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ETHANEDIOIC ACID

ETHANEDIOIC ACID = OXALIC ACID


CAS Number: 144-62-7 / 6153-56-6
EC Number: 205-634-3
MDL number: MFCD00002573
Molecular Formula: C2H2O4 or (COOH)2 or HOOCCOOH


Ethanedioic acid is an organic acid with the IUPAC name ethanedioic acid and formula HO2C−CO2H. 
Ethanedioic acid is the simplest dicarboxylic acid. 
Ethanedioic acid is a white crystalline solid that forms a colorless solution in water. 
Ethanedioic acid's name comes from the fact that early investigators isolated Ethanedioic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels. 


Ethanedioic acid occurs naturally in many foods. 
Ethanedioic acid has much greater acid strength than acetic acid.
Ethanedioic acid is a reducing agent and Ethanedioic acid's conjugate base, known as oxalate (C2O2−4), is a chelating agent for metal cations. 
Typically, Ethanedioic acid occurs as the dihydrate with the formula C2H2O4•2H2O.


Ethanedioic acid is an odorless white solid. 
Sinks and mixes with water. 
Ethanedioic acid is an alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2. 
Ethanedioic acid has a role as a human metabolite, a plant metabolite and an algal metabolite. 
Ethanedioic acid is a conjugate acid of an oxalate(1-) and an oxalate.


Ethanedioic acid, also called ethanedioic acid, a colourless, crystalline, toxic organic compound belonging to the family of carboxylic acids. 
The formula of Ethanedioic acid is (C2H2O4); Ethanedioic acid's usual form is that of the crystalline hydrate, (COOH)2•2H2O. 
Ethanedioic acid known as a constituent of wood sorrel as early as the 17th century, Ethanedioic acid was first prepared synthetically in 1776. 


Ethanedioic acid is manufactured by heating sodium formate in the presence of an alkali catalyst, by oxidizing carbohydrates with nitric acid, by heating sawdust with caustic alkalies, or by fermentation of sugar solutions in the presence of certain molds.
Ethanedioic acid is an organic, hydrophilic, toxic reducing agent; the simplest dicarboxylic acid. 
Ethanedioic acid is a strong dicarboxylic acid. 
Ethanedioic acid is the simplest dicarboxylic acid and has two hydrogen atoms, two carbon atoms, and four oxygen atoms. 


Ethanedioic acid’s molar mass of 90.03 g/mol and has two carboxylic acid (COOH) groups.
Ethanedioic acid is a naturally occurring organic acid in plants, vegetables, etc. 
Apart from that, Ethanedioic acid is also produced in the body by metabolism of ascorbic acid or glyoxylic acid. 
Ethanedioic acid is a colorless crystalline solid that dissolves in water to give colorless solutions.
Ethanedioic acid is mainly produced by the oxidation of carbohydrates or glucose in the presence of vanadium pentoxide using nitric acid or air. 


Various precursors can be used, including glycolic acid and ethylene glycol. 
A newer method requires oxidative carbonylation of alcohols to yield Ethanedioic acid diesters.
4 ROH + 4 CO + 02 → 2 (CO2R) 2 + 2H20
Ethanedioic acid is one of the most well-known plant-derived organic acids. 

Ethanedioic acid, which is shown with the chemical formula COOH2, is found in nature as a calcium salt in the rhubarb plant, in the plant called sorrel as the sodium salt, and in the sap of some plants. 
Most plant sources contain this organic acid. 
Plants such as spinach, tomatoes, sorrel are in it. 
Because Ethanedioic acid is an acid, Ethanedioic acid can form a salt with an ion in the environment. 


Ethanedioic acid, which enters a biologically living system and body, forms salts with ions there. 
Calcium oxalate, which is the most common salt, accumulates in the body, usually in the urinary system, especially in the kidneys, causing stone formation.
Ethanedioic acid is applied by mixing some Ethanedioic acid into the sugar syrup prepared with warm water and dripping on the bees when the bee is in clusters and there are no closed brood at an outdoor temperature below 10 degrees. 


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 each region. 
Ethanedioic acid is recommended to apply this once a year. 


Ethanedioic acid is recommended not to apply this in colonies with less than three frames, due to the deterioration of the cluster temperature balance in colonies where bees are weak.
When heat is applied on Ethanedioic acid dihydrate, Ethanedioic acid is a struggle with its sublimation property from solid state to gas state. 
In order to make these, there are evaporation apparatuses inside the hive, and Ethanedioic acid is evaporated outside and sent into the hive through a pipe.


Ethanedioic acid is an organic compound. 
Ethanedioic acid is a white crystalline solid that forms a colorless solution in water. 
Ethanedioic acid is an organic compound with the formula C2H2O4. 
Ethanedioic acid is a white crystalline solid that forms a colourless solution in water. 


Ethanedioic acid used in the control of varroa in honey bees is Ethanedioic acid hydrate with the chemical formula C2H2O4 - 2H2O. 
Ethanedioic acid is an important reagent in lanthanide chemistry. 
Hydrated lanthanide oxalate forms readily in very strongly acidic solutions, in a densely crystallized, easily leached state, primarily free of contamination by non-lanthanide elements. 
Thermal decomposition of this oxalate yields oxides, the most marketed form of these elements.


Ethanedioic acid dihydrate is a reducing agent. 
Ethanedioic acid, also known as Ethanedioic acid is a diprotic acid, which means it can give away 2 protons (hydrogen ions) to a base. 
Ethanedioic acid dihydrate has been evaluated as a treatment for reducing populations of naturally occurring microorganisms. 
Ethanedioic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. 


