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3.1. Lower olefins 3.1.3. Basic material in the manufacture of lower olefins. 3.1.4. Manufacture of ethylene.. High-temperature dehydrogenation of ethane Manufacture of ethylene from methane. Manufacture of ethylene from methanol Dehydration of ethanol.. 3.1.3. Manufacture of propylene Isolation of propylene from refinery and cracking gases.. f Fischer-Tropsch synthesis Thermal dehydrogenation of propane Catalytic dehydrogenation of propane and other lower alkanes (Oleflex process).. 3.1.4. Manufacture of 1-butene.. Isolation of 1-butene from hydrocarbon fractions C4 Catalytic dimerization of ethylene. 3.1.5. Manufacture of isobutylene. Isolation of isobutylene from hydrocarbon fractions 4 Dehydrogenation of isobutene... Isomerization of 1-butene.. Synthesis of isobutylene from acetone.. 3.2. Higher olefins Anionic dimerization of olefins Dimerization in the presence of organometallic catalysts Coordination-catalytic dimerization and codimerization of olefins Dimerization of n-butenes Codimerization of propylene and n-butenes 3.2.2. Disproportionation of olefins 3.2.3. Dimerization and disproportionation of olefins in a single technological process Synthesis of isopentenes from ethylene Manufacture of isopentenes from propylene Manufacture of isopentenes and higher olefins from ethylene, propylene, and their mixtures 3.2.4. Manufacture of higher olefins from synthesis gas.. 3.2.5. Manufacture of cycloolefins .. Synthesis of cyclopenten. Synthesis of cyclohexent. Synthesis of nonbornene Chapter 4. Diene monomers 4.1.3. Manufacture of butadiene from acetylene.. Synthesis of butadiene via aldol (the aldol method) Synthesis of butadiene via dimerization of acetylene.. 4.1.4. Industrial methods for the manufacture of butadiene One-step dehydrogenation of butane to butadiene.. Isolation of butadiene.. 4.2.Isoprene 4.2.1wo-step manufacture of isoprene from isobutylene and formaldehyde Reaction mechanism Transformation of 1,3-glycols into dioxanes... Formation of isopentene alcohols Transformation of 4,4-dimethyl-1,3-dioxane into isoprene 4.2.2. Manufacture of isoprene from isobutylene and formaldehyde via 3-methylbutanediol (MBD)... .. 4.2.3. Manufacture of isoprene from isobutylene and methylal.. 4.2.4. Manufacture of isoprene by dehydrogenation of hydrocarbons 5 Two-step dehydrogenation of isopentane to isoprene One-step dehydrogenation of isopentane to isoprene Two-step oxidative dehydrogenation of isopentane to isoprene.. 4.2.5. Manufacture of isoprene from propylene.. Dimerization of propylene Isomerization of 2-methyl-1-pentene to 2-methyl-2-pentene . Cracking of 2-methyl-2-pentene . Synthesis of isoprene from ethylene and propylene 4.2.6. Manufacture of isoprene from acetylene and acetone 4.2.7. Manufacture of isoprene by liquid-phase oxidation of hydrocarbons 4.2.8. Manufacture of isoprene from 2-butenes and synthesis gas.. 4.3. Diene monomers for the manufacture of ethylene-propylene-diene rubbers 4.3.1. Manufacture of nonconjugated dienes.. Synthesis of dicyclopentadiene Synthesis of 1,4-hexadiene.. Synthesis of 1,5-cyclooctadiene.. 4.3.2. Manufacture of norbornene derivatives. Synthesis of ethylidenenorbornene.. Synthesis of methylenenorbornene.. Synthesis of propenylnorbornene. Synthesis of 5-(buten-2-yl-4)-2-norbornene. Synthesis of cyclopentadienyl-5-endo-norbornen-2-yl-5-methan Chapter 5. Halogen-containing monomers 5.1. Chlorine-containing monomers.. 5.1.3. Theoretical backgrounds of hydrocarbon chlorination. 5.1.4. Oxidative chlorination.. 5.1.5 Hydrochlorination.. 5.1.4. Dehydrochlorination 5.1.5. Manufacture of chloroorganic compounds Gas-phase chlorination of hydrocarbons and chlorine derivatives Liquid-phase chlorination of hydrocarbons. Gas-phase decomposition of chlorine derivatives .. 5.1.6. Manufacture of vinyl chloride Balanced method of vinyl chloride synthesis from ethylene .. One-step of vinyl chloride synthesis from ethylene (Staffer proc.) Two-step synthesis of vinyl chloride from ethylene Synthesis of vinyl chloride from ethane.. Hydrochlorination of acetylene 5.1.7. Manufacture of vinylidene chloride 5.1.8. Manufacture of chloroprene Preparative methods of obtaining chloroprene Industrial methods for the synthesis of chloroprene. 5.1.9. Manufacture of epichlorohydrin 5.2. Fluorine-containing monomers 5.2.1. Theoretical backgrounds of fluorination processes 5.2.2. Mechanism of fluorination reactions.. 5.2.3. Methods of fluorination of alkanes Metal fluoride process . Cryogenic fluorination. Electrochemical fluorination 5.2.4. Fluorinating agents. Molecular fluorine Hypofluorites Hydrogen fluoride 5.2.5. Manufacture of vinyl fluoride 5.2.6. Manufacture of vinylidene fluoride .. 5.2.7. Manufacture of perfluoro-derivatives of hydrocarbons.

