2148:. Used as the "grout" by orthopedic surgeons to make the bone inserts fix into bone, it greatly reduces post-operative pain from the insertions but has a finite lifespan. Typically the lifespan of methylmethacrylate as bone cement is 20 years before revision surgery is required. Cemented implants are usually only done in elderly populations that require more immediate short term replacements. In younger populations, cementless implants are used because their lifespan is considerably longer. Also used in fracture repair in small exotic animal species using internal fixation.
364:
213:
31:
40:
647:
642:
823:
818:
1461:
in a primary distillation so that a crude MMA product stream, free from water, MeP and formaldehyde, is produced. Unreacted MeP and water are recycled via the formaldehyde dehydration process. MMA (>99.9%) is purified by vacuum distillations. The separated streams are returned to the process; there being only a small heavy ester purge stream, which is disposed of in a thermal oxidizer with heat recovered for use in the process.
822:
1053:
821:
1460:
on silica, achieves good selectivity to MMA from MeP. The formation of a small amount of heavy, relatively involatile compounds poisons the catalyst. The coke is easily removed and catalyst activity and selectivity restored by controlled, in-situ regeneration. The reactor product stream is separated
2183:
is 7–10 g/kg (oral, rat). It is an irritant to the eyes and can cause redness and pain. Irritation of the skin, eye, and nasal cavity has been observed in rodents and rabbits exposed to relatively high concentrations of methyl methacrylate. Methyl methacrylate is a mild skin irritant in humans and
2063:, as in the direct oxidation method. In the first step, methacrolein is produced in the same way as in the direct oxidation process by gas phase catalytic oxidation, is simultaneously oxidized and is esterified in liquid methanol to get MMA directly.
1464:
In 2008, Lucite
International commissioned an Alpha MMA plant on Jurong Island in Singapore. This process plant was cheaper to build and run than conventional systems, produces virtually no waste and the feedstocks can even be made from biomass.
1811:
and nitric acid at 5–10 °C in the liquid phase. After esterification and dehydration MMA is obtained. Challenges with this route, aside from yield, involve the handling of large amounts of nitric acid and
1140:
and his student W. A. Caspary in 1873, who noticed and described its tendency to change into a clear, hard, transparent substance especially in sunlight. Studies on acrylic esters slowly developed until the
846:
655:
2444:
Darabi
Mahboub, Mohammad Jaber; Dubois, Jean-Luc; Cavani, Fabrizio; Rostamizadeh, Mohammad; Patience, Gregory S. (2018). "Catalysis for the synthesis of methacrylic acid and methyl methacrylate".
622:
839:
2151:
MMA is a raw material for the manufacture of other methacrylates. These derivatives include ethyl methacrylate (EMA), butyl methacrylate (BMA) and 2-ethyl hexyl methacrylate (2-EHMA).
1681:
The reactions by the direct oxidation method consist of two-step oxidation of isobutylene or TBA with air to produce methacrylic acid and esterification by methanol to produce MMA.
2056:
Asahi
Chemical developed a process based on direct oxidative esterification of methacrolein, which does not produce by-products such as ammonium bisulfate. The raw material is
1346:
This technology affords more than 3 billion kilograms per year, and the economics have been heavily optimized. Nevertheless, the ACH route coproduces substantial amounts of
2813:
1165:
Given the scale of production, many methods have been developed starting from diverse two- to four-carbon precursors. Two principal routes appear to be commonly practiced.
1803:
A process using isobutylene as a raw material has been commercialized by
Escambia Co. Isobutylene is oxidized to provide α-hydroxy isobutyric acid. The conversion uses N
2381:
1401:
The MeP synthesis is conducted in a continuous-stirred tank reactor at moderate temperature and pressure using proprietary agitation and gas-liquid mixing arrangement.
824:
832:
1975:
Mitsubishi Gas
Chemicals proposed that MAN can be hydrated to methacrylamide without using sulfuric acid and is then esterified to obtain MMA by methylformate.
749:
2289:
2239:
968:
1641:, methyl acetylene is converted to MMA. As developed by Shell, this process produces MMA in one step reaction with 99% yield with a catalyst derived from
1066:
2308:
1486:, The condensation is catalyzed by a secondary amine. Air oxidation of methacrolein to methacrylic acid completes the synthesis of the acid:
2155:(MAA) is used as a chemical intermediate as well as in the manufacture of coating polymers, construction chemicals and textile applications.
