A colorless crystalline compound, oxalic acid has a melting point of Oxalic acid is poorly soluble in alcohol and ether and is insoluble in benzene and chloroform. Salts of oxalic acid are found in plants—for example, its acid potassium salt is found in sorrel genus Oxalishence the name. The acid forms in tissues as a metabolic product and, together with the oxalic acid in food, is excreted with urine as potassium oxalate.

Oxalates participate in the formation of stones in the kidneys and urinary bladder in cases of disorders of mineral metabolism. Oxalic acid is formed in oxalic acid fermentation. Oxalic acid was first synthesized in by F. It is used as mordant in cloth printing; it is also used in the production of dyes and inks, as a bleaching agent, and as a precipitating agent for rare earths.

Oxalic acid

Oxalic acid and oxalate salts are poisonous. Oxalic acid is found in many plants, e. Oxalic acid is the only possible compound in which two carboxyl groups carboxyl groupin chemistry, functional group that consists of a carbon atom joined to an oxygen atom by a double bond and to a hydroxyl group, OH, by a single bond.

Carboxylic acids are compounds whose molecules contain a carboxyl group that is joined to a hydrogen atom, an Click the link for more information.

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Unlike other carboxylic acids except formic acid formic acid or methanoic acidHCO 2 H, a colorless, corrosive liquid with a sharp odor; it boils at It has the lowest molecular weight and is the simplest of the carboxylic acids. Oxalic acid is usually prepared by heating sodium formate with sodium hydroxide to form sodium oxalate, which is converted to calcium oxalate and treated with sulfuric acid to obtain free oxalic acid.

Licensed from Columbia University Press. All rights reserved. The following article is from The Great Soviet Encyclopedia It might be outdated or ideologically biased. The Great Soviet Encyclopedia, 3rd Edition Formula: COOH 2.

Mentioned in? Encyclopedia browser? Full browser?While it is not usually a problem with normal diets, it is seen in high concentrations in certain ornamental plants such as Diffenbachiaas well as in some bleaches and antirust products. Persons or animals that chew on the plants or otherwise consume the chemical can be poisoned. Oxalic acid is highly toxic and if ingested vomiting should not be induced.

If the person is at home, a poison control center and emergency services should be contacted immediately. The acid can be neutralized by administration of calcium by either the oral or the intravenous route.


High urinary oxalate concentrations may cause deposition of kidney stones and other urinary calculi. All rights reserved.


An acid found in many plants and vegetables, particularly in buckwheat family Polygoniaceae and Oxalis family Oxalidaceae ; used as a hemostatic in veterinary medicine, but toxic in elevated levels when ingested by humans; also used in the removal of ink and other stains, and as a general reducing agent; salts of oxalic acid are found in renal calculi; accumulates in cases of primary hyperoxaluria. An acid found in many plants and vegetables; used as a hemostatic in veterinary medicine, but toxic when ingested by humans; also used in the removal of ink and other stains, and as a general reducing agent; salts of oxalic acid are found in renal calculi; accumulates in cases of primary hyperoxaluria.

Acid found in many plants and vegetables; toxic in elevated levels when ingested by humans; also used in the removal of ink and other stains, and as a general reducing agent.

Mentioned in? Benedict-Hopkins-Cole reagent binoxalate Bird's disease bistort bitter dock calcite calcium calcium acetate. Medical browser? Full browser?Questions are typically answered within 1 hour. Q: How many copper atoms are in a cube of copper metal measuring 1. The density of c A: Since you have asked multiple questions, we will solve the first question for you.

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Chemical Engineering. Civil Engineering. Computer Engineering. Computer Science. Electrical Engineering.Oxalic acidalso called ethanedioic acida colourless, crystalline, toxic organic compound belonging to the family of carboxylic acids. Oxalic acid is widely used as an acid rinse in laundries, where it is effective in removing rust and ink stains because it converts most insoluble iron compounds into a soluble complex ion. For the same reason, it is the chief constituent of many commercial preparations used for removing scale from automobile radiators.

Known as a constituent of wood sorrel as early as the 17th century, oxalic acid was first prepared synthetically in It is manufactured by heating sodium formate in the presence of an alkali catalystby oxidizing carbohydrates with nitric acidby heating sawdust with caustic alkalies, or by fermentation of sugar solutions in the presence of certain molds.

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oxalic acid

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Learn More in these related Britannica articles:. Some minerals, particularly those of a similar size and charge, compete with each other for absorption. For example, iron supplementation may reduce zinc absorption, while excessive intakes of zinc can interfere with copper absorption. On the other hand, the absorption….

Because one COOH group is still present in the compound, it has the properties of…. History at your fingertips. Sign up here to see what happened On This Dayevery day in your inbox! Email address. By signing up, you agree to our Privacy Notice.Oxalic acid is an organic compound with the formula C 2 H 2 O 4. It is a white crystalline solid that forms a colorless solution in water.

Its acid strength is much greater than that of acetic acid. It occurs naturally in many foods, but excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.


Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus Oxaliscommonly known as wood-sorrels. The preparation of salts of oxalic acid from plants had been known, at the latest, sincewhen the Dutch botanist and physician Herman Boerhaave isolated a salt from sorrel. ByScheele had shown that "sugar acid" and oxalic acid from natural sources were identical. Oxalic 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.

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These diesters are subsequently hydrolyzed to oxalic acid. Approximatelytonnes are produced annually. Historically oxalic acid was obtained exclusively by using caustics, such as sodium or potassium hydroxideon sawdust. Although it can be readily purchased, oxalic 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 oxalic acid; [18] this conversion uses carbon dioxide as a feedstock to generate oxalic acid. Anhydrous oxalic 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.

Oxalic acid is a relatively strong acid, despite being a carboxylic acid :. Oxalic acid undergoes many of the reactions characteristic of other carboxylic acids. It forms esters such as dimethyl oxalate m. Oxalate, the conjugate base of oxalic acid, is an excellent ligand for metal ions, e. Oxalic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction.

Oxalic acid's p K a values vary in the literature from 1. At least two pathways exist for the enzyme-mediated formation of oxalate. In one pathway, oxaloacetatea component of the Krebs citric acid cycleis hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase : [26].

What is the name of H2C2O4 (aq)?

It also arises from the dehydrogenation of glycolic acidwhich is produced by the metabolism of ethylene glycol. Calcium oxalate is the most common component of kidney stones.Questions are typically answered within 1 hour.

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