Electrocatalytic hydrogenation of organic compounds using a nickel sacrificial anode

Santana, Diogo S.; Melo, Givaldo O.; Lima, Márcio V.F.; Daniel, Jorge R.R.; Areias, Madalena C. C.; Navarro, Marcelo

doi:10.1016/j.jelechem.2004.02.015

Cited by 35 publications

(21 citation statements)

References 39 publications

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“…A pre-electrolysis was started and a constant current density (J = 350 mA dm À2 ) was applied until consumption of 60 C [6]; nickel deposition was observed on the cathode. The substrate (0.002 mol), dissolved in 5 mL of the electrolytic solution (H 2 O/co-solvent (1:1)), was added to the electrochemical system and the electrolysis was carried out using a current density gradient, initially at 350 mA dm À2 [6,9]. After passage of the first half charge necessary to a theoretical hydrogenation of a C@C bond, the current density was decreased to 300 mA dm À2 (passing the second half charge), and successively to 250 (third half charge), 200 (fourth half charge) and 175 mA dm À2 .…”

Section: Methodsmentioning

confidence: 99%

“…The reduction of natural terpenones in their respective alcohols is of great interest in food, pharmaceutical, chemical and cosmetic industries [39,40]. (+)-Pulegone belongs to the group of terpenones (flavours) that can be hydrogenated, generating (À)-menthone (1), (+)-isomenthone (2), (+)-neomenthol (3), (À)-menthol (4), (+)-neoisomenthol (5) and (À)-isomenthol (6). Scheme 1 illustrates the hydrogenation stages.…”

Section: Ech-sa Of the (+)-Pulegonementioning

confidence: 99%

“…Ni, Pt, Pd and Rh catalysts were used in the electrocatalytic hydrogenation (ECH) of a large variety of organic compounds, such as aromatic and unsaturated hydrocarbons [5][6][7][8][9][10], glucose [11,12], diamines and aminonitriles [13], aldehydes [9], ketones [6], diketones [14], nicotine [15] and unsaturated esters [16,17].…”

Section: Introductionmentioning

confidence: 99%

“…The electrochemical reduction of water proceeds according to a well-known mechanism involving three steps: Volmer, Tafel and Heyrovsky. The predominant step is determined by the reaction conditions and may also be a mixed process like Volmer-Tafel or Tafel 1 illustrates the complementary steps: the adsorption of the substrate on the cathodic surface (4), hydrogenation (5) and desorption of the hydrogenated product from the electrode (6) [17,19]. However, there is a competition between the hydrogenation process (step 5), and the molecular hydrogen desorption, either by electrochemical step (3) and/or chemically (step 2).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

Lima

Menezes

Neto

et al. 2008

Journal of Electroanalytical Chemistry

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Section: Methodsmentioning

confidence: 99%

Section: Ech-sa Of the (+)-Pulegonementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

Lima

Menezes

Neto

et al. 2008

Journal of Electroanalytical Chemistry

Self Cite

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“…As the reductive desorption mechanism was a hydrogenation, it was hypothesized that on stainless steel the potential would be near or above stainless steels hydrogen evolution point, which are greater than those on gold (-1.2 V for pall Acusep membranes). The electrocatalytic hydrogenation of various types of organics was investigated on iron electrodes with deposited nickel, which is similar to stainless steel surfaces, and showed the hydrogenation of similar long chain conjugated olefins, between 30 to 60% [124]. The cell voltage of the system increased over time, indicating the incomplete HER resulting in minor fouling.…”

