The Polarographic Reduction of Some Aryl Diketones

Philp, Robert H.; Flurry, R. L.; Day, R.

doi:10.1149/1.2426117

Cited by 70 publications

(14 citation statements)

References 17 publications

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“…In general, we expect molecules with conjugated carbon-carbon bonds and keto-and enolgroups that allow for the delocalization and rearrangement of the pi-electrons to undergo these redox transformations with extraordinary facility. 16 Typical organic redox couples are 1,2-benzoquinone-3,5-disulfonic acid (BQDS) and anthraquinone-2-sulfonic acid (AQS) (Eqs. 1 and 2).…”

Section: Factors Governing the Operation Of Orbatmentioning

confidence: 99%

An Inexpensive Aqueous Flow Battery for Large-Scale Electrical Energy Storage Based on Water-Soluble Organic Redox Couples

Yang

Hoober-Burkhardt

Wang

et al. 2014

J. Electrochem. Soc.

394

446

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We introduce a novel Organic Redox Flow Battery (ORBAT), for meeting the demanding requirements of cost, eco-friendliness, and durability for large-scale energy storage. ORBAT employs two different water-soluble organic redox couples on the positive and negative side of a flow battery. Redox couples such as quinones are particularly attractive for this application. No precious metal catalyst is needed because of the fast proton-coupled electron transfer processes. Furthermore, in acid media, the quinones exhibit good chemical stability. These properties render quinone-based redox couples very attractive for high-efficiency metal-free rechargeable batteries. We demonstrate the rechargeability of ORBAT with anthraquinone-2-sulfonic acid or anthraquinone-2,6-disulfonic acid on the negative side, and 1,2-dihydrobenzoquinone-3,5-disulfonic acid on the positive side. The ORBAT cell uses a membrane-electrode assembly configuration similar to that used in polymer electrolyte fuel cells. Such a battery can be charged and discharged multiple times at high faradaic efficiency without any noticeable degradation of performance. We show that solubility and mass transport properties of the reactants and products are paramount to achieving high current densities and high efficiency. The ORBAT configuration presents a unique opportunity for developing an inexpensive and sustainable metal-free rechargeable battery for large-scale electrical energy storage. The integration of electrical energy generated from solar and wind power into the grid is faced with the challenge of intermittent electricity output from these sources. This challenge can be effectively met by storing the electricity during times of excess production and releasing the electrical energy to the grid during times of peak demand. Rechargeable batteries are very attractive for energy storage because of their high energy efficiency and scalability.1-3 Since grid-scale electrical energy storage requires hundreds of gigawatt-hours to be stored, 4 the batteries for this application must be inexpensive, robust, safe and sustainable. None of today's mature battery technologies meet all of these requirements. The vanadium redox flow battery is one such battery technology that has reached an advanced level of development for grid-scale applications.5 However, the limited resources of vanadium, the high expense associated with the cell materials, and the toxicity hazard of using large quantities of soluble vanadium, have been the major challenges to the widespread adoption of the vanadium redox flow battery. 2,6,7 Aiming to overcome these disadvantages, we have demonstrated for the first time an aqueous redox flow battery that uses water-soluble organic redox couples at both electrodes that are metal-free. Such a battery has the potential to meet the demanding cost, durability, eco-friendliness, and sustainability requirements for grid-scale electrical energy storage. We have termed this battery an Organic Redox Flow Battery (ORBAT).In ORBAT, two different aqueous solutions...

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Section: Factors Governing the Operation Of Orbatmentioning

confidence: 99%

An Inexpensive Aqueous Flow Battery for Large-Scale Electrical Energy Storage Based on Water-Soluble Organic Redox Couples

Yang

Hoober-Burkhardt

Wang

et al. 2014

J. Electrochem. Soc.

394

446

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“…The electrochemical reduction of 1 has been reported in several papers (2)(3)(4)(5). In a waterethanol medium the polarograms of 1 show one, two, or three waves according to the p H (4).…”

Section: Polarography and Electrolysis Of 13-diphenyl-13-mentioning

confidence: 90%

“…propanediones and 1-phenyl-1,3-butanediones 2,2-Ditnetlzyl-1,3-cIi~~he11yl-l,3-~~ro~~aneclione, 3. and 2-Methyl-1,3-cliplzenyl-l,3-l~ropa1ze-cliorze, 2…”

Section: Polarography and Electrolysis Of 13-diphenyl-13-mentioning

confidence: 99%

Electrochemical reduction of 1,3-diketones in hydroorganic medium. Preparation of 1,2-cyclopropanediols

Armand¹,

Boulares²

1976

Can. J. Chem.