These are organic compounds containing exactly two carboxylic acid groups.
Ethanedioic acid is colorless, odorless powder or granular solid.
Ethanedioic acid is a strong dicarboxylic acid occurring in many plants and vegetables. 
Ethanedioic acid is produced in the body by metabolism of glyoxylic acid or ascorbic acid. 


Ethanedioic acid is not metabolized but excreted in the urine. 
Ethanedioic acid is used as an analytical reagent and general reducing agent (Pubchem). 
Ethanedioic acid (IUPAC name: oxalic acid, formula H2C2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). 
Because of the joining of two carboxyl groups, this is one of the strongest organic acids. 


Ethanedioic acid is also a reducing agent. 
The anions of Ethanedioic acid as well as Ethanedioic acid's salts and esters are known as oxalates. 
Bodily Ethanedioic acid may also be synthesized via the metabolism of either glyoxylic acid or unused ascorbic acid (vitamin C), which is a serious health consideration for long term megadosers of vitamin C supplements. 


80% of kidney stones are formed from calcium oxalate. 
Some Aspergillus species produce Ethanedioic acid, which reacts with blood or tissue calcium to precipitate calcium oxalate. 
Ethanedioic acid is an odorless white solid chemical. 
Ethanedioic acid can be found in powder or granule form. 


Ethanedioic acid has a minimum purity of 98%. 
Ethanedioic acid is an organic compound with the formula H2C2O4 also known as Ethanedioic acid. 
Ethanedioic acid is a colourless crystalline solid that dissolves in water to give colorless acidic solutions. 
Ethanedioic acid is classified as a dicarboxylic acid. 


Ethanedioic acid is the chemical compound with the formula H2C2O4. 
This dicarboxylic acid, Ethanedioic acid, is better described with the formula HO2CCO2H. 
Ethanedioic acidis a relatively strong organic acid, being about 10,000 times stronger than acetic acid. 
The di-anion, known as oxalate, is also a reducing agent as well as a ligand in coordination chemistry. 


Many metal ions form insoluble precipitates with oxalate, a prominent example being calcium oxalate, which is the primary constituent of the most common kind of kidney stone.
Although it can be readily purchased, 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. 
On a large scale, sodium oxalate is manufactured by absorbing carbon monoxide under pressure in hot sodium hydroxide.


Typically Ethanedioic acid is obtained as the dihydrate. 
This solid can be dehydrated with heat or by azeotropic distillation. 
Anhydrous Ethanedioic acid exists as two polymorphs; in one the hydrogen-bonding results in a chain-like structure whereas the hydrogen bonding pattern in the other form defines a sheet-like structure.


Ethanedioic acid is an organic compound. 
Ethanedioic acid is a white crystalline solid that forms a colorless solution in water. 
Leaves of the tea plant (Camellia sinensis) contain among the greatest measured concentrations of Ethanedioic acid relative to other plants. 
However the infusion beverage typically contains only low to moderate amounts of Ethanedioic acid per serving, due to the small mass of leaves used for brewing.


Ethanedioic acid Dihydrate is the simplest dicarboxylic acid and appears as a white solid powder. 
Ethanedioic acid is soluble in water and becomes colorless when dissolved in water.
Ethanedioic acid (CAS 6153-56-6), is an organic compound also known as ethanedioic acid. 
Ethanedioic acid forms a clear, colorless solution in water and has the chemical formula C2H2O4. 


Ethanedioic acid is also known as Ethanedioic acid and Ethanedioic acid is a colorless, crystalline, toxic organic  compound. 
The chemical formulation of Ethanedioic acid is C2H2O4 belonging to the family of carboxylic acids and the Ethanedioic acid's condensed  formula is HOOCCOOH, reflecting Ethanedioic acid's classification as the simplest dicarboxylic  acid. 


Ethanedioic acid is one of the  strongest organic acids with pKa values of 1.3 and 4.3 and is a widely  occurring natural product of animals, plants and other organisms. 
Ethanedioic acid was first reported to be  synthesized in 1776 and is known as a constituent of wood sorrel as early as  the 17th century.
Ethanedioic acid, which is otherwise known as ethanedioic acid, is a colorless, crystalline, organic compound from the dicarboxylic acid family found in many plants. 


The chemical formula of Ethanedioic acid is given by C2H2O4. 
Under standard temperature and pressure (STP) conditions, Ethanedioic acid is present as a white crystalline solid. 
When dissolved in water, Ethanedioic acid is known to form a colorless solution. 
Ethanedioic acid is considered to be the simplest dicarboxylic acid because Ethanedioic acid is composed of two carboxyl groups.  


-Ethanedioic acid occurs naturally in many plants like the following:
*Fruits
*Cocoa
*Leafy green vegetables
*Nuts
*Seeds
*Spinach
*Sweet potatoes
*Star fruit
*Turnip greens
*Endive
*Swiss chard
*Beet greens


When Ethanedioic acid mixes with other minerals, it forms oxalate. 
People regularly use the two terms interchangeably to refer to the same thing.  
Your body produces oxalate and also gets it from food sources. 
Vitamin C changes to oxalate when your body processes it.


The molecular weight of anhydrous Ethanedioic acid is  90.034 grams per mole. 
The molecular weight of the dihydrate of Ethanedioic acid is equivalent to 126.065 grams per mole.
Under standard conditions, Ethanedioic acid exists as an essentially crystalline white solid and is odorless. 
The density of anhydrous Ethanedioic acid is  1.90 grams / cubic centimeter. 
The density of Ethanedioic acid dihydrate is 1.653 grams per cubic centimeter. 


