Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives

429 Pages·2016·14.1 MB·English

by  Shannon S. Stahl and Paul L. Alsters

Editedby
ShannonS.StahlandPaulL.Alsters
LiquidPhaseAerobicOxidation
Catalysis
Editedby
ShannonS.StahlandPaulL.Alsters
Liquid Phase Aerobic Oxidation Catalysis
IndustrialApplicationsandAcademicPerspectives
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V
Contents
Preface XV
ListofContributors XVII
PartI RadicalChainAerobicOxidation 1
1 OverviewofRadicalChainOxidationChemistry 3
IveHermans
1.1 Introduction 3
1.2 ChainInitiation 6
1.3 ChainPropagation 7
1.4 FormationofRing-OpenedBy-ProductsintheCaseofCyclohexane
Oxidation 11
1.5 ComplicationsintheCaseofOlefinAutoxidation 12
1.6 SummaryandConclusions 13
References 14
2 NoncatalyzedRadicalChainOxidation:CumeneHydroperoxide 15
ManfredWeber,Jan-BerndGrosseDaldrup,andMarkusWeber
2.1 Introduction 15
2.2 ChemistryandCatalysis 15
2.2.1 CumeneRoutetoPhenolandAcetone:ChemistryOverview 16
2.2.2 ThermalDecompositionofCumeneHydroperoxide 17
2.2.3 OxidationofCumene 19
2.3 ProcessTechnology 21
2.3.1 ProcessOverview 21
2.3.2 ReactorsfortheCumeneOxidation 22
2.3.3 ReactorModeling 23
2.3.4 ProcessSafetyAspects 26
2.4 NewDevelopments 27
2.4.1 ProcessIntensificationbyModificationoftheOxidation
Reaction 27
2.4.2 ImprovementsofReactorandProcessDesign 29
References 30
VI Contents
3 CyclohexaneOxidation:HistoryofTransitionfromCatalyzed
toNoncatalyzed 33
JohanThomasTinge
3.1 Introduction 33
3.2 ChemistryandCatalysis 34
3.3 ProcessTechnology 35
3.3.1 TheTraditionalCatalyzedCyclohexaneOxidationProcess 35
3.3.2 TheNoncatalyzedDSMOxanone®CyclohexaneOxidation
Process 37
3.4 NewDevelopments 38
Epilogue 39
References 39
4 ChemistryandMechanismofOxidationofpara-XylenetoTerephthalic
AcidUsingCo–Mn–BrCatalyst 41
VictorA.AdamianandWilliamH.Gong
4.1 Introduction 41
4.2 ChemistryandCatalysis 42
4.2.1 Co–BrCatalysis 43
4.2.2 Cobalt–Manganese–BromideCatalysis(MCOxidation):TheNature
ofSynergybetweenCoandMn 48
4.2.3 TheRoleandNatureofBromineSpeciesinMCOxidation 50
4.2.4 NatureofCobalt(III)andMn(III)Species 52
4.2.5 ReactionsofCobalt(II)withPeroxyRadicalsandtheEffectofSolvent
onOxidationRate 52
4.2.6 PhenomenonofManganesePrecipitation 54
4.2.7 ConsolidatedViewofMCOxidationMechanism 54
4.2.8 OxidationBy-products 56
4.3 ProcessTechnology 58
4.3.1 Oxidation 58
4.3.2 Purification 58
4.4 NewDevelopments 61
4.4.1 HomogeneousBrominelessCatalysis 61
4.4.2 HeterogeneousBrominelessOxidationCatalysis 62
4.4.3 AlternativeSolvents 62
4.5 Conclusions 62
References 63
PartII Cu-CatalyzedAerobicOxidation 67
5 Cu-CatalyzedAerobicOxidation:OverviewandNew
Developments 69
DamianHruszkewycz,ScottMcCann,andShannonStahl
5.1 Introduction 69
5.2 ChemistryandCatalysis 70
Contents VII
5.2.1 Cu-CatalyzedOxydecarboxylativePhenolSynthesis 70
5.2.2 Cu-CatalyzedOxidativeCarbonylationofMethanolfortheSynthesis
ofDimethylCarbonate 72
5.3 ProcessTechnology 74
5.3.1 Cu-CatalyzedOxydecarboxylativePhenolSynthesis 74
5.3.2 Cu-CatalyzedOxidativeCarbonylationofMethanolfortheSynthesis
ofDimethylCarbonate 75