2136:). Methyl methacrylate is also used for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for
403:
2591:
2796:
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2622:
2548:
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2863:
2720:
378:
1073:
1035:
2343:
603:
1596:
Oxidative dehydrogenation of the isobutyric acid yields methacrylic acid. Metal oxides catalyse this process:
1157:, who investigated the topic for three decades, was finally able to start its industrial production in 1931.
118:
2873:
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695:
311:
208:
30:
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741:
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2133:
1125:
769:
220:
737:
869:
785:
359:
2833:
2125:
1149:
and his research into the nature of polyacrylates allowed to control the polymerization. Company
551:
641:
2858:
2145:
2598:
1456:
The reaction of MeP and formaldehyde takes place over a fixed bed of catalyst. This catalyst,
2738:
2566:
Scott D. Barnicki (2012). "Chapter 10. Synthetic
Organic Chemicals". In James A. Kent (ed.).
2141:
713:
669:
634:
527:
1174:
765:
320:
52:
2772:
757:
190:
8:
2124:
The principal application, consuming approximately 75% of the MMA, is the manufacture of
1882:, a related commodity chemical. MAN can be hydrated by sulfuric acid to methacrylamide:
1213:
84:
363:
212:
150:
94:
1561:
1296:
1142:
721:
130:
2534:
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2571:
2461:
2426:
2363:
2321:
2119:
1642:
1363:
1359:
1350:: roughly 1.1 kg/(kg MMA). Disposal of the salt is very energy intensive.
1017:
2253:
2530:
2521:
Nagai, Koichi (2001). "New developments in the production of methyl methacrylate".
2488:
2453:
2418:
2406:
2355:
2313:
2152:
1479:
1347:
1182:
1137:
1117:
1097:
1093:
516:
426:
2739:"Concise International Chemical Assessment Document 4 : METHYL METHACRYLATE"
2164:
1816:. This method was discontinued in 1965 after an explosion at an operation plant.
1638:
1557:
882:
583:
284:
239:
17:
709:
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540:
39:
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906:
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1457:
1217:
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has the potential to induce skin sensitization in susceptible individuals.
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1405:
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781:
858:
761:
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to give propanal, which is then condensed with formaldehyde to produce
838:
454:
221:
181:
2443:
777:
563:
331:
1043:
Except where otherwise noted, data are given for materials in their
2193:
804:
259:
2233:
797:
117:
2640:. New York: Lippincott Williams & Wilkins. pp. 401–419.
2159:
2129:
1178:
1121:
729:
683:
485:
271:
2306:
Bauer, Jr., William (2002). "Methacrylic Acid and
Derivatives".
675:
2479:
Wiley, Richard H.; Waddey, Walter E. (1949). "Methacrylamide".
161:
687:
2834:
National
Pollutant Inventory – Methyl methacrylate fact sheet
2286:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1113:
773:
590:
295:
141:
107:
705:
347:
2549:"New Catalyst for Methyl Methacrylate Process :: News"
2177:
2176:
In terms of the acute toxicity of methyl methacrylate, the
1005:
475:
250:
2171:
717:
2137:
2828:
2662:"Mpausa - Methacrylates & Why They Are Important"
2344:"Ueberführung der β-Bibrompropionsäure in Acrylsäure"
2290:
National
Institute for Occupational Safety and Health
2240:
National Institute for Occupational Safety and Health
1645:, phosphine ligands, and Bronsted acids as catalyst:
1632:
1408:
in a single heterogeneous reaction step to form MMA:
1404:
In a second set of reactions, MeP is condensed with
679:
2568:Handbook of Industrial Chemistry and Biotechnology
1878:This step is analogous to the industrial route to
1819:
2565:
2158:Wood can be impregnated with MMA and polymerized
2051:
2845:
2638:Basic Biomechanics of the Musculoskeletal System
1124:produced on a large scale for the production of
283:
820:
93:
2341:
2309:Ullmann's Encyclopedia of Industrial Chemistry
793:
2819:US Environmental Protection Agency, 1994 data
2839:CDC – NIOSH Pocket Guide to Chemical Hazards
1160:
2478:
2382:"New series: Acrylic patented 90 years ago"
2140:. Another application is as cement used in
1353:
2688:Centers for Disease Control and Prevention
2305:
362:
211:
189:
2516:
2514:
2512:
2510:
2508:
2506:
2504:
2502:
2342:Caspary, W.; Tollens, B. (January 1873).