Synthesis of tetrafluoroethylene.. Synthesis of hexafluorobutadiene Synthesis of perfluoroallenes.. 5.2.8. Manufacture of other fluoro-derivatives of hydrocarbons Synthesis of trifluorochloroethylene Synthesis of sym-dichlorodifluoroethylene. Synthesis of 3,3,3-trifluoropropylene.. 5.2.9. Manufacture of chladones (freons) Chapter 6. Vinylic monomers with aromatic and heterocyclic substituents.. 6.1. Styrene and its derivatives 6.1.1. Manufacture of styrene . Preparative methods of obtaining styrene Industrial methods for the manufacture of styrene . 6.1.2. Manufacture of -methylstyrene 6.2. Vinylpyridines. 6.2.1. General aspects of basic methods for the synthesis of vinylpyridines 6.2.2. Industrial methods for the manufacture of vinylpyridines Synthesis of 2-methyl-5-vinylpyridine Synthesis of 2- and 4-vinylpyridines and 2-vinyl-5-ethylpyridine 6.3. N-Vinylpyrrolidinone ... 6.3.1. Direct vinylation of -pyrrolidinone by acetylene. 6.3.2. Indirect vinylation of -pyrrolidinone ... 6.4. N-vinylcarbazole . 6.4.1. Manufacture of N-vinylcarbazole through vinylation by acetylene 6.4.2. Manufacture of N-vinylcarbazole by the vinyl exchange reaction 6.4.3. Manufacture of N-vinylcarbazoles by multi-step processes. Decomposition of N-(2-hydroxyethyl)carbazole Decomposition of 1-substituted N-ethylcarbazoles. 6.5. Other vinylic monomers.. 6.5.1. Manufacture of ethylidenenorbornene 6.5.2. Manufacture of vinyl toluene. 6.5.3. Manufacture of vinyl ketones Synthesis of vinyl methyl ketone Synthesis of isopropenyl methyl ketone. Synthesis of vinyl phenyl ketone Synthesis of vinylene carbonate. Chapter 7. Acrylic monomers. 7.1. Acrylonitrile 7.1.1Synthesis of acrylonitrile via ethylene oxide and ethylene cyanohydrin 7.1.2. Oxidative ammonolysis of propylene 7.1.3. Synthesis of acrylonitrile from acetylene and prussic acid .. 7.1.4. Synthesis of acrylonitrile via acetaldehyde and hydroxynitryl. 7.1.5. Synthesis of acrylonitrile from propylene and nitrogen oxides 7.1.6. Synthesis of acrylonitrile by direct interaction of ethylene, prussic acid, and oxygen 7.1.7. Oxidative ammonolysis of propane.. 7.2. Acrylamide. 7.2.1. Preparative methods of obtaining acrylamide... 7.2.2. Industrial methods for the manufacture of acrylamide 7.3. Acrylic acid ... 7.3.1. Hydrolysis of acrylonitrile 7.3.2. Hydrocarboxylation of acetylene. 7.3.3. Vapor-phase oxidation of propylene 7.3.4. Hydrolysis of ethylene cyanohydrin 7.3.5. Hydrolysis of -propiolactone 7.3.6. Oxidative carbonylation of ethylene 7.4.1. Gas-phase oxidation of isobutylene. 7.4.2. Oxidation of methacrolein .. 7.4.3. Gas-phase oxidation of methacrolein.. 7.5. Acrylates... 7.5.1. Manufacture of acrylates by esterification of acrylic and methacrylic acids .. Esterification by alcohols in the presence of sulfuric acid Esterification by alcohols in the presence of ion-exchange resins Esterification by olefins 7.5.2. Manufacture of acrylates via transesterification. Transesterification in the presence of acidic catalysts.. Transesterification in the presence of ion-exchange resins.. Transesterification in the presence other transesterification catalysts.. 7.5.3. Manufacture of acrylates from ethylene cyanohydrin.. 7.5.4. Manufacture of acrylates from acetylene by the Reppe reaction.. BASF process. 7.5.5. Manufacture of acrylates from ketene and formal 7.5.6. Manufacture of acrylates from acrylonitrile. 7.6. Methacrylates. 7.6.1. Manufacture of methacrylate from acetone and cyanohydrin.. Synthesis of cyanohydrin (prussic acid). Condensation of acetone and prussic acid . Synthesis of methacrylamide sulfate.. Hydrolysis or esterification of methacrylamide sulfate . 