Electrocatalytic hydrogenation of 4-phenoxyphenol on active powders highly dispersed in a reticulated vitreous carbon electrode

Dabo, Pierre; Cyr, André; Lessard, Jean; Brossard, L.; Ménard, Hugues

doi:10.1139/v99-120

Cited by 51 publications

(57 citation statements)

References 18 publications

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“…This result can be attributed to palladium's ability to both adsorb and absorb hydrogen (17). Similarly, Dabo et al (18) observed that palladium catalysts offered maximum current efficiencies in the ECH of 4-phenoxyphenol. Palladized carbon felt was found to be an efficient catalyst for the dechlorination of 4-chlorophenol (19) and 2,4-dichlorophenoxyacetic acid (7)(8)(9); in the latter studies, current efficiencies for dechlorination reaction followed the sequence Pd > Rh > Ru catalysts.…”

Section: Dechlorination Efficiency (Table 1)mentioning

confidence: 88%

“…At some point, we would expect a further increase in the amount of catalyst to be unproductive, due to clogging the pores of the RVC cathode; this is presumably the explanation for the lower current efficiency observed with 600 mg of catalyst. The electrocatalytic properties of various noble-metal catalysts -Raney nickel; palladium, platinum, ruthenium, and rhodium on aluminia; and palladium on calcium carbonate -were investigated ( Table 1, entries [14][15][16][17][18][19]. Catalysts on carbon powder supports were not included in the study because atrazine rapidly and strongly adsorbed to carbon powder resulting in its removal from solution without a chemical change.…”

Section: Dechlorination Efficiency (Table 1)mentioning

confidence: 99%

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Electrocatalytic dechlorination of atrazine

Stock¹,

Bunce²

2002

Can. J. Chem.

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Atrazine (2-chloro-4-ethylamino-6-isopropylamino-s-triazine), a photosynthetic inhibitor that is used in large quantities for weed control in corn and sorghum, is dechlorinated in aqueous solution upon electrolysis at a reticulated vitreous carbon cathode in the presence of noble-metal catalysts. Electrocatalytic hydrogenolysis to 2-ethylamino-4-isopropylamino-s-triazine occurs in quantitative yield, and is most efficient with palladium-based catalysts. Current efficiency increases with atrazine and catalyst concentration, and decreasing current density. A previously unobserved phenomenon with Pd catalysts is that current must be passed for a certain time before dechlorination commences. This lag time is explained in terms of the palladium lattice absorbing a finite amount of hydrogen before catalytically active hydrogen atoms appear on the catalyst surface.Résumé : Soumise à une électrolyse en solution aqueuse, au niveau d'une cathode de carbone vitreuse et réticulée et en présence de catalyseurs de métaux nobles, l'atrazine (la 2-chloro-4-éthylamino-6-isopropylamino-s-triazine), un inhibiteur de la photosynthèse utilisé en grandes quantités pour contrôler les mauvaises herbes dans le maïs et dans le shorgo, subit une déchloration. L'hydrogénolyse électrocatalytique en 2-éthylamino-4-isopropylamino-s-triazine se produit avec un rendement quantitatif et les catalyseurs à base de palladium sont les plus efficaces. L'efficacité de courant augmente avec les concentrations d'atrazine et de catalyseur et elle diminue avec la densité du courant. Avec les catalyseurs de Pd, il se produit un phénomène qui n'a pas été observé antérieurement; on doit faire passer le courant pour un certain temps avant que la déchloration ne débute. On explique ce décalage dans le temps en fonction d'une absorption dans un premier temps d'une quantité finie d'hydrogène par le réseau du palladium qui précéderait l'apparition d'atomes d'hydrogène catalytiquement actifs à la surface du catalyseur.

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Section: Dechlorination Efficiency (Table 1)mentioning

confidence: 88%

Section: Dechlorination Efficiency (Table 1)mentioning

confidence: 99%

Electrocatalytic dechlorination of atrazine

Stock¹,

Bunce²

2002

Can. J. Chem.

