37:
311:
204:
28:
802:
499:
500:
495:
605:
498:
688:, which is converted to methacrylamide sulfate using sulfuric acid. This derivative in turn is hydrolyzed to methacrylic acid, or esterified to methyl methacrylate in one step. Another route to methacrylic acid starts with
516:
523:
847:. Esterifications are brought about by acid-catalyzed condensations with alcohols, alkylations with certain alkenes, and transesterifications. Epoxide ring-opening gives hydroxyalkyl esters.
664:
with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its
501:
1132:"Aqueous enteric coatings with methacrylic acid copolymer type C on acidic and basic drugs in tablets and pellets, part I: Acetylsalicylic acid tablets and crystals"
943:
545:
618:
962:
887:
997:"Synthesis of Bio-Based Methacrylic Acid by Decarboxylation of Itaconic Acid and Citric Acid Catalyzed by Solid Transition-Metal Catalysts"
350:
774:
consisting partially of methacrylic acid are used in certain types of tablet coatings in order to slow the tablet's dissolution in the
1215:
832:
828:
as a thermally activated free-radical catalyst. Otherwise, MAA is relatively slow to polymerize thermally or photochemically.
738:
affords methacrylic acid. Salts of methacrylic acid have been obtained by boiling citra- or meso-brompyrotartaric acids with
1162:
911:
995:
Le Nôtre, Jérôme; Witte-van Dijk, Susan C. M.; van
Haveren, Jacco; Scott, Elinor L.; Sanders, Johan P. M. (September 2014).
613:
979:
1090:
325:
509:
1225:
625:
1106:
810:
268:
199:
133:
289:
895:
569:
556:
235:
1182:[II. Investigations on the unsaturated acids. On the characterisation of methacrylic acid.].
758:
673:
211:
840:
306:
229:
722:
Various green routes have been explored but they have not been commercialized. Specifically, the
825:
775:
996:
55:
1220:
1008:
277:
65:
181:
8:
685:
669:
99:
1012:
310:
203:
161:
109:
746:
1158:
1131:
1086:
1024:
975:
907:
806:
793:
779:
1191:
1180:"II. Untersuchungen über die ungesättigten Säuren. Zur Kenntnis der Methacrylsäure"
1150:
1078:
1051:
1016:
967:
899:
844:
765:
703:
and then methacrylic acid. Methacrolein for this purpose can also be obtained from
645:
455:
373:
1154:
892:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
886:
852:
786:
731:
723:
716:
712:
661:
257:
36:
848:
735:
596:
466:
939:
1209:
1195:
1082:
1055:
971:
727:
444:
434:
192:
1028:
1020:
836:
801:
704:
700:
693:
903:
522:
868:
689:
535:
508:
515:
396:
212:
172:
994:
771:
1179:
595:
Except where otherwise noted, data are given for materials in their
708:
481:
27:
937:
132:
856:
424:
244:
831:
Methacrylic acid undergoes several reactions characteristic of
739:
960:
William Bauer Jr. (2002). "Methacrylic Acid and
Derivatives".
1073:
Stickler, Manfred; Rhein, Thoma (2000). "Polymethacrylates".
665:
152:
122:
1060:
This article also describes pyrolysis of ethyl methacrylate.
1042:
W. P. Ratchford (1949). "Acrylic Acid I. Pyrolysis Method".
684:
In the most common route, methacrylic acid is prepared from
294:
582:
414:
757:
The main use of methacrylic acid is its polymerization to
1145:
Pham, Ha Q.; Marks, Maurice J. (2012). "Epoxy Resins".
439:
14 to 15 °C (57 to 59 °F; 287 to 288 K)
824:
For commercial applications, MAA is polymerized using
944:
National
Institute for Occupational Safety and Health
785:
MAA occurs naturally in small amounts in the oil of
959:
888:International Union of Pure and Applied Chemistry
1207:
859:form of methacrylic acid was described in 1880.
