1231:
370:
229:
33:
24:
654:
1123:
921:
1327:
in a medium-high temperature. Use of supercritical water instead of acetic acid as a solvent diminishes environmental impact and offers a cost advantage. However, the scope of such reaction systems is limited by the even more demanding conditions than the industrial process (300–400 °C,
1203:-xylene proceeds by a free radical process. Bromine radicals decompose cobalt and manganese hydroperoxides. The resulting oxygen-based radicals abstract hydrogen from a methyl group, which have weaker C–H bonds than does the aromatic ring. Many intermediates have been isolated.
1435:(PET). World production in 1970 was around 1.75 million tonnes. By 2006, global purified terephthalic acid (PTA) demand had exceeded 30 million tonnes. A smaller, but nevertheless significant, demand for terephthalic acid exists in the production of
1081:) opens the way for further oxidation to monomethyl terephthalate. In the Dynamit−Nobel process these two oxidations and the esterification were performed in a single reactor. The reaction conditions also lead to a second esterification, producing
1093:-toluic acid directly to terephthalic acid, without the need to isolate intermediates and still using air as the oxidant. Amoco (as Standard Oil of Indiana) purchased the Mid-Century/ICI technology, and the process is now known by their name.
1399:
process" or "Raecke process", named after the company and patent holder, respectively. This process involves the transfer of carboxylate groups. For example potassium benzoate disproportionates to potassium terephthalate, and
1921:
Karthikeyan, N.; Joseph Prince, J.; Ramalingam, S.; Periandy, S. (2015). "Electronic and vibrational investigation and NMR–mass spectroscopic analysis of terephthalic acid using quantum
Gaussian calculations".
662:
1456:. Polyester films are used widely in audio and video recording tapes, data storage tapes, photographic films, labels and other sheet material requiring both dimensional stability and toughness.
634:
1340:
Ketones act as promoters for formation of the active cobalt(III) catalyst. In particular, ketones with α-methylene groups oxidize to hydroperoxides that are known to oxidize cobalt(II). 2-
1250:
is common. The high temperature diminishes oxygen solubility in an already oxygen-starved system. Pure oxygen cannot be used in the traditional system due to hazards of flammable organic–O
2109:
Tomás, Rogério A. F.; Bordado, João C. M.; Gomes, João F. P. (2013). "p-Xylene
Oxidation to Terephthalic Acid: A Literature Review Oriented toward Process Optimization and Development".
1293:
environment allows for the use of pure oxygen directly, instead of air, with reduced flammability hazards. The solubility of molecular oxygen in solution is also enhanced in the CO
728:
1027:
Terephthalic acid was first isolated (from turpentine) by the French chemist Amédée
Cailliot (1805–1884) in 1846. Terephthalic acid became industrially important after
2039:
1336:
As with any large-scale process, many additives have been investigated for potential beneficial effects. Promising results have been reported with the following.
1528:, most notably the American M83 smoke grenade and M90 vehicle-employed smoke grenade, producing a thick white smoke that acts as an obscurant in the visual and
2144:
Wang, Qinbo; Cheng, Youwei; Wang, Lijun; Li, Xi (2007). "Semicontinuous
Studies on the Reaction Mechanism and Kinetics for the Liquid-Phase Oxidation of
1266:
before being released. Additionally, the corrosive nature of bromides at high temperatures requires the reaction be run in expensive titanium reactors.
2597:
934:
1994:
2374:
Ogata, Yoshiro; Hojo, Masaru; Morikawa, Masanobu (1960). "Further
Studies on the Preparation of Terephthalic Acid from Phthalic or Benzoic Acid".
2275:
2235:
2150:
419:
32:
1541:
Terephthalic acid is poorly soluble in water and alcohols; consequently, until about 1970 terephthalic acid was purified as its dimethyl
1861:
2347:
724:
2345:
Ogata, Yoshiro; Tsuchida, Masaru; Muramoto, Akihiko (1957). "The
Preparation of Terephthalic Acid from Phthalic or Benzoic Acid".
1230:
2582:
1356:
is a potential replacement for bromide, which is highly corrosive. The phthalimide functions by formation of the oxyl radical.
2510:
929:
603:
2447:"Biochemical and structural characterization of an aromatic ring–hydroxylating dioxygenase for terephthalic acid catabolism"
2047:
116:
2411:
2011:
2553:
2523:
2082:
Terephthalic acid is named on p. 29: "Je désignerai le premier de ces acides, celui qui est insoluble, sous le nom d'
384:
2312:
Pérez, Eduardo; Fraga
Dubreuil, Joan; García Verdugo, Eduardo; et al. (2011). "Selective Aerobic Oxidation of
941:
1359:
Guanidine inhibits the oxidation of the first methyl but enhances the usually slow oxidation of the toluic acid.