1220:-adduct, which is cracked to the ester:
387:InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3
319:
2829:Methacrylate Producers Association (MPA)
2234:NIOSH Pocket Guide to Chemical Hazards.
2172:Environmental issues and health hazards
1551:
358:
2846:
2795:: CS1 maint: archived copy as title (
2684:NIOSH Pocket Guide to Chemical Hazards
2635:
2621:: CS1 maint: archived copy as title (
2499:
2411:Industrial & Engineering Chemistry
2276:
2274:
2246:
2229:
2227:
2225:
2223:
2221:
2219:
1473:
1468:
877:435 °C (815 °F; 708 K)
510:101 °C (214 °F; 374 K)
500:−48 °C (−54 °F; 225 K)
202:
2672:
2570:(12th ed.). New York: Springer.
2520:
2404:
2301:
2299:
1676:
1112:. This colorless liquid, the methyl
390:Key: VVQNEPGJFQJSBK-UHFFFAOYSA-N
169:
149:
2700:
2559:
1564:of propene, using HF as a catalyst:
1168:
2731:
2713:International Chemical Safety Cards
2654:
2271:
2216:
863:2 °C (36 °F; 275 K)
274:
258:
13:
2296:
1633:Methyl acetylene (propyne) process
1556:As developed by Atochem and Röhm,
816:
14:
2885:
2807:
2721:International Labour Organization
2708:"ICSC 0300 - Methyl methacrylate"
2348:Justus Liebigs Annalen der Chemie
915:5000-7500 mg/kg (rabbit, dermal)
1173:The principal route begins with
1051:
645:
640:
438:
38:
29:
2758:
2629:
2584:
2541:
1820:Methacrylonitrile (MAN) process
1047:(at 25 °C , 100 kPa).
1036:Methyl methacrylate (data page)
2472:
2437:
2405:Neher, Harry T. (March 1936).
2398:
2374:
2335:
2052:Esterification of methacrolein
604:Occupational safety and health
444:
432:
1:
2814:Chemical data on Chemicalland
2535:10.1016/S0926-860X(01)00810-9
2209:
973:(US health exposure limits):
72:2-(methoxycarbonyl)-1-propene
2523:Applied Catalysis A: General
963:4567 ppm (guinea pig, 5 hr)
913:8420-10000 mg/kg (rat, oral)
57:Methyl 2-methylprop-2-enoate
7:
2187:
895:or concentration (LD, LC):
10:
2890:
2636:Nordin, Margareta (2001).
2117:
1153:founded by German chemist
1131:
15:
2725:World Health Organization
1358:The first stage involves
1161:Production and properties
1126:poly(methyl methacrylate)
1041:
1034:
1029:
967:
961:4207 ppm (rabbit, 4.5 hr)
891:
621:
601:
596:
576:
419:
399:
374:
77:
66:Methyl 2-methylpropenoate
63:
51:
46:
37:
28:
2864:Hazardous air pollutants
2493:10.15227/orgsyn.029.0061
2446:Chemical Society Reviews
2360:10.1002/jlac.18731670208
2318:10.1002/14356007.a16_441
1354:Methyl propionate routes
1030:Supplementary data page
1024:Methyl methacrylate MSDS
696:Precautionary statements
16:Not to be confused with
2312:. Weinheim: Wiley-VCH.
2146:total knee replacements
2126:polymethyl methacrylate
2113:
1824:MAN can be produced by
1362:of ethylene to produce
999:TWA 100 ppm (410 mg/m)
986:TWA 100 ppm (410 mg/m)
959:4400 ppm (rabbit, 8 hr)
552:Magnetic susceptibility
2142:total hip replacements
1136:MMA was discovered by
935:4447 ppm (mouse, 2 hr)
827:
2680:"Methyl methacrylate"
2282:"Methyl methacrylate"
2254:"Methyl methacrylate"
1498:CHO + HCHO → CH
933:18750 ppm (rat, 4 hr)
826:
545:29 mmHg (20 °C)
1552:From isobutyric acid
1197:CO + HCN → (CH
957:4400 ppm (rat, 8 hr)
927:median concentration
809:(fire diamond)
53:Preferred IUPAC name
24:Methyl methacrylate
2874:Commodity chemicals
2854:Methacrylate esters
2824:Intox Cheminfo data
2423:10.1021/ie50315a002
1474:Via propionaldehyde
1469:Other routes to MMA
1214:acetone cyanohydrin
1086:Methyl methacrylate
517:Solubility in water
462: g·mol
131:Beilstein Reference
68:methyl methacrylate
25:
2553:Chemistryviews.org
2458:10.1039/C8CS00117K
1828:from isobutylene:
1677:Isobutylene routes
1562:hydrocarboxylation
1478:Ethylene is first
1297:ammonium bisulfate
1074:Infobox references
1008:(Immediate danger)
939:4808 ppm (mammal)
828:
23:
2647:978-0-683-30247-9
2577:978-1-4614-4259-2
2555:. 22 August 2012.