256:
1113:. U.S. Food and Drug Administration. 2018-03-06
1041:
497:
108:
1147:Ullmann's Encyclopedia of Industrial Chemistry
1075:Ullmann's Encyclopedia of Industrial Chemistry
963:Ullmann's Encyclopedia of Industrial Chemistry
778:, and thus extend or delay the release of the
1072:
334:InChI=1S/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
1177:
1178:F. Engelhorn (1880). Rudolph Fittig (ed.).
699:. Isobutylene is oxidized sequentially to
540:77.2 °C (171.0 °F; 350.3 K)
1068:
1066:
309:
202:
180:
1144:
276:
1138:
938:NIOSH Pocket Guide to Chemical Hazards.
880:
800:
764:It is used in some nail primers to help
660:H. This colorless, viscous liquid is a
1063:
955:
953:
305:
234:
1208:
933:
931:
929:
927:
925:
923:
752:
449:161 °C (322 °F; 434 K)
193:
792:MMA is used in the synthesis of some
692:, which obtainable by dehydration of
337:Key: CERQOIWHTDAKMF-UHFFFAOYSA-N
160:
950:
749:efficiently gives methacrylic acid.
920:
247:
13:
493:
35:
26:
14:
1237:
1184:Justus Liebigs Annalen der Chemie
711:. Yet a third route involves the
603:
1171:
1107:"Products - Nail Care Products"
839:). These reactions include the
599:(at 25 °C , 100 kPa).
1216:Carboxylic acid-based monomers
1124:
1099:
1035:
988:
896:The Royal Society of Chemistry
1:
1155:10.1002/14356007.a09_547.pub2
874:
679:
550:(US health exposure limits):
819:
811:bisphenol A diglycidyl ether
7:
862:
22:
10:
1242:
768:adhere to the nail plate.
759:poly(methyl methacrylate)
674:poly(methyl methacrylate)
593:
544:
475:
401:86.09 g/mol
366:
346:
321:
92:
81:2-Methyl-2-propenoic acid
76:
70:2-Methylprop-2-enoic acid
64:
54:
49:
21:
1196:10.1002/jlac.18802000103
1083:10.1002/14356007.a21_473
1056:10.15227/orgsyn.029.0002
972:10.1002/14356007.a16_441
1226:Foul-smelling chemicals
1149:. Weinheim: Wiley-VCH.
966:. Weinheim: Wiley-VCH.
1021:10.1002/cssc.201402117
826:azobisisobutyronitrile
814:
576:TWA 20 ppm (70 mg/m)
504:
471:0.7 mmHg (20 °C)
87:2-Methylpropenoic acid
40:
31:
904:10.1039/9781849733069
833:α,β-unsaturated acids
813:and methacrylic acid.
804:
503:
39:
30:
841:Diels–Alder reaction
486:(fire diamond)
85:2-Methylacrylic acid
66:Preferred IUPAC name
1013:2014ChSCh...7.2712L
753:Uses and occurrence
686:acetone cyanohydrin
670:methyl methacrylate
648:with the formula CH
456:Solubility in water
18:
815:
794:vinyl ester resins
747:ethyl methacrylate
626:Infobox references
585:(Immediate danger)
505:
83:α-Methacrylic acid
41:
32:
16:
1164:978-3-527-30673-2
1044:Organic Syntheses
913:978-0-85404-182-4
845:Michael additions
807:vinyl ester resin
780:active ingredient
634:Chemical compound
632:
631:
419:Acrid, repulsive
409:Colorless liquid
290:CompTox Dashboard
134:Interactive image
45:
44:
17:Methacrylic acid
1233:
1201:
1199:
1175:
1169:
1168:
1142:
1136:
1135:
1128:
1122:
1121:
1119:
1118:
1103:
1097:
1096:
1070:
1061:
1059:
1039:
1033:
1032:
1007:(9): 2712–2720.
992:
986:
985:
957:
948:
947:
935:
918:
917:
884:
646:organic compound
638:Methacrylic acid
616:
610:
607:
606:
525:
518:
511:
496:
461:9% (25 °C)
374:Chemical formula
314:
313:
298:
296:
280:
260:
249:
238:
214:
206:
195:
184:
164:
136:
112:
79:Methacrylic acid
59:Methacrylic acid
23:
19:
15:
1241:
1240:
1236:
1235:
1234:
1232:
1231:
1230:
1206:
1205:
1204:
1176:
1172:
1165:
1143:
1139:
1130:
1129:
1125:
1116:
1114:
1105:
1104:
1100:
1093:
1071:
1064:
1040:
1036:
993:
989:
982:
958:
951:
936:
921:
914:
898:. p. 746.
