Платэ Н.А., Сливинский Е.В. Основы химии и технологии мономеров
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13.2.4 Manufacture of 4,4-diphenylmethane diisocyanate ……………… 511
Condensation of aniline with formaldehyde…………………… 512
Synthesis of aniline…………………………………………….. 513
13.2.5. Manufacture of other diisocyanates……………………………….. 516
13.2.6 Synthesis of isocyanates using organosilicon compounds ………… 519
Phosgenation of N-silylamines…………………………………. 519
Thermolysis of N-silylurethanes……………………………..... 522
Thermolysis of О-silylurethanes ………………………………. 522
13.3 Polyols and polyethers……………………………………………………… 524
13.3.1 Manufacture of
-diols…………………………………………….. 525
13.3.2. Manufacture of glycerol…………………………………………... 526
13.3.3. Manufacture of arylaliphatic diols ……………………………….. 528
13.3.4. Manufacture of monomers for poly(ether polyols)……………….. 528
Chapter 14. Monomers for polycarbonates………………………………….. 531
14.1 Bisphenols…………………………………………………………………. 535
14.1.1 Manufacture of bisphenol A………………………………………. 537
Condensation of phenol with acetone…………………………. 537
Condensation of phenol with acetone in the presence
of ion-exchange resins………………………………………… 544
Synthesis of bisphenol A from phenol and methylacetylene
or allene……………………………………………………….. 546
Synthesis of bisphenol A from phenol and
p-isopropenylphenol…………………………………………… 548
Synthesis of bisphenol A from phenol and 2-chloropropene-1… 549
Methods of purification of bisphenol A ………………………. 550
14.1.2 Manufacture of halogen-substituted bisphenols…………………... 550
Synthesis of tetrachlorobisphenol A…………………………... 551
Synthesis of tetrabromobisphenol A………………………….. 552
14.2 Diphenyl carbonate………………………………………………………… 552
14.2.1 Manufacture of diphenyl carbonate by phosgenation of phenols…. 553
14.2.2. Manufacture of diphenyl carbonate by
interaction of phenol with carbon tetrachloride…………………….. 555
14.3 Bisphenol S…………………………………………………………………. 556
14.4 Resorcinol…………………………………………………………………... 558
14.5 Cyclocarbonates…………………………………………………………….. 559
14.5.1. Manufacture of cyclocarbonates from
-oxides…………………... 564
14.5.2. Manufacture of cyclocarbonates from chlorohydrin ethers ………. 565
14.5.3. Manufacture of cyclocarbonates from diols………………………. 566
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14.5.4. Manufacture of multifunctional cyclocarbonates…………………. 567
Chapter 15. Monomers for phenol- and amino-aldehyde polymers………… 569
15.1. Monomers for phenol-aldehyde polymers…………………………………. 569
15.1.1. Manufacture of phenols…………………………………………… 569
Isolation of phenols from the products of coal processing…….. 570
Isolation of phenols from the products of oil refining…………. 573
Synthesis of phenols via sulfonation of benzene………………. 573
Alkaline hydrolysis of chlorobenzene (Dow Chemical method).. 574
Rachig modified method (Hooker Chem process)……………… 574
Cumene method………………………………………………… 575
Oxidation of benzene ………………………………………….. 584
15.1.2. Manufacture of bromophenols and their derivatives – antipyrenes.. 588
15.2. Monomers for carbamido-aldehyde polymers……………………………. 590
15.2.1. Manufacture of carbamide……………………………………….. 591
15.2.2. Manufacture of melamine………………………………………... 593
Chapter 16. Organosilicon monomers
………………………………………… 596
16.1. Methods of obtaining organosilicon monomers…………………………… 598
16.1.1. Organomagnesium synthesis …………………………………….. 598
16.1.2. Direct synthesis…………………………………………………... 598
16.1.3. Dehydrocondensation of silicon hydrides with hydrocarbons…… 599
16.1.4. Condensation of silicon hydrides with halogen-derivatives……... 599
16.1.5. Hydrosilylation…………………………………………………… 599
16.2. Organochlorosilanes………………………………………………………. 601
16.2.1. Manufacture of methyl- and ethylchlorosilanes by direct synthesis 602
Synthesis of silicon-copper contact mass……………………… 603
Synthesis of methylchlorosilanes………………………………. 605
Synthesis of ethylchlorosilane ……………………………….. 607
Synthesis of ethyldichlorosilane ………………………………. 608
Synthesis of diethyldichlorosilane……………………………... 609
Synthesis of phenylchlorosilanes………………………………. 610
16.2.2. Manufacture of organochlorosilanes by thermocatalytic silylation 610
Synthesis of methylphenyldichlorosilane……………………… 611
Hydrosilylation of unsaturated compounds……………………. 611
High-temperature condensation method……………………….. 612
16.2.3.Manufacture of organochlorosilanes by disproportionation reactions 612
16.2.4. Pyrolytic methods for the synthesis of organochlorosilanes ……… 613
16.2.5. Manufacture of organosilicon monomers by chemical
713
transformations of organochlorosilanes…………………………………… 614
16.2.6. Manufacture of tetrachlorosilane………………………………….. 615
16.2.7. Purification of diorganodichlorosilanes ………………………….. 616
16.3.
