932:
361:
188:
204:
957:
145:
116:
1075:
1324:
Bonamico, M.; Dessy, G.; Fares, V.; Scaramuzza, L. (1975). "Structural
Studies of Metal Complexes with Sulphur-Containing Bidentate Ligands. Part I. Crystal and Molecular Structures of Trimeric Bis-(dithiobenzoato)-nickel(II) and -palladium(II)".
890:
752:
657:
346:
447:
517:
1229:
Klaus
Huthmacher, Dieter Most "Cyanuric Acid and Cyanuric Chloride" Ullmann's Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. doi 10.1002/14356007.a08 191
452:
Then in the second step, cyanic acid polymerizes to form cyanuric acid, which condenses with the liberated ammonia from the first step to release melamine and water.
1035:. The reaction illustrates the competition between trimerization and polymerization. The polymer and trimer are formally derived from the
198:. This reaction is catalyzed by traces of bromine, metal salts, acids and bases. For this reason, experimentalists avoid brownish samples.
1293:
767:
662:
This water then reacts with cyanic acid present, which helps drive the trimerization reaction, generating carbon dioxide and ammonia.
668:
194:
The bromide has an extended shelflife when refrigerated. Like the chloride, it undergoes ab exothermic trimerisation to form
1262:
523:
228:
931:
1214:
377:
1249:
1181:
1148:
1354:
458:
938:
1260:
Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic
Syntheses, Collected Volume 2, p.610 (1943).
916:
57:
1036:
89:
1032:
110:
8:
124:
1009:
1287:
1245:
1210:
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908:
179:
171:
165:
1330:
1308:
1202:
1169:
1136:
983:
975:
967:
195:
178:
each trimerize at elevated temperatures over a carbon catalyst. The chloride gives
175:
77:
30:
1206:
1173:
939:
Breaking carbon-hetero double bonds forms symmetrical saturated 1,3,5-heterocycles
222:, with release of ammonia. The conversion commences at approximately 175 °C:
1269:
963:
920:
360:
1108:
1056:
948:
187:
157:
93:
1348:
1140:
1001:
211:
203:
1323:
911:, which has some industrial importance is obtained by cyclotrimerization of
990:
979:
944:
144:
119:
The trimerization cyclization reaction can be understood with this scheme.
1334:
994:
971:
956:
923:
896:
368:
1013:
758:
1164:
Morris, Joel; Kovács, Lajos; Ohe, Kouichi (2015). "Cyanogen
Bromide".
912:
215:
132:
20:
68:
62:
1103:
352:
115:
85:
84:
of the same substance. In technical jargon, a trimer is a kind of
73:
885:{\displaystyle {\ce {6 HCNO + 3 NH3 -> C3H6N6 + 3 CO2 + 3NH3}}}
1005:
161:
136:
1241:, Klaus Weissermel, Hans-Jurgen Arpe John Wiley & Sons; 3rd
16:
Molecule consisting of three identical molecules bound together
48:
1074:
219:
80:
formed by combination or association of three molecules or
42:
878:
858:
838:
825:
812:
796:
747:{\displaystyle {\ce {3 HOCN + 3 H2O -> 3 CO2 + 3NH3}}}
740:
720:
697:
642:
622:
609:
596:
580:
560:
505:
435:
410:
397:
334:
314:
276:
247:
81:
1196:
966:
is the cyclic trimer of the otherwise unstable species
1197:
Joel Morris; Lajos Kovács (2008). "Cyanogen
Bromide".
978:
and thioether groups. It is prepared by treatment of
652:{\displaystyle {\ce {3 + 3 NH3 -> C3H6N6 + 3 H2O}}}
1313:. New York, USA: D. Van Nostrand Company. p. 57.
770:
671:
526:
461:
380:
231:
1327:
Journal of the
Chemical Society, Dalton Transactions
341:{\displaystyle {\ce {3 H2N-CO-NH2 -> 3 + 3 NH3}}}
39:
36:
45:
33:
884:
746:
651:
511:
441:
340:
1130:
974:consists of a six-membered ring with alternating
442:{\displaystyle {\ce {(NH2)2CO -> HOCN + NH3}}}
1346:
1047:, although this species is not an intermediate.
