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Ethanedioic Acid is an organic acid whose systematic name is ethanedioic acid and has the formula HO 2 C−CO 2 H, also written as (CO 2 H) 2.
Ethanedioic Acid is the simplest dicarboxylic acid.
Ethanedioic Acid is a white crystalline solid that forms a colorless solution in water.
CAS Number: 6153-56-6
EC Number: 205-634-3
IUPAC Name: 1,2-ethanedioic acid
Chemical Formula: C2H2O4
Other names: 144-62-7, Aktisal, Aquisal, Oxiric acid, Kyselina stavelova, Oxaalzuur, Oxalsaeure, Acidum oxalicum, Acide oxalique, Acido ossalico, Ethanedionic acid, NCI-C55209, Ethane-1,2-dioic acid, DTXSID0025816, NSC-62774, Oxalic acid, anhydrous, 9E7R5L6H31, DTXCID805816, CHEBI:16995, Acid, Oxalic, hydron;oxalate, 2-oxo-2-oxonioacetate, Oxalic acid (aqueous), Oxalate, Ferric, Oxalate, Sodium, Oxalate, Iron, Oxalate, Aluminum, Oxalate, Chromium, Oxalate, Disodium, Oxalate, Dilithium, Oxalate, Magnesium, Oxalate, Potassium, Oxalate, Diammonium, Oxalate, Monosodium, Oxalate, Dipotassium, Oxalate, Monoammonium, Oxalate, Monopotassium, RefChem:6477, Oxalate, Potassium Chromium, Oxalate, Monohydrogen Monopotassium, 205-634-3, Caswell No. 625, Oxaalzuur [Dutch], Oxalsaeure [German], Oxalic acid anhydrous, Acide oxalique [French], C2H2O4, Acido ossalico [Italian], Kyselina stavelova [Czech], NSC 62774, CCRIS 1454, EPA Pesticide Chemical Code 009601, HSDB 1100, AI3-26463, BRN 0385686, HOOCCOOH, Ultraplast Activate S 52, Oxalic acid /Ethanedioic acid, Oxalicacid, bis(5-azaspiro[2.5]octan-8-ol), bis((2R)-azetidine-2-carbonitrile), MFCD00002573, bis(1-(3-methyloxetan-3-yl)ethan-1-amine), C00209, Oxalic acid alpha polymorph, Oxalic acid diammonium salt, CAS-144-62-7, OXD, NSC115893, EINECS 205-634-3, Ethandisaeure, Ethanedionate, Ascorbic Acid EP Impurity E, Oxagel, Oxalic, DeerClean, UNII-9E7R5L6H31, 2dua, 2hwg, H2ox, Oxalic Acid Dianion, Oxalic acid solution, Anhydrous oxalic acid, Ethane-1,2-dioate, Oxalic acid, 98%, Oxalic acid (8CI), oxalic acid 2 hydrate, Oxalic acid 2-Hydrate, 1o4n, 1t5a, WLN: QVVQ, Ethanedioic acid (9CI), OXALIC ACID [MI], Oxalic acid dihydrate ACS, SCHEMBL776, bmse000106, EC 205-634-3, OXALIC ACID [HSDB], NCIOpen2_000770, NCIOpen2_001022, NCIOpen2_001042, NCIOpen2_001202, NCIOpen2_008831, OXALIC ACID [VANDF], OXALIC ACID, 99%, 4-02-00-01819 (Beilstein Handbook Reference), OXALIC ACID [WHO-DD], SCHEMBL812380, Oxalic acid, AR, >=99%, Oxalic acid, LR, >=98%, CHEMBL146755, orb1222692, orb1304742, orb3025233, Oxalic acid, 99% (Standard), Oxalic acid, analytical standard, SCHEMBL10471058, BDBM14674, HY-Y0262R, MeSH ID: D019815, HMS5086K21, HY-Y0262, NSC62774, STR01359, Tox21_202122, Tox21_303346, BBL003000, EBC-04354, NSC 76990, s9354, STK379550, AKOS005449445, CCG-266020, DB03902, FO26604, NSC 132055, NSC 151956, SB40938, SB40959, SB40985, T2O2680, Oxalic acid, ReagentPlus(R), >=99%, MSK000232-1000W, NCGC00249170-01, NCGC00257376-01, NCGC00259671-01, BP-21133
Ethanedioic Acids name derives from the fact that early researchers isolated Ethanedioic Acid from flowering plants of the genus Oxalis, commonly known as wood sorrel.
