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Electroanalytical Chemistry of Some Organometallic Compounds of Tin, Lead and Germanium

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Electroanalytical Chemistry of Some Organometallic Compounds of Tin, Lead and Germanium ELECTROANALYTICAL CHEMISTRY OF SOME ORGANOMETALLIC COMPOUNDS OF TIN, LEAD AND GERMANIUM by Nani Bhushan Fouzder M.Sc. (Rajshahi) A Thesis Submitted for the Degree of Doctor of Philosophy of the University of London. Chemistry Department, Imperial College of Science and Technology, London S.W.7. September, 1975. 11 ABSTRACT. The present thesis concerns the investigation into the electrochemical behaviour of some industrially important organometallic compounds of tin, lead and germanium and development of suitable electrochemical methods for the analysis of these compounds at formula- tion and at trace level. The basic principles of the electrochemical techniques used inthis investigation have been given in the first part of the 'Introduction', while the various factors which control the electrode process have been discussed in the second part of the 'Introduction' in chapter 1. The electrochemical behaviour and analytical determination of some important organotin fungicides and pesticides such as tri-n-butyltin oxide, triphenyl- tin acetate, etc., some antihelminthic compounds such as dibutyltin dilaureate and dibutyltin dimaleate and some widely used PVC-stabilizers such as di-n-Octyltin dithioglycollic acid ester (Irgastab 17 MOK), Irgastab 17M and Irgastab 15 MOR have been described in the following three chapters. For each type of compound a detailed mechanism of the electrochemical process has been proposed and established. The electrochemical behaviour of organolead compounds and of the organogermanium compounds have been described in the next three chapters. In each case, the mechanism of reduction of these compounds has been established and methods 9fc their determina- tion at ordinary and at trace level have been developed. Finally, in the eighth chapter a brief intro- duction into the highspeed liquid chromatographic technique has been given and analysis of organotin compounds by this method using a wall-jet electrode detector has been described. iv ACKNOWLEDGEMENTS. The research work described in this thesis is entirely original except where due reference is made. I would like to thank Professor T. S. West for his interest and encouragement and for placing the facili- ties available in the Analytical Chemistry Department of the Imperial College at my disposal. I am particu- larly indebted to my immediate supervisor. Dr. B. Fleet for his help, advice and guidance throughout the entire research programme. I would also like to thank all my colleagues particularly Drs. S.Dasgupta and G.P.Bound and Messrs. J.Bland, T.Berger and J.Andrews for many stimulating discussions, Dr. C.J.Little of Roche Products, Welwyn Garden city and Dr. P. Bristow of I.C.I. (Pharmaceuticals Division) Macclesfield for their help in connection with HPLC experiments. My thanks are also due to E.D.T. Research, London, for the loan of a PAR Polarograph during HPLC experiments. My grateful thanks are due to the Ministry of the Overseas Development, Govt. of the U.K., for the award of a study fellowship, to the British Council for their cooperation and to the University of Rajshahi, Bangla- desh, for study leave. I am also grateful to my wife, Gita, for her constant encouragement throughout this investigation and particularly for her active and very useful help during preparation of this thesis. N. B. Fouzder. To APU with love and affection. CONTENTS Page. Title page. Abstract. ii Acknowledgements. iv CHAPTER 1. INTRODUCTION 1 1.1 D.c. polarography 3 Different types of limiting currents. 8 Interpretation of the polarogram and elucidation of electrode process 10 1.2 Diffusion controlled electrode process at solid electrodes: Determination of diffusion coefficient 12 1.3 Determination of n—values and identification of products. 13 Controlled Potential Electrolysis. 13 Controlled potential coulometry. 15 Microcoulometry. 18 1.4 Reversibility of the polarographic wave and identification of the intermediates 20 Oscillographic polarography and cyclic voltammetry 22 A.c. polarography 26 1.5 Polarography as a trace analytical technique. 27 Pulse polarography 27 Differential pulse polarography 29 1.6 Factors influencing the electrode process. 32 The electrical double layer and the role of adsorption. 32 The solvent effect. 39 vi The pH-effect. 42 The influence of the electrode material 45 Effect of temperature. 46 Effect of background electrolyte. 46 CHAPTER 2. ETECTROCHEMICAL BEHAVIOUR OF Bis (TRI- n-BUTYLTIN) OXIDE AND TRIPHENYLTIN COMPOUNDS AND THEIR ANALYTICAL DETERMINATIONS BOTH AT FORMULATION AND AT TRACE LEVELS. 2.1 Introduction. 49 2.2 Experimental technique. 50 2.3 Results and discussions 53 General polarographic behaviour. 