Ethanedioic acid is very soluble in water. 
The solubility of Ethanedioic acid in water ranges from 90 to 100 grams per liter at a temperature of 20 degrees Celsius.  
Ethanedioic acid is soluble in both ethanol and diethyl ether.
Ethanedioic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.


Leafy greens, legumes, and most other plant foods contain a nutrient called oxalate or Ethanedioic acid. 
Ethanedioic acid's a naturally occurring chemical you get through your diet. 
The body also produces Ethanedioic acid as waste. 
Foods rich in oxalates also contain other nutrients that your body needs for good health.


USES and APPLICATIONS of ETHANEDIOIC ACID:
-Ethanedioic acid's main applications include cleaning or bleaching, especially for the removal of rust (iron complexing agent). 
-Ethanedioic acid's utility in rust removal agents is due to Ethanedioic acid's forming a stable, water-soluble salt with ferric iron, ferrioxalate ion. 
-The cleaning product contains Ethanedioic acid. 
-Ethanedioic acid is an ingredient in some tooth whitening products. 


-About 25% of produced Ethanedioic acid will be used as a mordant in dyeing processes. 
-Ethanedioic acid is also used in bleaches, especially for pulpwood, and for rust removal and other cleaning, in baking powder, and as a third reagent in silica analysis instruments.
-Niche uses:
Ethanedioic acid is used by some beekeepers as a miticide against the parasitic varroa mite. 


-Dilute solutions (0.05–0.15 M) of Ethanedioic acid can be used to remove iron from clays such as kaolinite to produce light-colored ceramics.
-Ethanedioic acid is used to clean minerals.
-Ethanedioic acid is sometimes used in the aluminum anodizing process, with or without sulfuric acid. 
Compared to sulfuric acid anodizing, the coatings obtained are thinner and exhibit lower surface roughness.


-Ethanedioic acid is a strong dicarboxylic acid occurring in many plants and vegetables and can be used as an analytical reagent and general reducing agent.
-Ethanedioic acid is also widely used as a wood bleach, most often in its crystalline form to be mixed with water to Ethanedioic acid's proper dilution for use.


-Semiconductor industry:
Ethanedioic acid is also used in electronic and semiconductor industries. 
In 2006 Ethanedioic acid was reported being used in electrochemical–mechanical planarization of copper layers in the semiconductor devices fabrication process.


-Ethanedioic acid is widely used as an acid rinse in laundries, where Ethanedioic acid is effective in removing rust and ink stains because Ethanedioic acid converts most insoluble iron compounds into a soluble complex ion. 
-Ethanedioic acid is the chief constituent of many commercial preparations used for removing scale from automobile radiators.
-Available in various quantities, purities, and reagent grades; used as a mordant, acid rinse, rust removal agent, bleach component, lanthanide chemistry reagent, etc.


-Ethanedioic acid is one of the organic compounds and occurs in various vegetables and plants. 
-There are various uses of Ethanedioic acid and the most significant one is in the cleaning industry i.e. in places like laundries, bleaching, dyeing, etc
-Ethanedioic acid, a pathogenicity factor for sclerotinia sclerotiorum, suppresses the Oxidative burst of the host plant and directly inhibits the OGA-stimulated production of H2O2 by soybean cells, even in the absence of other fungal components.


-Uses of Ethanedioic acid:
*Metal Cleaner
*Radiator Cleaner
*Leather Tanning
*Bleaching Agent
*Rust Remover
*Stain & Ink Remover


-Ethanedioic acid is used in bleaches, especially for pulpwood. 
-Ethanedioic acid is also used in baking powder and as a third reagent in silica analysis instruments.
-Ethanedioic acid's main applications include cleaning or bleaching, especially for the removal of rust. 
Ethanedioic acid's utility in rust removal agents is due to Ethanedioic acid's forming a stable, water-soluble salt with ferric iron, ferrioxalate ion. 


-Effectively bleaches unfinished or stripped wood quickly and easily. 
-Ethanedioic acid's also excellent for removing black water spots and tannin stains in wood. 
-Ethanedioic acid is Suitable for outdoor use.
-Ethanedioic acid is used as a mordant in dyeing processes. 


-Ethanedioic acid naturally occurs in many plants and vegetables and is often used in freckle and bleaching cosmetic preparations. 
-Ethanedioic acid is used as a bleaching agent for leather and wood.
-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 Ethanedioic acid's 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's usefulness in rust removal agents is that ferrous iron forms a stable, water-soluble salt with the ferrioxalate ion.
-Instead of products containing heavy metals and residues, Ethanedioic acid hydrate from reliable places should be used.


-Ethanedioic acid main applications include cleaning or bleaching (iron complexing agent), especially to remove rust. 
-Evaporated Ethanedioic acid or a 3.2% solution of Ethanedioic acid in sugar syrup is used by some beekeepers as a killer against parasitic insects.
-Ethanedioic acid is rubbed on the finished marble sculptures and seals the surface and adds shine. 


-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 stains caused by water penetration.
-Ethanedioic acid dihydrate is a diprotic reducing agent used as a buffer
-Ethanedioic acid is used as a buffer in chromatographic separation, dechelation and deproteinization in tandem with acetonitrile and/or other solvents.


-Ethanedioic acid is generally used as a mordant, reducing agent and bleaching agent for the dyeing and printing industry. 
-Ethanedioic acid is used in the synthesis of cleaning products. 
-Ethanedioic acid is used as a cleaning chemical in coating processes. 


