CHEMICAL KINETICS C.H. BAMFORD C.F.H. TIPPER WSSSKUH EDITED BY

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1 CHEMICAL KINETICS EDITED BY C.H. BAMFORD M.A., Ph.D., Sc.D. (Cantab.), F.R.I.C., F.R.S. Campbell-Brown Professor of Industrial Chemistry, Uniuersity of Liverpool AND C.F.H. TIPPER Ph.D. (Bristol), D.Sc. (Edinburgh) Senior Lecturer in Physical Chemistry, University of Liverpool VOLUME 16 LIQUID-PHASE OXIDATION WSSSKUH ELSEVIER SCIENTIFIC PUBLISHING COMPANY AMSTERDAM OXFORD NEW YORK 1980

2 Contents Preface vii Chapter 1 (T. Mill and D.G. Hendry) Kinetics and mechanisms of free radical oxidation of alkanes and olefins in the liquid phase 1 1. Introduction 1 2. Historical basis of oxidation kinetics 1 3. The elementary rate steps in oxidation Oxidation of cyclohexene. The hydroperoxide chain Oxidation of styrene. The peroxy radical addition mechanism The oxidation of isobutane. Competition among alkylperoxy and alkoxy radical chains and olefin formation Oxidation of cumene (isopropylbenzene). The role of alkoxy radicals n-butane. Oxidation at secondary and primary C H bonds ,4-Dimethylpentane. Intramolecular oxidation Elementary rate steps. Absolute rate coefficients Measurement of absolute rate coefficients Overall kinetics of oxygen consumption Evaluation of ft t independent of k p Measurement of k t and fe p dependently Evaluation of k p using added hydroperoxide The reaction of carbon radicals with oxygen Formation of peroxy radicals Olefin formation Propagation Hydrogen atom transfer to R0 2 ' radicals Addition of RO2' radicals to carbon double bonds: formation of di- and polyperoxides Intramolecular H-atom transfer to peroxy radicals Ring closures of peroxy radicals H-Atom transfer to alkoxy radicals Absolute rate coefficients and Parameters for C C cleavage of alkoxy radicals (RO') Intramolecular H-atom transfer by RO* Peroxy radical interactions Chemistry of R02 - radical interactions Structure reactivity relationships in radical interactions Thermochemistry of radical interactions Absolute rate coefficients for termination Special features of initiation Autocatalysis Co-oxidation Kinetic relations 64

3 6.2 Reactivity ratios, r x and r Evaluation of the cross-termination parameter, Inhibition of oxidation Chemistry of inhibition Kinetics of inhibition by phenols and amines Rate coefficients and Parameters for inhibition Synergetic effects of phenols Inhibition by metal complexes, Photooxidations involving singlet molecular oxygen ('0 2 ) Introduction Chemistry of photooxidations with ' Kinetic relations and rate coefficients 81 References 83 Chapter 2 (L. Sajus and I. Seree de Roch) The liquid phase oxidation of aldehydes Introduction Analytical aspects Operational techniques Oxidation products Oxidation of normal saturated aldehydes Oxidation of n-decanal Oxidation of acetaldehyde Oxidation of heptaldehyde Oxidation of n-butanal Oxidation of unsaturated aldehydes Oxidation of 2-butenal Oxidation of acrolein and methacrolein Oxidation of benzaldehyde Autoxidation of benzaldehyde alone Photochemical oxidation Thermal oxidation Catalytic oxidation Co-oxidation of substituted benzaldehydes Benzaldehyde olefin co-oxidation in benzene Solution Co-oxidation of benzaldehyde with cyclohexanone Direct determination of kinetic coefficients Catalytic aldehyde oxidation without a chain mechanism Conclusions 118 References 122 Chapter 3 (E.T. Denisov) The oxidation of alcohols, ketones, ethers, esters, and acids in Solution Introduction Oxidation of alcohols The kinetics and products of alcohol oxidation Primary alcohols Secondary alcohols Chain mechanism of alcohol oxidation The formation of free radicals in alcohol oxidation Generation of chains Decomposition of hydrogen peroxide to free radicals Mechanism of cyclohexanol oxidation 134

4 2.4 Photo-oxidation and radiation-induced oxidation of alcohols Photo-oxidation Radiation-induced oxidation Oxidation with ozone Inhibitors of alcohol oxidation Mechanism of reaction of alcohol peroxy radicals with phenols and aromatic amines Regeneration of aromatic amines in alcohol oxidation Inhibition of alcohol oxidation by quinones Chemiluminescence in oxidations inhibited by aromatic amines in the presence of alcohols Negative catalysis in alcohol oxidation Negative redox catalysis Inhibition by bases Catalysis in the oxidation of alcohols Catalysis by transition metals Catalysis by bromide ions Catalysis by hydrogen ions Oxidation of alcohols with palladium salts Oxidation of alcohols in the presence of heterogeneous catalysts Oxidation of alcohols in basic solvents Co-oxidation of alcohols and aromatics Oxidation of ketones The products of ketone oxidation Acetone Methyl ethyl ketone and other aliphatic ketones Cyclohexanone Other ketones a-ketohydroperoxide The formation of acids by the oxidation of ketones Elementary Steps of ketone oxidation Chain propagation Chain termination Generation of chains Degenerate chain branching Formation of free radicals by reactions of ketones with hydroperoxides Oxidation of ketones in the presence of acids and bases Oxidation of ketones with ozone Oxidation of ethers Oxidation products Aliphatic ethers Cyclic ethers Ethers of benzyl alcohol The chain mechanism of ether oxidation Oxidation of acids Oxidative decarboxylation of acids Oxidation of acids 175 ö. Oxidation of esters The products of ester oxidation The chain mechanism of ester oxidation Oxidation of phenols Oxidation of phenols in hydrocarbon Solutions 181

5 7.2 Oxidation of phenols in polar Solutions Catalytic oxidation of phenols The role of hydrogen bonds in oxidation Hydrogen bonding and the formation of free radicals, Formation of hydrogen bonds with and abstraction of hydrogen atoms from O H and N H bonds Hydrogen bonding with peroxy radicals Reactions of peroxy radicals with polyfunctional molecules 191 References 195 Chapter 4 (D.L. Trimm) The liquid phase oxidation of sulphur, nitrogen, and chlorine Compounds Introduction Autoxidation of organic Compounds containing nitrogen Co-oxidation with hydrocarbons Inhibition by complex formation Inhibition by hydrogen abstraction Factors affecting inhibitor efficiency Electron-directing and steric effects: solvents Oxidation reduction Potentials Autoxidation of nitrogen-containing Compounds Autoxidation of organic Compounds containing sulphur Co-oxidation with hydrocarbons Autoxidation of sulphur-containing Substrates in the absence of other hydrocarbon free radical chain reactions Metal catalysis Reactions of sulphoxide products Autoxidation of organic Compounds containing chlorine 238 References 244 Index 249

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