53 Mechanism of reduction. 61 2.4 Analytical determinations. 66 CHAPTER 3. ELECTROCHEMICAL BEHAVIOUR OF DIBUTYLTIN DILAUREATE AND DIBUTYLTIN DIMALEATE AND THEIR ANALYTICAL DETERMINATIONS. 3.1 Introduction. 68 3.2 Experimental technique. 71 3.3 Results and discussions. 73 General polarographic behaviour. 73 Mechanism of reduction. 80 3.4 Analytical determinations. 82 CHAPTER 4. ETRCTROCHEMICAL BEHAVIOUR OF ORGANOTIN SULPHUR COMPOUNDS AND THEIR ANALYTICAL DETERMINATIONS. 4.1 Introduction. 90 4.2 Experimental technique. 91 4 3 Results and discussions 91 ,Differential pulse polarography. 94 Mechanism of reduction process. 96 4.4 Analytical determinations. 100 vii CHAPTER 5. ELECTROCHEMICAL BEHAVIOUR OF TRIPHENYLLEAD ACETATE AND ITS ANALYTICAL DETERMINATION. 5.1 Introduction. 102 5.2 Experimental technique. 105 5.3 Results and discussions. 105 General polarographic behaviour. 105 Voltammetry at glassy carbon electrode. 117 Mechanism of electrode process. 119 5.4 Analytical determinations. 123 CHAPTER 6. ELECTROCHEMICAL BEHAVIOUR OF DIBUTYL- LEAD DIACETATE AND ITS ANALYTICAL DETERMINATION AT ORDINARY AND AT SUBMICROMOLAR LEVEL. 6.1 Introduction. 126 6.2 Experimental technique. 128 6.3 Results and discussions. 128 General polarographic behaviour. 128 Voltammetry and cyclic voltammetry at a glassy carbon electrode. 136 Mechanism of reduction at the DME. 139 6.4 Analytical determinations. 140 CHAPTER 7. ELECTROCHEMICAL BEHAVIOUR OF TRIPHENYL - GERMANIUM BROMIDE AND ITS ANALYTICAL DETERMINATION . 7.1 Introduction. 145 7.2 Experimental technique. 148 7.3 Results and discussions. 149 General polarographic behaviour. Mechanism of reduction. 158 7.4 Analytical determinations. 160 viii CHAPTER 8. THE ANALYSIS OF ORGANOTIN COMPOUNDS BY HIGH PRESSURE LIQUID CHROMATOGRAPHY USING A VOLTAMEETRIC DETECTOR SYSTEM. 8.1 Introduction. 163 8.2 Theoretical principles. 164 8.3 Polarographic and other voltammetric detectors. 168 Wall-jet electrode principles. 170 8.4 Application of the WJED to the analysis of organotin compounds by HPIC method. 174 Experimental technique. 174 Results and discussions. 176 Conclusion. 183 REFERENCES. 187 LIST OF PUBLICATIONS. 207 1 CHAPTER 1. INTRODUCTION The formation of organic derivatives of metals having carbon-metal 6 -bond is a general phenomenon among the metals. Consequently a very large number of organometallic compounds are known. The organo- metallic chemistry is supposed to have begunl with the famous researches of Robert Bunsen on cacodyl, (CH ) As in 1841. Bunsen found the chemical beha- 3 4 2 viour of this compound to be very interesting. Since then many significant contributions were made for the newly discovered organometallic compounds of mercury, silicon, Tin, Lead and many other metals. Early industrial interest in these compounds was aroused from a series of brilliant discoveries in the application of these compounds in chemotherapy2 and in organic synthesis3. Midgley's discovery4 in 1922 of the highly effectiveness of organolead compounds as "antiknock" agent and subsequently its wide application as gasoline additive in internal combustion engines brought organometallic chemistry very much into public view. The Ziegler-Natta disco- very that organometallic compounds can be used very effectively as catalyst for low pressure polNhmeri- zation of olefins5-7 has further enhanced the industrial importance of these compounds and has led 2 to the growth of many new chemical industries during recent years. Finally the preparation of ferrocene and other metallocenes8'9 and elucidation of their structures10-15 have opened up a new area of organo- metallic chemistry which has broadened the horizon of our knowledge about the nature of chemical bon- ding as well as industrial applications16 of these compounds. The ever-increasing use of organometallic compounds in industry, medicine and agriculture has also increased the dangerous risk of environmental pollution and consequent ecological concern17. This as well as the quality control factor in industrial concerns have demanded highly sensitive specific methods of analysis of these compounds particularly at trace level. Several analytical techniques have so far been tried more or less successfully for this purpose. The present thesis is concerned with the development of suitable electrochemical methods of analysis of some industrially important organo- metallic compounds of Tin, Lead and Germanium at both macro and trace level. For the development of electroanalytical procedures it is desirable to elucidate as com- pletely as possible the mechanism of the electrode process. So a detailed investigation into the mechanism of electrochemical reduction of these compounds was undertaken. A variety of 3 electrochemical techniques have been_ extensively employed for this purpose. So a brief account of each will also be given. Finally, a general intro- duction will be given
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