Knowledge

Transalkylation

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756: 322:. This is the ratio of the number of methyl groups to the number of benzene rings in all of the substrates. For example, in the disproportionation of toluene, the M/R ratio is 1. Side reactions in which alkanes are produced reduce the number of methyl groups available which decreases the M/R ratio. This can be mitigated by adding compounds with higher numbers of methyl groups, such as trimethylbenzene. The ratio of products produced depends only on the M/R ratio so different starting materials can produce the same compounds via transalkylation. 886: 103:
reaction of toluene in which one toluene molecule transfers its methyl group to another one. The reaction is not selective, and the xylene produced can be ortho, meta, or para. There is a higher demand for para xylene, so it is often separated, and the mixture is allowed to reequilibrate to give more
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because of their channel openings are often between 0.4 and 1.5 nanometers, just enough for the molecules to pass through. Aromatics molecules enter and exit these channels at different rates, also called diffusion. In addition to their molecular sieving effect, zeolites have weakly bonded protons
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Transalkylation reactions of six to ten carbon methylated aromatics are often performed with the cofeed of hydrogen gas, over a zeolite based solid catalyst. Industrial processes operate the transalkylation reactor at elevated temperature and pressure to achieve desired process economics. Zeolites
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Diethylbenzenes arise as side-products of the alkylation of benzene with ethylene, which is conducted on a very large scale. Since there is only a limited market for diethylbenzene, much of it is recycled by transalkylation to give ethylbenzene:
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Al-Khattaf, Sulaiman; Ali, Syed A.; Aitani, Abdullah M.; Žilková, Naděžda; Kubička, David; Čejka, Jiří (2014). "Recent Advances in Reactions of Alkylbenzenes over Novel Zeolites: The Effects of Zeolite Structure and Morphology".
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to produce xylene. The reaction occurs via equilibrium, so the product is not pure xylene. Many products are produced with varying numbers of methyl groups. The quantities in which each product is produced depends on the
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Zeolites of varying sizes are used to perform transalkylation on different substrates. For example, zeolites with a pore size of 5.5Ă… are suitable for benzene, toluene, xylenes and trimethylbenzenes transalkylations.
735: 884:, Goncalvez De Almeida; Jose Luis & Berna Tejero et al., "Catalytic transalkylation of dialkyl benzenes", published 2010-01-28, assigned to Petroquimica Espanola, S.A. Petresa 963:
Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives".
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Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons".
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Transalkylation, as used by the petrochemical industry, is often used to convert toluene into benzene and xylenes. This is achieved through a
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building blocks. These crystals are porous in nature with characteristic micropore channels, cavities. Zeolite is known as one class of
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Tsai, Tseng-Chang "Disproportionation and Transalkylation of Alkylbenzenes over Zeolite Catalysts". Elsevier Science, 1999
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originated from its chemical composition. These are chemical active centers for acid-catalyzed transalkylation reaction.
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Transalkylation is employed in the commercial production of aromatics beyond the usual BTX feedstocks. For example,
1077: 75:. Transalkylation can convert toluene, which is overproduced, into benzene and xylene, which are under-produced. 67:. Motivation for using transalkylation reactions is based on a difference in production and demand for benzene, 1907: 881: 2031: 779: 1480: 1070: 1517: 1990: 1890: 745: 52: 1997: 1885: 755: 1966: 1411: 8: 1272: 789: 945: 741: 373: 100: 64: 913: 1956: 1926: 1684: 1306: 1014: 979: 827: 784: 28: 20: 949: 900:
Harmer, Mark A.; Sun, Qun (2001). "Solid acid catalysis using ion-exchange resins".
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Process and apparatus for ethylbenzene production and transalkylation to xylene
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is produced in part via two transalkylation reactions. In one example,
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Chemical reaction which transfers an alkyl group between molecules
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This type of reaction can also be performed with toluene and
811: 1204: 286:{\displaystyle {\ce {C6H4(C2H5)2 + C6H6 -> 2 C6H5C2H5}}} 926: 962: 723: 710: 689: 676: 656: 643: 627: 614: 601: 575: 562: 512: 499: 478: 465: 449: 436: 423: 410: 279: 266: 253: 240: 220: 207: 191: 178: 165: 147: 134: 998: 519:{\displaystyle {\ce {(CH3)3COC6H5 -> HOC6H4C(CH3)3}}} 759:
1,3-Diisopropylbenzene is produced via transalkylation.