7.6.2. Manufacture of methyl methacrylate from tert-butyl alcohol Esterification of methacrylic acid to methyl methacrylate.. 7.6.4. Manufacture of methyl methacrylate from isobutylene 7.6.5. New methods for the synthesis of methyl methacrylate Synthesis of methyl methacrylate via isobutyraldehyde. Methoxycarbonylation of allene and methylacetylene-allene 7.6.5. Manufacture of other alkyl methacrylates. 8.2. Backgrounds of vinylation processes 8.3.1. Manufacture of vinyl ethers by vinylation of alcohols. Synthesis of vinyl acetate from acetylene and acetic acid.. Synthesis of vinyl acetate from acetaldehyde Synthesis of vinyl acetate from ethylene and acetic acid 8.5 Derivatives of polyvinyl alcohol polyvinylacetals 9.1. Formaldehyde. 9.1.1 Mechanism and catalysts of oxidative dehydrogenation of methanol Mechanism of oxidative dehydrogenation of methanol.. Catalysts of oxidative dehydrogenation of methanol.. 9.2.1. Manufacture of ethylene oxide via ethylene chlorohydrin. 9.3.1 Manufacture of propylene oxide by direct oxidation with oxygen.. Noncatalytic liquid-phase oxidation of propylene.. 9.3.2. Manufacture of propylene oxide by oxidation Manufacture of epichlorohydrin from allyl chloride..

MONOMERS FOR POLYCONDENSATION POLYMERS

10.1. Terephthalic acid and dimethyl terephthalate.. Intermediate and side products in oxidation of p-xylene 10.1.5. Manufacture of aromatic and heterocyclic carboxylic acids by thermal transformation of their alkali salts... Transformations of alkali salts. Synthesis of terephthalic acid from toluene and xylenes. 10.1.6. Mitsubishi process 10.1.7. Manufacture of terephthalic acid from coal. 10.2. Maleic anhydride... 10.2.1. Manufacture of maleic anhydride by gas-phase oxidation of benzene 10.2.3. Manufacture of maleic anhydride by oxidation of butane.. 10.2.3. Manufacture of maleic anhydride by oxidation of n-butenes. 10.2.4. Isolation of maleic anhydride as a side product in the manufacture of phthalic anhydride 10.3. Phthalic anhydride. 10.3.1. Vapor-phase oxidation of o-xylene or naphthalene. 10.3.3. Liqid-phase oxidation of o-xylene or naphthalene.. 10.3.3. VNIIOS process.. 10.4. Fumaric acid. 10.5. Dichloromaleic and dichlorofumaric acids and their derivatives. 10.5.1. Manufacture of dichloromaleic acid and its anhydride 10.5.2. Manufacture of dichlorofumaric acid and its anhydride.. 10.6. 2,6-Naphthalenedicarboxylic acid. 10.7. Thiophene-2,5-dicarboxylic acid.. 10.8. Azelaic acid.. 10.9. Diols. 10.9.1. Manufacture ethylene glycol.. Hydration of ethylene oxide Other methods for the synthesis of ethylene glycol 10.9.2. Manufacture of 1,2-propanediol.. Hydration of propylene oxide. Other methods for the synthesis of 1,2-propanediol .. 10.9.3 Manufacture of 1,4-butanediol. Synthesis of 1,4-butanediol from acetylene and formaldehyde.. Synthesis of 1,4-butanediol from propylene.. Synthesis of 1,4-butanediol from renewable raw material (Cvaker Oatz process).. Propylene of 1,4-butanediol by acetoxylation of butadiene (Mitsubishi process). Synthesis of 1,4-butanediol through chlorination of butadiene ( Soda process).. Synthesis of 1,4-butanediol through hydroformylation of allyl alcohol (urare process) 10.9.4. Manufacture of 1,4-dimethylcyclohexane.. 11.1. Monomers for polymerization polyamides . 11.1.3. Manufacture of 7-aminoheptanoic acid.. 11.1.5. Manufacture of 9-aminopelargonic acid 11.1.6. Manufacture of 11-aminoundecanoic acid.. 11.2. Monomers for polycondensation polyamides derived from dicarboxylic Other industrial methods for the synthesis of adipic acid Synthesis of adiponitrile from acrylonitrile 11.2.3. Manufacture of hexamethylenediamine. Synthesis of hxamethylenediamine from adipic acid. Synthesis of hxamethylenediamine via 1,6-hexanediol. Synthesis of hxamethylenediamine from butadiene.. Dimerization of acrylonitrile... 