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      Translated title: Electrochemical chlorination of phenylnonane

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          Abstract

          Usando la técnica de catálisis de transferencia entre fases, se reporta la cloración anódica del fenilnonano en un sistema de dos líquidos inmiscibles (diclorometano-agua) utilizando iones de tetrabutilamonio como agente de transferencia entre fases del ion cloruro. Se obtuvo como producto principal el pclorononilbenceno, con un rendimiento (47%) mayor al obtenido de las electrólisis en un medio orgánico sencillo (24%). La formación de este producto es dependiente del tipo y concentración del agente de transferencia, pH, temperatura y potencial de oxidación. Los valores óptimos obtenidos fueron: Bu4NHSO4 (0.3 M), pH: 4 - 6, t = 35°C, E = 1.70 V vs Ag/Ag+. De acuerdo a nuestros resultados, a potenciales de oxidación menores que el del aromático, la formación del producto clorado se debe a la reacción química de la especie clorante generada electroquímicamente y el fenilnonano en solución mientras que a potenciales mayores, la reacción ocurre entre la especie clorante y una especie catiónica proveniente de la electrooxidación del fenilnonano. Experimentos realizados en un medio acetonitrilo-agua confirman estas propuestas de reacción; en este caso a bajos potenciales (1.40 V) se forma el p-clorononilbenceno (20%) por reacción de especies clorante-fenilnonano, mientras que a potenciales mayores se obtienen p-clorononilbenceno (27%) y nonilacetanilida (34%) por reacción de la especie clorante y el medio electrolítico con la especie catiónica intermediaria orgánica.

          Translated abstract

          By using phase transference catalysis, anodic chlorination of phenylnonane in a two immiscible liquids (dichloromethane-water) with tetrabutylammonium as the transference agent; pchlorononylbenzene was obtained as the main product with an organic yield of 47%, which means an improvement compared with 24% obtained when using a single solvent. Formation of p-chlorononylbenzene depends upon the nature and concentration of the transference agent, pH, temperature, and oxidation potential. The best conditions were reached using 0.3M Bu4NHSO4, at a pH ranging within 4 and 6, at 35°C and 1.70 V vs Ag/Ag+. Our results suggest that at those potentials below the oxidation peak of the aromatic, the formation of the chlorinated species is due to a chemical reaction between the electrochemically generated chlorinating species and the neutral molecule of phenylnonane. On the other hand, at those potentials above the oxidation peak, the reaction occurs between the chlorinating species and a cationic species generated by oxidation of phenylnonane. To confirm our results, experiments were run in acetonitrile-water, showing that at low potentials (~1.40 V vs Ag/Ag+), 20% of p-chlorononylbenzene is formed by direct reaction between the chlorinating species and the phenylnonane while at higher potentials, 27% of p-chlorononylbenzene and 34% of nonylacetamide is produced by reaction of the chlorinating species and the electrolytic medium with the organic cationic intermediate species.

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          Most cited references14

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          Instrumental Methods in Electrochemistry

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            Electrosynthesis in systems of two immiscible liquids and a phase transfer catalyst. VII. The chlorination of substituted naphthalenes

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              Kinetics of the anodic oxidation of benzyl alcohol in dichloromethane in the presence of redox mediator and phase transfer catalyst

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                Author and article information

                Contributors
                Role: ND
                Role: ND
                Role: ND
                Role: ND
                Journal
                rtfiuz
                Revista Técnica de la Facultad de Ingeniería Universidad del Zulia
                Rev. Téc. Ing. Univ. Zulia
                Facultad de Ingeniería, Universidad del Zulia (Maracaibo )
                0254-0770
                August 2002
                : 25
                : 2
                : 108-117
                Affiliations
                [1 ] Universidad de Los Andes Venezuela
                Article
                S0254-07702002000200006
                fbfc870c-b4b0-4a00-ac9a-badda5c9ace2

                http://creativecommons.org/licenses/by/4.0/

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                Product

                SciELO Venezuela

                Self URI (journal page): http://www.scielo.org.ve/scielo.php?script=sci_serial&pid=0254-0770&lng=en
                Categories
                ENGINEERING, MULTIDISCIPLINARY

                General engineering
                electrochemical chlorination,phenylnonane,Funcionalización de hidrocarburos,cloración electroquímica,oxidación anódica,fenilnonano,Hydrocarbons fictionalization,anodic oxidation

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