054:(C
2044:(C
2034:(C
1800:(C
1790:(C
1786:,
1776:(C
1766:(C
1762:,
1752:(C
1748:,
1738:(C
1675:16
1673:(C
1663:(C
1653:(C
1643:(C
1633:(C
1623:(C
1248:49
1244:40
1173:39
1169:30
1096:29
1092:20
1018:19
1014:10
536:.
528:.
503:89
501:.
474:82
472:.
468:.
445:.
435:89
433:.
429:.
387:.
383:.
359:93
357:.
304:.
284:⟶
268::
187:.
2158:)
2156:7
2148:)
2146:6
2138:)
2136:6
2128:)
2126:6
2118:)
2116:6
2108:)
2106:5
2098:)
2096:5
2088:)
2086:5
2078:)
2076:4
2068:)
2066:4
2058:)
2056:3
2048:)
2046:2
2038:)
2036:1
2024:7
2020:1
2018:C
1804:)
1802:7
1794:)
1792:6
1780:)
1778:5
1770:)
1768:4
1756:)
1754:3
1742:)
1740:2
1677:)
1667:)
1665:5
1657:)
1655:4
1647:)
1645:3
1637:)
1635:2
1627:)
1625:1
1242:C
1167:C
1090:C
1012:C
949:9
945:1
943:C
928:n
887:N
879:N
877:,
875:N
577:e
570:t
563:v
546:.
532::
513:.
509::
486:.
480::
453:.
441::
412::
398:.
369:.
365::
291:2
279:2
179:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
