Reactivity of carbon dioxide with quinones

Simpson, T. C.; Durand, Richard R.

doi:10.1016/0013-4686(90)85012-c

Cited by 39 publications

(38 citation statements)

References 19 publications

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“…Surprisingly, when AQDS is dissolved in an acidic electrolyte, regardless of chemical supplier (Combi-Chem, TCI, or Santa Cruz Biotechnology), we observed CO 2 gas evolution, determined via gas chromatography (Figure S8). Previous research on quinones has shown that CO 2 is bound as a 1:1 quinone adduct. − To determine if anthraquinone-CO 2 adducts were present in our AQDS powder, we performed a high concentration 13 C NMR experiment and found an additional peak present in the range for a carbonyl carbonate (Figure S9). In addition, acid titration of AQDS revealed an initial buffering of the solution at 9.73 followed by another plateau at 6.51.…”

Section: Resultsmentioning

confidence: 99%

Concentration-Dependent Dimerization of Anthraquinone Disulfonic Acid and Its Impact on Charge Storage

et al. 2017

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9,10-Anthraquinone-2,7-disulfonic acid (AQDS) is considered a benchmark active material for aqueous organic redox flow batteries. At low concentration, AQDS demonstrates two-electron transfer at near ideal electrochemical reversibility; however, at higher concentration, AQDS displays more complex behavior presumably due to the emergence of intermolecular reactions. Here, we systematically examine the electrochemical and physical properties of AQDS solutions using a suite of electrochemical, analytical, and spectroscopic techniques. Depending on the AQDS pretreatment, concentration, solution pH, and electrolyte composition, coupled chemical and electrochemical reactions lead to different charge storage capabilities. To elucidate the underlying cause of these differences, we performed various pretreatments of AQDS, examined chemical speciation by NMR, and investigated the corresponding electrochemical properties through cyclic voltammetry and bulk electrolysis. In all cases, reversible intermolecular dimerization was detected at solution concentrations greater than 10 mM. Moreover, we found that the charge state of the formed dimers was dependent on the AQDS pretreatment and the solution pH. Under acidic conditions, 1.5 electrons per molecule of AQDS were reversibly accessible, whereas under buffered mild-alkaline conditions, only one electron per molecule of AQDS was accessible. Because of insufficient proton concentration, AQDS did not cycle reversibly in unbuffered neutral electrolyte. Even when employing chemical oxidants during a chemical titration, charge storage of two electrons per molecule could not be realized. We hypothesize that adduct formation between AQDS and CO2, along with solution pH, play important roles in the charge accessibility.

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Section: Resultsmentioning

confidence: 99%

Concentration-Dependent Dimerization of Anthraquinone Disulfonic Acid and Its Impact on Charge Storage

et al. 2017

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“…Several classes of redox-active carriers have been investigated for eCCC applications including bipyridines, [7][8][9] thiols, 10 and quinones. [11][12][13][14][15][16][17][18] However, eCCC systems generally degrade from aerobic input streams because the reduced carriers react with oxygen (O2) resulting in unproductive carrier oxidation and the generation of superoxide, which can cause destructive radical reactions with the carrier, solvent, or electrolyte (red reaction in Scheme 1). 19,20 Since oxygen is present in flue gas and atmospheric CO2 sources, practical eCCC methods must overcome this limitation.…”

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confidence: 99%

Oxygen Stable Electrochemical CO2 Capture and Concentration through Alcohol Additives

Yang

Barlow

2021

Preprint

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Current methods for CO2 capture and concentration (CCC) are energy intensive due to their reliance on thermal cycles, which are intrinsically Carnot limited in efficiency. In contrast, electrochemically driven CCC (eCCC) can operate at much higher theoretical efficiencies. However, most reported systems are sensitive to O2, precluding their practical use. In order to achieve O2 stable eCCC, we pursued the development of molecular redox carriers with reduction potentials positive of the O2/O2- redox couple. Prior efforts to chemically modify redox carriers to operate at milder potentials resulted in a loss in CO2 binding. To overcome these limitations, we used common alcohols additives to anodically shift the reduction potential of a quinone redox carrier, 2,3,5,6-tetrachloro-p-benzoquinone (TCQ), by up to 350 mV, conferring O2 stability. Intermolecular hydrogen-bonding interactions to the dianion and CO2-bound forms of TCQ were correlated to alcohol pKa to identify ethanol as the optimal additive, as it imparts beneficial changes to both the reduction potential and CO2 binding constant, the two key properties for eCCC redox carriers. We demonstrate a full cycle of eCCC in aerobic simulated flue gas using TCQ and ethanol, two commercially available compounds. Based on the system properties, an estimated minimum of 21 kJ/mol is required to concentrate CO2 from 10% to 100%, or twice as efficient as state-of-the-art thermal amine capture systems and other reported redox carrier-based systems. Furthermore, this approach of using hydrogen-bond donor additives is general and can be used to tailor the redox properties of other quinones/alcohol combinations for specific CO2 capture applications.

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“…All O 1s spectra were normalized in area with respect to the integrated area of C 1s. Comparing the potential dependence of the O 1s spectrum for the Pt-free GC electrode (Figure ) with that of the Pt/GC electrode (Figure ), the broad peak from 532 to 534 eV can be mainly assigned to functional groups on the carbon, such as quinone, carboxyl, and carbonyl. − For the detection of the O 1s spectrum from the Pt particles, the use of the detection angle of 75° was quite beneficial. As shown in Figure S3, the intensity of the spectrum in the region from 531 to 529 eV (assigned to oxygen species adsorbed on Pt) increased with the detection angle of 75° compared with that at 0°.…”

Section: Resultsmentioning

confidence: 99%

Analysis of the Surface Oxidation Process on Pt Nanoparticles on a Glassy Carbon Electrode by Angle-Resolved, Grazing-Incidence X-ray Photoelectron Spectroscopy

Miyashita¹,

Wakisaka²,

Iiyama³

et al. 2017

Langmuir

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We have analyzed the surface oxidation process of Pt nanoparticles that were uniformly dispersed on a glassy carbon electrode (Pt/GC), which was adopted as a model of a practical Pt/C catalyst for fuel cells, in N-purged 0.1 M HF solution by using angle-resolved, grazing-incidence X-ray photoelectron spectroscopy combined with an electrochemical cell (EC-ARGIXPS). Positive shifts in the binding energies of Pt 4f spectra were clearly observed for the surface oxidation of Pt nanoparticles at potentials E > 0.7 V vs RHE, followed by a bulk oxidation of Pt to form Pt(II) at E > 1.1 V. Three types of oxygen species (HO, OH, and O) were identified in the O 1s spectra. It was found for the first time that the surface oxidation process of the Pt/GC electrode at E < ca. 0.8 V (OH formation) is similar to that of a Pt(111) single-crystal electrode, whereas that in the high potential region (O formation) resembles that of a Pt(110) surface or polycrystalline Pt film.

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Reactivity of carbon dioxide with quinones

Cited by 39 publications

References 19 publications

Concentration-Dependent Dimerization of Anthraquinone Disulfonic Acid and Its Impact on Charge Storage

Concentration-Dependent Dimerization of Anthraquinone Disulfonic Acid and Its Impact on Charge Storage

Oxygen Stable Electrochemical CO2 Capture and Concentration through Alcohol Additives

Analysis of the Surface Oxidation Process on Pt Nanoparticles on a Glassy Carbon Electrode by Angle-Resolved, Grazing-Incidence X-ray Photoelectron Spectroscopy

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