Carbonyl Compounds

Reactants, Catalysts and Products

Inbunden, Engelska, 2021

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Carbonyl Compounds Discover how carbonyl compounds bridge reactants, catalysts, and specific productsCarbonyl-containing molecules represent some of the most versatile functionalities in organic chemistry, with applications in a wide variety of areas.In Carbonyl Compounds: Reactants, Catalysts and Products, accomplished chemists and authors Feng Shi, Hongli Wang, and Xingchao Dai deliver a comprehensive treatment of these multi-functional compounds. You’ll discover how to build carbonyl molecules with traditional and non-traditional methods, how to transform carbonyl-containing molecules into fine chemicals, and how to use carbonyl-containing molecules as catalytic materials for the synthesis of fine chemicals.The book is a comprehensive and systematic treatment of carbonyl compounds as reactants, catalysts, and products. From the use of carbon monoxide in the hydroformylation of alkenes and alkynes to the reactions via carbonyl and hydroxyl groups recycling, you’ll find everything you need to know about these versatile compounds.Readers will also benefit from the inclusion of: A thorough introduction to carbonyl molecules as reactants, including treatments of carbon monoxide, carbon dioxide, HCHO, HCOOH, and CO surrogatesAn exploration of carbonyl compounds as catalysts, including acid catalyzed reactions with -CO2H and reactions via carbonyl and hydroxyl groups recyclingA practical discussion of the synthetic applications of carbonyl compounds, including the synthesis of functional molecules and the synthesis of functional materialsA concise treatment of future perspectives and potential research trends for carbonyl moleculesPerfect for organic, catalytic, pharmaceutical, and physical chemists, Carbonyl Compounds will also earn a place in the libraries of chemical engineers and materials scientists seeking a one-stop reference for up-to-date information about the building, transformation, and applications of carbonyl-containing molecules.

Produktinformation

Utgivningsdatum2021-09-01
Mått170 x 244 x 24 mm
Vikt879 g
FormatInbunden
SpråkEngelska
Antal sidor384
FörlagWiley-VCH Verlag GmbH
ISBN9783527347360

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Feng Shi, PhD, is Professor at Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (CAS). His research is focused on catalytic synthesis of N/O-containing fine chemicals.Hongli Wang, PhD, is Associate Professor at Lanzhou Institute of Chemical Physics, CAS. His research is focused on catalytic synthesis of high value-added chemicals with C1 molecules. Xingchao Dai, PhD, is Assistant Professor at Lanzhou Institute of Chemical Physics, CAS. His research is focused on the construction of heterogeneous catalytic systems in the high value-added utilization of renewable biomass-based molecules.

