Die elektrochemische Oxydation aromatischer Kohlenwasser‐stoffe und Phenole

Fichter, Fr.; Stocker, Rob

doi:10.1002/cber.19140470296

Cited by 23 publications

(21 citation statements)

References 22 publications

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“…The catholyte was analysed by vapour phase chromatography (vpc). The 100% mass balance obtained in the vast majority of experiments show that the sole process competing with hydrogenation (reactions [3] and [4]) was hydrogen evolution (reactions [6] and/or [7]). The current efficiency is then a measure of the relative importance of the two processes.…”

Section: Resultsmentioning

confidence: 99%

“…efficiency of the ECH process. The positive influence of boric acid could be related to an activation of the hydrogenation process (reactions [3] and [4]) and/or to an inhibition of hydrogen evolution (reactions [6] and/or [7]) due to a pH effect or to other effects which have to be investigated. At concentrations higher than 0.1 M, adsorption of boric acid could become important enough to slow down the hydrogenation process.…”

Section: Ech Of Phenanthrenementioning

confidence: 99%

“…and [4]) and the formation of molecular hydrogen from chemisorbed hydrogen (reactions [6] and/or [7], respectively the Heyrovskf and Tafel steps of the hydrogen evolution reaction (29)) (9,10,30).…”

Section: Introductionmentioning

confidence: 99%

“…For example, electrohydrogenations of interest in synthesis have been reported at various high area catalytic electrodes: nickel (1-3, 7, 9-11, 33-44), platinum (4,6,10,21,30,(44)(45)(46)(47)(48)(49)(50)(51), palladium (4,5,30,34,35,44,50), and rhodium (30,44). The functional groups electrohydrogenated include triple bonds (33,37,38), double bonds (4,7,34,37,41,42), aromatic rings (1,5,6,21,30,(45)(46)(47)(48), carbonyl groups (1,9,10,16,37,40,44,(49)(50)…”

Section: Introductionmentioning

confidence: 99%

“…The efficiency of electrocatalytic hydrogenations is determined by the competition between hydrogenation (reactions [3] and [4]) and hydrogen evolution (reactions [6] and/or [7]). The relative rates of these two processes are affected by the strength of the bond to be hydrogenated and by a number of factors which influence the adsorption of the organic substrate, the coverage of the electrode by chemisorbed hydrogen, and/or the activity of chemisorbed hydrogen such as the electrode material (17,30,44), the electrode surface and, for a given electrode, the current density (polarization of the electrode) (44), the concentration of the substrate (9)(10)(11)30), the pH of the solution (9,31), the organic cosolvent (30) and the presence of any molecule that can be adsorbed on the electrode (1 l), the supporting electrolyte, and the temperature (36).…”

Section: Introductionmentioning

confidence: 99%

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The electrocatalytic hydrogenation of fused poly cyclic aromatic compounds at Raney nickel electrodes: the influence of catalyst activation and electrolysis conditions

Robin¹,

Comtois²,

Martel³

et al. 1990

Can. J. Chem.

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. The electrocatalytic hydrogenation (ECH) of phenanthrene, anthracene, and naphthalene has been investigated under constant current at Raney nickel electrodes in a mixed aqueous organic medium. The influence of various parameters on the efficiency of the process determined by the current efficiency (a measure of the competition between hydrogenation and hydrogen evolution, the only two electrochemical processes occumng), the extent of hydrogenation (yield of octahydro-derivatives), and the conversion rate was studied with phenanthrene. The best conditions were ethylene glycol or propylene glycol as cosolvent containing between 1.5 to 5% of water, a neutral or slightly acidic medium containing boric acid (0.1 M) as buffer (initial pH of 2.6, final pH of 6.0-6.2), sodium chloride or tetrabutylamonium chloride as supporting electrolyte, a temperature of 80°C, and a current density of 42 to 84 m~/ c r n~. The most active electrodes (consisting of Raney Ni particles dispersed in a nickel matrix and surrounded by a layer of porous nickel) were obtained by leaching the dispersed alloy particles at 75°C for 7 h in 30% aqueous sodium hydroxide. The electrohydrogenation stopped at derivatives with a single aromatic ring, namely the octahydrophenanthrenes, octahydroanthracenes, and tetralin. In a non-buffered medium, tetrahydrophenanthrene could be obtained with selectivities of 80% or better.

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Section: Resultsmentioning

confidence: 99%

Section: Ech Of Phenanthrenementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The electrocatalytic hydrogenation of fused poly cyclic aromatic compounds at Raney nickel electrodes: the influence of catalyst activation and electrolysis conditions

Robin¹,

Comtois²,

Martel³

et al. 1990

Can. J. Chem.

