24:
383:
238:
33:
42:
702:
611:
606:
698:
703:
848:
701:
1524:
1019:, an application that takes advantage of its structure. It is difunctional in terms of the amine groups and tetra functional with respect to the amine hydrogens. The great majority of the diamine is consumed by the production of
619:
586:
719:
673:
1007:
as the catalyst and adiponitrile that is diluted with hexamethylenediamine itself (as the solvent). This process operates without ammonia and at lower pressure and temperature.
1276:"Surface amine-functionalization of UHMWPE fiber by bio-inspired polydopamine and grafted hexamethylene diamine: Surface amine-functionalization of UHMWPE fiber by PDA and HMDA"
861:
992:. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include
1477:
Lainioti, Georgia Ch.; Savva, Panagiota; Druvari, Denisa; Avramidis, Pavlos; Panagiotaras, Dionisios; Karellou, Eva Iris
Eleftheria; Kallitsis, Joannis K. (2021-08-01).
704:
1062:
of 792–1127 mg/kg. Nonetheless, like other basic amines, it can cause serious burns and severe irritation. Such injuries were observed in the accident at the
422:
1203:
726:
32:
23:
555:
41:
1229:"Hexamethylene diamine-modified epoxidized natural rubber and its effect on cure characteristics and properties of natural rubber blends"
925:. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.
397:
1088:
669:
868:
659:
330:
1165:
Robert A. Smiley "Hexamethylenediamine" in
Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
361:
1135:
712:
610:
1028:
1204:"SRIC Report - Report 31C - Advances in Adiponitrile (ADN) and Hexamethylenediamine (HMDA) Processes | IHS Markit"
1479:"Cross-linking of antimicrobial polymers with hexamethylene diamine to prevent biofouling in marine applications"
245:
281:
275:
1185:(Synthesis of 1,3-diaminopropane and 1,6-diaminohexane from glutaric acid and suberic acid, respectively),
1182:
605:
233:
1083:
993:
175:
633:
598:
536:
1315:"Aqueous dispersion of polyurethane ionomers from hexamethylene diisocyanate and trimellitic anhydride"
1142:. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records
1478:
677:
54:
378:
89:
1585:
1506:
1389:
1362:"Synthesis and structure investigation of hexamethylene diisocyanate (HDI)-based polyisocyanates"
1342:
1295:
1256:
1056:
997:
665:
135:
1123:
1636:
1631:
1577:
1569:
1498:
1459:
1408:
1381:
1334:
1248:
195:
1561:
1490:
1451:
1420:
1373:
1326:
1287:
1240:
1166:
922:
888:
822:
525:
445:
339:
123:
934:
748:
264:
99:
382:
237:
155:
1275:
1183:"Synthese des 1,3-Diaminopropans und 1,6-Diaminohexans aus Glutarsäure resp. Korksäure"
839:
827:
647:
1613:
1602:
1439:
1625:
1510:
1455:
1393:
1260:
514:
504:
226:
1589:
1346:
1299:
1494:
1036:
1032:
1004:
977:
938:
1409:"Curing of epoxy resins. II. Curing of bisphenol a diglycidyl ether with diamines"
303:
1074:(UK) on 4 January 2007 in which 37 persons were injured, one of them seriously.
1044:
1024:
915:
812:
772:
738:
651:
1244:
1377:
1071:
1067:
1040:
817:
473:
186:
1573:
1502:
1463:
1385:
1338:
1252:
1228:
1170:
1549:
1424:
1361:
643:
350:
1581:
1274:
Hu, Juncheng; Feng, Xia; Liu, Zhengyi; Zhao, Yiping; Chen, Li (July 2017).
1020:
725:
718:
711:
684:
206:
215:
1360:
Hu, Jin; Chen, Zhuo; He, Yong; Huang, Hong; Zhang, Xinya (2017-05-01).
1330:
1016:
981:
908:
494:
290:
246:
1565:
1015:
Hexamethylenediamine is used almost exclusively for the production of
1314:
1291:
985:
912:
166:
838:
Except where otherwise noted, data are given for materials in their
639:
919:
314:
146:
122:
112:
1063:
989:
1438:
Dušek, K.; Pleštil, J.; Lednický, F.; Luňák, S. (1978-04-01).