11.2.4 Manufacture of other monomers for the synthesis of polyamides.. 11.2.5. Manufacture of m-xylylenediamine Bromination of xylene. Oxidative ammonolysis 11.3. Monomers for other fiber-forming polyamides 11.3.1. Manufacture of fiber-forming polyamides based on suberic acid and 1,4-diaminomethylcyclohexane.. Synthesis of suberic acid . Synthesis of 1,4-diaminomethylcyclohexane.. 11.3.2. Manufacture of fiber-forming polyamides based on decanedicarboxylic acid and 4,4-diaminodicyclohexylmethane. Synthesis of decanedicarboxylic acid.. Synthesis of 4,4-diaminodicyclohexylmethane.. 11.4. Monomers for fully aromatic polyamides. 11.4.1. Manufacture of aromatic acid chlorides.. Synthesis of acid chlorides from xylenes Thionyl method... 11.4.2. Manufacture of monomers for fiber-forming polyamides by polycondensation of 4,4-diaminodiphenyl sulfone. .. 11.4.3. Manufacture of 2,5-bis-(p-aminophenyl)-1,3,4-oxadiazole. 11.4.4.Manufacture of 5,5-bis(m-aminophenyl)-2,2-bis(1,3,4-oxadiazolyl) 11.4.5. Manufacture of 4,4-bis-(p-aminophenyl)-2,2-dithiazole 11.4.6. Manufacture of bis-(m-aminophenyl)-thiazolo(5,4-d)thiazole 11.4.7. Manufacture of monomers for polyamides based on piperazine and diacids. Synthesis of piperazine Synthesis of 4,4-diphenyldicarboxylic acid. Chapter 12. Monomers for polyimides.. 12.1. Pyromellitic dianhydride.. 12.1.1. Manufacture of durene 12.1.2. Manufacture of pyromellitic dianhydride... 12.2. Diphenyltetracarboxylic dianhydrides.. 12.2.1. Manufacture of 2,2,3,3-diphenyltetracarboxylic dianhydride 12.2.2. Manufacture of 2,3,5,6-diphenyltetracarboxylic dianhydride.. 12.2.3. Manufacture of 2,2,6,6-diphenyltetracarboxylic dianhydride 12.2.4. Manufacture of 3,3,4,4-diphenyltetracarboxylic dianhydride .. 12.3. Naphthalenetetracarboxylic dianhydrides. 12.3.1. Manufacture of 1,4,5,8-naphthalenetetracarboxylic dianhydride 12.3.2. Manufacture of 2,3,6,7-naphthalenetetracarboxylic dianhydride 12.4. Benzophenone- and perylenetetracarboxylic dianhydrides... 12.4.1. Manufacture of 3,3,4,4-benzophenonetetracarboxylic dianhydride 12.4.2. Manufacture of 3,4,9,10-perylenetetracarboxylic dianhydride 12.5.1. Manufacture of o- and m-phenylenediamines.. 12.5.4. Manufacture of 4,4-diaminodiphenylmethane 12.5.5. Manufacture of 4,4-diaminodiphenyl oxide 12.6.1. Manufacture of anilinophthalein... Chapter 13. Monomers for polyurethanes. 13.1.1 Manufacture of diamines by reduction of dinitriles.. 13.1.2 Manufacture of diamines by reduction of aromatic Reduction of dinitro compounds by metals in alkaline medium.. 13.2.2 Curtius, Hofmann and Lossen rearrangements. 13.2.3 Manufacture of tolylene diisocyanates. Other industrial methods for the manufacture of 13.2.4 Manufacture of 4,4-diphenylmethane diisocyanate 13.2.5. Manufacture of other diisocyanates.. 13.2.6 Synthesis of isocyanates using organosilicon compounds 13.3.3. Manufacture of arylaliphatic diols .. 13.3.4. Manufacture of monomers for poly(ether polyols).. Chapter 14. Monomers for polycarbonates.. Condensation of phenol with acetone in the presence Synthesis of bisphenol A from phenol and methylacetylene Synthesis of bisphenol A from phenol and 2-chloropropene-1 14.1.2 Manufacture of halogen-substituted bisphenols... 14.2.1 Manufacture of diphenyl carbonate by phosgenation of phenols. 14.2.2. Manufacture of diphenyl carbonate by interaction of phenol with carbon tetrachloride.. 14.5.1. Manufacture of cyclocarbonates from -oxides... 14.5.2. Manufacture of cyclocarbonates from chlorohydrin ethers . 14.5.3. Manufacture of cyclocarbonates from diols. 