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“…According to the literature [5][6][7][8][9][10], the overall mechanism of the electrocatalytic hydrogenation of an unsaturated organic molecule, Z=Y, on a metal/carbon supported electrode involved three steps: the formation of adsorbed hydrogen, MH ads , on the metal, the adsorption of the organic molecule on carbon, and the catalytic hydrogenation of the adsorbed organic molecule by the adsorbed hydrogen.…”

Section: Introductionmentioning

confidence: 99%

Electrocatalytic hydrogenation of acetophenone using a Polymer Electrolyte Membrane Electrochemical Reactor

Sáez

García-García

Solla-Gullón

et al. 2013

Electrochimica Acta

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Please cite this article as: A. Sáez, V. García-García, J. Solla-Gullón, A. Aldaz, V. Montiel, Electrocatalytic hydrogenation of acetophenone using a Polymer Electrolyte Membrane Electrochemical Reactor, Electrochimica Acta (2010Acta ( ), doi:10.1016Acta ( /j.electacta.2012 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.Page 1 of 20 A c c e p t e d M a n u s c r i p t 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 AbstractThe use of a solid polymeric electrolyte, spe, is not commonly found in organic electrosynthesis despite its inherent advantages such as the possible elimination of the electrolyte entailing simpler purification processes, a smaller sized reactor and lower energetic costs. In order to test if it were possible to use a spe in industrial organic electrosynthesis, we studied the synthesis of 1-phenylethanol through the electrochemical hydrogenation of acetophenone using Pd/C 30% wt with different loadings as cathode and a hydrogen gas diffusion anode. A Polymer ElectrolyteMembrane Electrochemical Reactor, PEMER, with a fuel cell structure was chosen to carry out electrochemical reduction with a view to simplifying an industrial scale-up of the electrochemical process. We studied the influence of current density and cathode catalyst loading on this electroorganic synthesis. Selectivity for 1-phenylethanol was around 90% with only ethylbenzene and hydrogen detected as by-products.

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“…Therefore, more emphasis is placed on improving the nature of the building material of the electrodes in order to increase ECH efficiency. A variety of materials have been developed; including: Raney Ni/Ni, Raney Ni/Hg pool, Pt/Pt, Pt/C, Rh/C [7], Pt/Pt and Pt/C with different concentrations of Pt [8]; different types of composite materials incorporated in reticulated vitreous carbon (RVC) like fractal nickel (Ni), crystalline nickel boride (Ni 2 B), and metallic nanoaggregates deposited on non-conductive powders like alumina, aluminum hydroxide, barium carbonate, and barium sulphate [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…Competitive reactions such as production of molecular hydrogen can also take place (steps 5 or 6). Thus, in the case of supported electrocatalysts, the matrix (inorganic powder), which supports the metallic nanoaggregates and which monitors the adsorption of unsaturated molecules, was non-conductive until now [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Effect of support conductivity of catalytic powder on electrocatalytic hydrogenation of phenol

et al. 2008

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Metallic nanoaggregates deposited on nonconductive oxides powders as catalysts have shown good efficiency in electrocatalytic hydrogenation (ECH). In this process, the polarization of the metallic nanoaggregates is very important. This polarization can be improved when the electrode material is conductive. Thus, the goal of this work was to study the effect of the conduction of the supported material on the ECH process. Tin dioxide was chosen as oxide because it can be obtained in non-conductive or conductive form by doping with fluorine. Palladium supported catalysts powders were prepared by the sol-gel method. These electrocatalysts were characterized by XRD, SEM, TGA/DSC, FTIR and electrical conductivity. The effects of temperature and time of calcination were also investigated. Comparison of nonconductive and conductive catalysts for ECH of phenol shows that conductive F-doped SnO 2 increases the rate of electrohydrogenation.

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Electrocatalytic hydrogenation of 4-phenoxyphenol on active powders highly dispersed in a reticulated vitreous carbon electrode

Cited by 51 publications

References 18 publications

Electrocatalytic dechlorination of atrazine

Electrocatalytic dechlorination of atrazine

Electrocatalytic hydrogenation of acetophenone using a Polymer Electrolyte Membrane Electrochemical Reactor

Effect of support conductivity of catalytic powder on electrocatalytic hydrogenation of phenol

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