1461:
291:
172:
1477:
51:
484:
469:
1379:
1187:
479:
474:
42:
728:
1350:). Besides the rosin resins with about 60% share of world consumption, long chain diketenes called alkylketene dimers (AKD) are with 16% share the most important synthetic paper sizes, they are usually used in concentrations of 0.15%, meaning 1.5 kg solid AKD/
1193:
Diketene is an important industrial intermediate used for the production of acetoacetate esters and amides as well as substituted 1-phenyl-3-methylpyrazolones. The latter are used in the manufacture of dyestuffs and pigments. A typical reaction is:
492:
449:
1321:
1128:
1159:
971:
1662:
Rafael Gómez-Bombarelli; Marina González-Pérez; María Teresa Pérez-Prior; José A. Manso; Emilio Calle; Julio Casado (2008). "Kinetic Study of the
Neutral and Base Hydrolysis of Diketene".
634:
1838:
Rafael Gómez-Bombarelli; Marina González-Pérez; María Teresa Pérez-Prior; José A. Manso; Emilio Calle; Julio Casado (2008). "Chemical
Reactivity and Biological Activity of Diketene".
741:
622:
1767:
340:
1460:
1823:
630:
558:
1705:
1691:
1601:
1617:
Susana Breda; Igor Reva; Rui Fausto (2012). "UV Induced
Unimolecular Photochemistry of Diketene Isolated in Cryogenic Inert Matrices".
1788:
1200:
1177:
to the corresponding acetoacetic acid derivatives. The process is sometimes called acetoacetylation. An example is the reaction with
305:
1720:
Kiran Kumar
Solingapuram Sai; Thomas M. Gilbert; Douglas A. Klumpp (2007). "Knorr Cyclizations and Distonic Superelectrophiles".
1483:
The industrial synthesis of the sweetener acesulfam-K is based on the reaction of diketene with sulfamic acid and cyclization by
1132:
614:
1023:
626:
1378:
602:
748:
610:
552:
238:
850:
1880:
269:
1418:
674:
483:
1828: Process for the preparation of the non-toxic salts of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxide.
1571:
1186:
179:
797:
704:
570:
662:
468:
646:
473:
167:
578:
1445:
1386:
506:
478:
461:
1468:
129:
1819:
1347:
1628:
650:
638:
69:
1365:) to give the corresponding acid chlorides and subsequent elimination of HCl by amines (for example
1840:
1664:
1433:
1170:
594:
286:
95:
566:
1544:
1513:
1003:
999:
678:
586:
1804:
1548:
1508:
582:
1528:
598:
1890:
1885:
1856:
1784:
1738:
1701:
1644:
1597:
1455:
Exemplary for the synthesis of arylides by the reaction of diketenes with aromatic amines is:
1429:
1331:
821:
768:
50:
1848:
1776:
1730:
1672:
1636:
1619:
1589:
1540:
1476:
1441:
1362:
980:
764:
670:
363:
654:
247:
149:
1484:
1406:
1390:
618:
1357:
The preparation of AKD is carried out by chlorination of long chain fatty acids (such as
642:
105:
1632:
290:
171:
1327:
719:
1017:
At one time acetic anhydride was prepared by the reaction of ketene with acetic acid:
1874:
1722:
1498:
1437:
1366:
424:
414:
160:
1584:
Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes".
686:
41:
1358:
590:
211:
1755:
Ashford's
Dictionary of Industrial Chemicals, Third Edition, 2011, pages 3241-2.
1440:(especially toxic to bees). Diketenes react with substituted aromatic amines to
1414:
1394:
693:
544:
1551:, diketene is inactive as a carcinogen, possibly due to the instability of its
666:
1552:
1503:
1410:
1402:
1007:
562:
391:
140:
17:
1780:
1593:
1772:
1697:
1518:
984:
606:
574:
434:
258:
1860:
1742:
1648:
512:
976:
Alkylated ketenes also dimerize with ease and form substituted diketenes.
