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Fig. 5.55 Different paths of anodic oxidation dependent on electrolyte composition. (According to L. E. Eberson and N. L. Weinberg)
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387 reduction of nitrobenzene, azoxybenzene and hydrazobenzene are produced as a result of interactions among the adsorbed intermediates. If azobenzene is reduced in acid medium to hydrazobenzene, then the product rearranges in a subsequent chemical reaction in solution to give benzidine. An example of dimerization of the intermediates of an electrode reaction is provided by the reduction of acrylonitrile in a sufficiently concentrated aqueous solution of tetraethylammonium p -toluene sulphonate at a mercury or lead electrode. The intermediate in the reaction is probably the dianion CH 2 =CHCN + 2 e ^ CH2 CHCN (5.9.4)
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which reacts in the vicinity of the electrode with another acrylonitrile molecule CH2 CHCN + CH 2 =CHCN-* NCCHCH2CH2CHCN (5.9.5) (-) (-) NCCHCH2CH2CHCN + 2H 2 O-^ NC(CH2)4CN + 2OH~ finally to form adiponitrile (an important material in the synthesis of Nylon 606). Carbonyl compounds are reduced to alcohols, hydrocarbons or pinacols (cf., for example, Eq. 5.1.8), where the result of the electrode process depends on the electrode potential. The electrocatalytic oxidation of methanol was discussed on page 364. The extensively studied oxidation of simple organic substances is markedly dependent on the type of crystal face of the electrode material, as indicated in Fig. 5.56 for the oxidation of formic acid at a platinum electrode. M. Faraday was the first to observe an electrocatalytic process, in 1834, when he discovered that a new compound, ethane, is formed in the electrolysis of alkali metal acetates (this is probably the first example of electrochemical synthesis). This process was later named the Kolbe reaction, as Kolbe discovered in 1849 that this is a general phenomenon for fatty acids (except for formic acid) and their salts at higher concentrations. If these electrolytes are electrolysed with a platinum or irridium anode, oxygen evolution ceases in the potential interval between +2.1 and +2.2 V and a hydrocarbon is formed according to the equation 2 R C O O " ^ R2 + 2CO2 + 2e (5.9.6)
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In addition to hydrocarbons, other products have also been found, especially in the reactions of the higher fatty acids. In steady state, the current density obeys the Tafel equation with a high value of constant 6 0.5. At a constant potential the current usually does not depend very much on the sort of acid. The fact that the evolution of oxygen ceases in the
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Fig. 5.56 Triangular-pulse voltammograms of oxidation of 0.1 M formic acid in 0.5 M H2SO4 at various faces of a single-crystal platinum electrode, 22 C, dE/dt = 50 mV s"1. (According to C. Lamy) potential range where the Kolbe reaction proceeds can be explained in two ways. The anion of the fatty acid or an oxidation intermediate may block the surface of the electrode (cf. page 361), or as a second alternative, the acid may react with an intermediate of anodic oxygen evolution, which then cannot occur. The mechanism of this interesting process has not yet been completely elucidated; the two main hypotheses are illustrated in the following schemes: RCOO--*RCOOadsRCOO a d s "-> RCOO a d s + e RCOO a d s ->R a d s + CO 2 (5-9-7) Rads"* products, for example R 2
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RCOCT RCOCT + 2e > R + CO2 + e > R+ + CO2 (5.9.8) further products Similarly as for other chemical reactions, the activation energy for the electrode reactions of organic substances depends on the nature and position of the substituents on the aromatic ring of an organic molecule. As the standard potentials are not known for many of these mostly irreversible processes and as they were mainly investigated by polarography, their basic data is the half-wave potential (Eq. 5.4.27). The difference of the half-wave potential of the tested substance, i, and of the reference substance (which is, for example, non-substituted) for the same type of electrode reaction (e.g. nitrogroup reduction) is given by the equation RT k^ Ew - i/2,ref = AE1/2 = AE0' + - In - ^ (5.9.9) anF k^f We assume that neither the preexponential factor of the conditional electrode reaction rate constant nor the charge transfer coefficient changes markedly in a series of substituted derivatives and that the diffusion coefficients are approximately equal. In view of (5.2.52) and (5.2.53), (5.9.10) where AAHl is the difference between the activation energies of the electrode reactions of substance i and of the reference substance. R. W. Brockman and D. E. Pearson, S. Koide and R. Motoyama and P. Zuman applied the Hammett equation, originally deduced for chemical reactions, to electrode processes. In this concept the activation energy or standard Gibbs energy of a reaction where members of a homologous series participate is given by the relationship AAHl = 0:0/, (5 9 11) where py and p) characterize the type of the reaction and ok the substituent. The values of ok which are the same for all reaction types have been listed by L. Hammett. Thus, for the series of half-wave potentials of the same electrode reaction type we have (5.9.12)
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390 where p" characterizes the electrode reaction type (reduction of the nitro, aldehydic, chlorine, etc., group) and ok the substituent (mainly in the para or meta position on the benzene ring).