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A study of the elctrochemical reduction of nitrobenzene and o-halonitrobenzes in acidic media

A study of the elctrochemical reduction of nitrobenzene and o-halonitrobenzes in acidic media
A study of the elctrochemical reduction of nitrobenzene and o-halonitrobenzes in acidic media

The electrochemical reduction of nitrobenzene and o-halonitrobenzenes has been studied in aqueous organic solvents containing sulphuric acid. The reaction products and their maximum rate of production depend upon the solvent, cathode metal, electrode potential, concentration of acid and the rate of stirring of the catholyte. 

From studies in a glass batch reactor it was possible to find conditions (i.e. using 1:1 1-propanol/water, a copper cathode, a 3M sulphuric acid and rapid stirring at low electrode potentials) where the yield of p-aminophenol was over 75% at a current density of 150 mA.cm-2. Conditions for the complete 6e- reduction to the corresponding anilines were also defined. The highest yield was obtained with a mercury electrode, 0.114M H2SO4, slow stirring and a higher negative electrode potential. With nitrobenzene, o-fluoronitrobenzene and the o-chlorocompound, the anilines were formed in yields exceeding 75% and current densities above 100 mA.cm-2. With o-bromonitrobenzene the yield was lower because of competing cleavage of the C-Br bond. 

The reactions were also investigated in a parallel plate reactor with recycled electrolyte flow and conditions closer to those in an industrial electrochemical cell. The study revealed that p-aminophenol could be produced with a 76% material yield and 5.7 Kwh Kg-1 energy consumption, and anilines at 95% material yield and 10 Kwh Kg-1 energy consumption. The results compare very favourably with other attempts to produce these compounds.

University of Southampton
Marquez, Jairo
6b69cbcb-7922-4505-bc71-bbbc90b5ae24
Marquez, Jairo
6b69cbcb-7922-4505-bc71-bbbc90b5ae24
Pletcher, D.
8f934180-8464-46d8-a79b-6e89fe693bad

Marquez, Jairo (1981) A study of the elctrochemical reduction of nitrobenzene and o-halonitrobenzes in acidic media. University of Southampton, Doctoral Thesis, 151pp.

Record type: Thesis (Doctoral)

Abstract

The electrochemical reduction of nitrobenzene and o-halonitrobenzenes has been studied in aqueous organic solvents containing sulphuric acid. The reaction products and their maximum rate of production depend upon the solvent, cathode metal, electrode potential, concentration of acid and the rate of stirring of the catholyte. 

From studies in a glass batch reactor it was possible to find conditions (i.e. using 1:1 1-propanol/water, a copper cathode, a 3M sulphuric acid and rapid stirring at low electrode potentials) where the yield of p-aminophenol was over 75% at a current density of 150 mA.cm-2. Conditions for the complete 6e- reduction to the corresponding anilines were also defined. The highest yield was obtained with a mercury electrode, 0.114M H2SO4, slow stirring and a higher negative electrode potential. With nitrobenzene, o-fluoronitrobenzene and the o-chlorocompound, the anilines were formed in yields exceeding 75% and current densities above 100 mA.cm-2. With o-bromonitrobenzene the yield was lower because of competing cleavage of the C-Br bond. 

The reactions were also investigated in a parallel plate reactor with recycled electrolyte flow and conditions closer to those in an industrial electrochemical cell. The study revealed that p-aminophenol could be produced with a 76% material yield and 5.7 Kwh Kg-1 energy consumption, and anilines at 95% material yield and 10 Kwh Kg-1 energy consumption. The results compare very favourably with other attempts to produce these compounds.

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Marquez 1981 Thesis - Version of Record
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Published date: 1981

Identifiers

Local EPrints ID: 459556
URI: http://eprints.soton.ac.uk/id/eprint/459556
PURE UUID: 6db5c224-52ab-490c-99be-c23133f43c7d

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Date deposited: 04 Jul 2022 17:14
Last modified: 23 Jan 2023 18:05

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Contributors

Author: Jairo Marquez
Thesis advisor: D. Pletcher

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