366:
696:
509:
39 to 42 °C (102 to 108 °F; 312 to 315 K)
856:
1227:
Longseng, Rutchanon; Khaokong, Chuanpit (2020-12-01).
1313:Kim, C. K.; Kim, B. K.; Jeong, H. M. (1991-09-01).
302:
1055:Hexamethylenediamine is moderately toxic, with
1000:, and the triamine bis(hexamethylenetriamine).
700:
98:
8:
1413:Journal of Polymer Science: Polymer Symposia
1035:as a monomer feedstock in the production of
933:Hexamethylenediamine was first reported by
519:204.6 °C; 400.2 °F; 477.7 K
937:. It is produced by the hydrogenation of
381:
236:
194:
15:
1161:
1159:
1157:
976:The hydrogenation is conducted on molten
338:
1181:Curtius, Theodor and Clemm, Hans (1900)
1031:(HDI) is generated from this diamine by
406:InChI=1S/C6H16N2/c7-5-3-1-2-4-6-8/h1-8H2
1440:"Are cured epoxy resins inhomogeneous?"
1100:
427:
402:
377:
280:
214:
1136:"1,6-diaminohexane - Compound Summary"
227:
743:80 °C (176 °F; 353 K)
409:Key: NAQMVNRVTILPCV-UHFFFAOYSA-N
174:
154:
7:
1407:Luňák, S.; Dušek, K. (2007-03-08).
984:, typical catalysts being based on
293:
1550:"Toxicity of hexamethylenediamine"
1366:Research on Chemical Intermediates
14:
846:
609:
604:
463:
457:
40:
31:
22:
1039:. The diamine also serves as a
842:(at 25 °C , 100 kPa).
1495:10.1016/j.porgcoat.2021.106336
1280:Surface and Interface Analysis
451:
1:
1187:Journal für praktische Chemie
1089:2-Methylpentamethylenediamine
1554:Drug and Chemical Toxicology
1483:Progress in Organic Coatings
1456:10.1016/0032-3861(78)90243-4
1003:An alternative process uses
1548:Kennedy, Gerald L. (2005).
1319:Colloid and Polymer Science
761:or concentration (LD, LC):
1653:
1245:10.1007/s13726-020-00865-x
1029:hexamethylene diisocyanate
1378:10.1007/s11164-016-2795-1
836:
798:
757:
585:
580:
548:
438:
418:
393:
82:
65:
53:
48:
39:
30:
21:
1171:10.1002/14356007.a12_629
660:Precautionary statements
1425:10.1002/polc.5070530108
1233:Iranian Polymer Journal
1084:1,2-Diaminocyclohexane
1023:via condensation with
994:1,2-diaminocyclohexane
918:chain terminated with
707:
706:
17:Hexamethylenediamine
1529:www.sigmaaldrich.com
907:. The molecule is a
881:Hexamethylenediamine
689:(fire diamond)
489:Colourless crystals
55:Preferred IUPAC name
805:Related alkanamines
526:Solubility in water
481: g·mol
136:Beilstein Reference
18:
1331:10.1007/BF00657306
998:hexamethyleneimine
911:, consisting of a
891:with the formula H
885:hexane-1,6-diamine
869:Infobox references
799:Related compounds
708:
59:Hexane-1,6-diamine
16:
1566:10.1081/dct-39681
1239:(12): 1113–1121.
1193: : 189–211.
923:functional groups
877:Chemical compound
875:
874:
791:
785:
634:Hazard statements
362:CompTox Dashboard
282:1,6-diaminohexane
124:Interactive image
74:1,6-Hexanediamine
71:1,6-Diaminohexane
1644:
1616:
1611:
1605:
1600:
1594:
1593:
1545:
1539:
1538:
1536:
1535:
1521:
1515:
1514:
1474:
1468:
1467:
1435:
1429:
1428:
1404:
1398:
1397:
1372:(5): 2799–2816.