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to produce xylene. In this example, the M/R ratio is 2.
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Styrene process with recycle from dehydrogenation zone
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are micro-crystalline solids composed of tetrahedral
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to another. The reaction is used for the transfer of
729: 518: 285: 999:K. W. Schmiedel; D. Decker (2012). "Resorcinol". 95:Reaction of toluene to produce benzene and xylene 2023: 384:-butylphenyl ether is isomerized to the phenol: 1002:Ullmann's Encyclopedia of Industrial Chemistry 967:Ullmann's Encyclopedia of Industrial Chemistry 815:Ullmann's Encyclopedia of Industrial Chemistry 1078: 1058:Transalkylation in the Petrochemical Industry 1085: 1071: 807: 805: 51:rings. This is of particular value in the 899: 665: 229: 754: 740:Transalkylation in conjunction with the 300: 90: 802: 2024: 867: 865: 863: 861: 1092: 1066: 86: 325: 1053:Exxon Mobil Transalkylation Process 858: 13: 992: 107: 14: 2043: 1048:Transalkylation of dialkylbenzene 1031: 744:contributes to the production of 537:-butylphenol by treatment with 533:-butylphenol is converted to 4- 305:Transalkylation of toluene and 956: 920: 893: 882:US application 20100022814 874: 840: 713: 697: 659: 617: 604: 588: 580: 502: 486: 452: 413: 397: 223: 181: 152: 83:in transalkylation reactions. 1: 1011:10.1002/14356007.a23_111.pub2 914:10.1016/S0926-860X(01)00794-3 795: 31:involving the transfer of an 942:10.1080/01614940.2014.946846 902:Applied Catalysis A: General 296: 7: 763: 10: 2048: 367: 1980: 1939: 1859: 1836: 1798: 1775: 1670: 1591: 1461: 1438: 1394: 1337: 1260: 1235: 1100: 976:10.1002/14356007.a19_313 824:10.1002/14356007.a13_227 1991:chemical classification 1043:Transalkylation process 1005:. Weinheim: Wiley-VCH. 970:. Weinheim: Wiley-VCH. 818:. Weinheim: Wiley-VCH. 780:Friedel–Crafts reaction 760: 746:1,3-diisopropylbenzene 731: 520: 310: 287: 96: 53:petrochemical industry 1998:chemical nomenclature 758: 732: 529:Additionally, 2,4-di- 521: 304: 288: 94: 548: 541:by transalkylation: 391: 120: 1454:not C, H or O) 790:Transesterification 725: 712: 691: 678: 658: 645: 629: 616: 603: 577: 564: 514: 501: 480: 467: 451: 438: 425: 412: 281: 268: 255: 242: 222: 209: 193: 180: 167: 149: 136: 2032:Addition reactions 1896:Hypervalent iodine 852:2012-03-20 at the 761: 742:Hock rearrangement 727: 700: 695: 679: 666: 646: 633: 591: 586: 578: 565: 552: 516: 489: 484: 468: 455: 439: 426: 400: 395: 311: 283: 269: 256: 243: 230: 210: 197: 168: 155: 150: 137: 124: 101:disproportionation 97: 87:Disproportionation 79:are often used as 65:aromatic compounds 2019: 2018: 