1085:, which could be hydrolysed to terepthalic acid. In 1955, Mid-Century Corporation and ICI announced the bromide-
2316:-Xylene in Sub- and Supercritical Water. Part 1. Comparison with Ortho-xylene and the Role of the Catalyst".
1837:
903:
2233:-Toluic Acid under Mild Conditions: Synergistic Effects of Cobalt, Zirconium, Ketones, and Carbon Dioxide".
2592:
2376:
1298:
698:
327:
224:
186:
2577:
348:
23:
1992:
Sheehan, Richard J. (June 15, 2000). "Terephthalic Acid, Dimethyl
Terephthalate, and Isophthalic Acid".
1452:
Polyester fibers based on PTA provide easy fabric care, both alone and in blends with natural and other
716:
1924:
1494:
In the research laboratory, terephthalic acid has been popularized as a component for the synthesis of
1436:
1432:
1016:
991:
887:
653:
543:
2318:
236:
2069:
1106:
In the Amoco process, which is widely adopted worldwide, terephthalic acid is produced by catalytic
1242:
Approximately 5% of the acetic acid solvent is lost by decomposition or "burning". Product loss by
778:
752:
365:
2229:
Zuo, Xiaobin; Subramaniam, Bala; Busch, Daryle H. (2008). "Liquid-Phase
Oxidation of Toluene and
1495:
1408:
562:
134:
2587:
1428:
1122:
1082:
891:
1828:
1509:
occasionally comes as a terephthalate salt; however, the more usual salt of oxycodone is the
1463:
1254:
mixtures. Atmospheric air can be used in its place, but once reacted needs to be purified of
1222:
792:
676:
646:
744:
2458:
1933:
1353:
1215:
1004:
740:
336:
45:
2265:
Zuo, Xiaobin; Niu, Fenghui; Snavely, Kirk; et al. (2010). "Liquid Phase
Oxidation of
836:
732:
206:
8:
2562:
2427:
1833:
1316:
92:
82:
2462:
1937:
369:
228:
166:
2481:
2446:
2208:
1812:
1710:
1688:
1462:
Terephthalic acid is used as a raw material to make terephthalate plasticizers such as
146:
2549:
2519:
2486:
2407:
2191:
2126:
2007:
1949:
984:
830:
2212:
2476:
2466:
2385:
2356:
2327:
2292:
2284:
2244:
2200:
2159:
2118:
1999:
1941:
1484:
1453:
1153:
1149:
1058:
961:
957:
860:
522:
442:
2542:
2086:." (I will designate the first of these acids, which is insoluble, by the name of
998:. Several million tons are produced annually. The common name is derived from the
2269:-Xylene to Terephthalic Acid at Medium-high Temperatures: Multiple Benefits of CO
1309:
1259:
1243:
1218:
850:
586:
300:
255:
2445:
Kincannon, William M.; Zahn, Michael; Clare, Rita; et al. (29 March 2022).
1312:
production, less decarboxylation and higher purity than the commercial process.
1350:
salts enhance the activity of Co-Mn-Br catalysts. Selectivity is also improved.
1278:
overcomes many of the problems with the original industrial process. Because CO
1275:
1165:
1145:
995:
912:
704:
2204:
2177:
Xiao, Y.; Luo, W.-P.; Zhang, X.-Y.; et al. (2010). "Aerobic Oxidation of
1945:
1469:
It is used in the pharmaceutical industry as a raw material for certain drugs.
818:
2571:
2003:
1666:
1529:
1525:
1510:
1401:
1385:
1263:
1208:
1047:
1009:
868:
856:
712:
511:
501:
217:
2471:
1168:
serves as the oxidant. The combination of bromine and acetic acid is highly
2490:
2130:
1953:
1412:
1389:
1247:
1157:
1028:
864:
1920:
1849:
1644:
1622:
1377:
1214:, which is less reactive than the p-xylene owing to the influence of the
1184:
1161:
1039:
767:
736:
2389:
2360:
720:
2331:
2311:
2040:"Polybutylene Terephthalate (PBT) Material Guide & Properties Info"
1477:
1473:
1308:= 31 °C) has more complete oxidation with fewer byproducts, lower
1283:
999:
533:
470:
237:
197:
2297:
2248:
2163:
2122:
1368:
Terephthalic acid can be prepared in the laboratory by oxidizing many
2515:
2288:
1506:
1502:
1347:
1169:
1134:
1107:
1086:
988:
981:
393:
InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
1411:) has reported a route from the dinitrile, which can be obtained by
1395:
Although not commercially significant, there is also the so-called "
911:
Except where otherwise noted, data are given for materials in their
403:
InChI=1/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
1808:
1578:
1488:
1440:
1341:
1188:
1177:
1173:
1141:
1111:
1032:
883:
275:
2540:
Tedder, J. M.; Nechvatal, A.; Tubb, A. H., eds. (1975).