5.4 NewDevelopments:PharmaceuticalApplicationsofCu-Catalyzed
AerobicOxidationReactions 76
References 82
6 Copper-CatalyzedAerobicAlcoholOxidation 85
JanelleE.StevesandShannonS.Stahl
6.1 Introduction 85
6.2 ChemistryandCatalysis 86
6.3 ProspectsforScale-Up 91
6.4 Conclusions 93
References 94
7 PhenolOxidations 97
7.1 PolyphenyleneOxidesbyOxidativePolymerizationofPhenols 97
PatrickGamez
7.1.1 Introduction 97
7.1.2 ChemistryandCatalysis 99
7.1.3 ProcessTechnology 102
7.1.4 NewDevelopments 104
7.2 2,3,5-TrimethylhydroquinoneasaVitaminEIntermediatevia
OxidationofMethyl-SubstitutedPhenols 106
JanSchützandThomasNetscher
References 109
PartIII Pd-CatalyzedAerobicOxidation 113
8 Pd-CatalyzedAerobicOxidationReactions:IndustrialApplications
andNewDevelopments 115
DianWang,JonathanN.Jaworski,andShannonS.Stahl
8.1 Introduction 115
8.2 ChemistryandCatalysis:IndustrialApplications 117
8.2.1 AcetoxylationofAlkenestoVinylorAllylAcetates 117
8.2.2 OxidativeCarbonylationofAlcoholstoCarbonates,Oxalates,
andCarbamates 118
8.2.3 OxidativeCouplingofArenestoBiarylCompounds 121
8.3 ChemistryandCatalysis:ApplicationsofPotentialIndustrial
Interest 122
8.3.1 OxidationofAlcoholstoAldehydes 122
VIII Contents
8.3.2 OxidationofArenestoPhenolsandPhenylEsters 123
8.3.3 BenzylicAcetoxylation 125
8.3.4 AreneOlefination(OxidativeHeckReaction) 126
8.4 ChemistryandCatalysis:NewDevelopmentsand
Opportunities 128
8.4.1 Ligand-ModulatedAerobicOxidationCatalysis 128
8.4.2 UseofNO asCocatalyst 130
x
8.4.3 MethaneOxidation 132
8.5 Conclusion 133
References 133
9 AcetaldehydefromEthyleneandRelatedWacker-TypeReactions 139
ReinhardJira
9.1 Introduction 139
9.2 ChemistryandCatalysis 140
9.2.1 OxidationofOlefinicCompoundstoCarbonylCompounds 140
9.2.2 KineticsandMechanism 140
9.2.3 CatalyticOxidationofEthylene 145
9.2.3.1 OxidationofEthylenetoAcetaldehydeinthePresenceof
CuCl 145
2
9.2.3.2 OxidationofEthyleneto2-Chloroethanol 147
9.3 ProcessTechnology(WackerProcess) 148
9.3.1 Single-StageAcetaldehydeProcessfromEthylene 148
9.3.2 Two-StageAcetaldehydeProcessfromEthylene 149
9.4 OtherDevelopments 151
References 155
FurtherReading 158
10 1,4-Butanediolfrom1,3-Butadiene 159
YusukeIzawaandToshiharuYokoyama
10.1 Introduction 159
10.2 ChemistryandCatalysis 160
10.2.1 ShortOverviewofNon-butadiene-BasedRoutesto
1,4-Butanediol 160
10.2.1.1 Acetylene-BasedReppeProcess 160
10.2.1.2 Butane-BasedProcess;SelectiveOxidationofButanetoMaleic
Anhydride 161
10.2.1.3 Propylene-BasedProcess:HydroformylationofAllylAlcohol 161
10.2.2 Butadiene-BasedRoutesto1,4-Butanediol 162
10.2.2.1 Oxyhalogenationof1,3-Butadiene 162
10.2.2.2 OxidativeAcetoxylationof1,3-Butadiene 162
10.3 ProcessTechnology 164
10.3.1 MitsubishiChemical’s1,4-ButanediolManufacturingProcess:
First-GenerationProcess 165
10.3.1.1 OxidativeAcetoxylationStep 165
Contents IX
10.3.1.2 HydrogenationStep 165
10.3.1.3 HydrolysisStep 166
10.3.2 MitsubishiChemical’s1,4-ButanediolManufacturingProcess:
Second-GenerationProcess 167
10.4 NewDevelopments 168
10.4.1 ImprovementoftheCurrentProcess 168
10.4.2 DevelopmentofAlternativeProcesses 169