1523:
1342:
Diketenes with two alkyl chains are used in the manufacture of paper for
801:
528:
1449:
1370:
817:
813:
404:
198:
180:
1852:
1734:
1640:
524:
1676:
1343:
1178:
844:
Heating or irradiation with UV light regenerates the ketene monomer:
833:
1693:
1467:
Aromatic diazonium coupling with arylides to form azo dyes, such as
718:
Except where otherwise noted, data are given for materials in their
520:
1174:
1011:
540:
516:
222:
128:
118:
1316:{\displaystyle {\ce {ArNH2 + (CH2CO)2 -> ArNHC(O)CH2C(O)CH3}}}
682:
536:
532:
1398:
1351:
832:
Diketene is produced on commercial scale by dimerization of
658:
274:
49:
40:
990:
1309:
1282:
1252:
1236:
1215:
1123:{\displaystyle {\ce {H2C=C=O + CH3COOH -> (CH3CO)2O}}}
1113:
1097:
1073:
1038:
956:
899:
883:
870:
736:
923:
1203:
1135:
1026:
853:
1765:
Hunger, K.; Herbst, W. (2012). "Pigments, Organic".
1346:
of paper in order to improve their printability (by
1154:{\displaystyle \qquad \Delta H={\text{−63 kJ/mol}}}
1315:
1153:
1122:
987:in water is approximately 45 min. a 25 °C at
966:{\displaystyle {\ce {(C2H2O)2 <=> 2 CH2CO}}}
965:
931:
930:
913:
912:
210:
104:
1768:Ullmann's Encyclopedia of Industrial Chemistry
1586:Ullmann's Encyclopedia of Industrial Chemistry
979:Diketene readily hydrolyzes in water forming
8:
289:
170:
148:
29:
1308:
1303:
1288:
1281:
1276:
1261:
1251:
1246:
1235:
1230:
1222:
1214:
1209:
1204:
1202:
1146:
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1112:
1107:
1096:
1091:
1083:
1072:
1067:
1052:
1044:
1037:
1032:
1027:
1025:
1006:(AKDs), are used industrially to improve
955:
950:
945:
932:
925:
924:
922:
914:
907:
905:
904:
902:
898:
893:
882:
877:
869:
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856:
854:
852:
246:
1326:These acetoacetamides are precursors to
807:
792:
788:
781:
777:
773:
1564:
906:
345:
310:
285:
1696:(in German) (6th ed.), Weinheim:
429:127 °C (261 °F; 400 K)
161:
27:Organic compound with formula (CH2CO)2
317:Key: WASQWSOJHCZDFK-UHFFFAOYSA-N
314:InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
7:
1361:, using chlorinating agents such as
785:, and which is sometimes written as
698:33 °C (91 °F; 306 K)
419:−7 °C (19 °F; 266 K)
324:InChI=1/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
1413:but are now largely obsolete. With
1385:Furthermore, diketenes are used as
327:Key: WASQWSOJHCZDFK-UHFFFAOYAM
201:
1539:Despite its high reactivity as an
1494:Drugs made from Diketene include:
1137:
25:
1543:, and unlike analogue β-lactones
1448:for mostly yellow, orange or red
1475:
1459:
1436:to the highly toxic insecticide
1377:
1185:
726:
482:
477:
472:
467:
375:
1136:
722:(at 25 °C , 100 kPa).
1295:
1289:
1268:
1262:
1255:
1242:
1223:
1103:
1084:
1079:
933:
908:
889:
857:
812:. Diketene is a member of the
381:
369:
1:
1405:are formed from substituted
824:. It is a colorless liquid.