760:
115:
1845:
1373:
1138:
708:
491:
287:
1836:, a common natural product, via a reaction pathway initiated by
1841:
1396:
1381:
1130:
177:
690:
2444:
2406:(3rd ed.). Saltash, UK: Wavelength. 2011. p. 8805.
1600:
1542:
1427:
Virtually the entire world's supply of terephthalic acid and
1297:
environment. Because more oxygen is available to the system,
1255:
748:
311:
157:
105:
353:
1172:, requiring specialized reactors, such as those lined with
686:
266:
1319:
medium, the oxidation can be effectively catalyzed by MnBr
1053:, which resists further air-oxidation. Esterification of
2264:
1864:
a thermoplastic polyester formed from terephthalic acid
1807:
Terephthalic acid and its dimethyl ester have very low
1524:
Terephthalic acid is used as a filler in some military
1472:
In addition to these end uses, Terephthalic acid based
2533:
2344:
2544:
Basic Organic Chemistry: Part 5, Industrial Products
1015:
Terephthalic acid is also used in the production of
682:
2539:
2228:
2541:
1487:saturated polyesters for powder and water-soluble
2373:
2108:
1031:. Terephthalic acid was produced by oxidation of
133:
2569:
2072:[Studies of the essence of turpentine].
1459:Terephthalic acid is used in paint as a carrier.
1225:(4-CBA), which is often a problematic impurity.
1191:system, and compressed air is fed to a reactor.
1156:. Bromine functions as a regenerative source of
299:
2451:Proceedings of the National Academy of Sciences
2276:Industrial & Engineering Chemistry Research
2236:Industrial & Engineering Chemistry Research
2176:
2151:Industrial & Engineering Chemistry Research
2143:
1832:strain E6, terephthalic acid is biodegraded to
506:300 °C (572 °F; 573 K) Sublimes
91:
1995:Ullmann's Encyclopedia of Industrial Chemistry
756:
1269:
2404:Ashford's Dictionary of Industrial Chemicals
1483:PTA is an important raw material for lower
2260:
2258:
2224:
2222:
1862:Polycyclohexylenedimethylene terephthalate
1331:
368:
227:
205:
2598:Substances discovered in the 19th century
2548:. Chichester, UK: John Wiley & Sons.
2480:
2470:
2296:
2181:-Toluic Acid to Terephthalic Acid over T(
1987:
1985:
1983:
1981:
987:, used principally as a precursor to the
335:
2348:Journal of the American Chemical Society
2170:
2067:
1017:PBT plastic (polybutylene terephthalate)
2563:International Chemical Safety Card 0330
2255:
2219:
1991:
1404:rearranges to potassium terephthalate.
364:
2570:
2070:"Études sur l'essence de térébenthine"
2025:
2023:
1978:
1513:. Pharmacologically, one milligram of
786:496 °C (925 °F; 769 K)
772:260 °C (500 °F; 533 K)
218:
2511:CRC Handbook of Chemistry and Physics
2104:
2102:
2100:
2098:
2096:
1880:
1878:
1840:. Combined with the previously known
1363:
1221:group. Incomplete oxidation produces
396:Key: KKEYFWRCBNTPAC-UHFFFAOYSA-N
185:
165:
1480:are also used in hot melt adhesives.
538:polar organic solvents aqueous base
2020:
406:Key: KKEYFWRCBNTPAC-UHFFFAOYAF
290:
274:
13:
2534:External links and further reading
2093:
1875:
1553:Solubility (g/100 g solvent)
14:
2609:
1821:
1517:is equivalent to 1.13 mg of
1282:is a better flame inhibitor than
2508:Haynes, William M., ed. (2016).
2501:
2074:Annales de Chimie et de Physique
1229:
1121:
1101:
919:
652:
454:
31:
22:
2438:
2428:"GTDB – Genome GCF_001010305.1"
2420:
2396:
2367:
2338:
2305:
2148:-Xylene to Terephthalic Acid".
2137:
2061:
2032:
1852:degradation can be engineered.
1818:>1 g/kg (oral, mouse).
1422:
915:(at 25 °C , 100 kPa).
2583:Carboxylic acid-based monomers
1969:
1960:
1914:
1905:
1896:
1887:
1439:and several other engineering
1431:are consumed as precursors to
1372:-disubstituted derivatives of
825:>1 g/kg (oral, mouse)
460:
448:
1:
1868:
1838:terephthalate 1,2-dioxygenase
1536:
1446:
1237:
904:Terephthalic acid (data page)
50:Benzene-1,4-dicarboxylic acid
2377:Journal of Organic Chemistry
2189:Under Moderate Conditions".
