Browse
Submit Data
Databases
API
Help

Dataset Information

24 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

2-Methoxyhydroquinone from Vanillin for Aqueous Redox-Flow Batteries.

ABSTRACT: We show the synthesis of a redox-active quinone, 2-methoxy-1,4-hydroquinone (MHQ), from a bio-based feedstock and its suitability as electrolyte in aqueous redox flow batteries. We identified semiquinone intermediates at insufficiently low pH and quinoid radicals as responsible for decomposition of MHQ under electrochemical conditions. Both can be avoided and/or stabilized, respectively, using H₃ PO₄ electrolyte, allowing for reversible cycling in a redox flow battery for hundreds of cycles.

SUBMITTER: Schlemmer W

PROVIDER: S-EPMC7891622 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

2-Methoxyhydroquinone from Vanillin for Aqueous Redox-Flow Batteries.

Schlemmer Werner W Nothdurft Philipp P Petzold Alina A Riess Gisbert G Frühwirt Philipp P Schmallegger Max M Gescheidt-Demner Georg G Fischer Roland R Freunberger Stefan A SA Kern Wolfgang W Spirk Stefan S

Angewandte Chemie (International ed. in English) 20201008 51

We show the synthesis of a redox-active quinone, 2-methoxy-1,4-hydroquinone (MHQ), from a bio-based feedstock and its suitability as electrolyte in aqueous redox flow batteries. We identified semiquinone intermediates at insufficiently low pH and quinoid radicals as responsible for decomposition of MHQ under electrochemical conditions. Both can be avoided and/or stabilized, respectively, using H<sub>3</sub> PO<sub>4</sub> electrolyte, allowing for reversible cycling in a redox flow battery for h ...[more]

PMID: 32815619

Similar Datasets

Organic Redox Species in Aqueous Flow Batteries: Redox Potentials, Chemical Stability and Solubility.

Project description:Organic molecules are currently investigated as redox species for aqueous low-cost redox flow batteries (RFBs). The envisioned features of using organic redox species are low cost and increased flexibility with respect to tailoring redox potential and solubility from molecular engineering of side groups on the organic redox-active species. In this paper 33, mainly quinone-based, compounds are studied experimentially in terms of pH dependent redox potential, solubility and stability, combined with single cell battery RFB tests on selected redox pairs. Data shows that both the solubility and redox potential are determined by the position of the side groups and only to a small extent by the number of side groups. Additionally, the chemical stability and possible degradation mechanisms leading to capacity loss over time are discussed. The main challenge for the development of all-organic RFBs is to identify a redox pair for the positive side with sufficiently high stability and redox potential that enables battery cell potentials above 1 V.

| S-EPMC5155426 | biostudies-literature

Benzidine Derivatives as Electroactive Materials for Aqueous Organic Redox Flow Batteries.

Project description:This paper presents a theoretical and experimental evaluation of benzidine derivatives as electroactive molecules for organic redox flow batteries. These redox indicators are novel electroactive materials that can perform multielectron transfers in aqueous media. We performed the synthesis, electrochemical characterization, and theoretical study of the dimer of sodium 4-diphenylamine sulfonate, a benzidine derivative with high water solubility properties. The Pourbaix diagram of the dimer shows a bielectronic process at highly acidic pH values (≤ 0.9) and two single-electron transfers in a pH range from 0 to 9. The dimer was prepared in situ and tested on a neutral electrochemical flow cell as a stability diagnostic. To improve cell performance, we calculate and calibrate, with experimental data, the Pourbaix diagrams of benzidine derivatives using different substitution patterns and functional groups. A screening process allowed the selection of those derivatives with a bielectronic process in the entire pH window or at acidic/neutral pH values. Given the redox potential difference, they can be potential catholytes or anolytes in a flow cell. The couples formed with the final candidates can generate a theoretical cell voltage of 0.60 V at pH 0 and up to 0.68 V at pH 7. These candidate molecules could be viable as electroactive materials for a full-organic redox flow battery.

| S-EPMC10500672 | biostudies-literature

Sulfonated tryptanthrin anolyte increases performance in pH neutral aqueous redox flow batteries.

