27:
1049:
1034:
36:
205:
490:
485:
908:
1429:
1126:
MDI, like the other isocyanates, is an allergen and sensitizer. Persons developing sensitivity to isocyanates may have dangerous systemic reactions to extremely small exposures, including respiratory failure. Handling MDI requires strict engineering controls and personal protective equipment. It is
1070:
The positions of the isocyanate groups influences their reactivity. In 4,4′-MDI, the two isocyanate groups are equivalent but in 2,4′-MDI the two groups display highly differing reactivities. The group at the 4-position is approximately four times more reactive than the group at the 2-position due to
1075:
1043:
to form a mixture of isocyanates, the isomer ratio being determined by the isomeric composition of the diamine. Two different reaction mechanisms for this transformation are possible, namely "phosgenations first" and "step-wise phosgenations".
498:
465:
616:
1187:
1160:
779:
921:
612:
1362:
1010:, Kumho Mitsui Chemicals. All major producers of MDI are members of the International Isocyanate Institute, whose aim is the promotion of the safe handling of MDI and
1284:
319:
26:
1396:
608:
1427:, Smith, A. K.; Goddard, R. J.; Paulsen, E. J. L., "MDI-based polyurethane prepolymer with low monomeric MDI content", issued 2005-04-26
135:
1501:
1118:
4,4′-MDI is also used as an industrial strength adhesive, which is available to end consumers as various high-strength bottled glue preparations.
1238:
142:
1379:
1536:
1108:
648:
294:
963:. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. This isomer is also known as
604:
1292:
588:
1313:
Boros, R. Zsanett; Koós, Tamás; Wafaa, Cheikh; Nehéz, Károly; Farkas, László; Viskolcz, Béla; Szőri, Milán (2018-08-16).
928:
564:
534:
554:
271:
640:
489:
584:
660:
1048:
484:
1026:
870:
803:
790:
1033:
546:
212:
1407:
1202:
865:
644:
596:
636:
1059:
875:
624:
35:
620:
200:
1256:
1445:"Preventing Asthma and Death from MDI Exposure During Spray-on Truck Bed Liner and Related Applications"
1074:
987:
959:
are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and
512:
477:
1424:
1526:
1314:
1100:
1011:
1003:
999:
860:
48:
975:. It is the most produced diisocyanate, accounting for 61.3% of the global market in the year 2000.
101:
1454:. The National Institute for Occupational Safety and Health. DHHS (NIOSH) Publication No. 2006–149
1058:, and a mixture of MDI isomers which has a low 2,4′ isomer content. Further purification entails
1342:
1092:
572:
1480:
628:
568:
983:
Total world production of MDI and polymeric MDI is over 7.5 million tonnes per year (in 2017).
580:
1531:
1375:
1334:
1234:
1007:
592:
1511:
1444:
1367:
1326:
1255:
431:
347:
632:
280:
204:
600:
182:
1475:
111:
656:
162:
1488:, from the website of the National Institute for Occupational Safety and Health (NIOSH)
899:
560:
442:
1520:
1346:
420:
410:
193:
1502:
MDI and the
Environment - 2005 presentation by Center for the Polyurethanes Industry
1054:
Distillation of the mixture gives a mixture of oligomeric polyisocyanates, known as
668:
303:
InChI=1S/C15H10N2O2/c18-10-16-14-5-1-12(2-6-14)9-13-3-7-15(8-4-13)17-11-19/h1-8H,9H2
1096:
1088:
1022:
972:
890:
576:
522:
1330:
244:
1496:
1485:
1128:
948:
735:
717:
699:
675:
538:
652:
1156:
952:
851:
374:
173:
1371:
1338:
1315:"A theoretical study on the phosgenation of methylene diphenyl diamine (MDA)"
1179:
526:
1112:
1104:
542:
1040:
1029:
and other diamine precursors, as well as their corresponding polyamines:
991:
1018:
396:
231:
213:
518:
968:
956:
898:
Except where otherwise noted, data are given for materials in their
1127:
a potentially violently reactive material towards water and other
530:
255:
153:
141:
134:
124:
77:
995:
832:
664:
1506:
1184:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1087:
The major application of 4,4′-MDI is the production of rigid
1073:
1017:
The first step of the production of MDI is the reaction of
1491:
1203:"4,4'-Diphenylmethane diisocyanate | C15H10N2O2 - PubChem"
1099:
worldwide, as well as buildings. Typical polyols used are
916:
1492:
Isofact
American Chemistry Council Diisocyanates Panel
1512:
1481:
1257:"C&EN's Global Top 50 chemical companies of 2018"
1188:
National
Institute for Occupational Safety and Health
1161:
National
Institute for Occupational Safety and Health
1025:, using hydrochloric acid as a catalyst to produce
1091:. These rigid polyurethane foams are good thermal
1497:Azom Chemical database on Polyurethane chemistry
243:
110:
1404:Eco-Profiles of the European Plastics Industry
1363:Ullmann's Encyclopedia of Industrial Chemistry
1360:Six, C.; Richter, F. "Isocyanates, Organic".