1806:Sizing Agents in Fine Paper
998:Certain diketenes with two
36:
1907:
1690:Arpe, Hans-Jürgen (2007),
1428:which is chlorinated with
1169:Diketene also reacts with
716:
448:
443:
356:
336:
301:
88:
80:
74:4-Methylideneoxetan-2-one
68:
63:
35:
1781:10.1002/14356007.a20_371
1594:10.1002/14356007.a15_063
816:family. It is used as a
553:Precautionary statements
83:γ-Methylenepropiolactone
1809:Retrieved 1 March 2012.
1426:-dimethylacetoacetamide
1444:, which are important
1389:in the manufacture of
1317:
1155:
1124:
967:
54:
45:
1318:
1156:
1125:
968:
53:
44:
1417:diketenes reacts to
1409:, they were used as
1201:
1133:
1024:
851:
70:Preferred IUPAC name
1841:Chem. Res. Toxicol.
1665:J. Phys. Org. Chem.
1633:2012JPCA..116.2131B
1434:trimethyl phosphite
1373:or other solvents:
1311:
1284:
1254:
1238:
1217:
1115:
1099:
1075:
1040:
1004:alkyl ketene dimers
958:
919:
901:
885:
872:
796:. It is formed by
399: g·mol
32:
1881:Alkene derivatives
1700:, pp. 200–1,
1574:E III/IV 17: 4297.
1452:and azo pigments.
1332:diarylide pigments
1313:
1299:
1272:
1226:
1221:
1205:
1151:
1120:
1087:
1082:
1063:
1028:
963:
946:
938:
873:
860:
855:
749:Infobox references
55:
46:
30:
1853:10.1021/tx800153j
1847:(10): 1964–1969.
1803:Wolf S. Schultz:
1735:10.1021/jo7013092
1729:(25): 9761–9764.
1707:978-3-527-31540-6
1641:10.1021/jp211249k
1603:978-3-527-30385-4
1469:Pigment Yellow 74
1442:acetoacetanilides
1432:and reacted with
1430:sulfuryl chloride
1302:
1294:
1287:
1275:
1267:
1260:
1241:
1229:
1208:
1149:
1148:−63 kJ/mol
1118:
1102:
1090:
1078:
1066:
1059:
1051:
1043:
1031:
961:
949:
940:
888:
876:
863:
822:organic chemistry
769:molecular formula
757:Chemical compound
755:
754:
507:Hazard statements
270:CompTox Dashboard
130:Interactive image
59:
58:
16:(Redirected from
1898:
1865:
1864:
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1710:
1687:
1681:
1680:
1677:10.1002/poc.1483
1659:
1653:
1652:
1627:(9): 2131–2140.
1620:J. Phys. Chem. A
1614:
1608:
1607:
1581:
1575:
1569:
1541:alkylating agent
1479:
1463:
1407:phenylhydrazines
1381:
1363:thionyl chloride
1348:hydrophobization
1322:
1320:
1319:
1314:
1312:
1310:
1307:
1300:
1298:
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1234:
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1206:
1189:
1165:Acetoacetylation
1160:
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1147:
1129:
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1119:
1116:
1114:
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1064:
1057:
1056:
1049:
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1041:
1039:
1036:
1029:
1000:aliphatic chains
994:
981:acetoacetic acid
972:
970:
969:
964:
962:
959:
957:
954:
947:
941:
939:
937:
936:
929:
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903:
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874:
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868:
861:
811:
795:
784:
765:organic compound
739:
733:
730:
729:
688:
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672:
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534:
530:
526:
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518:
514:
486:
481:
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471:
398:
383:
377:
371:
364:Chemical formula
294:
293:
278:
276:
250:
214:
203:
182:
174:
163:
152:
132:
108:
37:
33:
21:
1906:
1905:
1901:
1900:
1899:
1897:
1896:
1895:
1871:
1870:
1869:
1868:
1837:
1836:
1832:
1824:
1818:
1817:
1813:
1802:
1798:
1791:
1764:
1763:
1759:
1754:
1750:
1719:
1718:
1714:
1708:
1689:
1688:
1684:
1661:
1660:
1656:
1616:
1615:
1611:
1604:
1583:
1582:
1578:
1570:
1566:
1561:
1549:β-butyrolactone
1537:
1490:
1485:sulfur trioxide
1391:pharmaceuticals
1340:
1199:
1198:
1167:
1131:
1130:
1022:
1021:
988:
849:
848:
842:
830:
809:
805:
794:
790:
786:
783:
779:
775:
771:
758:
751:
746:
745:
744: ?)