1957:Sulfenyl chloride 1935: 1934: 1434: 1433: 1253:(only C, H and O) 1094:Functional groups 930:Catalysis Reviews 785:Hydrodealkylation 748:, a precursor to 703: 694: 682: 669: 649: 636: 594: 585: 568: 555: 492: 483: 471: 458: 442: 429: 403: 326:Zeolite catalysts 272: 259: 246: 233: 213: 200: 171: 158: 140: 127: 29:chemical reaction 21:organic chemistry 2039: 1986: 1891:Trifluoromethoxy 1459: 1458: 1455: 1258: 1257: 1254: 1107: 1087: 1080: 1073: 1064: 1063: 1025: 1024: 996: 990: 989: 960: 954: 953: 924: 918: 917: 897: 891: 890: 889: 885: 878: 872: 869: 856: 844: 838: 837: 809: 736: 734: 733: 728: 726: 724: 721: 716: 711: 708: 701: 692: 690: 687: 680: 677: 674: 667: 657: 654: 647: 644: 641: 634: 628: 625: 620: 615: 612: 607: 602: 599: 592: 583: 576: 573: 566: 563: 560: 553: 525: 523: 522: 517: 515: 513: 510: 505: 500: 497: 490: 481: 479: 476: 469: 466: 463: 456: 450: 447: 440: 437: 434: 427: 424: 421: 416: 411: 408: 401: 354: 353: 352: 342: 341: 340: 315:trimethylbenzene 307:trimethylbenzene 292: 290: 289: 284: 282: 280: 277: 270: 267: 264: 257: 254: 251: 244: 241: 238: 231: 221: 218: 211: 208: 205: 198: 192: 189: 184: 179: 176: 169: 166: 163: 156: 148: 145: 138: 135: 132: 125: 37:organic compound 2047: 2046: 2042: 2041: 2040: 2038: 2037: 2036: 2022: 2021: 2020: 2015: 1984: 1976: 1931: 1886:Trichloromethyl 1881:Trifluoromethyl 1855: 1832: 1794: 1771: 1666: 1635:Phosphine oxide 1587: 1453: 1451: 1450: 1448: 1446: 1444: 1442: 1440: 1430: 1390: 1333: 1252: 1251: 1246: 1241: 1231: 1105: 1104: 1096: 1091: 1034: 1029: 1028: 1021: 997: 993: 986: 961: 957: 925: 921: 898: 894: 887: 879: 875: 870: 859: 854:Wayback Machine 845: 841: 834: 810: 803: 798: 775:BTX (chemistry) 766: 722: 717: 709: 704: 696: 688: 683: 675: 670: 655: 650: 642: 637: 626: 621: 613: 608: 600: 595: 587: 579: 574: 569: 561: 556: 551: 549: 546: 545: 511: 506: 498: 493: 485: 477: 472: 464: 459: 448: 443: 435: 430: 422: 417: 409: 404: 396: 394: 392: 389: 388: 370: 357:molecular sieve 351: 348: 347: 346: 344: 339: 336: 335: 334: 332: 328: 299: 278: 273: 265: 260: 252: 247: 239: 234: 219: 214: 206: 201: 190: 185: 177: 172: 164: 159: 151: 146: 141: 133: 128: 123: 121: 118: 117: 110: 108:Diethylbenzenes 89: 55:to manufacture 25:transalkylation 17: 12: 11: 5: 2045: 2035: 2034: 2017: 2016: 2014: 2013: 2012: 2011: 2006: 1994: 1987: 1981: 1978: 1977: 1975: 1974: 1972:Sulfinylamines 1969: 1964: 1959: 1954: 1952:Phosphoramides 1949: 1947:Isothiocyanate 1943: 1941: 1937: 1936: 1933: 1932: 1930: 1929: 1924: 1923: 1922: 1912: 1911: 1910: 1900: 1899: 1898: 1893: 1888: 1883: 1878: 1867: 1865: 1857: 1856: 1854: 1853: 1848: 1842: 1840: 1834: 1833: 1831: 1830: 1825: 1823:Selenenic acid 1820: 1818:Seleninic acid 1815: 1813:Selenonic acid 