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Monsanto process

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and methyl iodide, which in turn affords, through carbonylation, acetyl iodide. Acetyl iodide reacts with acetate salts or acetic acid to give the anhydride. Rhodium iodides and lithium salts are employed as catalysts. Because acetic anhydride hydrolyzes, the conversion is conducted under anhydrous
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Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. (1992). "Eastman Chemical Company Acetic Anhydride Process".
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in a process that is similar to the Monsanto acetic acid synthesis. Methyl acetate is used in place of methanol as a source of methyl iodide.
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Hartwig, J. F. Organotransition Metal Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010.
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of 150–200 Â°C and gives a selectivity greater than 99%. It was developed in 1960 by the German chemical company
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https://web.archive.org/web/20050412040850/http://www.uyseg.org/catalysis/ethacid/ethacid2.htm
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involves two non-organometallic steps: conversion of methanol to
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Hosea Cheung, Robin S. Tanke, G. Paul Torrence "Acetic Acid" in
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to form the six-coordinate dicarbonyl complex, which undergoes
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conditions in contrast to the Monsanto acetic acid synthesis.
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Arene complexes of univalent gallium, indium, and thallium
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complex . This five-coordinate complex then reacts with
333:"The Cativa Process for the Manufacture of Acetic Acid" 44: 117:species . This anion rapidly transforms, via the 70:in 1966, which introduced a new catalyst system. 722: 23:is an industrial method for the manufacture of 256:Ullmann's Encyclopedia of Industrial Chemistry 175:with respect to methyl iodide and . Hence the 418: 432: 330: 82:The catalytic cycle of the Monsanto process 519:Oxidative addition / reductive elimination 425: 411: 283:. Archived from the original on 2014-08-11 187:Tennessee Eastman acetic anhydride process 277:"Production method: The Monsanto process" 16:Method for the manufacture of acetic acid 468:Polyhedral skeletal electron pair theory 723: 406: 575:Transition metal fullerene complexes 179:of methyl iodide is proposed as the 13: 610:Transition metal carbyne complexes 605:Transition metal carbene complexes 570:Transition metal indenyl complexes 171:The reaction has been shown to be 77: 73: 14: 762: 620:Transition metal alkyne complexes 615:Transition metal alkene complexes 391: 625:Transition-metal allyl complexes 132:, affording the pentacoordinate 600:Transition metal acyl complexes 359: 324: 308: 269: 248: 1: 258:, 2002, Wiley-VCH, Weinheim. 242: 97:- (top of scheme). The first 382:10.1016/0920-5861(92)80188-S 43:-based process developed by 7: 676:Shell higher olefin process 483:Dewar–Chatt–Duncanson model 281:www.greener-industry.org.uk 234:converts methyl acetate to 50:This process operates at a 10: 767: 565:Cyclopentadienyl complexes 529:β-hydride elimination 503:Metal–ligand multiple bond 353:10.1595/003214000X44394105 160:and the hydrolysis of the 689: 643: 630:Transition metal carbides 547: 511: 440: 300:: CS1 maint: unfit URL ( 731:Organometallic chemistry 434:Organometallic chemistry 264:10.1002/14356007.a01_045 595:Half sandwich compounds 710:Bioinorganic chemistry 90:active species is the 83: 681:Ziegler–Natta process 585:Metal tetranorbornyls 331:Jones, J. H. (2000). 181:rate-determining step 168:and hydrogen iodide. 