-Ethanedioic acid is used to remove rust in the plumbing pipes and kitchen counters. 
-Ethanedioic acid is the main component of commercial rust removers used to remove metal rust stains from sinks and tubs. 
-Ethanedioic acid is also used as a marble polishing and grinding agent. 


-The polishing powder obtained is applied on the marble and processed. 
A chemical reaction occurs. 
After polishing, polishing is done. 
In this way, it protects the marble against external effects for a long time. 


-In the beekeeping industry, Ethanedioic acid's evaporated form or Ethanedioic acid's 3.2% solution in sugar syrup can be used by some beekeepers as a killing agent against parasitic varroa mite.
-Wood bleach - To bleach old and stained wood removing tannin stains and water stains
-Ethanedioic acid is used together with stearic acid in the production of marble polishing powder. 
-Ethanedioic acid is used as a grinding agent in preparing & polishing stones & marble in restoring furniture


-Rust removal- in removing rust on boats, in automotive shops and in restoring antiques in rust stain removal without harming Gel coat, fibre glass, steel and other metal surfaces for pre-treating stainless steel
-For removing hard water stains from tiles and plumbing fixtures as a precipitator in rare earth mineral processing 
-Ethanedioic acid is an important reagent in Lanthanide chemistry.
-Ethanedioic acid is used as a mordant in dyeing processes.


-Ethanedioic acid can be used as a reducing agent in photography.
-Ethanedioic acid is a relatively strong organic acid with many commercial uses especially in the carpentry and joinery trades in the UK. 
-Ethanedioic acid can also be used to freshen wood colour if Ethanedioic acid has become grayed due to external exposure. 
-In the refinishing of wooden furniture, Ethanedioic acid can be used after stripping to lighten darker stained areas. 
-Ethanedioic acid can also be used as a rust remover and a stain remover in many other applications. 


-How to use Ethanedioic acid:
Prepare a solution by dissolving 60g of Ethanedioic acid in 1 litre of water, apply to stain or rust and allow to work for 20-30 minutes. 
Always rinse thoroughly with clean water. 
For wood bleaching it is recommended to neutralize after treatment with a borax solution (3 tablespoons of borax dissolved in 1 litre of water).


-When using on wood the wood must be free of all coatings, waxes & oils. 
-Ethanedioic acid is necessary to use appropriate strippers and cleaners to remove coatings. 
-In wood restorers where the acid dissolves away a layer of dry surface wood to expose fresh material underneath.


-As an additive to automotive wheel cleaners.
-As a mordant in dyeing processes.
-Vaporized Ethanedioic acid, or a 6% solution of Ethanedioic acid in sugar syrup, is used by some beekeepers as an insecticide against the parasitic Varroa mite.
-As a rust remover in such applications as automotive shops and for the restoration of antiques.


-As a recommended surface pretreatment for stainless steels (surface etch) before application of solid metal or polymer self-lubricating coatings.
-For polishing stones and marble.
-Ethanedioic acid is used to destroy warts.
-Ethanedioic acid is used as a mordant in dyeing processes.


-Ethanedioic acid is used in bleaches, especially for pulpwood. 
-Ethanedioic acid is also used in baking powder and as a third reagent in silica analysis instruments.
-Ethanedioic acid’s main applications include cleaning or bleaching, especially for the removal of rust. 
-Ethanedioic acid's utility in rust removal agents is due to its forming a stable, water-soluble salt with ferric iron, ferrioxalate ion.


-Effectively bleaches unfinished or stripped wood quickly and easily. 
-Ethanedioic acid’s also excellent for removing black water spots and tannin stains in wood. 
-Ethanedioic acid is Suitable for outdoor use.


-Industrial use of Ethanedioic acid:
In industry, Ethanedioic acid is primarily used in mineral processing mechanisms. 
In addition, Ethanedioic acid can be used to sterilize equipment, and people in the textile industry use Ethanedioic acid to bleach clothes. 
Ethanedioic acid is also used in factories for removing rust from metallic equipment. 


-Medical use of Ethanedioic acid:
In the medical field, companies use acids to further purify or dilute certain chemicals. 
However, there is little data on the health benefits of Ethanedioic acid. 
-Ethanedioic acid is mainly used as a reducing element in the development of photographic film. 
-Ethanedioic acid is also used in wastewater treatment plants to effectively remove lime from water.


-There are many Ethanedioic acid applications that we can take from various sources. 
Up to 25% of Ethanedioic acid produced will be used as a mordant in dyeing processes. 
-Ethanedioic acid is used as bleach, especially for pulpwood. 
-Also, Ethanedioic acid is used in baking powder and as the third reagent in silica analysis instruments.


-Cleaning:
Ethanedioic acid application mainly includes bleaching or cleaning, especially Ethanedioic acid as a rust remover (an iron complexing agent). 
Ethanedioic acid's utility in rust removal agents is because Ethanedioic acid forms a stable, water-soluble salt with ferrioxalate ion and ferric iron.


-Extractive Metallurgy:
Ethanedioic acid is a primary reagent in lanthanide chemistry. 
Hydrated lanthanide oxalates readily form in very strongly acidic solutions in easily filtered form, a densely crystalline, and as largely free of contamination by non-lanthanide elements. 
This oxalate thermal decomposition gives the oxides, the most commonly marketed form of these elements.


