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Usage

Uses

Used in Chemical Industry:
1,1,2,2-Ethanetetracarboxylic acid is used as a chelating agent for its ability to form stable complexes with metal ions, which is crucial in various chemical processes and applications.
Used in Synthesis of Metal-Organic Frameworks (MOFs):
1,1,2,2-Ethanetetracarboxylic acid is used as a building block in the synthesis of MOFs, contributing to the creation of structures with high porosity and surface area, which are valuable for gas storage, catalysis, and drug delivery.
Used in Coordination Polymers:
1,1,2,2-Ethanetetracarboxylic acid is used as a ligand in the formation of coordination polymers, which are important materials in areas such as catalysis, magnetism, and luminescence.
Used in Pharmaceuticals:
1,1,2,2-Ethanetetracarboxylic acid has potential applications in pharmaceuticals, where its unique chemical properties may be leveraged for the development of new drugs or drug delivery systems.
Used in Catalysis:
1,1,2,2-Ethanetetracarboxylic acid is used in catalysis, where its ability to chelate metal ions can enhance the efficiency and selectivity of catalytic processes.
Used in Material Science:
1,1,2,2-Ethanetetracarboxylic acid is utilized in material science for the development of new materials with specific properties, such as high thermal stability or unique electronic characteristics.

Upstream product

• 141-82-2 malonic acid 

Downstream Products

• 3508-52-9 (+/-)-cis-tetrahydro-furo[3,4-c]furan-1,4-dione 
• 110-15-6 succinic acid 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

Ce4+-malonic acid reaction in the presence of O2. Reaction channels leading to tartronic and oxalic acid intermediates

The effect of oxygen on the Ce4+-malonic acid reaction was studied in a semibatch reactor. That effect is important for the Belousov-Zhabotinsky (BZ) chemical oscillator. The Ce4+ reagent inflow and consequently the rate of the reaction itself was controlled by a peristaltic pump. The reaction products were analyzed by HPLC. With this technique two major oxidation pathways were identified. One is significant at high Ce4+ inflow rates only; the product of this channel is tartronic acid. The other pathway leading to oxalic acid is active at all flow rates but dominant when the feed is slow. A great part of oxalic acid is oxidized further to carbon dioxide and water. A reaction mechanism compatible with these findings is presented. A key step of this mechanism is the fate of the peroxymalonyl radical which is the first intermediate for both channels. It is proposed that at high Ce4+ concentrations a fast reaction of this intermediate with Ce4+ leads to tartronic acid. At low Ce4+ concentrations, however, the peroxymalonyl radical has a longer lifetime to decarboxylate before reacting with a second Ce4+ and giving oxalic acid this way. Two mechanistic schemes proposed for this low Ce4+ channel were tested with further HPLC and kinetic experiments. From the high and low Ce4+ channels it is only the low one which plays a significant role in oxygen-perturbed BZ systems. The effect of that channel and its intermediates on BZ oscillators is discussed briefly.

Chemical mechanism of the radical feedback loop in the classical BZ reaction. Malonyl bromite and oxalic acid as flow-through intermediates

High-pressure liquid chromatography (HPLC) and measurements of the CO2 produced were performed in the induction period of the classical Belousov-Zhabotinsky (BZ) reaction (malonic acid-bromate-cerium catalyst in sulfuric acid medium). It was found that oxalic acid is a flow-through intermediate of the reaction. This was confirmed with an independent qualitative test with thiobarbituric acid. The concentration of oxalic acid grows in the induction period together with that of bromomalonic acid and dibromomalonic acid intermediates. It is known that there are two negative feedback loops in the BZ reaction: one is via bromide and the other via organic free radicals. Oxalic acid and also CO2 are products of this second loop where organic radicals react with BrO2 radicals. The induction period was chosen for the present experimental studies because the above radical-radical reactions are most intense during that time. Based on the experimental results mechanistic proposals are made for the radical feedback loop. A method to accumulate multivalent organic acids present in very low concentrations in the BZ reaction was also developed. Applying this and a thermal decomposition method ethenetetracarboxylic acid (EETA) was identified as an oxidation product of ethanetetracarboxylic acid (ETA).

HPLC studies on the photochemical formation of free radicals from malonic acid

In the Belousov Zhabotinsky reaction, malonyl radicals formed during the oxidation of malonic acid by Ce4+ play an important role in the mechanism of the negative feedback loop. In the past, we have analyzed the end products in the Ce4+-malonic acid reaction applying HPLC technique. For comparison, we generated malonyl radicals by UV irradiation of solutions of malonic acid and we identified the reaction products. Two of these are the same as in the Ce4+-malonic acid reaction, but some additional products are also formed. To explain our experimental results, a new reaction path is proposed where malonyl radicals and hydrogen atoms are the first intermediates in the photochemical decomposition of the malonic acid. Mechanistic differences between this photochemical decomposition and the Ce4+-malonic acid reaction are also discussed.

Stoichiometric Fingerprinting as an Aid in Understanding Complex Reactions: The Oxidation of Malonic Acid by Cerium(IV)

The stoichiometry of the Ce(IV) oxidation of malonic acid (MA) under aerobic and anaerobic conditions was investigated.The Ce(IV)/MA consumption ratio is found to vary from about 3.5 to 7, depending nonlinearly on the initial concentration of malonic acid as well as dissolved oxygen.The observed data can be quantitatively explained by a model that employs the characteristic structure of branching pathways in the overall mechanism and does not require the exact knowledge of the rate constants.It is concluded that a systematic study of consumption ratios provides an important aid for elucidating mechanisms of complex reactions.