2481:Organic Syntheses
2452:(20): 7703–7738.
2120:Acrylate polymers
1643:palladium acetate
1364:methyl propionate
1360:carboalkoxylation
1169:Cyanohydrin route
1082:Chemical compound
1080:
1079:
1018:Safety data sheet
670:Hazard statements
470:Colorless liquid
343:CompTox Dashboard
119:Interactive image
2881:
2801:
2800:
2794:
2786:
2784:
2783:
2777:
2771:. Archived from
2770:
2762:
2756:
2755:
2753:
2752:
2743:
2735:
2729:
2728:
2704:
2698:
2697:
2695:
2694:
2676:
2670:
2669:
2658:
2652:
2651:
2633:
2627:
2626:
2620:
2612:
2610:
2609:
2603:
2597:. Archived from
2596:
2588:
2582:
2581:
2563:
2557:
2556:
2545:
2539:
2538:
2529:(1–2): 367–377.
2518:
2497:
2496:
2476:
2470:
2469:
2441:
2435:
2434:
2407:"Acrylic Resins"
2402:
2396:
2395:
2393:
2392:
2386:www.k-online.com
2378:
2372:
2371:
2339:
2333:
2331:
2303:
2294:
2293:
2278:
2269:
2268:
2266:
2264:
2250:
2244:
2243:
2231:
2153:Methacrylic acid
2088:
2087:
2083:
1870:)CN + 3 H
1857:
1856:
1852:
1743:
1742:
1738:
1530:
1529:
1525:
1348:ammonium sulfate
1212:then hydrolyzes
1183:hydrogen cyanide
1175:the condensation
1138:Bernhard Tollens
1118:methacrylic acid
1094:organic compound
1064:
1058:
1055:
1054:
951:lowest published
883:Explosive limits
848:
841:
834:
819:
799:
795:
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703:
689:
685:
681:
677:
649:
644:
558:-57.3·10 cm/mol
461:
446:
440:
434:
427:Chemical formula
367:
366:
351:
349:
323:
287:
276:
262:
240:Gmelin Reference
223:
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22:
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2788:
2787:
2781:
2779:
2775:
2768:
2766:"Archived copy"
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2763:
2759:
2750:
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2741:
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2592:"Archived copy"
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2165:stabilized wood
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2116:
2108:
2104:
2100:
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1639:Reppe chemistry
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1615:
1612:H + O → CH
1611:
1607:
1603:
1591:
1587:
1583:
1579:
1575:
1571:
1560:is produced by
1558:isobutyric acid
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1538:
1534:
1527:
1523:
1522:
1520:
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1509:
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1501:
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1493:
1480:hydroformylated
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1471:
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18:methyl acrylate
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2809:
2808:External links
2806:
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2628:
2583:
2576:
2558:
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2498:
2471:
2436:
2417:(3): 267–271.
2397:
2373:
2354:(2): 240–257.