-Removing marks, stains and rust:
Ethanedioic acid is mainly used for the most demanding cleaning operations. 
Ethanedioic acid effectively removes all kinds of marks and stains from the surface of the object. 
Ethanedioic acid is a gentle stain remover that eats up stains but leaves the base as it is. 
Acids have similar properties to bleach and can be used, for example, to remove rust on metals such as plumbing pipes, kitchen countertops etc. 
Some cleaning agents, laundry detergents, and bleaches contain some of this acid. 
Ethanedioic acid is also ideal for polishing virtually all stones and disposing of waste wood.


-What Ethanedioic acid is Used to Remove Rust?
To remove the rust for the products like iron, some strong acids will be helpful.
-Ethanedioic acid is widely used in laundry to effectively remove ink stains and in industries for the removal of rust. 
-For the same reason, Ethanedioic acid is the main component of many commercial preparations used to remove scale from car radiators. 


-Ethanedioic acid is used in the following products: pH regulators and water treatment products, laboratory chemicals, metal surface treatment products, leather treatment products, textile treatment products and dyes, non-metal-surface treatment products, washing & cleaning products, water softeners, water treatment chemicals and polymers.
-Ethanedioic acid has an industrial use resulting in manufacture of another substance (use of intermediates).
-Ethanedioic acid is used in the following areas: building & construction work and formulation of mixtures and/or re-packaging.


-Release to the environment of Ethanedioic acid can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, in the production of articles, formulation of mixtures and manufacturing of the substance.
-Ethanedioic acid is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.


-Ethanedioic acid is used in the following products: coating products, polishes and waxes and washing & cleaning products.
-Other release to the environment of Ethanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
-Ethanedioic acid is used in the following products: non-metal-surface treatment products, metal surface treatment products, washing & cleaning products, coating products, metal working fluids, polishes and waxes, laboratory chemicals and pH regulators and water treatment products.


-Ethanedioic acid is used in the following areas: building & construction work.
-Ethanedioic acid is used for the manufacture of: chemicals, metals, machinery and vehicles and furniture.
-Ethanedioic acid is used for the manufacture of: furniture, wood and wood products, pulp, paper and paper products and chemicals.
-Niche Uses:
Ethanedioic acid is also used by a few beekeepers as a miticide against the parasitic varroa mite


-Ethanedioic acid is used to clean minerals.
-Ethanedioic acid is also sometimes used in the aluminum anodizing process, with or without sulfuric acid. 
Compared to the sulfuric acid anodizing, the coatings obtained are thinner and exhibit a lower surface roughness.
-Other release to the environment of Ethanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use


PREPARATION of ETHANEDIOIC ACID:
Ethanedioic acid is mainly manufactured by the oxidation of carbohydrates or glucose using nitric acid or air in the presence of vanadium pentoxide. 
A variety of precursors can be used including glycolic acid and ethylene glycol.
A newer method entails oxidative carbonylation of alcohols to give the diesters of Ethanedioic acid:

4 ROH + 4 CO + O2 → 2 (CO2R)2 + 2 H2O
These diesters are subsequently hydrolyzed to Ethanedioic acid. 
Approximately 120,000 tonnes are produced annually.
Historically Ethanedioic acid was obtained exclusively by using caustics, such as sodium or potassium hydroxide, on sawdust, followed by acidification of the oxalate by mineral acids, such as sulfuric acid.
Ethanedioic acid can also be formed by the heating of sodium formate in the presence of an alkaline catalyst.


LABORATORY METHODS of ETHANEDIOIC ACID:
Although Ethanedioic acid can be readily purchased, 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 with heat or by azeotropic distillation.
Developed in the Netherlands, an electrocatalysis by a copper complex helps reduce carbon dioxide to Ethanedioic acid; this conversion uses carbon dioxide as a feedstock to generate Ethanedioic acid.

Anhydrous Ethanedioic acid exists as two polymorphs; in one the hydrogen-bonding results in a chain-like structure, whereas the hydrogen bonding pattern in the other form defines a sheet-like structure. 
Because the anhydrous material is both acidic and hydrophilic (water seeking), it is used in esterifications.


DIHYDRATE:
The dihydrate H2C2O4.2H2O has space group C52h–P21/n, with lattice parameters a = 611.9 pm, b = 360.7 pm, c = 1205.7 pm, β = 106°19', Z = 2. 
The main inter-atomic distances are: C−C 153 pm, C−O1 129 pm, C−O2 119 pm.

Theoretical studies indicate that Ethanedioic acid dihydrate is one of very few crystalline substances that exhibit negative area compressibility. 
Namely, when subjected to isotropic tension stress (negative pressure), the a and c lattice parameters increase as the stress decreases from −1.17 GPa to −0.12 GPa and from −1.17 GPa to −0.51 GPa, respectively.


REACTIONS of ETHANEDIOIC ACID:
Acid-base properties:
Ethanedioic acid's pKa values vary in the literature from 1.25–1.46 and 3.81–4.40. 
Ethanedioic acid is relatively strong compared to other carboxylic acids:

C2O4H2 ⇌ C2O4H− + H+                  pKa = 1.27
C2O4H− ⇌ C2O2−4 + H+                  pKa = 4.27

Ethanedioic acid undergoes many of the reactions characteristic of other carboxylic acids. 
Ethanedioic acid forms esters such as dimethyl oxalate (m.p. 52.5 to 53.5 °C, 126.5 to 128.3 °F). 
Ethanedioic acid forms an acid chloride called oxalyl chloride.
Ethanedioic acid is a relatively strong "weak acid" with pKa1=1.27 and pKa2=4.28. 
Ethanedioic acid exhibits many of the reactions characteristic of other carboxylic acids. 