1163:
1157:
997:, a cyclic trimer containing C-O single bonds.
1199:Encyclopedia of Reagents for Organic Synthesis
1166:Encyclopedia of Reagents for Organic Synthesis
1133:Ullmann's Encyclopedia of Industrial Chemistry
1023:Dimethylsilanediol dehydrates to a trimer of
1232:
1126:
1124:
1050:
867:
847:
785:
775:
729:
709:
686:
676:
631:
569:
466:
323:
236:
160:are prepared by trimerization of certain
1073:
371:and ammonia in an endothermic reaction:
151:
114:
1306:
1223:
104:
1347:
1292:: CS1 maint: archived copy as title (
1121:
902:
512:{\displaystyle {\ce {3 HOCN -> 3}}}
1131:Hillis O. Folkins (2005). "Benzene".
1071:crystallize as trimers (M = Ni, Pd).
907:The 1,5,9-trans-trans-cis isomer of
1190:
139:. This process was commercialized:
13:
14:
1366:
1310:Systematic organic chemistry (3E)
955:
930:
359:
355:can be understood in two steps.
202:
186:
143:
29:
1018:
1317:
1300:
1254:
1000:Catalyzing and dehydrating by
799:
703:
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127:reported the first example of
1:
1207:10.1002/047084289X.rc269.pub2
1174:10.1002/047084289X.rc269.pub3
1114:
757:In total, the second step is
351:The endothermic synthesis of
88:derived from three identical
1239:Industrial Organic Chemistry
367:First, urea decomposes into
7:
1097:
895:but the overall process is
99:
10:
1371:
108:
92:often in competition with
66: 'three' and
1141:10.1002/14356007.a03_475
1078:Structure of the trimer
1307:Cumming, W. M. (1937).
1135:. Weinheim: Wiley-VCH.
210:An industrial route to
1094:
1051:Coordination chemistry
943:Cyclotrimerization of
917:titanium tetrachloride
886:
748:
653:
513:
443:
342:
120:
1077:
887:
749:
654:
514:
444:
343:
216:thermal decomposition
152:Nitrile trimerization
118:
109:Further information:
1335:10.1039/DT9750002250
1033:polydimethylsiloxane
768:
669:
524:
459:
378:
229:
131:, the conversion of
111:Alkyne trimerisation
105:Alkyne trimerisation
72: 'parts') is a
1355:Trimers (chemistry)
1004:, trimerization of
989:Three molecules of
903:Diene trimerisation
880:
860:
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827:
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742:
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125:Marcellin Berthelot
1095:
1010:aldol condensation
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387:
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129:cyclotrimerization
121:
1329:(21): 2250–2255.
993:condense to form
976:methylene bridges
909:cyclododecatriene
871:
851:
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778:
733:
713:
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180:cyanuric chloride
172:Cyanogen chloride
166:cyanogen chloride
1362:
1339:
1338:
1321:
1315:
1314:
1304:
1298:
1297:
1291:
1283:
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1268:. Archived from
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1236:
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1227:
1221:
1220:
1194:
1188:
1187:
1168:. pp. 1–8.
