461:
264:
169:
460:
24:
456:
627:
484:
459:
1289:
Herzberger, Jana; Niederer, Kerstin; Pohlit, Hannah; Seiwert, Jan; Worm, Matthias; Wurm, Frederik R.; Frey, Holger (2016). "Polymerization of
Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation".
954:
477:
688:. Being simple to make and bifunctional, it has a variety of industrial uses. The compound is a colorless, slightly viscous liquid that is slightly unstable and is not often encountered in pure form.
828:
462:
803:
Glycidyl fatty acid esters that are thought to contaminate some edible oils could be a source of traces of glycidol in the diet. These esters are formed during the
995:
926:
844:
554:
640:
1099:
1072:
Bruce H. Lipshutz, Robert
Moretti, and Robert Crow (1990). "Mixed Higher-Order Cyanocuprate-Induced Epoxide Openings: 1-Benzyloxy-4-Penten-2-Ol".
1204:
836:
1044:
Guenter Sienel, Robert Rieth, Kenneth T. Rowbottom "Epoxides" in
Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
313:
772:
Glycidol can be O-benzylated in the presence of strong base. More typically, such glycidol ethers are produced by reaction of
823:
Glycidol is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. Exposure to glycidol may also cause
1157:"Glycidyl Fatty Acid Esters in Refined Edible Oils: A Review on Formation, Occurrence, Analysis, and Elimination Methods"
1395:
1279:
1026:
278:
1320:
1114:
635:
647:
807:, which uses vapor and high temperatures to remove impurities. The reaction conditions in that step can allow
1355:
Hanson, Robert M. (1991). "The synthetic methodology of nonracemic glycidol and related 2,3-epoxy alcohols".
965:
470:
769:
Glycidol is used as a chemical intermediate in the synthesis of other glycidyl ethers, esters, and amines.
221:
164:
242:
847:
840:
804:
578:
565:
1208:
1390:
950:
1060:
259:
1319:
Sutter, Marc; Silva, Eric Da; Duguet, Nicolas; Raoul, Yann; Métay, Estelle; Lemaire, Marc (2015).
1113:
Sutter, Marc; Silva, Eric Da; Duguet, Nicolas; Raoul, Yann; Métay, Estelle; Lemaire, Marc (2015).
824:
1093:
230:
146:
36:
106:
8:
682:
82:
72:
263:
168:
126:
1321:"Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies"
1115:"Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies"
946:
815:(MAG, DAG) naturally present in the oil to rearrange into glycidyl fatty acid esters.
711:
Some useful products derived from glycidol are 2,3-epoxypropyloxy chloroformate (from
23:
1385:
1343:
1307:
1275:
1229:
1186:
1178:
1137:
1022:
705:
603:
1364:
1335:
1299:
1168:
1129:
1081:
1045:
1014:
685:
663:
416:
336:
1230:"List of Classifications, Agents classified by the IARC Monographs, Volumes 1–124"
1071:
210:
859:
773:
1303:
827:
depression, followed by central nervous system stimulation. It is listed as an
609:
864:
618:
427:
1254:
922:
540:
520:
1379:
1182:
1085:
1049:
1018:
987:
874:
808:
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697:
405:
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157:
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1311:
1190:
1141:
792:
780:
483:
869:
812:
496:
1368:
469:
788:
784:
716:
476:
364:
137:
1339:
1133:
617:
Except where otherwise noted, data are given for materials in their
1155:
Cheng, Wei-wei; Liu, Guo-qin; Wang, Li-qing; Liu, Zeng-she (2017).
712:
442:
185:
920:
105:
678:
385:
197:
1288:
1269:
1009:
Johnson, Roy A.; Burgos-Lepley, Carmen E. (2001). "Glycidol".
992:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
117:
95:
247:
591:
176:
977:
AMA Archives of
Industrial Health. Vol. 14, Pg. 250, 1956
1318:
1112:
1161:
Comprehensive
Reviews in Food Science and Food Safety
996:
National
Institute for Occupational Safety and Health
927:
National
Institute for Occupational Safety and Health
845:
National
Institute for Occupational Safety and Health
1008:
1234:
IARC Monographs on the
Evaluation of Risk to Humans
843:at 50 ppm over an eight-hour work shift, while the
410:167 °C (333 °F; 440 K) (decomposes)
1377:
209:
1154:
458:
81:
1011:Encyclopedia of Reagents for Organic Synthesis
1272:Glycidol: Properties, Reactions, Applications
837:Occupational Safety and Health Administration
835:". In regards to occupational exposures, the
691:
1255:CDC - NIOSH Pocket Guide to Chemical Hazards
1098:: CS1 maint: multiple names: authors list (
955:Institute for Occupational Safety and Health
696:Glycidol is prepared by the epoxidation of
262:
167:
145:
1172:
1040:
1038:
850:at 25 ppm over an eight-hour work shift.
805:deodorization step of edible oil refining
715:) and glycidyl urethanes (by addition of
704:, and a typical O-atom source is aqueous
229:
1270:Axel Kleemann, Rudolf M. Wagner (1981).