Ethanedioic acidforms esters such as dimethyloxalate (m.p. 52.5–53.5 °C). 
Ethanedioic acid forms an acid chloride called oxalyl chloride.
Oxalate, the conjugate base of Ethanedioic acid, is an excellent ligand for metal ions. 
Ethanedioic acid usually binds as a bidentate ligand forming a 5-membered MO2C2 ring. 
An illustrative complex is potassium ferrioxalate, K3[Fe(C2O4)3]. 


METAL-BINDING PROPERTIES of ETHANEDIOIC ACID:
Transition metal oxalate complexes are numerous, e.g. the drug oxaliplatin. 
Ethanedioic acid has shown to reduce manganese dioxide MnO
2 in manganese ores to allow the leaching of the metal by sulfuric acid.

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 form, largely free of contamination by nonlanthanide elements:
2 Ln3+ + 3 C2O4H2 → Ln2(C2O4)3 + 6 H+
Thermal decomposition of these oxalates gives the oxides, which is the most commonly marketed form of these elements.

Other:
Ethanedioic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction.
Ethanedioic acid vapor decomposes at 125–175 °C into carbon dioxide CO2 and 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 in 2:1 molar ratio yields a solid crystalline compound H2C2O4.
[CO(NH2)2]2, consisting of stacked two-dimensional networks of the neutral molecules held together by hydrogen bonds with the oxygen atoms.


OCCURRENCE of ETHANEDIOIC ACID:
Biosynthesis:
At least two pathways exist for the enzyme-mediated formation of oxalate. 

In one pathway, oxaloacetate, a component of the Krebs citric acid cycle, is hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase:
[O2CC(O)CH2CO2]2− + H2O → C2O2−4 + CH3CO−2 + H+
It also arises from the dehydrogenation of glycolic acid, which is produced by the metabolism of ethylene glycol.

Ethanedioic acid and oxalates are abundantly present in many plants, most notably fat hen (lamb's quarters), sour grass, and sorrel (including Oxalis). 
The root and/or leaves of rhubarb and buckwheat are listed being high in Ethanedioic acid.

Foods that are edible but that still contain significant concentrations of Ethanedioic acid include—in decreasing order—star fruit (carambola), black pepper, parsley, poppy seed, rhubarb stalks, amaranth, spinach, chard, beets, cocoa, chocolate, most nuts, most berries, and beans. 
The gritty “mouth feel” one experiences when drinking milk with a rhubarb dessert is caused by precipitation of calcium oxalate. 
Thus even dilute amounts of Ethanedioic acid can readily "crack" the casein found in various dairy products.


OCCURRENCE IN FOODS AND PLANTS of ETHANEDIOIC ACID:
Early investigators isolated Ethanedioic acid from wood-sorrel (Oxalis). 
Members of the spinach family and the brassicas (cabbage, broccoli, brussels sprouts) are high in oxalates, as are sorrel and umbellifers like parsley. 

The leaves and stems of all species of the genus Chenopodium and related genera of the family Amaranthaceae, which includes quinoa, contain high levels of Ethanedioic acid. 
Rhubarb leaves contain about 0.5% Ethanedioic acid, and jack-in-the-pulpit (Arisaema triphyllum) contains calcium oxalate crystals. 

Similarly, the Virginia creeper, a common decorative vine, produces Ethanedioic acid in its berries as well as oxalate crystals in the sap, in the form of raphides. 
Bacteria produce oxalates from oxidation of carbohydrates.
Plants of the genus Fenestraria produce optical fibers made from crystalline Ethanedioic acid to transmit light to subterranean photosynthetic sites.

Carambola, also known as starfruit, also contains Ethanedioic acid along with 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.
The formation of naturally occurring calcium oxalate patinas on certain limestone and marble statues and monuments has been proposed to be caused by the chemical reaction of the carbonate stone with Ethanedioic acid secreted by lichen or other microorganisms.

Production by fungi:
Many soil fungus species secrete Ethanedioic acid, resulting in greater solubility of metal cations, increased availability of certain soil nutrients, and can lead to the formation of calcium oxalate crystals. 
Some fungi such as Aspergillus niger have been extensively studied for the industrial production of Ethanedioic acid; however, those processes are not yet economically competitive with production from oil and gas.


BIOCHEMISTRY of ETHANEDIOIC ACID:
The conjugate base of Ethanedioic acid is the hydrogenoxalate anion, and Ethanedioic acid's conjugate base (oxalate) is a competitive inhibitor of the lactate dehydrogenase (LDH) enzyme. 

LDH catalyses the conversion of pyruvate to lactic acid (end product of the fermentation (anaerobic) process) oxidising the coenzyme NADH to NAD+ and H+ concurrently. 
Restoring NAD+ levels is essential to the continuation of anaerobic energy metabolism through glycolysis. 

As cancer cells preferentially use anaerobic metabolism (see Warburg effect) inhibition of LDH has been shown to inhibit tumor formation and growth, thus is an interesting potential course of cancer treatment.
Ethanedioic acid plays an key role in the interaction between pathogenic fungi and plants. 
Small amounts of Ethanedioic acid enhances plant resistance to fungi, but higher amounts cause widespread programmed cell death of the plant and help with fungi infection. 

Plants normally produce Ethanedioic acid in small amounts, but some pathogenic fungi such as Sclerotinia sclerotiorum cause a toxic accumulation.
Oxalate, besides being biosynthesised, may also be biodegraded. 
Oxalobacter formigenes is an important gut bacteria that helps animals (including humans) degrade oxalate.