14.5.4. Manufacture of multifunctional cyclocarbonates. Chapter 15. Monomers for phenol- and amino-aldehyde polymers 15.1. Monomers for phenol-aldehyde polymers. Isolation of phenols from the products of coal processing.. Alkaline hydrolysis of chlorobenzene (Dow Chemical method).. 15.1.2. Manufacture of bromophenols and their derivatives antipyrenes.. 15.2. Monomers for carbamido-aldehyde polymers. 16.1. Methods of obtaining organosilicon monomers 16.1.1. Organomagnesium synthesis .. 16.1.2. Direct synthesis... 16.1.3. Dehydrocondensation of silicon hydrides with hydrocarbons 16.1.4. Condensation of silicon hydrides with halogen-derivatives... 16.1.5. Hydrosilylation 16.2. Organochlorosilanes. 16.2.1. Manufacture of methyl- and ethylchlorosilanes by direct synthesis Synthesis of silicon-copper contact mass Synthesis of methylchlorosilanes. Synthesis of ethylchlorosilane .. Synthesis of ethyldichlorosilane . Synthesis of diethyldichlorosilane... Synthesis of phenylchlorosilanes. 16.2.2. Manufacture of organochlorosilanes by thermocatalytic silylation Synthesis of methylphenyldichlorosilane Hydrosilylation of unsaturated compounds. High-temperature condensation method.. 16.2.3.Manufacture of organochlorosilanes by disproportionation reactions 16.2.4. Pyrolytic methods for the synthesis of organochlorosilanes 16.2.5. Manufacture of organosilicon monomers by chemical transformations of organochlorosilanes 16.2.6. Manufacture of tetrachlorosilane.. 16.2.7. Purification of diorganodichlorosilanes .. 16.3. Monomers for siloxane rubbers. 16.3.1. Manufacture of siloxane rubbers . 16.3.2. Manufacture of siloxane monomers by hydrolysis of diorganodichlorosilanes... General aspects of hydrolysis of diorganodichlorosilanes . diorganodichlorosilanes.. 16.3.3. Other methods of obtaining siloxane monomers . Thermal rearrangement of linear polysiloxanes... Catalytic rearrangement of linear polysiloxanes.. 16.4. Monomers for modified siloxane rubbers. 16.4.1. Manufacture of hexaorganocyclotrisiloxanes.. 16.4.2. Manufacture of organosilicon urethanes.. Synthesis of O-silylurethanes.. Synthesis of N-silylurethanes.. Synthesis of urethanes from glycoxysilanes.... Synthesis of carbofunctional organosilicon diols Synthesis of products of condensation of organosilicon isocyanates with hydroxyl-containing compounds. Synthesis of monomers for organosilicon polyurethanes prepared by hydrosilylation reaction Synthesis of monomers for organosilicon polyurethanes prepared from organosilicon bis(chloroformates) 16.5. Monomers for polysilicohydrocarbons permselective polymers Chapter 17. Other organoelement monomers 17.1. Monomers for sulfur-containing polymers .. 17.1.1. Manufacture of sodium sulfide and polysulfides. 17.1.2. Manufacture of 1,2-dichloroethane 17.1.3. Manufacture of p-dichlorobenzene. 17.2. Phosphazenes (phosphonitriles) 17.4. Nitrogen-containing monomers 17.4.1. Manufacture of monomers with azole cycles . Synthesis of 2,5-bis(p-aminopheny)-1,3,4-oxadiazole Synthesis of 4,4-bis(p-aminophenyl)-2,2-dithiazole. Synthesis of 5,5-di(m-aminophenyl)-2,2-bis(1,3,4-oxadiazolyl) Synthesis of 5,5-di(p-aminophenyl)-2,2-bis(1,3,4-oxadiazolyl).. 17.4.2. Manufacture of di- and tetracarboxylic acids.. 17.5. Metal-containing monomers and the related polymers 17.5.1. Manufacture of monomers containing covalently bound metals. Synthesis of unsaturated nontransition-metal Synthesis of unsaturated nontransition-metal 17.5.2. Manufacture of ionic metal-containing monomers 17.5.3. Manufacture of etal-containing monomers containing 17.5.4 Manufacture of -tipe metal-containing monomers

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