Project description:Aqueous organic redox flow batteries (AORFBs) hold great promise as low-cost, environmentally friendly and safe alternative energy storage media. Here we present aqueous organometallic and all-organic active materials for RFBs with a water-soluble active material, sulfonated tryptanthrin (TRYP-SO3H), working at a neutral pH and showing long-term stability. Electrochemical measurements show that TRYP-SO3H displays reversible peaks at neutral pH values, allowing its use as an anolyte combined with potassium ferrocyanide or 4,5-dihydroxy-1,3-benzenedisulfonic acid disodium salt monohydrate as catholytes. Single cell tests show reproducible charge-discharge cycles for both catholytes, with significantly improved results for the aqueous all-organic RFB reaching high cell voltage (0.94 V) and high energy efficiencies, stabilized during at least 50 working cycles.

| S-EPMC9814137 | biostudies-literature

Substituent Pattern Effects on the Redox Potentials of Quinone-Based Active Materials for Aqueous Redox Flow Batteries.

Project description:Quinone-based, aqueous redox flow batteries are a promising technology for large-scale, low-cost energy storage. To understand the influence of substituent and substituent pattern effects of quinone-based derivatives on the redox potential, a screening study was performed that included benzoquinone, naphtaquinone, and anthraquinone derivatives. The order of substituent influence is -OH>-Me/-OMe for decreasing the redox potential and -F<-SO3 - <-CN, -NO2 for increasing the redox potential, which is in agreement with general expectations. We found that the consideration of resonance and inductive effects design strategies of redox-active materials can be extended by the ability of intramolecular hydrogen bond formation, steric hindrance, and energetic differences of conformers for oxidized and reduced species. Due to the complexity and overlap of these effects, theoretical screening studies can provide guidance for the design of new molecular materials. In addition to the redox potential, other parameters such as stability, solubility, and kinetic rate constant or synthetic accessibility are crucial to consider.

| S-EPMC7702104 | biostudies-literature

Development of efficient aqueous organic redox flow batteries using ion-sieving sulfonated polymer membranes.

Project description:Redox flow batteries using aqueous organic-based electrolytes are promising candidates for developing cost-effective grid-scale energy storage devices. However, a significant drawback of these batteries is the cross-mixing of active species through the membrane, which causes battery performance degradation. To overcome this issue, here we report size-selective ion-exchange membranes prepared by sulfonation of a spirobifluorene-based microporous polymer and demonstrate their efficient ion sieving functions in flow batteries. The spirobifluorene unit allows control over the degree of sulfonation to optimize the transport of cations, whilst the microporous structure inhibits the crossover of organic molecules via molecular sieving. Furthermore, the enhanced membrane selectivity mitigates the crossover-induced capacity decay whilst maintaining good ionic conductivity for aqueous electrolyte solution at pH 9, where the redox-active organic molecules show long-term stability. We also prove the boosting effect of the membranes on the energy efficiency and peak power density of the aqueous redox flow battery, which shows stable operation for about 120 h (i.e., 2100 charge-discharge cycles at 100 mA cm-2) in a laboratory-scale cell.

| S-EPMC9177609 | biostudies-literature

Charge-Dependent Crossover in Aqueous Organic Redox Flow Batteries Revealed Using Online NMR Spectroscopy.

Project description:Aqueous organic redox-flow batteries (AORFBs) are promising candidates for low-cost grid-level energy storage. However, their wide-scale deployment is limited by crossover of redox-active material through the separator membrane, which causes capacity decay. Traditional membrane permeability measurements do not capture all contributions to crossover in working batteries, including migration and changes in ion size and charge. Here we present a new method for characterizing crossover in operating AORFBs using online 1H NMR spectroscopy. By the introduction of a separate pump to decouple NMR and battery flow rates, this method opens a route to quantitative time-resolved monitoring of redox-flow batteries under real operating conditions. In this proof-of-concept study of a 2,6-dihydroxyanthraquinone (2,6-DHAQ)/ferrocyanide model system, we observed a doubling of the 2,6-DHAQ crossover during battery charging, which we attribute to migration effects. This new membrane testing methodology will advance our understanding of crossover and accelerate the development of improved redox-flow batteries.