1014:in the workplace, community and environment.
8:
1443:Almaguer, D.; et al. (September 2006).
1486:NIOSH Safety and Health Topic: Isocyanates
1406:. Brussels: PlasticsEurope. Archived from
203:
181:
18:
1224:
1222:
279:
1155:NIOSH Pocket Guide to Chemical Hazards.
1476:International Chemical Safety Card 0298
1140:
324:
299:
1174:
1172:
1170:
1150:
1148:
1146:
1144:
1039:Then, these diamines are treated with
425:314 °C (597 °F; 587 K)
194:
53:1,1′-Methylenebis(4-isocyanatobenzene)
986:As of 2019, the largest producer was
415:40 °C (104 °F; 313 K)
327:O=C=NC(C=C2)=CC=C2CC1=CC=C(N=C=O)C=C1
306:Key: UPMLOUAZCHDJJD-UHFFFAOYSA-N
161:
20:4,4′-Methylene diphenyl diisocyanate
7:
1254:Tullo, Alexander H. (29 July 2019).
1095:and used in nearly all freezers and
71:4,4′-Methylene diphenyl diisocyanate
234:
1507:International Isocyanate Institute
1066:Reactivity of the isocyanate group
83:Methylene bis(4-phenyl isocyanate)
14:
1109:poly(tetramethylene ether) glycol
332:O=C=N\c1ccc(cc1)Cc2ccc(\N=C=O)cc2
74:4,4′-Diphenylmethane diisocyanate
1180:"Methylene bisphenyl isocyanate"
1047:
1032:
906:
680:212–214 °C (Cleveland open cup)
488:
483:
34:
25:
1262:Chemical & Engineering News
941:Methylene diphenyl diisocyanate
902:(at 25 °C , 100 kPa).
65:Bis(4-isocyanatophenyl)methane
1:
1229:Randall, D.; Lee, S. (2003).
784:(US health exposure limits):
1331:10.1016/j.cplett.2018.06.024
990:. Other major producers are
1264:. Vol. 97, no. 30
1062:of the MDI isomer mixture.
688:or concentration (LD, LC):
391:White or pale yellow solid
1553:
871:Hexamethylene diisocyanate
1397:"Polyurethane rigid foam"
896:
843:
778:
724:31,690 mg/kg (rat, oral)
706:2200 mg/kg (mouse, oral)
684:
464:
459:
340:
315:
290:
94:
59:
47:
42:
33:
24:
1537:IARC Group 3 carcinogens
1372:10.1002/14356007.a14_611
1319:Chemical Physics Letters
1207:pubchem.ncbi.nlm.nih.gov
866:Naphthalene diisocyanate
555:Precautionary statements
1366:. Weinheim: Wiley-VCH.
1078:MDI isomers and polymer
1027:4,4'-Methylenedianiline
876:Isophorone diisocyanate
1289:ICIS Chemical Business
1283:Gal, J. (2012-02-20).
1231:The Polyurethanes Book
1079:
971:in the manufacture of
797:C 0.2 mg/m (0.02 ppm)
68:1-Isocyanato-4-benzene
1425:US patent 6884904
1395:Boustead, I. (2005).
1077:
988:Wanhua Chemical Group
222:4,4'-: 202-966-0
16:Aromatic diisocyanate
1101:polyethylene adipate
861:Toluene diisocyanate
736:median concentration
49:Preferred IUPAC name
1233:. New York: Wiley.