885:
881:
877:
865:
853:isobutyric acid
822:
787:Roman chamomile
776:digestive tract
755:
736:mesaconic acids
732:citraconic acid
724:decarboxylation
717:Isobutyric acid
713:dehydrogenation
682:
662:carboxylic acid
659:
655:
651:
635:
628:
623:
622:
621: ?)
612:
608:
604:
600:
586:
573:
560:
530:
529:
528:
527:
520:
513:
506:
502:
494:
458:
390:
386:
382:
376:
362:
359:
354:
353:
342:
339:
338:
335:
329:
328:
317:
299:
292:
283:
263:
250:
224:
187:
167:
139:
126:
115:
102:
88:
86:
84:
82:
80:
72:
71:
60:
12:
11:
5:
1239:
1229:
1228:
1223:
1218:
1203:
1202:
1170:
1163:
1137:
1123:
1098:
1091:
1062:
1034:
987:
981:978-3527306732
980:
949:
919:
912:
878:
876:
873:
872:
871:
864:
861:
851:reduces it to
849:Sodium amalgam
821:
818:
817:
816:
754:
751:
681:
678:
672:(MMA), and to
657:
653:
649:
640:, abbreviated
633:
630:
629:
624:
602:
601:
597:standard state
594:
591:
590:
587:
581:
578:
577:
574:
568:
565:
564:
561:
555:
552:
551:
542:
541:
538:
532:
531:
521:
514:
507:
492:
491:
490:
489:
487:
478:
477:
473:
472:
469:
467:Vapor pressure
463:
462:
459:
454:
451:
450:
447:
441:
440:
437:
431:
430:
427:
421:
420:
417:
411:
410:
407:
403:
402:
399:
393:
392:
388:
384:
380:
377:
372:
369:
368:
364:
363:
361:
360:
357:
349:
348:
347:
344:
343:
341:
340:
336:
333:
332:
324:
323:
322:
319:
318:
316:
315:
302:
300:
288:
285:
284:
282:
281:
273:
271:
265:
264:
262:
261:
253:
251:
243:
240:
239:
232:
226:
225:
223:
222:
218:
216:
208:
207:
197:
189:
188:
186:
185:
177:
175:
169:
168:
166:
165:
157:
155:
149:
148:
145:
144:Abbreviations
141:
140:
138:
137:
129:
127:
120:
117:
116:
114:
113:
105:
103:
98:
95:
94:
90:
89:
78:
74:
73:
69:
68:
62:
61:
58:
52:
51:
47:
46:
43:
42:
33:
9:
6:
4:
3:
2:
1238:
1227:
1224:
1222:
1219:
1217:
1214:
1213:
1211:
1197:
1193:
1189:
1185:
1181:
1174:
1166:
1160:
1156:
1152:
1148:
1141:
1133:
1127:
1112:
1108:
1102:
1094:
1092:3-527-30673-0
1088:
1084:
1080:
1076:
1069:
1067:
1057:
1053:
1049:
1045:
1038:
1030:
1026:
1022:
1018:
1014:
1010:
1006:
1002:
998:
991:
983:
977:
973:
969:
965:
964:
956:
954:
945:
941:
934:
932:
930:
928:
926:
924:
915:
909:
905:
901:
897:
893:
889:
883:
879:
870:
867:
866:
860:
858:
854:
850:
846:
842:
838:
834:
829:
827:
812:
809:derived from
808:
803:
799:
798:
797:
795:
790:
788:
783:
781:
777:
773:
769:
767:
766:acrylic nails
762:
760:
750:
748:
745:Pyrolysis of
743:
741:
737:
733:
729:
728:itaconic acid
725:
720:
718:
714:
710:
706:
702:
698:
696:
691:
687:
677:
675:
671:
668:, especially
667:
663:
647:
643:
639:
627:
620:
615:
598:
592:
588:
584:
580:
579:
575:
572:(Recommended)
571:
567:
566:
562:
559:(Permissible)
558:
554:
553:
549:
548:
543:
539:
537:
534:
533:
526:
519:
512:
488:
485:
484:
480:
479:
474:
470:
468:
465:
464:
460:
457:
453:
452:
448:
446:
445:Boiling point
443:
442:
438:
436:
435:Melting point
433:
432:
428:
426:
423:
422:
418:
416:
413:
412:
408:
405:
404:
400:
398:
395:
394:
378:
375:
371:
370:
365:
356:
355:
352:
345:
331:
330:
327:
320:
312:
308:
307:DTXSID3025542
304:
303:
301:
291:
287:
286:
279:
275:
274:
272:
270:
267:
266:
259:
255:
254:
252:
246:
242:
241:
237:
233:
231:
228:
227:
220:
219:
217:
215:
210:
209:
205:
201:
198:
196:
194:ECHA InfoCard
191:
190:
183:
179:
178:
176:
174:
171:
170:
163:
159:
158:
156:
154:
151:
150:
146:
143:
142:
135:
131:
130:
128:
124:
119:
118:
111:
107:
106:
104:
101:
97:
96:
91:
75:
67:
63:
57:
53:
48:
38:
34:
29:
25:
24:
20:
1187:
1183:
1173:
1146:
1140:
1126:
1115:. Retrieved
1110:
1101:
1074:
1047:
1043:
1037:
1004:
1000:
990:
961:
891:
882:
837:acrylic acid
830:
823:
791:
784:
770:
763:
756:
744:
721:
705:formaldehyde
701:methacrolein
694:
683:
641:
637:
636:
546:
482:
358:CC(C(O)=O)=C
93:Identifiers
77:Other names
1221:Enoic acids
1111:www.fda.gov
1001:ChemSusChem
869:Lactic acid
690:isobutylene
536:Flash point
429:1.015 g/cm
406:Appearance
367:Properties
200:100.001.096
162:CHEBI:25219
1210:Categories
1117:2019-04-03
875:References
772:Copolymers
680:Production
397:Molar mass
278:1CS02G8656
173:ChemSpider
121:3D model (
100:CAS Number
56:IUPAC name
857:polymeric
820:Reactions
676:(PMMA).
221:201-204-4
213:EC Number
1029:25045161
946:(NIOSH).
890:(2014).
863:See also
805:Typical
709:ethylene
697:-butanol
644:, is an
483:NFPA 704
476:Hazards
1009:Bibcode
940:"#0386"
740:alkalis
619:what is
617: (
425:Density
391:
245:PubChem
236:C008384
110:79-41-4
1190:: 70.
1161:
1089:
1027:
978:
910:
734:, and
666:esters
614:verify
611:
351:SMILES
50:Names
1050:: 2.
835:(see
652:=C(CH
589:N.D.
563:none
547:NIOSH
326:InChI
153:ChEBI
123:JSmol
1159:ISBN
1087:ISBN
1025:PMID
976:ISBN
908:ISBN
855:. A
843:and
707:and
695:tert
583:IDLH
415:Odor
269:UNII
258:4093
230:MeSH
182:3951
147:MAA
1192:doi
1188:200
1151:doi
1079:doi
1052:doi
1017:doi
968:doi
900:doi
726:of
715:of
656:)CO
642:MAA
570:REL
557:PEL
295:EPA
248:CID
1212::
1186:.
1157:.
1109:.
1085:.
1077:.
1065:^
1048:29
1046:.
1023:.
1015:.
1003:.
999:.
974:.
952:^
942:.
922:^
906:.
894:.
796:.
789:.
782:.
761:.
742:.
730:,
719:.
1200:.
1198:.
1194::
1167:.
1153::
1134:.
1120:.
1095:.
1081::
1058:.
1054::
1031:.
1019::
1011::
1005:7
984:.
970::
916:.
902::
658:2
654:3
650:2
609:N
524:2
517:2
510:3
389:2
387:O
385:6
383:H
381:4
379:C
297:)
293:(
125:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