1407:Lummus (now a subsidiary of
1299:supercritical carbon dioxide
1194:
1144:. The bromide source can be
1096:
994:, used to make clothing and
7:
2507:
1855:
1802:
1545:. It sublimes when heated.
807:or concentration (LD, LC):
10:
2616:
1925:Spectrochimica Acta Part A
1466:and dibutyl terephthalate.
1437:polybutylene terephthalate
1433:polyethylene terephthalate
1270:Alternative reaction media
1022:
888:Polyethylene terephthalate
2205:10.1007/s10562-009-0227-1
2068:Cailliot, Amédée (1847).
1946:10.1016/j.saa.2014.11.112
1515:hydrochloridum oxycodonae
909:
902:
897:
842:
803:
633:
628:
596:
579:
486:White crystals or powder
435:
415:
380:
75:
56:
44:
39:
30:
21:
2004:10.1002/14356007.a26_193
1496:metal-organic frameworks
1207:-xylene is converted to
980:. This white solid is a
898:Supplementary data page
699:Precautionary statements
528:0.065 g/L at 25 °C
2472:10.1073/pnas.2121426119
2044:omnexus.specialchem.com
1998:. Weinheim: Wiley-VCH.
1519:terephthalas oxycodonae
1409:McDermott International
1332:Promotors and additives
563:Magnetic susceptibility
1429:dimethyl terephthalate
1083:dimethyl terephthalate
892:Dimethyl terephthalate
427:O=C(O)c1ccc(C(O)=O)cc1
1848:, a full pathway for
1829:Comamonas thiooxydans
1532:spectrum when burned.
1464:dioctyl terephthalate
1223:4-carboxybenzaldehyde
793:Threshold limit value
2273:-expanded Liquids".
1354:N-Hydroxyphthalimide
1216:electron-withdrawing
1005:Pistacia terebinthus
46:Preferred IUPAC name
2593:Commodity chemicals
2463:2022PNAS..11921426K
2457:(13): e2121426119.
2432:gtdb.ecogenomic.org
2390:10.1021/jo01082a003
2361:10.1021/ja01579a043
2084:acide téréphtalique
1938:2015AcSpA.139..229K
1834:protocatechuic acid
1739:
1554:
1402:potassium phthalate
1328:>200 bar).
1317:supercritical water
1164:is the solvent and
1129:The process uses a
1042:. Air oxidation of
523:Solubility in water
478: g·mol
147:Beilstein Reference
18:
2578:Dicarboxylic acids
2332:10.1039/C1GC15137A
2185:-Cl)PPMnCl/Co(OAc)
1737:
1711:Dimethyl sulfoxide
1689:Dimethyl formamide
1552:
1364:Alternative routes
942:Infobox references
843:Related compounds
17:Terephthalic acid
16:
2514:(97th ed.).
2384:(12): 2082–2087.
2355:(22): 6005–6008.
2326:(12): 2389–2396.
2249:10.1021/ie070896h
2192:Catalysis Letters
2164:10.1021/ie0615584
2158:(26): 8980–8992.
2123:10.1021/cr300298j
2088:terephthalic acid
1800:
1799:
1794:
1793:
1731:
1730:
1199:The oxidation of
954:Terephthalic acid
950:Chemical compound
948:
947:
879:Related compounds
831:Safety data sheet
677:Hazard statements
349:CompTox Dashboard
117:Interactive image
59:Terephthalic acid
2605:
2559:
2547:
2529:
2495:
2494:
2484:
2474:
2442:
2436:
2435:
2424:
2418:
2417:
2400:
2394:
2393:
2371:
2365:
2364:
2342:
2336:
2335:
2309:
2303:
2302:
2300:
2289:10.1039/B920262E
2262:
2253:
2252:
2226:
2217:
2216:
2199:(1–2): 155–161.