1810: 1804: 1802: 1796: 1795: 1793: 1792: 1787: 1781: 1779: 1773: 1772: 1770: 1769: 1764: 1759: 1754: 1749: 1744: 1739: 1734: 1729: 1724: 1719: 1714: 1709: 1704: 1699: 1694: 1693: 1692: 1682: 1676: 1674: 1668: 1667: 1665: 1664: 1659: 1654: 1649: 1648: 1647: 1637: 1632: 1627: 1622: 1621: 1620: 1610: 1609: 1608: 1606:Phosphodiester 1597: 1595: 1589: 1588: 1586: 1585: 1580: 1575: 1570: 1565: 1560: 1555: 1550: 1545: 1540: 1535: 1530: 1525: 1520: 1515: 1510: 1505: 1500: 1495: 1490: 1485: 1484: 1483: 1478: 1467: 1465: 1456: 1452:(one element, 1436: 1435: 1432: 1431: 1429: 1428: 1427: 1426: 1416: 1415: 1414: 1409: 1398: 1396: 1392: 1391: 1389: 1388: 1383: 1378: 1377: 1376: 1366: 1365: 1364: 1359: 1354: 1343: 1341: 1335: 1334: 1332: 1331: 1329:Methylenedioxy 1326: 1321: 1320: 1319: 1314: 1304: 1303: 1302: 1297: 1287: 1286: 1285: 1275: 1270: 1264: 1262: 1255: 1233: 1232: 1230: 1229: 1224: 1219: 1218: 1217: 1212: 1202: 1201: 1200: 1195: 1190: 1185: 1180: 1175: 1165: 1164: 1163: 1158: 1148: 1147: 1146: 1141: 1136: 1131: 1126: 1121: 1110: 1108: 1106:(only C and H) 1098: 1097: 1090: 1089: 1082: 1075: 1067: 1061: 1060: 1055: 1050: 1045: 1040: 1033: 1032:External links 1030: 1027: 1026: 1020:978-3527306732 1019: 991: 985:978-3527306732 984: 955: 936:(4): 333–402. 919: 908:(1–2): 45–62. 892: 873: 857: 839: 833:978-3527306732 832: 800: 799: 797: 794: 793: 792: 787: 782: 777: 772: 765: 762: 738: 737: 720: 715: 707: 699: 686: 673: 664: 661: 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1735: 1733: 1730: 1728: 1727:Sulfinic acid 1725: 1723: 1722:Thiosulfonate 1720: 1718: 1715: 1713: 1712:Thiosulfinate 1710: 1708: 1707:Sulfenic acid 1705: 1703: 1700: 1698: 1695: 1691: 1688: 1687: 1686: 1683: 1681: 1678: 1677: 1675: 1673: 1669: 1663: 1662:Phosphaallene 1660: 1658: 1657:Phosphaalkyne 1655: 1653: 1652:Phosphaalkene 1650: 1646: 1643: 1642: 1641: 1638: 1636: 1633: 1631: 1628: 1626: 1623: 1619: 1616: 1615: 1614: 1611: 1607: 1604: 1603: 1602: 1599: 1598: 1596: 1594: 1590: 1584: 1581: 1579: 1576: 1574: 1571: 1569: 1566: 1564: 1561: 1559: 1556: 1554: 1551: 1549: 1546: 1544: 1541: 1539: 1536: 1534: 1531: 1529: 1526: 1524: 1521: 1519: 1516: 1514: 1511: 1509: 1506: 1504: 1501: 1499: 1496: 1494: 1491: 1489: 1486: 1482: 1479: 1477: 1474: 1473: 1472: 1469: 1468: 1466: 1464: 1460: 1457: 1437: 1425: 1422: 1421: 1420: 1417: 1413: 1410: 1408: 1405: 1404: 1403: 1400: 1399: 1397: 1393: 1387: 1384: 1382: 1379: 1375: 1372: 1371: 1370: 1367: 1363: 1360: 1358: 1355: 1353: 1350: 1349: 1348: 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1447:hydrogen, 1443:not being 1424:Orthoester 1317:Dioxiranes 1295:Enol ether 1183:1-Propenyl 796:References 770:Alkylation 750:resorcinol 2004:inorganic 1838:Tellurium 1752:Thioester 