2334:
2327:978-3527306732
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2118:Main article:
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1957:
1953:
1949:
1945:
1941:
1937:
1933:
1929:
1926:
1923:
1919:
1915:
1911:
1907:
1903:
1899:
1895:
1891:
1887:
1876:
1875:
1871:
1867:
1863:
1859:
1845:
1841:
1837:
1833:
1821:
1818:
1813:
1808:
1804:
1801:
1800:
1796:
1792:
1788:
1784:
1780:
1776:
1772:
1768:
1764:
1761:
1757:
1753:
1749:
1745:
1731:
1727:
1723:
1722:
1718:
1714:
1710:
1706:
1702:
1698:
1694:
1690:
1686:
1678:
1675:
1674:
1673:
1670:
1666:
1662:
1658:
1654:
1650:
1634:
1631:
1630:
1629:
1625:
1621:
1617:
1613:
1609:
1605:
1601:
1594:
1593:
1589:
1585:
1581:
1577:
1573:
1569:
1553:
1550:
1549:
1548:
1544:
1540:
1536:
1532:
1518:
1514:
1511:
1507:
1503:
1499:
1495:
1491:
1475:
1472:
1470:
1467:
1454:
1453:
1449:
1445:
1441:
1437:
1433:
1429:
1425:
1421:
1417:
1413:
1399:
1398:
1395:
1391:
1387:
1383:
1379:
1375:
1371:
1355:
1352:
1344:
1343:
1340:
1336:
1332:
1328:
1324:
1320:
1316:
1312:
1308:
1304:
1290:
1289:
1285:
1281:
1277:
1273:
1269:
1265:
1261:
1257:
1253:
1249:
1245:
1241:
1237:
1233:
1232:C(OH)CN + 2H
1229:
1225:
1207:
1206:
1202:
1198:
1194:
1190:
1170:
1167:
1162:
1159:
1147:macromolecules
1133:
1130:
1109:
1105:
1101:
1081:
1078:
1077:
1072:
1050:
1049:
1045:standard state
1042:
1039:
1038:
1032:
1031:
1027:
1026:
1021:
1014:
1013:
1010:
1004:
1001:
1000:
997:
991:
988:
987:
984:
978:
975:
974:
965:
964:
955:
946:
944:
941:
940:
937:3750 ppm (rat)
931:
922:
920:
917:
916:
911:
902:
900:
897:
896:
889:
888:
885:
879:
878:
875:
868:
865:
864:
861:
855:
854:
844:
837:
830:
815:
814:
813:
812:
810:
801:
800:
750:P303+P361+P353
699:
694:
691:
690:
673:
668:
665:
664:
659:
654:
651:
650:
638:
633:
630:
629:
619:
618:
615:
612:
609:
608:
599:
598:
594:
593:
587:
582:
579:
578:
574:
573:
572:at 20 °C
566:
560:
559:
556:
550:
547:
546:
543:
541:Vapor pressure
537:
536:
533:
524:
523:
520:
515:
512:
511:
508:
502:
501:
498:
492:
491:
488:
482:
481:
480:acrid, fruity
478:
472:
471:
468:
464:
463:
457:
451:
450:
447:
441:
435:
430:
425:
422:
421:
417:
416:
414:
413:
410:
402:
401:
400:
397:
396:
394:
393:
389:
386:
385:
377:
376:
375:
372:
371:
369:
368:
355:
353:
341:
338:
337:
334:
328:
327:
325:
324:
316:
314:
308:
307:
305:
304:
300:
298:
292:
291:
289:
288:
280:
278:
270:
267:
266:
264:
263:
255:
253:
247:
246:
243:
238:
235:
234:
232:
231:
227:
225:
217:
216:
206:
198:
197:
195:
194:
186:
184:
178:
177:
175:
174:
166:
164:
158:
157:
155:
154:
146:
144:
138:
137:
134:
129:
126:
125:
123:
122:
114:
112:
105:
102:
101:
99:
98:
90:
88:
83:
80:
79:
75:
74:
65:
61:
60:
56:
55:
49:
48:
44:
43:
35:
34:
9:
6:
4:
3:
2:
2886:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2859:Methyl esters