Ethanedioic Acid occurs naturally in many foods.
Excessive ingestion of Ethanedioic Acid or prolonged skin contact can be dangerous.
Ethanedioic Acid has much greater acid strength than acetic acid.
Ethanedioic Acid is a reducing agent and its conjugate base known as oxalate (C2O).
Ethanedioic Acid is a chelating agent for metal cations.
Typically, Ethanedioic Acid occurs as the dihydrate with the formula C2H204·2H20.
The preparation of Ethanedioic Acid (crab acid) salts from plants has been known since at least 1745, when Dutch botanist and physician Herman Boerhaave isolated wood sorrel salt, similar to the kraft process.
In 1773, François Pierre Savary of Friborg, Switzerland, isolated Ethanedioic Acid from the salt of sorrel.
In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman produced Ethanedioic Acid by reacting sugar with concentrated nitric acid; Scheele called the resulting acid socker-syra or såcker-syra (sugar acid).
By 1784, Scheele had shown that "sugar acid" obtained from natural sources and Ethanedioic Acid were the same.
In 1824, German chemist Friedrich Wöhler obtained Ethanedioic Acid by reacting cyanogen with ammonia in aqueous solution.
This experiment may represent the first synthesis of a natural product.
Ethanedioic Acid is mainly produced by the oxidation of carbohydrates or glucose using nitric acid or air in the presence of vanadium pentoxide.
Various precursors can be used, including glycolic acid and ethylene glycol.
A newer method requires oxidative carbonylation of alcohols to give diesters of Ethanedioic Acid:
4ROH + 4CO + O2 → 2(CO 2R )2 + 2H2O
These diesters are then hydrolyzed to Ethanedioic Acid.
About 120,000 tons are produced annually.
Historically, Ethanedioic Acid was only produced by using caustics such as sodium or potassium hydroxide on sawdust and then acidifying the oxalate with mineral acids such as sulfuric acid.
Ethanedioic Acid can also be formed by heating sodium formate in the presence of an alkaline catalyst.
Although readily available for purchase, Ethanedioic Acid can be prepared in the laboratory by oxidizing sucrose using nitric acid in the presence of a small amount of vanadium pentoxide as a catalyst.
The hydrated solid can be dehydrated by heat or by azeotropic distillation.
Electrocatalysis of a copper complex developed in the Netherlands helps reduce carbon dioxide to Ethanedioic Acid; In this conversion, carbon dioxide is used as a raw material to produce Ethanedioic Acid.
The pKa values of Ethanedioic Acid vary between 1.25-1.46 and 3.81-4.40 in the literature.
The 100th edition of the CRC, published in 2019, has values of 1.25 and 3.81.
Ethanedioic Acid is relatively strong compared to other carboxylic acids:
Ethanedioic Acid undergoes many of the reactions characteristic of other carboxylic acids.
Forms esters such as dimethyl oxalate ( mp 52.5 to 53.5 °C, 126.5 to 128.3 °F).
Ethanedioic Acid forms an acid chloride called oxalyl chloride.
Transition metal oxalate complexes are numerous, for example the drug oxaliplatin.
Ethanedioic Acid has been shown to reduce manganese dioxide MnO.
Ethanedioic Acid is an important reagent in lanthanide chemistry.
Hydrated lanthanide oxalates form readily in very strongly acidic solutions as a densely crystalline, easily filtered, largely uncontaminated form by non-lanthanide elements:
2 Ln 3+ + 3 C 2 Ö 4 H 2 → Ln 2 (C 2 Ö 4 ) 3 + 6 H +
Thermal decomposition of these oxalates yields oxides, the most widely marketed form of these elements.
Ethanedioic Acid and oxalates can be oxidized by permanganate in an autocatalytic reaction.
Ethanedioic Acid vapor decomposes into carbon dioxide CO at 125–175 °C formic acid HCOOH.
Photolysis with 237–313 nm UV light also produces carbon monoxide CO and water.