1717:Sulfoxide 1702:Disulfide 1690:Sulfonium 1640:Phosphine 1618:Phosphite 1601:Phosphate 1533:Carbamate 1508:Hydrazone 1441:element, 1439:Only one 1412:Anhydride 1151:Methylene 660:⟶ 453:⟶ 320:M/R ratio 297:M/R Ratio 224:⟶ 81:catalysts 35:from one 2026:Category 1985:See also 1920:Chloride 1846:Tellurol 1800:Selenium 1767:Xanthate 1481:Ammonium 1463:Nitrogen 1445:carbon, 1402:Carboxyl 1369:Aldehyde 1357:Acryloyl 1339:carbonyl 1243:hydrogen 1198:Cumulene 950:97415930 850:Archived 764:See also 77:Zeolites 57:p-xylene 47:between 2009:organic 1808:Selenol 1732:Sulfone 1685:Sulfide 1583:NONOate 1578:Nitroso 1568:Nitrite 1563:Nitrate 1553:Cyanate 1543:Nitrile 1528:Amidine 1523:Imidate 1493:Nitrene 1488:Hydrazo 1476:Enamine 1407:Acetoxy 1395:carboxy 1362:Benzoyl 1300:Epoxide 1283:Methoxy 1273:Alcohol 1227:Carbene 1161:Methine 368:Phenols 73:xylenes 69:toluene 61:styrene 49:benzene 1908:Iodide 1828:Selone 1672:Sulfur 1381:Ketone 1374:Ketene 1352:Acetyl 1307:Peroxy 1278:Alkoxy 1268:Acetal 1249:oxygen 1238:carbon 1222:Alkyne 1215:Benzyl 1210:Phenyl 1193:Allene 1188:Crotyl 1168:Alkene 1156:Bridge 1144:Pentyl 1129:Propyl 1119:Methyl 1017:  982:  948:  888:  830:  539:phenol 71:, and 41:methyl 1940:Other 1777:Boron 1747:Thial 1680:Thiol 1573:Nitro 1538:Imide 1518:Amide 1503:Oxime 1498:Imine 1471:Amine 1419:Ester 1386:Ynone 1290:Ether 1261:R-O-R 1236:Only 1178:Allyl 1173:Vinyl 1139:Butyl 1124:Ethyl 1114:Alkyl 946:S2CID 27:is a 1862:Halo 1347:Acyl 1247:and 1205:Aryl 1015:ISBN 980:ISBN 828:ISBN 535:tert 531:tert 382:tert 376:tert 343:and 43:and 1513:Azo 1007:doi 972:doi 938:doi 910:doi 906:221 820:doi 668:HOC 635:HOC 554:HOC 457:HOC 428:COC 345:SiO 333:AlO 19:In 2028:: 1245:, 1240:, 1013:. 978:. 944:. 934:56 932:. 904:. 860:^ 826:. 804:^ 752:. 702:CH 593:CH 491:CH 402:CH 374:4- 59:, 23:, 1086:e 1079:t 1072:v 1023:. 1009:: 988:. 974:: 952:. 940:: 916:. 912:: 836:. 822:: 719:3 714:) 706:3 698:( 693:C 685:4 681:H 672:6 663:2 652:5 648:H 639:6 631:+ 623:2 618:) 610:3 605:) 597:3 589:( 584:C 581:( 571:3 567:H 558:6 508:3 503:) 495:3 487:( 482:C 474:4 470:H 461:6 445:5 441:H 432:6 419:3 414:) 406:3 398:( 350:4 338:4 275:5 271:H 262:2 258:C 249:5 245:H 236:6 232:C 227:2 216:6 212:H 203:6 199:C 195:+ 187:2 182:) 174:5 170:H 161:2 157:C 153:( 143:4 139:H 130:6 126:C

Index

organic chemistry
chemical reaction
alkyl group
organic compound
methyl
ethyl groups
benzene
petrochemical industry
p-xylene
styrene
aromatic compounds
toluene
xylenes
Zeolites
catalysts

disproportionation

trimethylbenzene
trimethylbenzene
M/R ratio
molecular sieve
4-tert-butylphenol
phenol
Hock rearrangement
1,3-diisopropylbenzene
resorcinol

Alkylation
BTX (chemistry)

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