2857:
2855:
2852:
2851:
2849:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2811:
2798:
2792:
2778:on 2013-01-24
2774:
2767:
2761:
2747:
2740:
2734:
2726:
2722:
2719:
2715:
2714:
2709:
2703:
2689:
2685:
2681:
2675:
2667:
2663:
2657:
2649:
2643:
2639:
2632:
2624:
2618:
2604:on 2015-09-24
2600:
2593:
2587:
2579:
2573:
2569:
2562:
2554:
2550:
2544:
2536:
2532:
2528:
2524:
2517:
2515:
2513:
2511:
2509:
2507:
2505:
2503:
2494:
2490:
2486:
2482:
2475:
2467:
2463:
2459:
2455:
2451:
2447:
2440:
2432:
2428:
2424:
2420:
2416:
2412:
2408:
2401:
2387:
2383:
2377:
2369:
2365:
2361:
2357:
2353:
2349:
2345:
2338:
2329:
2323:
2319:
2315:
2311:
2310:
2302:
2300:
2291:
2287:
2283:
2277:
2275:
2259:
2255:
2249:
2241:
2237:
2230:
2228:
2226:
2224:
2222:
2220:
2215:
2205:
2202:
2200:
2199:Methacrylates
2197:
2195:
2192:
2191:
2185:
2182:
2169:
2167:
2166:
2161:
2156:
2154:
2149:
2147:
2143:
2139:
2135:
2131:
2127:
2121:
2066:
2065:
2064:
2062:
2060:
2038:
2004:
1978:
1977:
1976:
1927:
1885:
1884:
1883:
1881:
1880:acrylonitrile
1831:
1830:
1829:
1827:
1817:
1762:
1725:
1724:
1684:
1683:
1682:
1648:
1647:
1646:
1644:
1640:
1599:
1598:
1597:
1567:
1566:
1565:
1563:
1559:
1512:
1489:
1488:
1487:
1485:
1481:
1466:
1462:
1459:
1458:caesium oxide
1411:
1410:
1409:
1407:
1402:
1369:
1368:
1367:
1365:
1361:
1351:
1349:
1302:
1301:
1300:
1298:
1294:
1223:
1222:
1221:
1219:
1218:sulfate ester
1215:
1211:
1210:Sulfuric acid
1188:
1187:
1186:
1184:
1180:
1176:
1166:
1158:
1156:
1152:
1151:Rohm and Haas
1148:
1145:'s theory of
1144:
1139:
1129:
1127:
1123:
1119:
1115:
1099:
1095:
1091:
1087:
1075:
1068:
1063:
1046:
1040:
1037:
1033:
1028:
1025:
1022:
1019:
1016:
1015:
1011:
1007:
1003:
1002:
998:
995:(Recommended)
994:
990:
989:
985:
982:(Permissible)
981:
977:
976:
972:
971:
966:
956:
952:
943:
942:
932:
928:
919:
918:
912:
908:
899:
898:
894:
890:
886:
884:
881:
880:
876:
873:
867:
866:
862:
860:
857:
856:
849:
842:
835:
811:
808:
807:
803:
802:
700:
697:
693:
692:
674:
671:
667:
666:
663:
660:
657:
653:
652:
648:
643:
639:
636:
632:
631:
627:
625:
620:
616:
611:
610:
606:
605:
600:
595:
592:
588:
585:
584:Dipole moment
581:
580:
575:
571:
567:
565:
562:
561:
557:
553:
549:
548:
544:
542:
539:
538:
534:
532:
531:
526:
525:
522:1.5 g/100 ml
521:
518:
514:
513:
509:
507:
506:Boiling point
504:
503:
499:
497:
496:Melting point
494:
493:
489:
487:
484:
483:
479:
477:
474:
473:
469:
466:
465:
458:
456:
453:
452:
431:
428:
424:
423:
418:
411:O=C(OC)C(=C)C
409:
408:
405:
398:
384:
383:
380:
373:
365:
361:
360:DTXSID2020844
357:
356:
354:
344:
340:
339:
335:
333:
330:
329:
322:
318:
317:
315:
313:
310:
309:
302:
301:
299:
297:
294:
293:
286:
282:
281:
279:
273:
269:
268:
261:
257:
256:
254:
252:
249:
248:
244:
241:
237:
236:
229:
228:
226:
224:
219:
218:
214:
210:
207:
205:
203:ECHA InfoCard
200:
199:
192:
188:
187:
185:
183:
180:
179:
172:
168:
167:
165:
163:
160:
159:
152:
148:
147:
145:
143:
140:
139:
135:
132:
128:
127:
120:
116:
115:
113:
109:
104:
103:
96:
92:
91:
89:
86:
82:
81:
76:
62:
54:
50:
45:
41:
36:
32:
27:
19:
2780:. Retrieved
2773:the original
2760:
2749:. Retrieved
2745:
2733:
2711:
2702:
2691:. Retrieved
2683:
2674:
2665:
2656:
2637:
2631:
2606:. Retrieved
2599:the original
2586:
2567:
2561:
2552:
2543:
2526:
2522:
2484:
2480:
2474:
2449:
2445:
2439:
2414:
2410:
2400:
2389:. Retrieved
2385:
2376:
2351:
2347:
2337:
2307:
2285:
2261:. Retrieved
2257:
2248:
2175:
2163:
2157:
2150:
2123:
2058:
2055:
1974:
1877:
1826:ammoxidation
1823:
1802:
1680:
1653:+ CO + CH
1636:
1595:
1555:
1484:methacrolein
1477:
1463:
1455:
1406:formaldehyde
1403:
1400:
1378:+ CO + CH
1357:
1345:
1293:Methanolysis
1291:
1208:
1172:
1164:
1135:
1120:(MAA), is a
1089:
1085:
1084:
969:
892:
870:Autoignition
805:
661:
623:
613:Main hazards
602:
529:
296:RTECS number
78:Identifiers
64:Other names
2263:30 November
2258:Chemsrc.com
2162:to produce
2144:as well as
1657:OH → CH
1580:O → (CH
1576:+ CO + H
1382:OH → CH
1323:OH → CH
1216:(ACH) to a
907:median dose
893:Lethal dose
872:temperature
859:Flash point
656:Signal word
607:(OHS/OSH):
467:Appearance
420:Properties
209:100.001.180
171:ChEMBL49996
151:CHEBI:34840
2848:Categories
2782:2013-10-29
2751:2021-11-30
2693:2020-01-26
2666:Mpausa.org
2608:2013-10-29
2391:2024-02-27
2210:References
2075:)–CHO + CH
1991:O → CH
1432:O → CH
1143:Staudinger
887:1.7%-8.2%
635:Pictograms
617:Flammable
577:Structure
490:0.94 g/cm
455:Molar mass
321:196OC77688
182:ChemSpider
106:3D model (
85:CAS Number
2431:0019-7866
2368:0075-4617
2017:+ HCOOCH
1987:)CN + H
1717:)–CHO + H
1705:C–OH) + O
1521:)CHO +
1299:and MMA:
1155:Otto Röhm
1096:with the
1012:1000 ppm
790:P403+P235
786:P403+P233
782:P370+P378
770:P333+P313
766:P332+P313
754:P304+P340
746:P302+P352
626:labelling
589:1.6–1.97
564:Viscosity
332:UN number
303:OZ5075000
230:201-297-1
222:EC Number
2869:Monomers
2791:cite web
2617:cite web
2466:30211916
2292:(NIOSH).
2242:(NIOSH).
2194:Acrylate
2188:See also
2130:plastics
2128:acrylic
2061:-butanol
1624:H + H
1506:)CHO + H
1331:)C(O)OCH
1315:H)C(O)NH
1276:H)C(O)NH
1252:H)C(O)NH
1240:→ ((CH
1128:(PMMA).
1092:) is an
806:NFPA 704
597:Hazards
554:(χ)
2746:Who.int
2236:"#0426"
2160:in situ
2101:)–COOCH
2089: O
2084:⁄
2033:+ HCONH
1952:OH → CH
1894:)CN + H
1858: O
1853:⁄
1779:OH → CH
1744: O
1739:⁄
1734:)CHO +
1697:(or (CH
1531: O
1526:⁄
1366:(MeP):
1264:→ (CH
1205:C(OH)CN
1179:acetone
1132:History
1122:monomer
1098:formula
1067:what is
1065: (
486:Density
460:100.117
272:PubChem
136:605459
95:80-62-6
2644:
2574:
2487:: 61.