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JOSEPH ARMAND and LINE BOULARES. Can. J. Chem. 54, 1197Chem. 54, (1976. The electrochemical reduction of 1,3-diketones C6H5-CO-CRIR2-CO-R3 (R1 = H, CH3; RZ = CH3, CH2C6H5; R3 = CH3, C6H5) in an hydroorganic medium corresponds to a bielectronic process and leads to I,?-cyclopropanediols which, in most cases, are obtained in good yields. The polarographic results are presented and the mechanisms are discussed, JOSEPH ARMAND et LINE BOULARES. Can. J. Chem. 54, 1197 (1976). La r6duction 6lectrochimique des dicetones-1,3, C6H5-CO-CRIR2-CO-R3 (R1 = H, CH3; R2 = CH,, CH2C6H5 ; et R3 = CH,, C6H5), dans un milieu hydroorganique correspond k' un processus bi6Lectronique et conduit aux cyclopropanediols-l,2 qui sont obtenus dans la plupart des cas avec de bons rendements. On prisente les risultats polarographiques et on discute des micanismes.[Traduit par le journal]

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“…En premier lieu, on doit rejeter l'hypothese d'une hydrolyse de 12 en a-dicetone et la reduction de cette derniere en 17 par l'intermediaire de l'tne-diol (16) (21). Nous avons en effet verifie par ultraviolet la stabilitk de l'oxime (12b) dans les conditions operatoires utilisees.…”

Section: 2unclassified

Préparation, réduction chimique et électrochimique d'α-nitrostyrylcétones — synthèse d'hétérocycles azotés

Marcot¹,

Rabaron²,

Viel³

et al. 1981

Can. J. Chem.

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1224 (1981).La nitration par le peroxyde d'azote des styrylcetones conduit avec de bons rendements aux cetones a-nitroethyleniques correspondantes. Toutefois, lorsque des groupes methoxyles sont presents sur le noyau, la nitration s'effectue sur celui-ci.La reduction par LiAIH, des a-nitrostyrylcetones fournit les aminoalcools krythro et thrko rackmiques correspondants. Apres acylation puis cyclisation, on obtient une dihydroisoquinolCine ou une oxazoline-2.La reduction electrochimique de ces nitrostyrylcCtones engendre selectivement les a-cttoximes, elles-mkmes Clectroreductibles en a-aminocetones. Ces dernieres conduisent en milieu neutre, par condensation de deux molCcules, aux dihydro-2,5 pyrazines qui s'aromatisent e n pyrazines correspondantes. En milieu acide on isole un a-cetol.Un mecanisme de reduction faisant intervenir un iniermediaire enaminol est propose.BERNARD MARGOT, ALAIN RABARON, CLAUDE VIEL, CHRISTIAN BELLEC, STEPHANE DESWARTE, and PIERRE MAITTE. Can. J. Chem. 59, 1224 (1981).Nitration of styryl ketones with nitrogen peroxide leads to the correspondinga-nitroethylenic ketones in good yield. However, the presence of methoxy groups involves a nitration on the aromatic nucleus.LiAIH, reduction ofa-nitrostyrylketones yields the corresponding racemic erythro-and threo-aminoalcohols; after acylation and cyclisation a dihydro-quinoline or a 2-oxazoline is obtained.Electrochemical reduction of these nitrostyryl-ketones selectively provides the a-ketoximes, which are themselves reduced electrolytically to a-aminoketones, These latter compounds dimerise in neutral medium to dihydro-2,Spyrazines which aromatise to the corresponding pyrazines. In acid medium an a-ketol is obtained.A mechanism for the reduction is proposed implicating an enaminol intermediate. [Journal translation]

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The Polarographic Reduction of Some Aryl Diketones

Cited by 70 publications

References 17 publications

An Inexpensive Aqueous Flow Battery for Large-Scale Electrical Energy Storage Based on Water-Soluble Organic Redox Couples

An Inexpensive Aqueous Flow Battery for Large-Scale Electrical Energy Storage Based on Water-Soluble Organic Redox Couples

Electrochemical reduction of 1,3-diketones in hydroorganic medium. Preparation of 1,2-cyclopropanediols

Préparation, réduction chimique et électrochimique d'α-nitrostyrylcétones — synthèse d'hétérocycles azotés

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