1357:
1351:
1350:
1310:
1304:
1303:
1292:10.1002/sia.6203
1271:
1265:
1264:
1224:
1218:
1217:
1215:
1214:
1200:
1194:
1179:
1173:
1163:
1152:
1151:
1149:
1147:
1140:PubChem Compound
1132:
1126:
1121:
1115:
1110:, 11th Edition,
1105:
889:organic compound
859:
853:
850:
849:
823:Methylhexanamine
790:(dermal, rabbit)
789:
783:
749:Explosive limits
728:
721:
714:
699:
679:
675:
671:
667:
653:
649:
645:
641:
613:
608:
572:
549:Thermochemistry
480:
465:
459:
453:
446:Chemical formula
386:
385:
370:
368:
342:
306:
295:
284:
265:Gmelin Reference
248:
240:
229:
218:
198:
178:
158:
126:
102:
44:
35:
26:
19:
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1651:
1647:
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1622:
1621:
1620:
1619:
1612:
1608:
1601:
1597:
1547:
1546:
1542:
1533:
1531:
1525:"MSDS - H11696"
1523:
1522:
1518:
1476:
1475:
1471:
1437:
1436:
1432:
1406:
1405:
1401:
1359:
1358:
1354:
1312:
1311:
1307:
1273:
1272:
1268:
1226:
1225:
1221:
1212:
1210:
1202:
1201:
1197:
1180:
1176:
1164:
1155:
1145:
1143:
1134:
1133:
1129:
1122:
1118:
1106:
1102:
1097:
1080:
1060:
1053:
1013:
972:
968:
964:
960:
956:
952:
948:
935:Theodor Curtius
931:
906:
902:
898:
894:
878:
871:
866:
865:
864: ?)
855:
851:
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843:
832:
806:
794:
776:
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733:
732:
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730:
723:
716:
709:
705:
697:
662:
636:
622:
601:
573:
570:
564:
560:
557:
556:Std enthalpy of
528:
478:
468:
462:
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448:
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431:
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425:
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410:
407:
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138:
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116:
105:
92:
78:
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61:
60:
12:
11:
5:
1650:
1648:
1640:
1639:
1634:
1624:
1623:
1618:
1617:
1606:
1595:
1540:
1516:
1469:
1450:(4): 393–397.
1430:
1399:
1352:
1325:(9): 895–900.
1305:
1286:(7): 640–646.
1266:
1219:
1195:
1189:, 2nd series,
1174:
1153:
1127:
1116:
1099:
1098:
1096:
1093:
1092:
1091:
1086:
1079:
1076:
1058:
1052:
1049:
1012:
1009:
974:
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962:
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954:
950:
946:
930:
927:
904:
900:
896:
892:
876:
873:
872:
867:
845:
844:
840:standard state
837:
834:
833:
831:
830:
828:Tuaminoheptane
825:
820:
815:
809:
807:
804:
801:
800:
796:
795:
793:
792:
786:
779:
777:
768:
766:
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762:
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741:
735:
734:
724:
717:
710:
695:
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692:
690:
681:
680:
674:P305+P351+P338
663:
658:
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637:
632:
629:
628:
623:
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27:
13:
10:
9:
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4:
3:
2:
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1234:
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1223:
1220:
1209:
1208:ihsmarkit.com
1205:
1199:
1196:
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1178:
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1154:
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1128:
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1120:
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1101:
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1085:
1082:
1081:
1077:
1075:
1073:
1069:
1065:
1061:
1050:
1048:
1046:
1042:
1041:cross-linking
1038:
1034:
1030:
1026:
1022:
1018:
1010:
1008:
1006:
1001:
999:
995:
991:
987:
983:
980:diluted with
979:
944:
943:
942:
940:
936:
928:
926:
924:
921:
917:
914:
913:hexamethylene
910:
890:
886:
882:
870:
863:
858:
841:
835:
829:
826:
824:
821:
819:
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515:Boiling point
513:
512:
508:
506:
505:Melting point
503:
502:
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492:
488:
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477:
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379:DTXSID5024922
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232:
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228:ECHA InfoCard
225:
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38:
34:
29:
25:
20:
1609:
1598:
1560:(1): 15–33.
1557:
1553:
1543:
1532:. Retrieved
1528:
1519:
1486:
1482:
1472:
1447:
1443:
1433:
1419:(1): 45–55.