Evaporation of a solution of urea and Ethanedioic Acid at a molar ratio of 2:1 gives a solid crystalline compound H
2C2S4. [CO(NH2)2]2 It consists of stacked two-dimensional networks of neutral molecules held together by hydrogen bonds with oxygen atoms.
Early researchers isolated Ethanedioic Acid from wood sorrel (Oxalis).
Members of the spinach family and brassicas (cabbage, broccoli, brussels sprouts) are high in oxalates, as are the umbrella leaves of sorrel and parsley.
Plants of the genus Fenestraria produce optical fibers made of crystalline Ethanedioic Acid to transmit light to photosynthetic sites underground.
Carambola, also known as star fruit, contains Ethanedioic Acid as well as caramboxin.
Citrus juice contains small amounts of Ethanedioic Acid.
Citrus fruits produced in organic agriculture contain less Ethanedioic Acid than those produced in conventional agriculture.
Ethanedioic Acid has been suggested that the formation of naturally occurring calcium oxalate patinas in some limestone and marble statues and monuments is due to the chemical reaction of carbonate stone with Ethanedioic Acid secreted by lichen or other microorganisms.
Ethanedioic Acid is mainly produced by the oxidation of carbohydrates or glucose of vanadium pentoxides using nitric acid or air.
Three different titles are available, including glycolic acid and ethylene glycol.
A newer method requires oxidative carbonylation of alcohols to yield Ethanedioic Acid diesters.
Ethanedioic Acid is one of the known plant root organic acids.
Ethanedioic Acid, which is prepared with the chemical formula COOH2, is found in the rhubarb plant as the sought salt, in the so-called sorrel plant as the sodium salt, and in some procedural sap.
Ethanedioic Acid is a plant-produced organic acid.
Plants such as spinach, tomatoes, sorrel are in it.
Due to being acid, they form salts with an ion in the environment.
Ethanedioic Acid is a biologically living system and the Ethanedioic Acid entering the system forms salts with ions here.
Calcium oxalate, the most common salt, accumulates in the body, usually in the urinary system, especially in the kidneys, causing stone formation.
Some Ethanedioic Acids into the sugar syrup provided as lukewarm were run on the bees in the form of dripping at a temperature below 10 degrees Celsius when the bee was in clusters and the closed brood was present.
While the amount of sugar and water in the solution remains the same, the Ethanedioic Acid ratio may change according to the regional temperature.
In other words, the rates vary for the region.
Ethanedioic Acid makes it weaken once a year.
Ethanedioic Acid is recommended to apply this in colonies with less than three frames, depending on the amount of cluster temperature in colonies where bees are weak.
When heat is given to Ethanedioic Acid dihydrate, it becomes a solid amount of gas, that is, it is a struggle with its sublimation feature.
In order to make these, there are evaporation apparatuses inside the hive, oxalic is evaporated outside and sent into the hive with a pipe.
Ethanedioic Acid and its various oxalate derivatives are available from various natural sources.
Some of these resources are plants, vegetables, leaves, wood and coal etc.
Our body also produces it in our body through the metabolism process of glyoxylic acid or ascorbic acid.
Ethanedioic Acid is usually prepared with the aid of the oxidation of carbohydrates such as sucrose or glucose using nitric acid.
The catalysis in such reactions will be vanadium pentoxide.
Ethanedioic Acid can also be prepared by reacting alcohols with carbon monoxide in the presence of oxygen.
To give diesters of Ethanedioic Acid which are then hydrolyzed to give Ethanedioic Acid.
Ethanedioic Acid is an odorless, crystalline white solid compound.
Ethanedioic Acids density is 1.9 grams per mL.
Ethanedioic Acids melting point is 190°C.
Ethanedioic Acid is commonly found in the hydrate form, namely (COOH)2⋅2H2O.
Ethanedioic Acid dissolves easily in water and then forms a colorless and acidic solution in it.
Anhydrous Ethanedioic Acid is very hydrophilic and can absorb water.
Ethanedioic Acid is a strong acid by nature.
Ethanedioic Acid is the simplest dicarboxylic acid and can react like a typical carboxylic acid.
In this way, it can form acid chloride and ester derivatives.
Ethanedioic Acid is a good reducing agent and useful as a good chelating ligand for various metal cations.