HISTORY of ETHANEDIOIC ACID:
The preparation of salts of Ethanedioic acid (crab acid) from plants had been known, at least since 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from wood sorrel. 
By 1773, François Pierre Savary of Fribourg, Switzerland had isolated Ethanedioic acid from its salt in 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 acid that resulted socker-syra or såcker-syra (sugar acid). 
By 1784, Scheele had shown that "sugar acid" and Ethanedioic acid from natural sources were identical.
In 1824, the 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.


ALTERNATIVE PARENTS of ETHANEDIOIC ACID:
*Carboxylic acids 
*Organic oxides 
*Hydrocarbon derivatives 
*Carbonyl compounds 


SUBSTITUENTS of ETHANEDIOIC ACID:
*Dicarboxylic acid or derivatives
*Carboxylic acid
*Organic oxygen compound
*Organic oxide
*Hydrocarbon derivative
*Organooxygen compound
*Carbonyl group
*Aliphatic acyclic compound


PHYSICAL and CHEMICAL PROPERTIES of ETHANEDIOIC ACID:
Molecular Weight: 90.03
Molecular Weight: 90.03    
XLogP3-AA: -0.3
Hydrogen Bond Donor Count: 2    
Hydrogen Bond Acceptor Count: 4    
Rotatable Bond Count: 1    
Exact Mass: 89.99530854    
Monoisotopic Mass: 89.99530854    


Topological Polar Surface Area: 74.6 Ų    
Heavy Atom Count: 6    
Formal Charge: 0    
Complexity: 71.5
Isotope Atom Count: 0    
Defined Atom Stereocenter Count: 0    
Undefined Atom Stereocenter Count: 0    
Defined Bond Stereocenter Count: 0    
Undefined Bond Stereocenter Count: 0    


Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Appearance Form: powder
Color: white
Odor: odorless
Odor Threshold: Not applicable
pH: 1,3 at 9 g/l


Melting point/freezing point:
Melting point/range: 189,5 °C - dec.
Initial boiling point and boiling range: No data available
Flash point: No data available
Evaporation rate: No data available
Flammability (solid, gas): No data available
Upper/lowe flammability or explosive limits: No data available
Vapor pressure: No data available
Vapor density: No data available


Relative density: No data available
Water solubility: No data available
Partition coefficient: n-octanol/water: No data available
Autoignition temperature: No data available
Decomposition temperature: No data available
Viscosity 
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Explosive properties: No data available


Oxidizing properties: No data available
Other safety information: No data available
Molecular Formula: C2H6O6
Average mass: 126.065 Da
Monoisotopic mass: 126.016441 Da
Boiling point: 149 - 160 °C (1013 hPa) (decomposition)
Density    1.65 g/cm3 (20 °C)


Flash point: 157 °C (decomposition)
Melting Point: 98 - 100 °C
pH value: 1.5 (10 g/l, H₂O)
Vapor pressure: 0.000312 hPa (25 °C)
Bulk density: 813 kg/m3
Solubility: >100 g/l
Chemical formula: C2H2O4
Molar mass: 90.034 g•mol−1 (anhydrous), 126.065 g•mol−1 (dihydrate)
Appearance: White crystals


Odor: odorless
Density: 1.90 g•cm−3 (anhydrous, at 17 °C), 1.653 g•cm−3 (dihydrate)
Melting point: 189 to 191 °C, 101.5 °C (214.7 °F; 374.6 K) dihydrate
Solubility in water: 90-100 g/L (20 °C)
Solubility: 237 g/L (15 °C) in ethanol, 14 g/L (15 °C) in diethyl ether 
Vapor pressure: <0.001 mmHg (20 °C)
Acidity (pKa): 1.25, 4.14
Conjugate base: Hydrogenoxalate
Magnetic susceptibility (χ): -60.05•10−6 cm3/mol


FIRST AID MEASURES of ETHANEDIOIC ACID:
-Description of first-aid measures:
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.

*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with water/ shower. 
Consult a physician.

*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Immediately call in ophthalmologist.
Remove contact lenses.

*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed:
No data available


ACCIDENTAL RELEASE MEASURES of ETHANEDIOIC ACID:
-Environmental precautions:
Do not let product enter drains.

-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Take up dry. 
Dispose of properly. 
Clean up affected area. 


FIRE FIGHTING MEASURES of ETHANEDIOIC ACID:
-Extinguishing media:
*Suitable extinguishing media:
Water 
Foam 
Carbon dioxide (CO2) 
Dry powder

*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.


EXPOSURE CONTROLS/PERSONAL PROTECTION of ETHANEDIOIC ACID:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:

*Eye/face protection:
Use equipment for eye protection. 
Tightly fitting safety goggles.

*Skin protection:
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

*Body Protection:
protective clothing
-Control of environmental exposure:
Do not let product enter drains


HANDLING and STORAGE of ETHANEDIOIC ACID:
-Precautions for safe handling:
*Advice on safe handling:
Work under hood. 

*Hygiene measures:
Immediately change contaminated clothing.  
Wash hands and face after working with substance.

-Conditions for safe storage, including any incompatibilities:
Storage conditions
Tightly closed. 
Dry.