432:Solubility in water
383:g/mol
21:
1080:
1071:steric hindrance.
967:. MDI reacts with
929:Infobox references
844:Related compounds
835:(Immediate danger)
19:
1240:978-0-470-85041-1
937:Chemical compound
935:
934:
886:Related compounds
513:Hazard statements
143:Interactive image
136:Interactive image
1544:
1463:
1462:
1460:
1459:
1449:
1440:
1434:
1433:
1432:
1428:
1421:
1415:
1414:
1412:
1401:
1392:
1386:
1385:
1357:
1351:
1350:
1310:
1304:
1303:
1301:
1300:
1291:. Archived from
1280:
1274:
1273:
1271:
1269:
1259:
1251:
1245:
1244:
1226:
1217:
1216:
1214:
1213:
1198:
1192:
1191:
1176:
1165:
1164:
1152:
1051:
1036:
919:
913:
910:
909:
825:
821:
817:
813:
770:
763:
759:
752:
748:
718:lowest published
670:
666:
662:
658:
654:
650:
646:
642:
638:
634:
630:
626:
622:
618:
614:
610:
606:
602:
598:
594:
590:
586:
582:
578:
574:
570:
566:
562:
548:
544:
540:
536:
532:
528:
524:
520:
492:
487:
454:
450:
404:
382:
348:Chemical formula
283:
247:
236:
215:
207:
196:
185:
165:
145:
138:
114:
38:
29:
22:
1552:
1551:
1547:
1546:
1545:
1543:
1542:
1541:
1517:
1516:
1472:
1467:
1466:
1457:
1455:
1447:
1442:
1441:
1437:
1430:
1423:
1422:
1418:
1410:
1399:
1394:
1393:
1389:
1382:
1359:
1358:
1354:
1312:
1311:
1307:
1298:
1296:
1285:"To the Rescue"
1282:
1281:
1277:
1267:
1265:
1253:
1252:
1248:
1241:
1228:
1227:
1220:
1211:
1209:
1200:
1199:
1195:
1178:
1177:
1168:
1154:
1153:
1142:
1137:
1124:
1085:
1068:
981:
938:
931:
926:
925:
924: ?)
915:
911:
907:
903:
887:
880:
854:
836:
823:
819:
815:
811:
807:
794:
774:
768:
761:
757:
750:
746:
739:
733:
721:
715:
703:
697:
557:
515:
501:
480:
452:
448:
434:
402:
380:
368:
364:
360:
356:
350:
336:
333:
328:
323:
322:
311:
308:
307:
304:
298:
297:
286:
266:
250:
237:
225:
188:
168:
148:
128:
117:
104:
90:
89:
55:
54:
17:
12:
11:
5:
1550:
1548:
1540:
1539:
1534:
1529:
1519:
1518:
1515:
1514:
1509:
1504:
1499:
1494:
1489:
1483:
1478:
1471:
1470:External links
1468:
1465:
1464:
1435:
1416:
1413:on 2013-09-25.