735:
731:
727:
723:
709:
706:
555:
509:
495:
464:
396:
386:
380:
374:
366:
352:
349:
344:
343:
332:
329:
328:
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319:
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315:
309:
308:
297:
279:
272:
253:
233:
217:
204:
192:
155:
135:
122:
111:
98:
84:
76:
75:
28:
23:
22:
15:
12:
11:
5:
1904:
1902:
1894:
1893:
1888:
1883:
1873:
1872:
1867:
1866:
1830:
1811:
1796:
1790:978-3527306732
1789:
1757:
1748:
1712:
1706:
1682:
1671:(5): 438–442.
1654:
1609:
1602:
1576:
1563:
1562:
1560:
1557:
1536:
1533:
1532:
1531:
1526:
1521:
1516:
1511:
1506:
1501:
1488:
1481:
1480:
1465:
1464:
1401:. For example
1383:
1382:
1339:
1336:
1328:arylide yellow
1324:
1323:
1306:
1297:
1291:
1279:
1270:
1264:
1257:
1249:
1244:
1233:
1225:
1220:
1212:
1191:
1190:
1166:
1163:
1162:
1161:
1145:
1142:
1139:
1110:
1105:
1094:
1086:
1081:
1070:
1062:
1055:
1047:
1035:
1008:hydrophobicity
974:
973:
953:
944:
935:
928:
917:
910:
896:
891:
880:
867:
859:
841:
838:
829:
826:
756:
753:
752:
747:
725:
724:
720:standard state
717:
714:
713:
710:
703:
700:
699:
696:
690:
689:
635:P305+P351+P338
623:P303+P361+P353
556:
551:
548:
547:
510:
505:
502:
501:
496:
491:
488:
487:
465:
460:
457:
456:
446:
445:
441:
440:
437:
431:
430:
427:
421:
420:
417:
411:
410:
407:
401:
400:
394:
388:
387:
384:
378:
372:
367:
362:
359:
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354:
353:
351:
350:
347:
339:
338:
337:
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331:
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295:
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261:
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90:
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82:
78:
77:
73:
72:
66:
65:
61:
60:
57:
56:
47:
26:
24:
18:Acetoacetylate
14:
13:
10:
9:
6:
4:
3:
2:
1903:
1892:
1889:
1887:
1884:
1882:
1879:
1878:
1876:
1862:
1858:
1854:
1850:
1846:
1843:
1842:
1834:
1831:
1821:
1815:
1812:
1808:
1807:
1800:
1797:
1792:
1786:
1782:
1778:
1774:
1770:
1769:
1761:
1758:
1752:
1749:
1744:
1740:
1736:
1732:
1728:
1725:
1724:
1723:J. Org. Chem.