1416:
1412:
1402:
1369:
1365:
1355:
1322:
1318:
1308:
1283:
1279:
1269:
1236:
1232:
1222:
1211:. Retrieved
1207:
1198:
1190:
1186:
1177:
1144:. Retrieved
1139:
1130:
1119:
1111:
1107:
1103:
1054:
1045:epoxy resins
1037:polyurethane
1033:phosgenation
1027:. Otherwise
1014:
1011:Applications
1005:Raney nickel
1002:
978:adiponitrile
975:
939:adiponitrile
932:
884:
880:
879:
758:
685:
625:
587:
576:−205 kJ mol
565:
538:
315:RTECS number
176:ChEMBL303004
83:Identifiers
66:Other names
1108:Merck Index
1025:adipic acid
916:hydrocarbon
813:Pentylamine
784:(oral, rat)
773:median dose
759:Lethal dose
739:Flash point
620:Signal word
486:Appearance
439:Properties
234:100.004.255
156:CHEBI:39618
1626:Categories
1534:2019-02-19
1489:: 106336.
1213:2019-02-19
1095:References
1072:Billingham
1068:Seal Sands
953:CN + 4 H
818:Cadaverine
788:1.11 g kg
782:750 mg kg
599:Pictograms
499:0.84 g/mL
474:Molar mass
340:ZRA5J5B2QW
187:ChemSpider
111:3D model (
90:CAS Number
1574:0148-0545
1511:236243177
1503:0300-9440
1464:0032-3861
1394:100565578
1386:1568-5675
1339:1435-1536
1261:221824894
1253:1735-5265
1043:agent in
929:Synthesis
887:, is the
753:0.7–6.3%
590:labelling
558:formation
351:UN number
322:MO1180000
255:204-679-6
247:EC Number
1637:Diamines
1632:Monomers
1614:BBC News
1603:BBC News
1590:84650430
1582:15720033
1347:94481368
1300:99804759
1078:See also
1066:site in
1021:nylon 66
1017:polymers
686:NFPA 704
581:Hazards
531:490 g L
430:NCCCCCCN
207:DrugBank
196:13835579
141:1098307
100:124-09-4
1444:Polymer
1070:, near
982:ammonia
909:diamine
862:what is
860: (
495:Density
479:116.208
291:PubChem
216:DB03260
1588:
1580:
1572:
1509:
1501:
1462:
1392:
1384:
1345:
1337:
1298:
1259:
1251:
1146:29 May
1051:Safety
986:cobalt
957:→ H
857:verify
854:
626:Danger
544:0.386
423:SMILES
167:ChEMBL
49:Names
1586:S2CID
1507:S2CID
1390:S2CID
1343:S2CID
1296:S2CID
1257:S2CID
945:NC(CH
920:amine
398:InChI
355:2280
304:16402
270:2578
147:ChEBI
113:JSmol
1578:PMID
1570:ISSN
1499:ISSN
1460:ISSN
1382:ISSN
1335:ISSN
1249:ISSN
1148:2012
1124:MSDS
1112:4614
1064:BASF
990:iron
988:and
961:N(CH
895:N(CH
678:P310
670:P280
666:P261
652:H335
648:H314
644:H312
640:H302
537:log
331:UNII
276:MeSH
1562:doi
1491:doi
1487:157
1452:doi
1421:doi
1374:doi
1327:doi
1323:269
1288:doi
1241:doi
1167:doi
883:or
588:GHS
569:298
367:EPA
294:CID
1628::
1584:.
1576:.
1568:.
1558:28
1556:.
1552:.
1527:.
1505:.
1497:.
1485:.
1481:.
1458:.
1448:19
1446:.
1442:.
1417:53
1415:.
1411:.
1388:.
1380:.
1370:43
1368:.
1364:.
1341:.
1333:.
1321:.
1317:.
1294:.
1284:49
1282:.
1278:.
1255:.
1247:.
1237:29
1235:.
1231:.
1206:.
1191:62
1156:^
1138:.
1059:50
1057:LD
1047:.
996:,
969:NH
941::
903:NH
769:50
767:LD
676:,
672:,
668:,
650:,
646:,
642:,
592::
561:(Δ
461:16
1592:.
1564::
1537:.
1513:.
1493::
1466:.
1454::
1427:.
1423::
1396:.
1376::
1349:.
1329::
1302:.
1290::
1263:.
1243::
1216:.
1169::
1150:.
1114:.
971:2
967:6
965:)
963:2
959:2
955:2
951:4
949:)
947:2
905:2
901:6
899:)
897:2
893:2
852:N
775:)
771:(
727:0
720:2
713:3
571:)
566:H
563:f
539:P
467:2
464:N
458:H
455:6
452:C
369:)
365:(
115:)
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