Monomers for siloxane rubbers……………………………………………. 617
16.3.1. Manufacture of siloxane rubbers ……………………………….… 617
16.3.2. Manufacture of siloxane monomers by hydrolysis of
diorganodichlorosilanes……………………………………….………….. 619
General aspects of hydrolysis of diorganodichlorosilanes ……. 620
Industrial methods for the hydrolysis of
diorganodichlorosilanes……………………………………….. 621
16.3.3. Other methods of obtaining siloxane monomers …………………. 623
Thermal rearrangement of linear polysiloxanes………………... 623
Catalytic rearrangement of linear polysiloxanes……………….. 624
16.4. Monomers for modified siloxane rubbers…………………………………. 626
16.4.1. Manufacture of hexaorganocyclotrisiloxanes…………………….. 628
16.4.2. Manufacture of organosilicon urethanes………………………….. 629
Synthesis of O-silylurethanes………………………………….. 629
Synthesis of N-silylurethanes………………………………….. 630
Synthesis of urethanes from glycoxysilanes……….…………... 631
Synthesis of carbofunctional organosilicon diols……………… 632
Synthesis of products of condensation of organosilicon
isocyanates with hydroxyl-containing compounds……………. 634
Synthesis of monomers for organosilicon polyurethanes
prepared by hydrosilylation reaction…………………………… 635
Synthesis of monomers for organosilicon polyurethanes
prepared from organosilicon bis(chloroformates)……………… 636
16.5. Monomers for polysilicohydrocarbons – permselective polymers………… 637
Chapter 17. Other organoelement monomers………………………………… 642
17.1.
Monomers for sulfur-containing polymers ……………………………….. 642
17.1.1.
Manufacture of sodium sulfide and polysulfides…………………. 642
17.1.2.
Manufacture of 1,2-dichloroethane ……………………………… 643
17.1.3.
Manufacture of p-dichlorobenzene………………………………. 643
17.2. Phosphazenes (phosphonitriles)…………………………………………… 646
17.3.
Boron-containing monomers……………………………………………… 649
17.4.
Nitrogen-containing monomers …………………………………………… 653
17.4.1.
Manufacture of monomers with azole cycles ……………………. 654
Synthesis of 2,5-bis(
p-aminopheny)-1,3,4-oxadiazole………… 655
Synthesis of 4,4-bis(p-aminophenyl)-2,2-dithiazole…………. 656
714
Synthesis of 5,5-di(m-aminophenyl)-2,2-bis(1,3,4-oxadiazolyl) 656
Synthesis of 5,5-di(p-aminophenyl)-2,2-bis(1,3,4-oxadiazolyl).. 657
17.4.2. Manufacture of di- and tetracarboxylic acids…………………….. 657
17.4.3. Manufacture of benzimidazoles………………………………….. 659
17.4.4. Manufacture of
benzoxazoles…………………………………….. 659
17.4.5. Manufacture of bis(maleimides)………………………………….. 660
17.5. Metal-containing monomers and the related polymers …………………… 661
17.5.1. Manufacture of monomers containing covalently bound metals…. 663
Synthesis of unsaturated nontransition-metal
organometallic monomers……………… …………………… 664
Synthesis of unsaturated nontransition-metal
organometallic monomers……………………………………… 664
17.5.2. Manufacture of ionic metal-containing monomers……………… 665
17.5.3. Manufacture of мetal-containing monomers containing
coordinatively bound metals…………………………………………….. 666
17.5.4 Manufacture of π-tipe metal-containing monomers ……………… 666
Subject index …………………………………………………………………… 670
Учебное издание
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Платэ Николай Альфредович
Сливинский Евгений Викторович
ОСНОВЫ ХИМИИ
И ТЕХНОЛОГИИ
МОНОМЕРОВ
Утверждено к печати
Ученым советом
Института нефтехимического синтеза
им. А.В. Топчиева
Российской академии наук
Редактор М.Л. Франк
Художник А.С. Скороход
Технический редактор В.В. Лебедева
Корректоры А.Б. Васильев, Р.В. Молоканова
,
Т.И. Шеповалова
Подписано к печати 05.11.2002
Тираж 1000 экз.
Издательство “Наука”
МАИК “Наука/Интерпериодика”