Section: Electrochemical Characterisationmentioning

confidence: 99%

Active anti-fouling and defouling of membranes using electrochemical methods

Mueller¹

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Industrial wastewater treatment from cattle slaughterhouses traditionally use dissolved air floatation (DAF) to remove the high organic content of fat, oil and grease (FOG) from wastewaters and recover them for producing other products, including tallow, gelatine and food additives. Dissolved air floatation presents several operating difficulties including the large size, high energy use and odour issues resulting in increased operation costs and decreased efficiency. Replacing a DAF unit with microfiltration or ultrafiltration membranes to recover FOG and protein could reduce operating costs and space, increase product quality through fractionation of various valuable nutrients and reduce or eliminate the smell. However, membranes have rarely been considered for such applications due to the high fouling propensity of the feed and the inability of conventional methods and membranes to effectively deal with this. One relatively unexplored fouling mitigation / cleaning technique involves electrochemistry to either prevent fouling through charge repulsion or remove fouling via electrochemical reactions. The key target of this work therefore is to investigate the suitability of conductive stainless steel membranes for filtration of a FOG / protein stream utilising electrochemical cleaning methods.In theory, in-situ membrane antifouling (the inhibition of fouling) and defouling (the removal of fouling) can be achieved by varying the applied potential on an electrochemically active and conductive membrane. Oils and organic matter tend to carry a negative charge in aqueous solutions at neutral pH and increase in negative charge density with alkali pH. For antifouling, maintaining a negative charge on a membrane surface repulses negatively charged molecules in solution, which in turn, both inhibits adsorption and/or induces them to migrate away from the electrode / membrane surface. The major finding here was that reductive potentials, at or below the hydrogen evolution reaction were successful in minimising fouling on an electrode and also succeeded in mitigating fouling by 67% in a full membrane setup. There is an ideal operating window for negative potential to achieve antifouling, enough to induce repulsion but not negative enough to initiate redox reactions at the membrane surface between -0.4 V to -1.2 V. However, to achieve the best performance antifouling probably requires constant operation at potentials negative enough to initiate the hydrogen evolution reaction or reductive desorption. The commercial implications of this are likely to be power requirements, on the order of 10W/m 2 . Or to put it another way, this translates to an energy requirement of 1 kWh/kL of permeate flux through the membrane, which for treating a stick water stream in typical abattoir.Defouling by contrast uses electrochemical reactions to either oxidise the organic foulants or produce gas bubbles which can lift off foulants through physical shear forces. The major finding iii here is that, when operated as anodic electrodes, me...

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Electrochemical‐Induced Hydrogenation of Electron‐Deficient Internal Olefins and Alkynes with CH₃OH as Hydrogen Donor

et al. 2021

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Efficient hydrogenation of electron‐deficient internal olefins and alkynes access to saturate ketone with CH3OH as a single hydrogen donor under electrochemical conditions has been successfully developed. This hydrogenation strategy can be used to convert electron‐deficient internal olefins and alkynes to saturate ketone under electrochemical conditions with exogenous‐reductant and a metal catalyst. Mechanistic studies reveal that radical hydrogenation was involved in this transformation. Notably, various electron‐deficient internal olefins and alkynes could be tolerated in such an electrochemical hydrogenation synthetic strategy and can be easily scaled up with good efficiency.

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Electrocatalytic hydrogenation of organic compounds using a nickel sacrificial anode

Cited by 35 publications

References 39 publications

A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

Active anti-fouling and defouling of membranes using electrochemical methods

Electrochemical‐Induced Hydrogenation of Electron‐Deficient Internal Olefins and Alkynes with CH₃OH as Hydrogen Donor

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Electrocatalytic hydrogenation of organic compounds using a nickel sacrificial anode

Cited by 35 publications

References 39 publications

A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

A factorial design analysis of (+)-pulegone electrocatalytic hydrogenation

Active anti-fouling and defouling of membranes using electrochemical methods

Electrochemical‐Induced Hydrogenation of Electron‐Deficient Internal Olefins and Alkynes with CH3OH as Hydrogen Donor

Contact Info

Product

Resources

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Electrochemical‐Induced Hydrogenation of Electron‐Deficient Internal Olefins and Alkynes with CH₃OH as Hydrogen Donor