942:
940:
938:
936:
921:NIOSH Pocket Guide to Chemical Hazards.
287:InChI=1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2
892:
890:
297:InChI=1/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2
258:
1378:
1354:
1035:
916:
914:
912:
910:
908:
400:−54 °C (−65 °F; 219 K)
158:
933:
787:of 2-methylquinazolin-4(3H)-one) and
501:66 °C (151 °F; 339 K)
290:Key: CTKINSOISVBQLD-UHFFFAOYSA-N
125:
887:
905:
300:Key: CTKINSOISVBQLD-UHFFFAOYAN
200:
184:
13:
1263:
454:
14:
1407:
625:
348:
22:
1248:
1222:
1197:
1148:
1106:
1065:
833:probably carcinogenic to humans
621:(at 25 °C , 100 kPa).
1205:"OSHA guidelines for glycidol"
1061:Glycidol at chemicalland21.com
1054:
1002:
980:
971:
959:
677:. The molecule contains both
354:
342:
1:
966:Food and Cosmetics Toxicology
880:
798:
559:(US health exposure limits):
529:1980 mg/kg (dermal, rabbit)
58:Hydroxymethyl ethylene oxide
7:
1304:10.1021/acs.chemrev.5b00441
853:
779:Glycidol is a precursor to
509:or concentration (LD, LC):
10:
1412:
841:permissible exposure limit
692:Synthesis and applications
1396:IARC Group 2A carcinogens
951:GESTIS Substance Database
818:
700:. A typical catalyst is
615:
553:
505:
436:
329:
309:
274:
65:
47:
35:
30:
21:
1086:10.15227/orgsyn.069.0080
1050:10.1002/14356007.a09_531
1019:10.1002/047084289X.rg005
968:. Vol. 19, Pg. 347, 1981
757:+ RNCO → RNHC(O)OCH
54:3-Hydroxypropylene oxide
1174:10.1111/1541-4337.12251
831:, meaning that it is "
825:central nervous system
572:TWA 50 ppm (150 mg/m)
465:
60:2-Hydroxymethyl oxiran
585:TWA 25 ppm (75 mg/m)
547:450 ppm (mouse, 4 hr)
527:420 mg/kg (oral, rat)
464:
1236:. IARC. July 7, 2019
549:580 ppm (rat, 8 hr)
541:median concentration
447:(fire diamond)
52:2,3-Epoxy-1-propanol
37:Preferred IUPAC name
1369:10.1021/cr00004a001
829:IARC Group 2A Agent
417:Solubility in water
372: g·mol
56:Epoxypropyl alcohol
18:
848:recommends a limit
791:(by alkylation of
648:Infobox references
594:(Immediate danger)
466:
16:
1340:10.1021/cr5004002
1334:(16): 8609–8651.
1134:10.1021/cr5004002
1128:(16): 8609–8651.
1074:Organic Syntheses
706:peroxyacetic acid
686:functional groups
666:with the formula
656:Chemical compound
654:
653:
604:Safety data sheet
243:CompTox Dashboard
107:Interactive image
1403:
1391:Primary alcohols
1372:
1357:Chemical Reviews
1351:
1328:Chemical Reviews
1325:
1315:
1298:(4): 2170–2243.
1292:Chemical Reviews
1285:
1257:
1252:
1246:
1245:
1243:
1241:
1226:
1220:
1219:
1217:
1216:
1207:. Archived from
1201:
1195:
1194:
1176:
1152:
1146:
1145:
1122:Chemical Reviews
1119:
1110:
1104:
1103:
1097:
1089:
1069:
1063:
1058:
1052:
1042:
1033:
1032:
1006:
1000:
999:
984:
978:
975:
969:
963:
957:
944:
931:
930:
918:
903:
899:, 11th Edition,
894:
776:with alkoxides.
765:
745:
676:
664:organic compound
638:
632:
629:
628:
486:
479:
472:
457:
432:0.9 mmHg (25°C)
371:
356:
350:
344:
337:Chemical formula
267:
266:
251:
249:
233:
213:
202:
188:
171:
160:
149:
129:
109:
85:
41:Oxiranylmethanol
26:
19:
15:
1411:
1410:
1406:
1405:
1404:
1402:
1401:
1400:
1376:
1375:
1323:
1282:
1266:
1264:Further reading
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1260:
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1228:
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1202:
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1111:
1107:
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1070:
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1055:
1043:
1036:
1029:
1007:
1003:
986:
985:
981:
976:
972:
964:
960:
945:
934:
919:
906:
895:
888:
883:
860:Epichlorohydrin
856:
821:
801:
774:epichlorohydrin
764:
760:
756:
752:
748:
743:
739:
735:
731:
727:
723:
694:
675:
671:
667:
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650:
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644:
643: ?)
634:
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595:
582:
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524:
518:
491:
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467:
463:
455:
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380:Viscous liquid
369:
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5:
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1374:
1373:
1363:(4): 437–475.
1352:
1316:
1286:
1280:
1265:
1262:
1259:
1258:
1247:
1221:
1196:
1167:(2): 263–281.