142:reductive elimination 125:group to an adjacent 81: 690:Related branches of 448:Crystal field theory 341:Platinum Metals Rev. 66:and improved by the 705:Inorganic chemistry 524:Migratory insertion 498:Agostic interaction 453:Ligand field theory 746:Chemical processes 590:Sandwich compounds 548:Types of compounds 473:Isolobal principle 177:oxidative addition 103:oxidative addition 84: 718: 717: 700:Organic chemistry 671:Olefin metathesis 661:Grignard reaction 560:Grignard reagents 758: 666:Monsanto process 463:d electron count 458:18-electron rule 427: 420: 413: 404: 403: 386: 385: 363: 357: 356: 337: 328: 322: 312: 306: 305: 299: 291: 289: 288: 273: 267: 252: 230:In this process 192:Acetic anhydride 68:Monsanto Company 45:BP Chemicals Ltd 21:Monsanto process 766: 765: 761: 760: 759: 757: 756: 755: 721: 720: 719: 714: 685: 639: 555:Gilman reagents 543: 539:Carbometalation 534:Transmetalation 507: 436: 431: 394: 389: 369:Catalysis Today 364: 360: 335: 329: 325: 313: 309: 293: 292: 286: 284: 275: 274: 270: 253: 249: 245: 236:lithium acetate 225: 221: 217: 213: 209: 194:is produced by 189: 154:catalytic cycle 151: 138:carbon monoxide 76: 74:Catalytic cycle 17: 12: 11: 5: 764: 754: 753: 748: 743: 738: 733: 716: 715: 713: 712: 707: 702: 696: 694: 687: 686: 684: 683: 678: 673: 668: 663: 658: 656:Cativa process 653: 647: 645: 641: 640: 638: 637: 632: 627: 622: 617: 612: 607: 602: 597: 592: 587: 582: 577: 572: 567: 562: 557: 551: 549: 545: 544: 542: 541: 536: 531: 526: 521: 515: 513: 509: 508: 506: 505: 500: 495: 490: 485: 480: 475: 470: 465: 460: 455: 450: 444: 442: 438: 437: 430: 429: 422: 415: 407: 401: 400: 393: 392:External links 390: 388: 387: 358: 323: 307: 268: 246: 244: 241: 232:lithium iodide 228: 227: 223: 219: 215: 211: 207: 200:methyl acetate 188: 185: 149: 115:hexacoordinate 113:- to form the 99:organometallic 75: 72: 37:Cativa process 15: 9: 6: 4: 3: 2: 763: 752: 749: 747: 744: 742: 739: 737: 734: 732: 729: 728: 726: 711: 708: 706: 703: 701: 698: 697: 695: 693: 688: 682: 679: 677: 674: 672: 669: 667: 664: 662: 659: 657: 654: 652: 651:Carbonylation 649: 648: 646: 642: 636: 633: 631: 628: 626: 623: 621: 618: 616: 613: 611: 608: 606: 603: 601: 598: 596: 593: 591: 588: 586: 583: 581: 578: 576: 573: 571: 568: 566: 563: 561: 558: 556: 553: 552: 550: 546: 540: 537: 535: 532: 530: 527: 525: 522: 520: 517: 516: 514: 510: 504: 501: 499: 496: 494: 491: 489: 486: 484: 481: 479: 478:Ď€ backbonding 476: 474: 471: 469: 466: 464: 461: 459: 456: 454: 451: 449: 446: 445: 443: 439: 435: 428: 423: 421: 416: 414: 409: 408: 405: 399: 396: 395: 383: 379: 375: 371: 370: 362: 354: 350: 347:(3): 94–105. 346: 343: 342: 334: 327: 321: 317: 311: 303: 297: 282: 278: 272: 265: 261: 257: 251: 247: 240: 237: 233: 218:+ CO → (CH 205: 204: 203: 201: 197: 196:carbonylation 193: 184: 182: 178: 174: 169: 167: 163: 162:acetyl iodide 159: 158:methyl iodide 155: 147: 146:acetyl iodide 143: 139: 135: 131: 128: 124: 120: 116: 112: 108: 107:methyl iodide 104: 100: 96: 93: 89: 88:catalytically 80: 71: 69: 65: 61: 57: 53: 48: 46: 42: 38: 34: 30: 29:carbonylation 27:by catalytic 26: 22: 665: 644:Applications 580:Metallocenes 376:(1): 73–91. 373: 367: 361: 344: 339: 326: 310: 285:. Retrieved 280: 271: 255: 250: 229: 190: 170: 152:C(O)I). The 110: 101:step is the 94: 85: 49: 39:, a similar 20: 18: 493:spin states 173:first-order 166:acetic acid 144:to release 60:temperature 25:acetic acid 725:Categories 441:Principles 320:189138953X 287:2014-08-27 243:References 741:Catalysis 692:chemistry 512:Reactions 488:Hapticity 119:migration 54:of 30–60 751:Monsanto 296:cite web 127:carbonyl 52:pressure 33:methanol 736:Rhodium 41:iridium 318:  134:acetyl 130:ligand 123:methyl 58:and a 336:(PDF) 121:of a 92:anion 316:ISBN 302:link 86:The 64:BASF 19:The 378:doi 349:doi 260:doi 222:CO) 198:of 164:to 148:(CH 111:cis 109:to 105:of 95:cis 56:atm 31:of 727:: 374:13 372:. 345:44 338:. 298:}} 294:{{ 279:. 214:CH 210:CO 206:CH 183:. 426:e 419:t 412:v 384:. 380:: 355:. 351:: 304:) 290:. 266:. 262:: 226:O 224:2 220:3 216:3 212:2 208:3 150:3

Index

acetic acid
carbonylation
methanol
Cativa process
iridium
BP Chemicals Ltd
pressure
atm
temperature
BASF
Monsanto Company
The catalytic cycle of the Monsanto process
catalytically
anion
organometallic
oxidative addition
methyl iodide
hexacoordinate
migration
methyl
carbonyl
ligand
acetyl
carbon monoxide
reductive elimination
acetyl iodide
catalytic cycle
methyl iodide
acetyl iodide
acetic acid

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