2174:
2168:
2167:
2141:
2135:
2134:
2111:Chemical Reviews
2106:
2091:
2081:
2065:
2059:
2058:
2056:
2055:
2046:. Archived from
2036:
2030:
2029:Haynes, p. 16.29
2027:
2018:
2017:
1989:
1976:
1975:Haynes, p. 16.42
1973:
1967:
1964:
1958:
1957:
1918:
1912:
1911:Haynes, p. 3.579
1909:
1903:
1900:
1894:
1893:Haynes, p. 5.163
1891:
1885:
1884:Haynes, p. 3.492
1882:
1740:
1736:
1555:
1551:
1548:
1547:
1485:molecular weight
1454:synthetic fibers
1380:or a mixture of
1233:
1154:tetrabromoethane
1150:hydrogen bromide
1125:
1059:methyl p-toluate
1057:-toluic acid to
1002:-producing tree
958:organic compound
932:
926:
923:
922:
861:Isophthalic acid
851:carboxylic acids
762:
758:
754:
750:
746:
742:
738:
734:
730:
726:
722:
718:
714:
710:
706:
692:
688:
684:
656:
620:
597:Thermochemistry
575:
573:
477:
462:
456:
450:
443:Chemical formula
373:
372:
357:
355:
339:
303:
292:
278:
256:Gmelin Reference
239:
231:
220:
209:
189:
169:
137:
119:
95:
35:
26:
19:
15:
2615:
2614:
2608:
2607:
2606:
2604:
2603:
2602:
2568:
2567:
2556:
2536:
2526:
2504:
2499:
2498:
2443:
2439:
2426:
2425:
2421:
2414:
2402:
2401:
2397:
2372:
2368:
2343:
2339:
2319:Green Chemistry
2310:
2306:
2272:
2263:
2256:
2227:
2220:
2188:
2175:
2171:
2142:
2138:
2117:(10): 7421–69.
2107:
2094:
2066:
2062:
2053:
2051:
2038:
2037:
2033:
2028:
2021:
2014:
1990:
1979:
1974:
1970:
1966:Haynes, p. 5.37
1965:
1961:
1919:
1915:
1910:
1906:
1902:Haynes, p. 5.96
1901:
1897:
1892:
1888:
1883:
1876:
1871:
1858:
1824:
1816:
1805:
1749:
1744:
1738:Vapor pressure
1539:
1449:
1425:
1366:
1334:
1326:
1322:
1310:carbon monoxide
1307:
1296:
1292:
1287:
1281:
1272:
1260:ozone depleters
1253:
1244:decarboxylation
1240:
1219:carboxylic acid
1197:
1176:. A mixture of
1104:
1099:
1080:
1076:
1072:
1068:
1064:
1025:
996:plastic bottles
979:
975:
971:
967:
951:
944:
939:
938:
937: ?)
928:
924:
920:
916:
890:
886:
880:
867:
863:
859:
853:
822:
816:
799:10 mg/m (STEL)
796:
783:
780:
701:
679:
665:
649:
621:
618:
612:
608:
605:
604:Std enthalpy of
589:
571:
569:
566:
552:
525:
475:
465:
459:
453:
445:
431:
428:
423:
422:
411:
408:
407:
404:
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388:
387:
376:
358:
351:
342:
322:
306:
293:
281:
258:
249:
212:
192:
172:
149:
140:
122:
109:
98:
85:
71:
69:
67:
65:
60:
52:
51:
12:
11:
5:
2613:
2612:
2601:
2600:
2595:
2590:
2585:
2580:
2566:
2565:
2560:
2554:
2535:
2532:
2531:
2530:
2524:
2503:
2500:
2497:
2496:
2437:
2419:
2413:978-0952267430
2412:
2395:
2366:
2337:
2304:
2283:(2): 260–267.
2270:
2254:
2243:(3): 546–552.
2218:
2186:
2169:
2136:
2092:
2060:
2031:
2019:
2013:978-3527306732
2012:
1977:
1968:
1959:
1913:
1904:
1895:
1886:
1873:
1872:
1870:
1867:
1866:
1865:
1857:
1854:
1823:
1822:Biodegradation
1820:
1814:
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1798:
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1776:
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1697:
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1678:
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1628:
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1619:
1618:
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1612:
1609:
1606:
1603:
1597:
1596:
1593:
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1587:
1584:
1581:
1575:
1574:
1571:
1568:
1565:
1562:
1559:
1538:
1535:
1534:
1533:
1526:smoke grenades
1522:
1499:
1492:
1481:
1470:
1467:
1460:
1457:
1448:
1445:
1424:
1421:
1365:
1362:
1361:
1360:
1357:
1351:
1345:
1344:is often used.