2464:
2429:
2366:
2324:
2043:→ NH
2029:)COOCH
2013:)–CONH
1999:)–CONH
1960:)COOCH
1936:)–CONH
1914:)–CONH
1906:O → CH
1862:→ CH
1775:H + CH
1649:CH≡CCH
1637:Using
1535:→ CH
1295:gives
1108:)COOCH
1062:verify
1059:
1020:(SDS)
662:Danger
535:1.35
404:SMILES
260:C14527
162:ChEMBL
47:Names
2776:(PDF)
2769:(PDF)
2742:(PDF)
2602:(PDF)
2595:(PDF)
2097:=C(CH
2079:OH +
2071:=C(CH
2039:HCONH
2025:=C(CH
2009:=C(CH
1995:=C(CH
1983:=C(CH
1956:=C(CH
1932:=C(CH
1910:=C(CH
1890:=C(CH
1866:=C(CH
1844:+ NH
1783:=C(CH
1767:=C(CH
1752:=C(CH
1748:→ CH
1730:=C(CH
1713:=C(CH
1709:→ CH
1689:=C(CH
1661:=C(CH
1616:=C(CH
1572:=CHCH
1539:=C(CH
1517:=C(CH
1502:=C(CH
1428:+ CH
1335:+ NH
1327:=C(CH
1319:+ CH
1311:C(OSO
1272:C(OSO
1248:C(OSO
1114:ester
1104:=C(CH
970:NIOSH
568:0.6 c
379:InChI
336:1247
245:2691
142:ChEBI
108:JSmol
2797:link
2723:and
2642:ISBN
2623:link
2572:ISBN
2462:PMID
2427:ISSN
2364:ISSN
2322:ISBN
2265:2021
2204:PMMA
2134:PMMA
2114:Uses
2093:→ CH
2059:tert
2047:+ CO
2021:→ CH
1964:+ NH
1948:+ CH
1840:C=CH
1608:CHCO
1588:CHCO
1448:+ H
1440:)CCO
1280:+ H
1185::
1181:and
1006:IDLH
798:P501
794:P405
778:P363
774:P362
762:P321
758:P312
742:P280
738:P272
734:P271
730:P264
726:P261
722:P243
718:P242
714:P241
710:P240
706:P233
702:P210
688:H335
684:H317
680:H315
676:H225
528:log
476:Odor
312:UNII
285:6658
251:KEGG
191:6406
2531:doi
2527:221
2489:doi
2454:doi
2419:doi
2356:doi
2352:167
2314:doi
2138:PVC
2105:+ H
1968:HSO
1902:+ H
1848:+
1832:(CH
1795:+ H
1787:)CO
1771:)CO
1756:)CO
1665:)CO
1620:)CO
1600:(CH
1543:)CO
1436:(CH
1339:HSO
1303:(CH
1224:(CH
1189:(CH
1177:of
1116:of
1090:MMA
993:REL
980:PEL
624:GHS
348:EPA
275:CID
70:MMA
2850::
2793:}}
2789:{{
2744:.
2718:UN
2716:.
2710:.
2686:.
2682:.
2664:.
2619:}}
2615:{{
2551:.
2525:.
2501:^
2485:29
2483:.
2460:.
2450:47
2448:.
2425:.
2415:28
2413:.
2409:.
2384:.
2362:.
2350:.
2346:.
2320:.
2298:^
2288:.
2284:.
2273:^
2256:.
2238:.
2218:^
2180:50
2178:LD
2168:.
2067:CH
2005:CH
1979:CH
1944:SO
1940:·H
1928:CH
1922:SO
1918:·H
1898:SO
1886:CH
1812:NO
1791:CH
1763:CH
1726:CH
1685:CH
1669:CH
1568:CH
1513:CH
1494:CH
1490:CH
1444:CH
1424:CH
1420:CO
1416:CH
1412:CH
1394:CH
1390:CO
1386:CH
1284:SO
1260:SO
1256:·H
1236:SO
1100:CH
947:Lo
945:LC
923:50
921:LC
903:50
901:LD
796:,
792:,
788:,
784:,
780:,
776:,
772:,
768:,
764:,
760:,
756:,
752:,
748:,
744:,
740:,
736:,
732:,
728:,
724:,
720:,
716:,
712:,
708:,
704:,
686:,
682:,
678:,
628::
2799:)
2785:.
2754:.
2727:.
2696:.
2668:.
2650:.
2625:)
2611:.
2580:.
2537:.
2533::
2495:.
2491::
2468:.
2456::
2433:.
2421::
2394:.
2370:.
2358::
2332:.
2330:.
2316::
2267:.
2132:(
2109:O
2107:2
2103:3
2099:3
2095:2
2091:2
2086:2
2082:1
2077:3
2073:3
2069:2
2045:3
2041:2
2035:2
2031:3
2027:3
2023:2
2019:3
2015:2
2011:3
2007:2
2001:2
1997:3
1993:2
1989:2
1985:3
1981:2
1970:4
1966:4
1962:3
1958:3
1954:2
1950:3
1946:4
1942:2
1938:2
1934:3
1930:2
1924:4
1920:2
1916:2
1912:3
1908:2
1904:2
1900:4
1896:2
1892:3
1888:2
1874:O
1872:2
1868:3
1864:2
1860:2
1855:2
1851:3
1846:3
1842:2
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