1387:
1381:978-3527306732
1380:
1352:
1305:
1275:
1246:
1239:
1218:
1193:
1166:
1139:
1138:
1136:
1133:
1123:
1120:
1084:
1081:
1067:
1064:
980:
977:
936:
933:
932:
927:
905:
904:
900:standard state
897:
894:
893:
888:
885:
882:
881:
879:
878:
873:
868:
863:
857:
855:
849:
846:
845:
841:
840:
837:
831:
828:
827:
808:
802:
799:
798:
795:
789:
786:
785:
776:
775:
773:
772:
765:
754:
742:
740:
731:
729:
726:
725:
722:
713:
711:
708:
707:
704:
695:
693:
690:
689:
682:
681:
678:
672:
671:
617:P305+P351+P338
558:
553:
550:
549:
516:
511:
508:
507:
502:
497:
494:
493:
481:
476:
473:
472:
462:
461:
457:
456:
445:
443:Vapor pressure
439:
438:
435:
430:
427:
426:
423:
417:
416:
413:
407:
406:
399:
393:
392:
389:
385:
384:
377:
371:
370:
366:
362:
358:
354:
351:
346:
343:
342:
338:
337:
335:
334:
331:
329:
326:
318:
317:
316:
313:
312:
310:
309:
305:
302:
301:
293:
292:
291:
288:
287:
285:
284:
276:
274:
268:
267:
265:
264:
260:
258:
252:
251:
249:
248:
240:
238:
230:
227:
226:
224:
223:
219:
217:
209:
208:
198:
190:
189:
187:
186:
178:
176:
170:
169:
167:
166:
158:
156:
150:
149:
147:
146:
139:
131:
129:
122:
119:
118:
116:
115:
107:
105:
100:
97:
96:
92:
91:
88:
87:
84:
81:
75:
72:
69:
66:
62:
61:
57:
56:
52:
51:
45:
44:
40:
39:
31:
30:
15:
13:
10:
9:
6:
4:
3:
2:
1549:
1538:
1535:
1533:
1530:
1528:
1525:
1524:
1522:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1487:
1484:
1482:
1479:
1477:
1474:
1473:
1469:
1453:
1446:
1439:
1436:
1426:
1420:
1417:
1409:
1405:
1398:
1391:
1388:
1383:
1377:
1373:
1369:
1365:
1364:
1356:
1353:
1348:
1344:
1340:
1336:
1332:
1328:
1324:
1320:
1316:
1309:
1306:
1295:on 2012-03-26
1294:
1290:
1286:
1279:
1276:
1263:
1258:
1250:
1247:
1242:
1236:
1232:
1225:
1223:
1219:
1208:
1204:
1197:
1194:
1189:
1185:
1181:
1175:
1173:
1171:
1167:
1162:
1158:
1151:
1149:
1147:
1145:
1141:
1134:
1132:
1130:
1121:
1119:
1116:
1114:
1110:
1106:
1102:
1098:
1097:refrigerators
1094:
1090:
1082:
1076:
1072:
1065:
1063:
1061:
1060:fractionation
1057:
1056:polymeric MDI
1052:
1050:
1045:
1042:
1037:
1035:
1030:
1028:
1024:
1020:
1015:
1013:
1009:
1005:
1001:
997:
993:
989:
984:
978:
976:
974:
970:
966:
962:
958:
954:
950:
946:
942:
930:
923:
918:
901:
895:
892:
889:
884:
883:
877:
874:
872:
869:
867:
864:
862:
859:
858:
856:
853:
848:
847:
842:
838:
834:
830:
829:
809:
806:(Recommended)
805:
801:
800:
796:
793:(Permissible)
792:
788:
787:
783:
782:
777:
766:
755:
744:
743:
741:
737:
728:
727:
723:
719:
710:
709:
705:
701:
692:
691:
687:
683:
679:
677:
674:
673:
559:
556:
552:
551:
517:
514:
510:
509:
506:
503:
500:
496:
495:
491:
486:
482:
479:
475:
474:
470:
468:
463:
458:
446:
444:
441:
440:
436:
433:
429:
428:
424:
422:
421:Boiling point
419:
418:
414:
412:
411:Melting point
409:
408:
400:
398:
395:
394:
390:
387:
386:
378:
376:
373:
372:
352:
349:
345:
344:
339:
330:
325:
321:
314:
300:
296:
289:
282:
278:
277:
275:
273:
270:
269:
262:
261:
259:
257:
254:
253:
246:
242:
241:
239:
233:
229:
228:
221:
220:
218:
216:
211:
210:
206:
202:
199:
197:
195:ECHA InfoCard
192:
191:
184:
180:
179:
177:
175:
172:
171:
164:
160:
159:
157:
155:
152:
151:
144:
140:
137:
133:
132:
130:
126:
121:
120:
113:
109:
108:
106:
103:
99:
98:
93:
85:
82:
79:
76:
73:
70:
67:
64:
63:
58:
50:
46:
41:
37:
32:
28:
23:
1456:. Retrieved
1451:
1438:
1419:
1408:the original
1403:
1390:
1361:
1355:
1322:
1318:
1308:
1297:. Retrieved
1293:the original
1288:
1278:
1266:. Retrieved
1261:
1249:
1230:
1210:. Retrieved
1206:
1196:
1183:
1129:nucleophiles
1125:
1117:
1089:polyurethane
1086:
1083:Applications
1069:
1055:
1053:
1046:
1038:
1031:
1023:formaldehyde
1016:
985:
982:
973:polyurethane
964:
960:
944:
940:
939:
891:Polyurethane
780:
760:mg/m (rat, 4
749:mg/m (rat, 4
685:
504:
466:
405:g/cm, solid
256:RTECS number
95:Identifiers
60:Other names
1527:Isocyanates
1452:NIOSH Alert
1325:: 568–576.