1333:
1330:
1324:
1320:
1305:
1294:
1290:
1285:
1279:
1276:carbon dioxide
1271:
1268:
1251:
1239:
1236:
1235:
1234:
1196:
1193:
1166:compressed air
1146:sodium bromide
1127:
1126:
1103:
1100:
1098:
1095:
1078:
1074:
1070:
1066:
1062:
1046:-xylene gives
1024:
1021:
977:
973:
969:
965:
949:
946:
945:
940:
918:
917:
913:standard state
910:
907:
906:
900:
899:
895:
894:
881:
878:
875:
874:
854:
848:
845:
844:
840:
839:
834:
827:
826:
823:
814:
812:
809:
808:
801:
800:
797:
791:
788:
787:
784:
777:
774:
773:
770:
764:
763:
729:P305+P351+P338
702:
697:
694:
693:
680:
675:
672:
671:
666:
661:
658:
657:
650:
645:
642:
641:
631:
630:
626:
625:
624:−816.1 kJ/mol
622:
616:
610:
602:
599:
598:
594:
593:
590:
585:
582:
581:
577:
576:
574:10 cm/mol
567:
561:
558:
557:
554:
550:
540:
539:
536:
530:
529:
526:
521:
518:
517:
514:
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498:
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487:
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457:
451:
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401:
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395:
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359:
347:
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308:
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304:
296:
294:
286:
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263:
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254:
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250:
248:
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233:
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222:
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202:
200:
194:
193:
191:
190:
182:
180:
174:
173:
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170:
162:
160:
154:
153:
150:
145:
142:
141:
139:
138:
130:
128:
124:
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120:
112:
110:
103:
100:
99:
97:
96:
88:
86:
81:
78:
77:
73:
72:
64:-Phthalic acid
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
9:
6:
4:
3:
2:
2611:
2610:
2599:
2596:
2594:
2591:
2589:
2588:Benzoic acids
2586:
2584:
2581:
2579:
2576:
2575:
2573:
2564:
2561:
2557:
2555:9780471850144
2551:
2546:
2545:
2538:
2537:
2527:
2525:9781498754293
2521:
2517:
2513:
2512:
2506:
2505:
2502:Cited sources
2492:
2488:
2483:
2478:
2473:
2468:
2464:
2460:
2456:
2452:
2448:
2441:
2433:
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2405:
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2315:
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2268:
2261:
2259:
2250:
2246:
2242:
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2210:
2206:
2202:
2198:
2194:
2193:
2184:
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2173:
2165:
2161:
2157:
2153:
2152:
2147:
2140:
2132:
2128:
2124:
2120:
2116:
2112:
2105:
2103:
2101:
2099:
2097:
2089:
2085:
2079:
2075:
2071:
2064:
2050:on 2023-11-24
2049:
2045:
2041:
2035:
2026:
2024:
2015:
2009:
2005:
2001:
1997:
1996:
1988:
1986:
1984:
1982:
1972:
1963:
1955:
1951:
1947:
1943:
1939:
1935:
1931:
1927:
1926:
1917:
1908:
1899:
1890:
1881:
1879:
1874:
1863:
1860:
1859:
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1847:
1843:
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1835:
1831:
1830:
1819:
1817:
1810:
1789:
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1781:
1778:
1777:
1773:
1770:
1769:
1765:
1762:
1761:
1757:
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1753:
1747:
1742:
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1735:
1734:
1733:
1726:
1723:
1720:
1717:
1714:
1712:
1709:
1708:
1704:
1701:
1698:
1695:
1692:
1690:
1687:
1686:
1682:
1679:
1676:
1673:
1670:
1668:
1667:Sulfuric acid
1665:
1664:
1660:
1657:
1654:
1651:
1648:
1646:
1643:
1642:
1638:
1635:
1632:
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1613:
1610:
1607:
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1602:
1599:
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1580:
1577:
1576:
1572:
1569:
1566:
1563:
1560:
1557:
1556:
1550:
1549:
1546:
1544:
1531:
1530:near-infrared
1527:
1523:
1520:
1516:
1512:
1511:hydrochloride
1508:
1504:
1500:
1497:
1493:
1490:
1486:
1482:
1479:
1475:
1471:
1468:
1465:
1461:
1458:
1455:
1451:
1450:
1444:
1442:
1438:
1434:
1430:
1420:
1418:
1414:
1410:
1405:
1403:
1398:
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1387:
1383:
1379:
1375:
1371:
1358:
1355:
1352:
1349:
1346:
1343:
1339:
1338:
1337:
1329:
1318:
1313:
1311:
1304:
1300:
1288:
1277:
1267:
1265:
1264:methylbromide
1261:
1257:
1249:
1245:
1232:
1228:
1227:
1226:
1224:
1220:
1217:
1213:
1211:
1206:
1202:
1192:
1190:
1186:
1182:
1180:
1175:
1171:
1167:
1163:
1159:
1158:free radicals
1155:
1151:
1147:
1143:
1140:
1136:
1132:
1124:
1120:
1119:
1118:
1116:
1114:
1109:
1102:Amoco Process
1094:
1092:
1089:oxidation of
1088:
1084:
1060:
1056:
1052:
1050:
1045:
1041:
1037:
1035:
1030:
1020:
1018:
1013:
1011:
1010:phthalic acid
1007:
1006:
1001:
997:
993:
990:
986:
983:
963:
959:
955:
943:
936:
931:
914:
908:
905:
901:
896:
893:
889:
885:
882:
877:
876:
873:
871:
866:
862:
858:
857:Phthalic acid
855:
852:
847:
846:
841:
838:
835:
832:
829:
828:
824:
820:
811:
810:
806:
802:
798:
794:
790:
789:
785:
782:
776:
775:
771:
769:
766:
765:
703:
700:
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695:
681:
678:
674:
673:
670:
667:
664:
660:
659:
655:
651:
648:
644:
643:
639:
637:
632:
627:
623:
615:
607:
601:
600:
595:
591:
588:
587:Dipole moment
584:
583:
578:
568:
564:
560:
559:
555:
549:
545:
542:
541:
537:
535:
532:
531:
527:
524:
520:
519:
515:
513:
512:Boiling point
510:
509:
505:
503:
502:Melting point
500:
499:
495:
493:
490:
489:
485:
482:
481:
474:
472:
469:
468:
447:
444:
440:
439:
434:
425:
424:
421:
414:
400:
390:
389:
386:
379:
371:
367:
366:DTXSID6026080
363:
362:
360:
350:
346:
345:
338:
334:
333:
331:
329:
326:
325:
318:
317:
315:
313:
310:
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297:
295:
289:
285:
284:
277:
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264:
260:
257:
253:
252:
245:
244:
242:
240:
235:
234:
230:
226:
223:
221:
219:ECHA InfoCard
216:
215:
208:
204:
203:
201:
199:
196:
195:
188:
187:ChEMBL1374420
184:
183:
181:
179:
176:
175:
168:
164:
163:
161:
159:
156:
155:
151:
148:
144:
143:
136:
132:
131:
129:
126:
125:
118:
114:
113:
111:
107:
102:
101:
94:
90:
89:
87:
84:
80:
79:
74:
63:
55:
47:
43:
38:
34:
29:
25:
20:
2543:
2509:
2454:
2450:
2440:
2431:
2422:
2403:
2398:
2381:
2375:
2369:
2352:
2346:
2340:
2323:
2317:
2313:
2307:
2280:
2274:
2266:
2240:
2234:
2230:
2196:
2190:
2182:
2178:
2172:
2155:
2149:
2145:
2139:
2114:
2110:
2087:
2083:
2077:
2073:
2063:
2052:. Retrieved
2048:the original
2043:
2034:
1993:
1971:
1962:
1929:
1923:
1916:
1907:
1898:
1889:
1827:
1825:
1806:
1573:240 °C
1540:
1518:
1514:
1426:
1423:Applications
1416:
1413:ammoxidation
1406:
1394:
1390:chromic acid
1376:, including
1369:
1367:
1335:
1314:
1302:
1273:
1248:benzoic acid
1241:
1212:-toluic acid
1209:
1204:
1200:
1198:
1178:
1128:
1112:
1105:
1090:
1054:
1051:-toluic acid
1048:
1043:
1038:with 30-40%
1033:
1029:World War II
1026:
1014:
1003:
953:
952:
872:-Toluic acid
869:
865:Benzoic acid
804:
779:Autoignition
668:
635:
613:
547:
312:RTECS number
76:Identifiers
61:
57:Other names
2076:. Série 3.
1932:: 229–242.
1850:PET plastic
1743:Temperature
1645:Formic acid
1623:Acetic acid
1570:200 °C
1567:160 °C
1564:120 °C
1378:caraway oil
1323:with pure O
1274:The use of
1185:acetic acid
1162:Acetic acid
1040:nitric acid
819:median dose
805:Lethal dose
781:temperature
768:Flash point
663:Signal word
556:3.54, 4.34
516:Decomposes
496:1.519 g/cm
483:Appearance
436:Properties
225:100.002.573
167:CHEBI:15702
2572:Categories
2298:1808/18532
2054:2023-11-24
1869:References
1561:25 °C
1537:Solubility
1478:polyamides
1474:polyesters
1447:Other uses
1238:Challenges
1000:turpentine
837:MSDS sheet
647:Pictograms
580:Structure
534:Solubility
471:Molar mass
337:6S7NKZ40BQ
198:ChemSpider
104:3D model (
83:CAS Number
2516:CRC Press
1507:oxycodone
1503:analgesic
1419:-xylene.
1348:Zirconium
1195:Mechanism
1170:corrosive
1135:manganese
1108:oxidation
1097:Synthesis
1087:catalysed
989:polyester
982:commodity
753:P403+P233
745:P337+P313
741:P332+P313
725:P304+P340
721:P302+P352
638:labelling
606:formation
319:WZ0875000
246:202-830-0
238:EC Number
2491:35312352
2213:95855968
2131:23767849
2080:: 27–40.