Preface xiPart I Carbonyl Molecules as Reactants 11 Carbon Monoxide 31.1 Hydroformylation of Alkenes and Alkynes 31.1.1 Co Catalysts 41.1.2 Rh Catalysts 51.1.3 Au Catalysts 71.1.4 Ligand-Modified Heterogeneous Catalysts 71.1.5 Single-Atom Catalysts 101.2 Hydroxy-, Alkoxy-, and Aminocarbonylation of Alkenes and Alkynes 111.2.1 Hydroxycarbonylation of Alkenes 111.2.2 Hydroxycarbonylation of Alkynes 131.2.3 Alkoxycarbonylation of Alkenes 141.2.4 Alkoxycarbonylation of Alkynes 161.2.5 Aminocarbonylation of Alkenes 171.2.6 Aminocarbonylation of Alkynes 191.3 The Pauson–Khand Reaction 201.3.1 The Catalytic Pauson–Khand Reaction 211.3.2 Stereoselective Pauson–Khand Reactions 231.3.3 Pauson–Khand Transfer Carbonylation Reactions 251.4 Synthesis of Acetic Acid 261.4.1 Process Considerations 261.4.2 Rhodium-Catalyzed Carbonylation 271.4.3 Iridium-Catalyzed Carbonylation 281.5 Carbonylation of C–X Bonds 301.5.1 Hydroxy-, Alkoxy-, and Aminocarbonylations of C–X Bonds 301.5.2 Reductive Carbonylations 341.5.3 Carbonylative Coupling Reactions with Organometallic Reagents 361.5.4 Carbonylative Sonogashira Reactions 411.5.5 Carbonylative C–H Activation Reactions 441.5.6 Carbonylative Heck Reactions 461.6 Carbonylation of Epoxides 481.6.1 Ring-expansion Carbonylation of Epoxides 481.6.2 Hydroformylation and Silylformylation of Epoxides 501.6.3 Alternating Copolymerization of Epoxides 501.6.4 Alkoxycarbonylation and Aminocarbonylation of Epoxides 511.7 Carbonylation of Aldehydes 521.7.1 Amidocarbonylations of Aldehydes 521.7.2 Hydroformylation and Silylformylation of Aldehydes 541.7.3 Hetero Pauson–Khand Reactions of Aldehydes 551.7.4 Reactions of Aldehydes with Acylanions 551.7.5 Miscellaneous of Aldehydes 561.8 Oxidative Carbonylation Reaction 571.8.1 Oxidative Carbonylation of Alkenes 571.8.2 Oxidative Carbonylation of Alkynes 591.8.3 Oxidative Carbonylation of Organometallic Reagents 631.8.4 Oxidative Carbonylation of Arenes 651.8.5 Oxidative Carbonylation of Amines 671.9 Other Reactions 691.9.1 Reactions of Diazoalkanes with Carbon Monoxide 701.9.2 Reaction of C–NO2 with CO 732 Carbon Dioxide 752.1 Synthesis of Urea Derivatives 752.1.1 Metal-free Catalyst Systems 752.1.2 Ph3SbO as Catalyst 752.1.3 Pd Catalyst Systems 762.1.4 Ionic Liquids as Catalyst 762.1.5 CeO2 as Catalyst 772.2 Synthesis of Carbamate Derivatives 782.2.1 Ru Catalyst Systems 782.2.2 Sn or Ni Catalyst Systems 792.2.3 Zeolite as Catalyst 792.2.4 Other Catalyst Systems 812.3 Synthesis of Carboxyl Acid Derivatives 822.4 Cycloaddition of Epoxide with CO2 882.4.1 Oxides Catalysts 932.4.2 Zeolite Catalysts 942.4.3 Supported Nanoparticle and Lewis Acid Catalysts 952.4.4 Carbon Catalysts 982.4.5 Salen, Porphyrins, and Phthalocyanines Catalysts 982.4.6 Ionic Liquid Catalysts 1012.4.7 Metal–Organic Framework (MOF) Catalysts 1062.4.8 Bifunctional Catalysts 1092.4.9 Other Catalysts 1172.5 Reaction of Polyalcohols/Olefins with CO2 1192.6 Formylation of Amines with CO2 1212.7 Reactions of Propargyl Alcohols/Propargyl Amines with CO2 1252.8 Other Reactions 1272.8.1 Reactions of Aromatic Halides with CO2 1272.8.2 Reactions of 2-Aminobenzonitriles with CO2 1303 Other C1 Carbonyl Molecules 1333.1 Formaldehyde (HCHO) 1333.1.1 Carbonylation of Halides with HCHO 1343.1.2 Carbonylation of Olefins with HCHO 1363.1.3 Carbonylation of Alkynes with HCHO 1423.2 Formic Acid (HCOOH) 1443.2.1 Hydroxycarbonylation of Arenes with Formic Acid 1443.2.2 Carbonylation of Alkenes with Formic Acid 1443.2.3 Carbonylation of Alkynes with Formic Acid 1483.2.4 N-Formylation Reactions with Formic Acid 1503.2.4.1 Metal Oxides Catalysts 1503.2.4.2 Brønsted Acidic as Catalyst 1513.2.4.3 Amberlite IR-120 Resins as Catalysts 1523.2.4.4 Magnetic Catalysts 1523.2.4.5 Zeolite as Catalyst 1533.2.4.6 Ionic Liquids (ILs) as Catalyst 1543.2.4.7 Other Catalysts 1563.2.5 Carbonylation of C–X with Formic Acid 1573.2.6 Other Reactions 1614 CO Surrogates 1634.1 Carbonyl Metal 1634.2 Formates 1654.3 Formamides 1684.4 Formic Anhydride 1694.5 Silacarboxylic Acid 1704.6 N-Formylsaccharin 1724.7 Acyl Chloride 1724.8 In Situ Generated Carbonyl Source 1744.8.1 Methanol 1744.8.2 Glycerol 1764.8.3 Aldoses 1784.8.4 Epoxide 1794.8.5 Chloroform 1814.8.5.1 Pd-catalyzed Carbonylation Reactions 1824.8.5.2 Fe-Catalyzed Carbonylation Reactions 1854.8.5.3 Zn-Catalyzed Carbonylation Reactions 