| S-EPMC10860123 | biostudies-literature

Phenyl Acrylate-Based Cross-Linked Anion Exchange Membranes for Non-aqueous Redox Flow Batteries

Project description: Not available

| S-EPMC10510496 | biostudies-literature

Molecular engineering of dihydroxyanthraquinone-based electrolytes for high-capacity aqueous organic redox flow batteries.

Project description:Aqueous organic redox flow batteries (AORFBs) are a promising technology for large-scale electricity energy storage to realize efficient utilization of intermittent renewable energy. In particular, organic molecules are a class of metal-free compounds that consist of earth-abundant elements with good synthetic tunability, electrochemical reversibility and reaction rates. However, the short cycle lifetime and low capacity of AORFBs act as stumbling blocks for their practical deployment. To circumvent these issues, here, we report molecular engineered dihydroxyanthraquinone (DHAQ)-based alkaline electrolytes. Via computational studies and operando measurements, we initially demonstrate the presence of a hydrogen bond-mediated degradation mechanism of DHAQ molecules during electrochemical reactions. Afterwards, we apply a molecular engineering strategy based on redox-active polymers to develop capacity-boosting composite electrolytes. Indeed, by coupling a 1,5-DHAQ/poly(anthraquinonyl sulfide)/carbon black anolyte and a [Fe(CN)6]3-/4- alkaline catholyte, we report an AORFB capable of delivering a stable cell discharge capacity of about 573 mAh at 20 mA/cm2 after 1100 h of cycling and an average cell discharge voltage of about 0.89 V at the same current density.

| S-EPMC9374662 | biostudies-literature

Estimation of activity coefficients for aqueous organic redox flow batteries: Theoretical basis and equations.

Project description:The field of aqueous organic redox flow batteries (AORFBs) has been developing fast in recent years, and many chemistries are starting to emerge as serious contenders for grid-scale storage. The industrial development of these systems would greatly benefit from accurate physics-based models, allowing to optimize battery operation and design. Many authors in the field of flow battery modeling have brought evidence that the dilute solution hypothesis (the assumption that aqueous electrolytes behave ideally) does not hold for these systems and that calculating cell voltage or chemical potentials through concentrations rather than activities, while serviceable, may become insufficient when greater accuracy is required. This article aims to provide the theoretical basis for calculating activity coefficients of aqueous organic electrolytes used in AORFBs to provide tools to predict the concentrated behavior of aqueous electrolytes, thereby improving the accuracy of physics-based models for flow batteries.

| S-EPMC9465363 | biostudies-literature

Polyoxovanadate-alkoxide clusters as multi-electron charge carriers for symmetric non-aqueous redox flow batteries.

Project description:Non-aqueous redox flow batteries have emerged as promising systems for large-capacity, reversible energy storage, capable of meeting the variable demands of the electrical grid. Here, we investigate the potential for a series of Lindqvist polyoxovanadate-alkoxide (POV-alkoxide) clusters, [V6O7(OR)12] (R = CH3, C2H5), to serve as the electroactive species for a symmetric, non-aqueous redox flow battery. We demonstrate that the physical and electrochemical properties of these POV-alkoxides make them suitable for applications in redox flow batteries, as well as the ability for ligand modification at the bridging alkoxide moieties to yield significant improvements in cluster stability during charge-discharge cycling. Indeed, the metal-oxide core remains intact upon deep charge-discharge cycling, enabling extremely high coulombic efficiencies (∼97%) with minimal overpotential losses (∼0.3 V). Furthermore, the bulky POV-alkoxide demonstrates significant resistance to deleterious crossover, which will lead to improved lifetime and efficiency in a redox flow battery.

| S-EPMC5890794 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data