852:Isocyanates
822:mg/m (0.020
814:mg/m (0.005
700:median dose
686:Lethal dose
676:Flash point
499:Signal word
388:Appearance
341:Properties
201:100.043.361
163:CHEBI:53218
80:Desmodur 44
1521:Categories
1458:2012-08-14
1299:2020-01-15
1268:15 January
1212:2017-06-25
1135:References
1093:insulators
979:Production
953:isocyanate
818:ppm) C 0.2
771:mg/m (rat)
478:Pictograms
375:Molar mass
281:B0LO6BBS8C
174:ChemSpider
123:3D model (
102:CAS Number
1347:102682388
1339:0009-2614
1201:Pubchem.
1113:polyether
1105:polyester
661:P403+P233
649:P342+P311
645:P337+P313
641:P333+P313
637:P332+P313
621:P308+P313
613:P304+P341
609:P304+P340
605:P304+P312
601:P302+P352
469:labelling
263:NQ9350000
214:EC Number
1532:Monomers
1190:(NIOSH).
1163:(NIOSH).
1041:phosgene
1004:Huntsman
992:Covestro
965:Pure MDI
961:4,4′-MDI
955:. Three
949:aromatic
947:) is an
850:Related
839:75 mg/m
810:TWA 0.05
460:Hazards
451:mmHg (20
447:0.000005
112:101-68-8
86:Pure MDI
1157:"#0413"
1019:aniline
969:polyols
957:isomers
922:what is
920: (
437:Reacts
397:Density
369:
232:PubChem
1431:
1378:
1345:
1337:
1237:
1122:Safety
1107:) and
917:verify
914:
826:ppm)
824:
820:
816:
812:
769:
762:
758:
751:
747:
505:Danger
453:
449:
403:
381:
379:250.25
320:SMILES
43:Names
1448:(PDF)
1411:(PDF)
1400:(PDF)
1343:S2CID
1008:Tosoh
781:NIOSH
401:1.230
295:InChI
154:ChEBI
125:JSmol
78:Bayer
1376:ISBN
1335:ISSN
1270:2020
1235:ISBN
1021:and
996:BASF
833:IDLH
669:P501
665:P405
657:P363
653:P362
633:P321
629:P314
625:P312
597:P285
593:P281
589:P280
585:P272
581:P271
577:P264
573:P261
569:P260
565:P202
561:P201
547:H373
543:H351
539:H335
535:H334
531:H332
527:H319
523:H317
519:H315
455:°C)
272:UNII
245:7570
183:7289
1368:doi
1327:doi
1323:706
1115:).
1111:(a
1103:(a
1012:TDI
1000:Dow
945:MDI
804:REL
791:PEL
767:178
764:hr)
756:380
753:hr)
745:369
467:GHS
235:CID
1523::
1450:.
1402:.
1374:.
1341:.
1333:.
1321:.
1317:.
1287:.
1260:.
1221:^
1205:.
1186:.
1182:.
1169:^
1159:.
1143:^
1131:.
1006:,
1002:,
998:,
994:,
951:di
732:50
730:LC
714:Lo
712:LD
696:50
694:LD
667:,
663:,
659:,
655:,
651:,
647:,
643:,
639:,
635:,
631:,
627:,
623:,
619:,
615:,
611:,
607:,
603:,
599:,
595:,
591:,
587:,
583:,
579:,
575:,
571:,
567:,
563:,
545:,
541:,
537:,
533:,
529:,
525:,
521:,
471::
359:10
355:15
1461:.
1384:.
1370::
1349:.
1329::
1302:.
1272:.
1243:.
1215:.
943:(
912:N
738:)
734:(
720:)
716:(
702:)
698:(
367:2
365:O
363:2
361:N
357:H
353:C
127:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