1954:25561302
1856:See also
1809:toxicity
1803:Toxicity
1748:Pressure
1579:Methanol
1489:coatings
1441:polymers
1342:Butanone
1262:such as
1189:catalyst
1174:titanium
1142:catalyst
985:chemical
884:p-Xylene
849:Related
629:Hazards
565:(χ)
152:1909333
93:100-21-0
2482:9060491
2459:Bibcode
1934:Bibcode
1846:MHETase
1811:, with
1558:Solvent
1386:cuminol
1374:benzene
1181:-xylene
1139:bromide
1115:-xylene
1036:-xylene
1023:History
962:formula
935:what is
933: (
669:Warning
544:Acidity
492:Density
476:166.132
288:PubChem
2552:
2522:
2489:
2479:
2410:
2211:
2129:
2010:
1952:
1842:PETase
1790:101.3
1750:(kPa)
1605:0.0019
1397:Henkel
1382:cymene
1289:, a CO
1256:toxins
1187:, the
1131:cobalt
956:is an
930:verify
927:
833:(SDS)
592:2.6D
420:SMILES
276:C06337
261:50561
178:ChEMBL
135:B00943
127:3DMet
40:Names
2209:S2CID
1782:53.3
1774:26.7
1766:13.3
1627:0.035
1601:Water
1543:ester
1505:drug
1388:with
960:with
795:(TLV)
570:−83.5
385:InChI
158:ChEBI
106:JSmol
2550:ISBN
2520:ISBN
2487:PMID
2408:ISBN
2314:para
2127:PMID
2008:ISBN
1950:PMID
1844:and
1758:1.3
1745:(°C)
1639:4.5
1633:0.75
1617:9.0
1611:0.38
1608:0.08
1501:The
1476:and
1384:and
1370:para
1258:and
1008:and
761:P501
757:P405
749:P362
737:P321
733:P312
717:P280
713:P271
709:P264
705:P261
691:H335
687:H319
683:H315
328:UNII
301:7489
267:KEGG
207:7208
62:para
2477:PMC
2467:doi
2455:119
2386:doi
2357:doi
2328:doi
2293:hdl
2285:doi
2245:doi
2201:doi
2197:134
2160:doi
2119:doi
2115:113
2000:doi
1942:doi
1930:139
1826:In
1787:404
1779:387
1771:370
1763:353
1755:303
1693:6.7
1649:0.5
1636:1.8
1630:0.3
1614:1.7
1589:2.9
1583:0.1
1415:of
1315:In
1246:to
1152:or
1110:of
1061:(CH
992:PET
972:(CO
636:GHS
617:298
354:EPA
291:CID
70:BDC
68:PTA
66:TPA
2574::
2518:.
2485:.
2475:.
2465:.
2453:.
2449:.
2430:.
2382:25
2380:.
2353:79
2351:.
2324:13
2322:.
2291:.
2281:12
2279:.
2257:^
2241:47
2239:.
2221:^
2207:.
2195:.
2156:46
2154:.
2125:.
2113:.
2095:^
2090:.)
2078:21
2042:.
2022:^
2006:.
1980:^
1948:.
1940:.
1928:.
1877:^
1815:50
1813:LD
1727:—
1715:20
1705:—
1683:—
1661:—
1595:—
1592:15
1443:.
1392:.
1183:,
1160:.
1148:,
1117::
1077:CH
1073:CO
1019:.
1012:.
976:H)
815:50
813:LD
759:,
755:,
751:,
747:,
743:,
739:,
735:,
731:,
727:,
723:,
719:,
715:,
711:,
707:,
689:,
685:,
640::
609:(Δ
553:)
546:(p
2558:.
2528:.
2493:.
2469::
2461::
2434:.
2416:.
2392:.
2388::
2363:.
2359::
2334:.
2330::
2301:.
2295::
2287::
2271:2
2267:p
2251:.
2247::
2231:p
2215:.
2203::
2187:2
2183:p
2179:p
2166:.
2162::
2146:p
2133:.
2121::
2057:.
2016:.
2002::
1956:.
1944::
1936::
1724:—
1721:—
1718:—
1702:—
1699:—
1696:—
1680:—
1677:—
1674:—
1671:2
1658:—
1655:—
1652:—
1586:—
1521:.
1498:.
1491:.
1417:p
1325:2
1321:2
1306:c
1303:T
1301:(
1295:2
1291:2
1286:2
1284:N
1280:2
1252:2
1210:p
1205:p
1201:p
1179:p
1137:–
1133:–
1113:p
1091:p
1079:3
1075:2
1071:4
1069:H
1067:6
1065:C
1063:3
1055:p
1049:p
1044:p
1034:p
978:2
974:2
970:4
968:H
966:6
964:C
925:N
870:p
821:)
817:(
619:)
614:H
611:f
572:×
551:a
548:K
464:4
461:O
458:6
455:H
452:8
449:C
356:)
352:(
108:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