10.5 SummaryandConclusions 169
References 170
11 MitsubishiChemicalsLiquidPhasePalladium-CatalyzedOxidation
Technology:OxidationofCyclohexene,Acrolein,andMethylAcrylate
toUsefulIndustrialChemicals 173
YoshiyukiTanaka,JunP.Takahara,TohruSetoyama,andHansE.B.Lempers
11.1 Introduction 173
11.2 ChemistryandCatalysis 174
11.2.1 AerobicPalladium-CatalyzedOxidationofCyclohexeneto
1,4-Dioxospiro-[4,5]-decane 174
11.2.1.1 OptimizationoftheReactionConditions 174
11.2.2 AerobicPalladium-CatalyzedOxidationofOtherTypesof
Olefins 176
11.2.3 AerobicPalladium-CatalyzedOxidationofAcroleinto
MalonaldehydeBis-(1,3-dioxan-2-yl)-acetalFollowedby
Hydrolysis/Hydrogenationto1,3-Propanediol 178
11.3 ProspectsforScale-Up 180
11.3.1 AerobicPalladium-CatalyzedOxidationofMethylAcrylate(MA)
to3,3-DimethoxyMethylPropionate:ProcessOptimizationand
Scale-Up 180
11.3.2 Small-ScaleReactionOptimization 181
11.3.3 Large-ScaleMethylAcrylateOxidationReactionandWork-Up 184
11.3.4 ReactionSimulationStudiesasAidforFurtherScale-Up 184
11.4 Conclusion 187
References 187
12 OxidativeCarbonylation:DiphenylCarbonate 189
GrigoriiL.Soloveichik
12.1 Introduction 189
12.1.1 DiphenylCarbonateintheManufacturingofPolycarbonates 189
12.1.2 HistoryofDirectDiphenylCarbonateProcessatGE 190
12.2 ChemistryandCatalysis 192
12.2.1 MechanismofOxidativeCarbonylationofPhenol 192
12.2.2 CatalystsforOxidativeCarbonylationofPhenol 193
12.2.3 CocatalystsforOxidativeCarbonylationofPhenol 196
12.2.3.1 OrganicCocatalysts 196
12.2.3.2 InorganicCocatalysts 196
X Contents
12.2.4 MulticomponentCatalyticPackages 199
12.2.5 RoleofBromideinDirectSynthesisofDiphenylCarbonate 199
12.3 ProspectsforScale-Up 201
12.3.1 CatalystOptimization 201
12.3.2 WaterRemovalinDirectDiphenylCarbonateProcess 202
12.3.3 DownstreamProcessingandCatalystRecovery 203
12.4 ConclusionsandOutlook 203
Acknowledgments 204
References 205
13 AerobicOxidativeEsterificationofAldehydeswithAlcohols:The
EvolutionfromPd–PbIntermetallicCatalyststoAu–NiO Nanoparticle
x
CatalystsfortheProductionofMethylMethacrylate 209
KenSuzukiandSetsuoYamamatsu
13.1 Introduction 209
13.2 ChemistryandCatalysis 210
13.2.1 DiscoveryofthePd–PbCatalyst 210
13.2.2 Pd–PbIntermetallicCompounds 210
13.2.3 Mechanism 212
13.2.4 TheRoleofPbinthePd–PbCatalyst 213
13.2.5 IndustrialCatalyst 213
13.3 ProcessTechnology 214
13.4 NewDevelopments 215
13.5 ConclusionandOutlook 217
References 218
PartIV OrganocatalyticAerobicOxidation 219
14 QuinonesinHydrogenPeroxideSynthesisandCatalyticAerobic
OxidationReactions 221
AlisonE.WendlandtandShannonS.Stahl
14.1 Introduction 221
14.2 ChemistryandCatalysis:AnthraquinoneOxidation(AO)
Process 223
14.2.1 AutoxidationProcess(HydroquinonetoQuinone) 223
14.2.2 HydrogenationProcess(QuinonetoHydroquinone) 225
14.3 ProcessTechnology 227
14.4 FutureDevelopments:SelectiveAerobicOxidationReactions
CatalyzedbyQuinones 229
14.4.1 AerobicDDQ-CatalyzedReactionsUsingNO Cocatalysts 229
x
14.4.2 AerobicQuinone-CatalyzedReactionsUsingOther
Cocatalysts 230
14.4.3 CAOMimicsandSelectiveOxidationofAmines 231
References 234