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ELECTEOLYTIC BEDUCTION OF OKGANIC COMPOUNDS 55 para position is unoccupied give jp-aminophenols, the yield amounting to about 40 per cent. It is necessary to dilute the sulphuric acid slightly or to keep the temperature low, otherwise sulphonation 1 2 Elbs was the first to prove that a considerable quantity of aniline is formed at the same time, and that a lead cathode increases the amount of this substance. Gattermann subsequently proved that phenylhydroxyl- amine is the primary reduction product, and this was de- monstrated by causing it to combine with benzaldehyde (which was present during reduction) as fast as formed, giving benzylidene-phenylhydroxylamine:— C6H5NHOH + C6H5CHO - C6H5 - N - OH - C6H5 + H2O. / \) With a platinum cathode in hydrochloric acid suspension 3 occurs and a #-aminophenol sulphonic acid results. nitrobenzene gives o- and ^-chloraniline, but L o b shown that with a lead cathode aniline is the only pro- duct. Probably o- and _p-chloraniline result from the molecular re-arrangement of the chloramine, C6H6 - NHC1, which is produced from the phenylhydroxylamine first 4 formed. Elbs and Silberman also found that, in acid solution, lead cathodes give more aniline than platinum when reducing nitrobenzene. This was confirmed by the reduction of the nitrotoluenes, 1 Noyes and Clement, Ber.,1893,26,990. Zeitsch. Elcktrochem., 1896, 2,4:72. 3 Ber.91896, 29,1894 ; Zeitsoh. Elektrochm., 1898, 4, 430. bid.t 1896,3?472. 2 hasPDF Image | MANUFACTURE OF CHEMICALS BY ELECTROLYSIS
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