Oxalic (ethanedioic) acid) is dibasic saturated carboxylic acid, a chemical substance in the form of colorless crystals, soluble in water, completely insoluble in diethyl and ethyl alcohol, insoluble in benzene, chloroform, petroleum ether.
This organic compound is found in many vegetables and herbs.
Ethanedioic Acid is the simplest dicarboxylic acid with the condensed formula HOOC-COOH and has a higher acidic strength than acetic acid.
Excessive consumption of Ethanedioic Acid can be dangerous.
Ethanedioic Acid is produced by the oxidation of carbohydrates.
Ethanedioic Acid can also be prepared in the laboratory by oxidation of sucrose in the presence of a catalyst such as nitric acid and vanadium pentoxide.
Ethanedioic Acid has a bipolymorphic structure and appears as a white crystalline solid that becomes a colorless solution when dissolved in water.
Ethanedioic Acid is a reducing agent and is used as a chelating agent with oxalate as its conjugate base.
Ethanedioic Acid is a dicarboxylic acid with the chemical formula C2H2O4.
Ethanedioic Acid is found in the cell sap of Oxalis and Rumex species as potassium and calcium salts.
In an aqueous solution, Ethanedioic Acid is a weak acid that can only partially ionize.
Ethanedioic Acid has two acidic protons.
Initial ionization yields a weak acid, HC2O4-, which will also ionize.
Ethanedioic Acid is one of the strongest of the organic acids and removes carbonic acid and many other acids from their salts.
Ethanedioic Acid is produced by the action of potash hydrate or nitric acid on most naturally occurring organic compounds.
Ethanedioic Acid is also called diprotic acid.
Ethanedioic Acid has a bipolymorphic structure and appears as a white crystalline solid that becomes a colorless solution when dissolved in water.
Ethanedioic Acid is a reducing agent and is used as a chelating agent with oxalate as its conjugate base.
Ethanedioic Acid is a dicarboxylic acid with the chemical formula C2H2O4.
Ethanedioic Acid is found in the cell sap of Oxalis and Rumex species as potassium and calcium salts.
In an aqueous solution, Ethanedioic Acid is a weak acid that can only partially ionize.
Ethanedioic Acid has two acidic protons.
Initial ionization yields a weak acid, HC2O4-, which will also ionize.
Ethanedioic Acid is one of the strongest of the organic acids and removes carbonic acid and many other acids from their salts.
Ethanedioic Acid is produced by the action of potash hydrate or nitric acid on most naturally occurring organic compounds.
Ethanedioic Acid is also called diprotic acid.
Ethanedioic Acid may be noted that in its anhydrous form, Ethanedioic Acid exists in two different polymorphs.
Hydrogen bonding occurs in the first polymorph of Ethanedioic Acid.
Due to this hydrogen bond, a chain-like structure develops at the intermolecular level.
The second polymorph of this compound is also subject to hydrogen bonding.
In this case, however, hydrogen bonding gives the compound a layer-like structure at the intermolecular level.
This compound is widely used in esterification reactions due to its two important properties.
The first feature that makes Ethanedioic Acid ideal for esterification reactions is its acidic nature.
The second and most important feature of Ethanedioic Acid is its hydrophilic structure.
Applications
Ethanedioic Acid and oxalates are used in the textile and leather industries.
metallurgical (for cleaning metals from scale, corrosion, rust, oxides);
chemical (in the production of paints, plastics, inks, pyrotechnics);
textiles (as a mordant when dyeing wool and silk);
microscopy (for bleaching sections);
agriculture (as insecticide);
pharmacology;
Wood work;
cosmetology (as part of whitening creams, masks and serums);
analytical chemistry (for precipitation of rare earth elements);
household chemicals (as the bleach and disinfectant component of detergents).
Also, the substance is used to form food additives and biologically active complexes (as a preservative).
The main applications of Ethanedioic Acid include cleaning or bleaching, especially to remove rust (iron complexing agent).
Ethanedioic Acid is an ingredient in some teeth whitening products.
Approximately 25% of the produced Ethanedioic Acid will be used as a mordant in dyeing processes.
Ethanedioic Acid is also used as a third reagent in bleaches, particularly in pulp, rust removal and other cleaning processes, baking soda, and silica analyzers.