186Part I References 187Part II Carbonyl Compounds as Catalysts 2175 Acid-Catalyzed Reactions with –CO2H 2195.1 Carboxylic Acid Molecules Catalyzed Reactions 2195.1.1 Hydrolysis/Aminolysis/Ethanolysis Reactions 2195.1.2 Mutarotation of 2,3,4,6-Tetramethyl-d-glucose (TM-G) 2215.1.3 Depolymerization of Polyoxymethylenes 2215.1.4 Elimination Reactions 2215.1.5 Hydrogen–Deuterium Exchange Reactions 2225.1.6 Reduction Reactions 2225.1.7 Decomposition of Diazodiphenylmethane 2225.1.8 Amino–Imino Tautomerism Reactions 2225.1.9 Aldol Reaction 2245.1.10 Friedel−Crafts Reaction 2245.1.11 Hydrogen Shifts Reaction 2255.1.12 Cyclization Reaction 2265.1.13 Hydroboration Reaction 2295.1.14 Trifluoromethylation Reaction 2295.2 Carbon Material–Catalyzed Reactions 2305.2.1 Reduction of Nitric Oxide 2305.2.2 Oxidative Coupling of Amines to Imines 2335.2.3 Depolymerization of Cellulose and Lignocellulose 2335.2.4 Nitrobenzene Reduction Reaction and Beckmann Rearrangement Reaction 2365.2.5 Ring-Opening Reaction of Styrene Oxide 2366 Reactions via Carbonyl and Hydroxyl Groups Recycling 2396.1 Carbon-Catalyzed Selective Oxidation Reactions 2396.1.1 Oxidative Dehydrogenation of Ethylbenzene 2396.1.2 Oxidative Dehydrogenation of n-Butane 2426.1.3 Oxidative Dehydrogenation of Isobutane 2436.1.4 Oxidative Dehydrogenation of Propane 2456.2 Polymer-Catalyzed Selective Oxidation Reactions 2456.2.1 Oxidative Dehydrogenation of Ethylbenzene 2456.2.2 Oxidative Dehydrogenation of Heterocyclic Compounds 2466.3 Aldehyde/Ketone-Catalyzed Borrowing-Hydrogen Reactions 2476.3.1 Dehydrative β-C-Alkylation Reaction of Methyl Carbinols with Alcohols 2476.3.2 Dehydrative α-Alkylation Reactions of Ketones with Alcohols 2486.3.3 Dehydrative Alkylation Reactions of Fluorenes with Alcohols 2486.3.4 Dehydrative N-Alkylation Reactions of Amines with Alcohols 2496.4 Carbon-Catalyzed Borrowing-Hydrogen Reactions 250Part II References 251Part III The Synthetic Applications of Carbonyl Compounds 2557 Synthesis of Functional Molecules 2577.1 Reduction of Carbonyl Compounds 2577.1.1 Aldehydes and Ketones to Alcohol 2577.1.2 Acids to the Alcohols and Aldehydes 2597.1.2.1 To Alcohols 2597.1.2.2 To Aldehydes 2617.1.3 Ester to Alcohols and Ethers 2637.1.3.1 To Alcohols 2637.1.3.2 To Ethers 2647.1.4 Amides to Amines 2647.1.5 Clemmensen Reduction 2677.1.6 Wolff–Kishner Reduction 2687.2 Nucleophilic Addition Reactions of Aldehydes and Ketones 2707.2.1 Carbon Nucleophiles 2707.2.1.1 Grignard Reagent and Other Organometallic Reagents 2707.2.1.2 Reformatsky Reaction 2717.2.1.3 Benzoin Condensation 2727.2.1.4 CN Group 2727.2.1.5 Aromatic and Aliphatic C–H Bond 2737.2.2 Nitrogen Nucleophiles 2757.2.3 Oxygen Nucleophiles 2777.2.3.1 H2O as a Nucleophile 2777.2.3.2 ROH as a Nucleophile 2777.3 Addition Elimination Reactions of Aldehydes and Ketones 2787.3.1 Aldol Reaction 2787.3.2 Perkin Reaction 2787.3.3 Knoevenagel Condensation 2807.4 Oxidation of Aldehydes and Ketones 2817.4.1 Baeyer–Villiger Oxidation 2817.4.2 To Acid 2827.5 Wittig Reaction 2857.6 Reductive Amination Reaction 2867.6.1 Homogeneous Catalyst System 2877.6.2 Heterogeneous Catalyst System 2907.7 Hydroboration/Hydrophosphonylation/Hydrosilylation/Hydroacylation of Aldehydes and Ketones 2937.7.1 Hydroboration 2937.7.2 Hydrophosphonylation 2967.7.3 Hydrosilylation Reactions 2977.7.4 Hydroacylation Reactions 3007.8 Oxidative Cross-Coupling Reaction of Aldehydes 3027.8.1 Homogeneous Catalyst System 3027.8.2 Heterogeneous Catalyst System 3047.9 Reductive Coupling Reactions of Aldehydes 3067.10 Reaction of Acids as Starting Materials 3107.10.1 Esterification Reactions 3107.10.2 Amidation Reactions 3107.10.3 Decarboxylation Coupling Reactions 3117.11 Reaction of Esters as Starting Materials 3177.11.1 Hydrolysis Reaction 3177.11.2 Transesterification Reaction 3187.11.3 Aminolysis Reaction 3197.12 Reaction of Amides as Starting Materials 3207.12.1 Hydrolysis Reaction 3207.12.2 Alcoholysis Reaction 3208 Synthesis of Functional Materials 3238.1 Polyamides 3238.1.1 Aliphatic Polyamides 3248.1.2 Aromatic Polyamides 3258.1.3 Long-Chain Semiaromatic Polyamides 3268.2 Phenol Formaldehyde Resins 3298.2.1 Novolac Resins 3298.2.2 Resole Resins 3308.3 Polyurethanes 3328.4 Polyesters 335Part III References 3399 Conclusion and Perspectives 3519.1 Conclusion 3519.2 Perspectives 352Index 355