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Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Jayan,

Thadathil,

Varghese

2023

Asian J Org Chem

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Conventional methods for hydrogenation of organic compounds generally use corrosive catalysts and reagents, along with extreme conditions like high temperatures and pressures. Quenching of corrosive materials does not deter its negative impact on the environment, nor is one safe when it comes to working with high temperature and pressure. Electrochemical hydrogenation has proven to be safe and green since most of the efficient reactions are conducted at ambient pressure and temperature, without or minimizing the use of toxic catalysts and corrosive reagents as compared to conventional methods. This review therefore presents the advances in electrochemical hydrogenation reactions of organic compounds, starting from simple aliphatic compounds to complex polyaromatics and heterocyclic aromatic compounds.

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Über m‐Nitrorhodan‐benzol und verwandte Verbindungen

Fichter¹,

Schonlau²

1915

Ber. Dtsch. Chem. Ges.

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Zur Vervollstiindigung der Untersuchungen uber die elektrolytische Reduktion von r?-Nitro-, 4-Nitround 2.4-Dinitro-rhodan-benzol yon Fr. F i c h t e r und T h e o d o r B e c k I) haben wir das m -N i t r or h o d a n -b e n z o l dargestellt und der elektrolytischen Reduktion uoterviorfen. 1~1 -N i t r o -r h od a nb e n z o I. . Die Uarstellung aus diazotierteni on-Nitroanilin durch Einwirkung vou Ithodanwasserstoff und Cuprorhodnnid verliiuit vie1 wen-iger glatt als die Gewinnung der beidcn Isomeren a); tlas untcr Stickstoftentwicklung sich nbsrhcidende untl niit &her aosgezogenc Kohprodukt ist ein dickfliissiges, dunkles 61, das eutweder cliirch Dcstillntioii unter vermindertem Drnck (Sdp. lS0" uiiter 13 Inm) oder durch Ubertreiben mit \Vassardampf untl hussalzen tles Destillates niit Kochsalz, xber in Iieitlen PRllen nicbt, ohne Verlust inFolge Zursetz ung gereinigt wirtl. Das /it -N i t r 0 -r h o d a nb e n z ol (Formel I) bildet weide verfilzte Nadeln; es laDt sich aus Alkohol oder noch vorteilhafter aus Petroliither, in dem es schwer lijslich ist, umkrystallisieren, ist leicht 163lich in Ather, Chloroform und Eisessig, fast unloslich in Wasser. und schmilzt bei 5G0. Der Schmelzpunkt liegt also bei.der meta-Verbindung erheblich niedriger als beim o-Nitro-rhodan-benzol (Scbmp. 132.5O) und beim p-Nitro-rhodan-benzol (Schmp. 133O), ein Verbalten. das auch bei anderen Schwefelverbindungen, z. B. bei den drei Tbiokresolen oder bei den drei Amino-phenyl-mercaptanen, beobachtet wird. C?H,O?NzS. Ber. N 15.59, S 17.80. Gef. 9 15.76, a 17.97. E 1 e k t r o 1 y t i s c h e R e tl u k t i o n d e s 111-N it r 0 -r h o d a nb e n z o 1 s. Reduziert man 4.5 g (== '/40 1101.) //i-Nitro-rhodan-benzol in 50 ccm etwa 7-fachnormaler alkoholischer Salzaure in einer Tonzelle a n einer kolbenformigen Bleiruhrerkathode mit der Stromdichte 0.044 bis 0.066 Amplqcm und mindestens dem Doppelten der nach der Gleichung: berechneten Strommenge bezw. mit einem so .groI3en StromiiberschuB, daB die anfanglich hellgelbe Flrrbe vollstiindig verschwindet, so laBt sich der Erfolg der beabsichtigten Reduktion durch das Auftreten der KO1. Ca Hc .SCN + 8 H = NH2. Cs Hc .SH + 2 HsO + HCN .~ B. 44, 3636 [1911]. *) 11. A. M i l l e r , Ztschr. f. Fnrben-Industrie 5, 357 [190(i].

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Die elektrochemische Oxydation aromatischer Kohlenwasser‐stoffe und Phenole

Cited by 23 publications

References 22 publications

The electrocatalytic hydrogenation of fused poly cyclic aromatic compounds at Raney nickel electrodes: the influence of catalyst activation and electrolysis conditions

The electrocatalytic hydrogenation of fused poly cyclic aromatic compounds at Raney nickel electrodes: the influence of catalyst activation and electrolysis conditions

Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Über m‐Nitrorhodan‐benzol und verwandte Verbindungen

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