1161:
1155:
1154:
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1070:
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984:hydrogen sulfide
968:thioformaldehyde
959:
934:
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196:cyanuric bromide
190:
176:cyanogen bromide
147:
78:polyatomic anion
55:
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51:
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44:
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1263:"Archived copy"
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1083:
1079:
1068:
1064:
1060:
1053:
1044:
1040:
1028:
1024:
1021:
964:1,3,5-Trithiane
941:
921:organoaluminium
905:
877:
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857:
852:
837:
832:
824:
819:
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806:
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158:1,3,5-triazines
154:
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32:
28:
17:
12:
11:
5:
1368:
1358:
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1340:
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1222:
1216:978-0471936237
1215:
1189:
1182:
1156:
1149:
1119:
1118:
1116:
1113:
1112:
1111:
1109:Protein trimer
1106:
1099:
1096:
1089:
1085:
1081:
1066:
1062:
1057:dithiobenzoate
1052:
1049:
1042:
1026:
1020:
1017:
961:
960:
949:1,3,5-Trioxane
940:
937:
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904:
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866:
863:
855:
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835:
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94:polymerization
15:
9:
6:
4:
3:
2:
1367:
1356:
1353:
1352:
1350:
1336:
1332:
1328:
1320:
1312:
1311:
1303:
1295:
1289:
1275:on 2012-03-29
1271:
1264:
1257:
1251:
1250:3-527-28838-4
1247:
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1183:9780470842898
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1101:
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1072:
1058:
1048:
1038:
1034:
1016:
1015:
1011:
1007:
1003:
1002:sulfuric acid
998:
996:
992:
987:
985:
981:
977:
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965:
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953:
952:
950:
946:
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723:
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683:
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271:
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217:
213:
212:cyanuric acid
205:
201:
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117:
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97:
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87:
83:
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75:
71:
70:
65:
64:
59:
58:Ancient Greek
53:
26:
22:
1326:
1319:
1309:
1302:
1277:. Retrieved
1270:the original
1256:
1242:
1238:
1234:
1225:
1198:
1192:
1165:
1159:
1132:
1054:
1039:sila-ketone
1037:hypothetical
1022:
1019:Trisiloxanes
999:
991:acetaldehyde
988:
980:formaldehyde
962:
945:formaldehyde
942:
906:
894:
756:
661:
451:
366:
350:
214:entails the
209:
193:
170:
156:Symmetrical
155:
128:
122:
67:
61:
24:
18:
1031:as well as
995:paraldehyde
972:heterocycle
924:co-catalyst
897:endothermic
369:cyanic acid
56:; from
1279:2014-05-05
1150:3527306730
1115:References
1059:complexes
1014:mesitylene
759:exothermic
90:precursors
1080:[Ni(S
913:butadiene
800:⟶
704:⟶
584:⟶
471:⟶
417:⟶
280:⟶
263:−
255:−
133:acetylene
123:In 1866,
21:chemistry
1349:Category
1288:cite web
1104:Oligomer
1098:See also
1061:[M(S
1012:affords
947:affords
353:melamine
164:such as
162:nitriles
100:Examples
86:oligomer
74:molecule
1006:acetone
970:. This
919:and an
137:benzene
1248:
1213:
1180:
1147:
25:trimer
1273:(PDF)
1266:(PDF)
982:with
915:with
60:
1294:link
1246:ISBN
1243:1997
1211:ISBN
1178:ISBN
1145:ISBN
1084:CPh)
1065:CPh)
1055:The
1045:Si=O
1008:via
777:HCNO
678:HOCN
468:HOCN
420:HOCN
220:urea
174:and
82:ions
69:-mer
63:tri-
23:, a
1331:doi
1203:doi
1170:doi
1137:doi
1029:SiO
218:of
135:to
76:or
19:In
1351::
1290:}}
1286:{{
1209:.
1201:.
1176:.
1143:.
1123:^
1041:Me
1025:Me
986:.
951::
926::
899:.
870:NH
850:CO
788:NH
761::
732:NH
712:CO
572:NH
548:NH
493:NH
427:NH
414:CO
389:NH
326:NH
302:NH
268:NH
259:CO
182::
168:.
96:.
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1337:.
1333::
1296:)
1282:.
1219:.
1205::
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1172::
1153:.
1139::
1093:.
1090:3
1088:]
1086:2
1082:2
1069:]
1067:2
1063:2
1043:2
1027:2
874:3
865:3
862:+
854:2
845:3
842:+
834:6
830:N
821:6
817:H
808:3
804:C
792:3
783:3
780:+
773:6
736:3
727:3
724:+
716:2
707:3
701:O
693:2
689:H
684:3
681:+
674:3
646:O
638:2
634:H
629:3
626:+
618:6
614:N
605:6
601:H
592:3
588:C
576:3
567:3
564:+
556:3
551:]
544:)
541:O
538:(
534:C
531:[
501:3
496:]
489:)
486:O
483:(
479:C
476:[
464:3
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423:+
406:2
401:)
393:2
385:(
330:3
321:3
318:+
310:3
305:]
298:)
295:O
292:(
288:C
285:[
272:2
251:N
243:2
239:H
234:3
52:/
46:m
40:r
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31:/
27:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