Ethanedioic Acid is used by some beekeepers as a miticide against the parasitic varroa mite.
Dilute solutions of Ethanedioic Acid (0.05-0.15 M) can be used to remove iron from clay such as kaolinite to produce light colored ceramics.
Ethanedioic Acid, like many other acids, can be used to clean minerals.
Two such examples are quartz crystals and pyrite.
Ethanedioic Acid is sometimes used with or without sulfuric acid in aluminum anodizing.
Compared to sulfuric acid anodizing, the resulting coatings are thinner and exhibit lower surface roughness.
Ethanedioic Acid is also commonly used as a wood bleach; often in crystalline form, it is mixed with water to the appropriate dilution for use.
The two aqueous dihydrates of Ethanedioic Acid are used in alkalimetry and manganometry, rarely in the separation of earth metals and in the quantitative analysis of calcium.
Ethanedioic Acid and its antimony salts are used as mordant in textile dyeing in industry.
Ethanedioic Acid is used in the control of varroa in organic and conventional beekeeping in the food field.
Ethanedioic Acid used in the control of varroa in honey bees is Ethanedioic Acid hydrate with the chemical formula C2H2O4 - 2H2O.
Reliably obtained Ethanedioic Acid hydrate was used instead of products containing heavy metals and residues.
Ethanedioic Acid main applications include cleaning or bleaching (iron complex replication agent), especially for rust removal.
Bar Keepers Friend is an example of a household cleaner that contains Ethanedioic Acid.
The useless ferrous iron in rust removal agents is a residual salt formation in water known as the ferrioxalate ion.
Ethanedioic Acid is an important reagent in lanthanide chemistry.
Hydrated lanthanide oxalate forms readily in very strongly acidic dissolutions, in a densely crystallized, easily filtered state, mainly free from contamination by non-established elements.
Thermal degradation of this oxalate yields oxides, the most marketed form of these elements.
Ethanedioic Acid evaporated in sugar syrup or a 3.2% solution of Ethanedioic Acid is used by some beekeepers as a disease against parasitic groups.
Ethanedioic Acid is rubbed on the finished marble sculptures and the surface becomes sealed and separated.
Ethanedioic Acid is also used to clean iron and manganese deposits from quartz crystals.
Ethanedioic Acid is used as a bleach for wood to remove black spots caused by submersion zones.
Ethanedioic Acid is an organic compound with the formula C2H2O4, known for its versatile applications and outstanding results.
In a world where cleanliness and hygiene are of great importance, Ethanedioic Acid appears as an indispensable product that facilitates the most difficult cleaning tasks.
Ethanedioic Acid is a white, crystalline solid that is highly soluble in water, forming a colorless solution.
Ethanedioic Acids acidic nature enables it to effectively tackle a wide variety of cleaning, bleaching and rust removal applications.
Available in a variety of sizes and packaging options, Ethanedioic Acid is the perfect solution for users from a variety of industries, including homeowners, professional cleaners and industrial businesses.
Superior Cleaning Performance:
Ethanedioic Acid is a powerful cleaning agent that is highly effective in removing stubborn stains and marks caused by iron, rust, calcium and lime deposits.
Ethanedioic Acid can be used to clean various surfaces such as metal, wood and plastic, as well as industrial equipment, boats and other vehicles.
Rust Removal: The unique properties of Ethanedioic Acid make it a go-to solution for rust removal as it quickly dissolves rust and restores metal surfaces to their original condition.
Ideal for use on bicycles, motorcycles, tools and other metal items prone to rust.
Ethanedioic Acid is an excellent wood bleaching agent that helps brighten and rejuvenate worn or discolored wood surfaces.
Ethanedioic Acid works wonders on outdoor wood furniture, fences and patios, giving them a fresh and new look.
Textile and Leather Care:
Ethanedioic Acid is very effective in removing stains and discoloration on textile and leather products.
Ethanedioic Acid gently penetrates fabric fibers and leather surfaces, removing stains without damaging the material.
Environmentally friendly:
Ethanedioic Acid, an organic compound, is a sustainable and environmentally friendly alternative to harsh chemicals.
Ethanedioic Acid breaks down naturally over time and poses minimal risk to the environment.