1716:
1713:
1709:
1703:
1699:
1695:
1694:
1686:
1683:
1678:
1674:
1670:
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1666:
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1613:
1610:
1605:
1599:
1595:
1591:
1587:
1580:
1577:
1573:
1568:
1565:
1558:
1556:
1554:
1550:
1546:
1545:propiolactone
1542:
1534:
1530:
1527:
1525:
1522:
1520:
1517:
1515:
1512:
1510:
1507:
1505:
1502:
1500:
1499:Lercanidipine
1497:
1496:
1495:
1492:
1486:
1478:
1474:
1473:
1472:
1470:
1462:
1458:
1457:
1456:
1453:
1451:
1447:
1443:
1439:
1438:monocrotophos
1435:
1431:
1427:
1425:
1421:
1416:
1412:
1408:
1404:
1400:
1396:
1392:
1388:
1387:intermediates
1380:
1376:
1375:
1374:
1372:
1368:
1367:triethylamine
1364:
1360:
1355:
1353:
1349:
1345:
1337:
1335:
1333:
1329:
1304:
1277:
1247:
1231:
1218:
1210:
1197:
1196:
1195:
1188:
1184:
1183:
1182:
1180:
1179:2-aminoindane
1176:
1172:
1164:
1143:
1140:
1108:
1092:
1068:
1060:
1053:
1045:
1033:
1020:
1019:
1018:
1015:
1013:
1009:
1005:
1001:
996:
992:
986:
982:
977:
951:
942:
926:
915:
894:
878:
865:
847:
846:
845:
839:
837:
835:
827:
825:
823:
819:
815:
803:
799:
770:
766:
762:
750:
743:
738:
721:
715:
711:
708:
702:
701:
697:
695:
692:
691:
557:
554:
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549:
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425:Boiling point
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418:
416:
415:Melting point
413:
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408:
406:
403:
402:
395:
393:
390:
389:
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831:
798:dimerization
760:
759:
705:Autoignition
498:
450:
348:O=C1OC(=C)C1
223:RTECS number
89:Identifiers
81:Other names
1553:DNA adducts
1514:Butoctamide
1415:methylamine
1403:pyrazolones
707:temperature
694:Flash point
493:Signal word
439:0.88 mPa.s
409:1.09 g cm
357:Properties
168:100.010.562
1875:Categories
1820:EP 0218076
1559:References
1509:Olaquindox
1504:Manidipine
1446:precursors
1411:analgetics
1002:, such as
828:Production
462:Pictograms
392:Molar mass
248:0DZ97C3Z7D
141:ChemSpider
117:3D model (
96:CAS Number
1773:Wiley-VCH
1698:Wiley-VCH
1572:Beilstein
1529:Ipramidil
1519:Ketazolam
1256:⟶
1138:Δ
1080:⟶
985:half-life
934:⇀
927:−
916:−
909:↽
840:Reactions
767:with the
679:P403+P235
675:P403+P233
671:P370+P378
663:P332+P313
631:P304+P340
627:P304+P312
619:P302+P352
615:P301+P312
611:P301+P310
453:labelling
435:Viscosity
259:UN number
230:RQ8225000
189:211-617-1
181:EC Number
31:Diketene
1891:Lactones
1886:Oxetanes
1861:18759502
1743:17999519
1649:22273010
1524:Carboxin
1450:azo dyes
1171:alcohols
761:Diketene
444:Hazards
106:674-82-8
1629:Bibcode
1371:toluene
1354:paper.
989:2 <
818:reagent
814:oxetane
742:what is
740: (
405:Density
199:PubChem
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1535:Safety
1344:sizing
1175:amines
993:< 7
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834:ketene
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763:is an
737:verify
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499:Danger
397:84.074
341:SMILES
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1259:ArNHC
1012:paper
810:C=C=O
306:InChI
263:2521
212:12661
150:12140
119:JSmol
1857:PMID
1785:ISBN
1739:PMID
1702:ISBN
1645:PMID
1598:ISBN
1547:and
1399:dyes
1397:and
1330:and
1207:ArNH
1173:and
1077:COOH
712:275
687:P501
683:P405
667:P362
659:P330
655:P321
651:P320
647:P312
643:P311
639:P310
607:P284
603:P280
599:P271
595:P270
591:P264
587:P261
583:P260
579:P243
575:P242
571:P241
567:P240
563:P233
559:P210
545:H335
541:H332
537:H331
533:H330
529:H318
525:H315
521:H302
517:H301
513:H226
239:UNII
1849:doi
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991:pH
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