1147:
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1027:
1001:
979:
970:
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932:
904:
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867:
865:Ethylene oxide
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746:
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624:
623:
619:standard state
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428:Vapor pressure
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1281:9783778507094
1277:
1273:
1268:
1267:
1256:
1251:
1235:
1231:
1225:
1211:on 2012-09-25
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1030:
1028:0-471-93623-5
1024:
1020:
1016:
1012:
1005:
997:
993:
989:
983:
974:
967:
962:
956:
952:
948:
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937:
928:
924:
917:
915:
913:
911:
909:
902:
898:
893:
891:
886:
876:
875:Glycidic acid
873:
871:
868:
866:
863:
861:
858:
857:
851:
849:
846:
842:
838:
834:
830:
826:
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814:
810:
809:monoglyceride
806:
796:
794:
790:
786:
782:
777:
775:
770:
747:
736:→ ClC(O)OCH
722:
721:
720:
718:
714:
709:
707:
703:
702:tungstic acid
699:
698:allyl alcohol
689:
687:
684:
680:
665:
661:
649:
642:
637:
620:
614:
611:
610:External MSDS
608:
605:
602:
601:
597:
593:
589:
588:
584:
581:(Recommended)
580:
576:
575:
571:
568:(Permissible)
567:
563:
562:
558:
557:
552:
546:
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425:
421:
418:
414:
413:
409:
407:
406:Boiling point
404:
403:
399:
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396:Melting point
394:
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260:DTXSID4020666
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159:ECHA InfoCard
156:
155:
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34:
29:
25:
20:
1360:
1356:
1331:
1327:
1295:
1291:
1271:
1250:
1238:. Retrieved
1233:
1224:
1213:. Retrieved
1209:the original
1199:
1164:
1160:
1150:
1125:
1121:
1108:
1094:cite journal
1077:
1073:
1067:
1056:
1010:
1004:
991:
982:
973:
961:
900:
896:
832:
822:
813:diglycerides
802:
793:theophylline
781:diproqualone
778:
771:
768:
710:
695:
659:
658:
555:
506:
443:
390:1.1143 g/cm
66:Identifiers
48:Other names
897:Merck Index
870:Glycidamide
717:isocyanates
521:median dose
507:Lethal dose
497:Flash point
377:Appearance
330:Properties
165:100.008.300
127:CHEBI:30966
1380:Categories
1274:. Hüthig.
1215:2006-10-20
988:"Glycidol"
881:References
839:has set a
799:Occurrence
789:dyphylline
785:alkylation
365:Molar mass
231:S54CF1DV9A
138:ChemSpider
94:3D model (
73:CAS Number
1183:1541-4337
422:miscible
17:Glycidol
1386:Epoxides
1348:26196761
1312:26713458
1240:July 14,
1191:33371535
1142:26196761
998:(NIOSH).
929:(NIOSH).
854:See also
713:phosgene
660:Glycidol
598:150 ppm
444:NFPA 704
437:Hazards
83:556-52-5
50:Glycidol
953:of the
949:in the
947:Record
923:"#0303"
761:CH(O)CH
753:CH(O)CH
740:CH(O)CH
732:+ COCl
728:CH(O)CH
683:alcohol
679:epoxide
641:what is
639: (
386:Density
321:OCC1OC1
198:PubChem
1346:
1310:
1278:
1189:
1181:
1140:
1080:: 80.
1025:
819:Safety
744:+ HCl
662:is an
636:verify
633:
606:(SDS)
370:74.079
314:SMILES
186:C10920
31:Names
1324:(PDF)
1118:(PDF)
672:CHOCH
556:NIOSH
279:InChI
211:11164
147:10691
118:ChEBI
96:JSmol
1344:PMID
1308:PMID
1276:ISBN
1242:2019
1187:PMID
1179:ISSN
1138:PMID
1100:link
1023:ISBN
901:4385
811:and
783:(by
749:HOCH
724:HOCH
681:and
668:HOCH
592:IDLH
222:UNII
177:KEGG
1365:doi
1336:doi
1332:115
1300:doi
1296:116
1169:doi
1130:doi
1126:115
1082:doi
1046:doi
1015:doi
795:).
579:REL
566:PEL
248:EPA
201:CID
1382::
1361:91
1359:.
1342:.
1330:.
1326:.
1306:.
1294:.
1232:.
1185:.
1177:.
1165:16
1163:.
1159:.
1136:.
1124:.
1120:.
1096:}}
1092:{{
1078:69
1076:.
1037:^
1021:.
1013:.
994:.
990:.
935:^
925:.
907:^
889:^
719::
708:.
537:50
535:LC
517:50
515:LD
1371:.
1367::
1350:.
1338::
1314:.
1302::
1284:.
1244:.
1218:.
1193:.
1171::
1144:.
1132::
1102:)
1088:.
1084::
1048::
1031:.
1017::
763:2
759:2
755:2
751:2
742:2
738:2
734:2
730:2
726:2
674:2
670:2
631:Y
543:)
539:(
523:)
519:(
485:3
478:2
471:4
358:2
355:O
352:6
349:H
346:3
343:C
250:)
246:(
98:)
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