STABILITY and REACTIVITY of ETHANEDIOIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .
-Conditions to avoid:
no information available
-Incompatible materials:
No data available


SYNONYMS:
oxalic acid
ethanedioic acid
Aktisal
Aquisal
oxalate
Oxiric acid
Oxalsaeure
Oxaalzuur
Kyselina stavelova
Acide oxalique
Acido ossalico
Acidum oxalicum
Caswell No. 625
Oxalicacid
NCI-C55209
Ethanedionic acid
Ethane-1,2-dioic acid
CCRIS 1454
EPA Pesticide Chemical Code 009601
HSDB 1100
AI3-26463
NSC 62774
UNII-9E7R5L6H31
BRN 0385686
HOOCCOOH
C2H2O4
Oxalic acid anhydrous
CHEBI:16995
9E7R5L6H31
C2-beta-polymorph
ETHANEDIOIC ACID DIHYDRATE
Ethanedioic acid-d2
Oxalic Acid Dianion
DSSTox_CID_5816
C00209
DSSTox_RID_77935
DSSTox_GSID_25816
Oxalic acid diammonium salt
Wood bleach
OXD
NSC115893
Ethandisaeure
Ethanedionate
Oxagel
2dua
2hwg
H2ox
Anhydrous oxalic acid
Ethane-1,2-dioate
Oxalic acid, 98%
Oxalic acid (8CI)
oxalic acid 2 hydrate
Oxalic acid, anhydrous
Oxalic acid 2-Hydrate
1o4n
1t5a
Oxalate standard for IC
WLN: QVVQ
Ethanedioic acid (9CI)
Oxalic acid dihydrate ACS
Ultraplast Activate S 52
bmse000106
Oxalic Acid Low Ash Grade
NCIOpen2_000770
NCIOpen2_001022
NCIOpen2_001042
NCIOpen2_001202
NCIOpen2_008831
TETRADECANOIC-D27ACID
4-02-00-01819 (Beilstein Handbook Reference)
Oxalic acid solution, 0.5 M
Oxalic acid, AR, >=99%
Oxalic acid, LR, >=98%
CHEMBL146755
DTXSID0025816
Oxalic acid solution, 0.05 M
Oxalic acid, analytical standard
BDBM14674
bis(5-azaspiro[2.5]octan-8-ol)
HY-Y0262
NSC62774
Oxalicacid,0.1NStandardizedSolution
STR01359
ZINC6021239
Tox21_202122
Tox21_303346
BBL003000
bis((2R)-azetidine-2-carbonitrile)
NSC-62774
s9354
STK379550
AKOS005449445
Oxalic acid, 5% w/v aqueous solution
CCG-266020
DB03902
MCULE-6647815245
SB40938
SB40959
SB40985
Oxalic acid, 10% w/v aqueous solution
Oxalic acid, ReagentPlus(R), >=99%
NCGC00249170-01
NCGC00257376-01
NCGC00259671-01
BP-21133
H158
Oxalic acid 10 microg/mL in Acetonitrile
Oxalic acid, 0.1N Standardized Solution
Oxalic acid, SAJ first grade, >=97.0%
bis(1-(3-methyloxetan-3-yl)ethan-1-amine)
CS-0013716
FT-0657506
Oxalic acid, Vetec(TM) reagent grade, 98%
Oxalic acid, purum, anhydrous, >=97.0% (RT)
Q184832
J-007978
F1B1B2D7-C290-4CE6-8550-F25B202AFADE
F2191-0257
Oxalic acid, puriss. p.a., anhydrous, >=99.0% (RT)
Oxalic acid, purified grade, 99.999% trace metals basis
Oxalate standard for IC, 1.000 g/L in H2O, analytical standard
Oxalic acid concentrate, 0.1 M (COOH)2 (0.2N)
Oxalic acidACIDO OSSALICO (s)
Acide oxaliqueAcide(S) 
Oxalique(S)
Acido OssalicoAcido 
Oxalico
Aktisal
Anhydrous Oxalic Acid
AquisalÁCido(S) 
OxáLico(S)
Ethanedioate
Ethanedioic Acid
Ethanedioic acid, conjugate acid (1:2)
Ethanedionic acid
Ethandisaeure    
Ethane-1,2-dioic acid    
Ethanedioic acid    
H2Ox    
HOOCCOOH    
Oxalsaeure    
Ethane-1,2-dioate    
Ethanedioate    
Oxalate    
Ammonium oxalate    
Ethanedioic acid dihydrate    
Ethanedionate    
Ethanedionic acid    
Kyselina stavelova    
Oxaalzuur    HMDB
Oxalic acid 2-hydrate    
Oxalic acid anhydrous    
Oxalic acid diammonium salt    
Oxalic acid dihydrate    
Acid, oxalic    
Aluminum oxalate    
Chromium (3+) oxalate (3:2)    
Dipotassium oxalate    
Iron oxalate    
Magnesium oxalate    
Magnesium oxalate (1:1)    
Oxalate, dilithium    
Oxalate, disodium    
Oxalate, monohydrogen monopotassium    
Oxalate, monopotassium    
Oxalate, potassium    
Chromium oxalate    
Dilithium oxalate    
Manganese (2+) oxalate (1:1)    
Monosodium oxalate    
Oxalate, chromium    
Oxalate, dipotassium    
Oxalate, magnesium    
Oxalate, monosodium    
Oxalate, potassium chromium    
Oxalate, sodium    HMDB
Potassium oxalate    
Potassium oxalate (2:1)    
Diammonium oxalate    
Disodium oxalate    
Oxalate, aluminum    
Oxalate, diammonium    
Oxalate, ferric    
Oxalate, monoammonium    
Potassium chromium oxalate    
Chromium (2+) oxalate    
Ferric oxalate    
Iron (2+) oxalate (1:1)    
Iron (3+) oxalate    
Monoammonium oxalate    
Monohydrogen monopotassium oxalate    
Monopotassium oxalate    
Oxalate, iron    
Sodium oxalate    
Oxalic acid
Oxalic Acid Dihydrate (Technical)
Wood Bleach
Crab Acid


 

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