Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Oxalic acid is an organic acid with the systematic name ethanedioic acid and chemical formula HO−C(=O)−C(=O)−OH, also written as (COOH)2 or (CO2H)2 or H2C2O4. It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels. It occurs naturally in many foods. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.
Oxalic acid has much greater acid strength than acetic acid. It is a reducing agent[9] and its conjugate bases hydrogen oxalate (HC2O−4) and oxalate (C2O2−4) are chelating agents for metal cations. It is used as a cleaning agent, especially for the removal of rust, because it forms a water-soluble ferric iron complex, the ferrioxalate ion. Oxalic acid typically occurs as the dihydrate with the formula H2C2O4·2H2O.
^ ab"Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^Apelblat, Alexander; Manzurola, Emanuel (1987). "Solubility of oxalic, malonic, succinic, adipic, maleic, malic, citric, and tartaric acids in water from 278.15 to 338.15 K". The Journal of Chemical Thermodynamics. 19 (3): 317–320. doi:10.1016/0021-9614(87)90139-X.
^Radiant Agro Chem. "Oxalic Acid MSDS". Archived from the original on 2011-07-15. Retrieved 2012-02-02.
^ abcdNIOSH Pocket Guide to Chemical Hazards. "#0474". National Institute for Occupational Safety and Health (NIOSH).
^Bjerrum, Jannik; Sillén, Lars Gunnar; Schwarzenbach, Gerold Karl; Anderegg, Giorgio (1958). Stability constants of metal-ion complexes, with solubility products of inorganic substances. London: Chemical Society.
^CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
^"Oxalic acid". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^Ullmann's Encyclopedia of Industrial Chemistry. Wiley. 2005. pp. 17624/28029. doi:10.1002/14356007. ISBN 9783527306732.
Oxalicacid is an organic acid with the systematic name ethanedioic acid and chemical formula HO−C(=O)−C(=O)−OH, also written as (COOH)2 or (CO2H)2 or...
"rhubarb" in English. The large, triangular leaves contain high levels of oxalicacid and anthrone glycosides, making them inedible. The small flowers are...
Cl−C(=O)−C(=O)−Cl. This colorless, sharp-smelling liquid, the diacyl chloride of oxalicacid, is a useful reagent in organic synthesis. Oxalyl chloride was first...
base of oxalicacid. At neutral pH in aqueous solution, oxalicacid converts completely to oxalate. The dissociation of protons from oxalicacid proceeds...
Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalicacid, glyoxylic acid is one of the C2 carboxylic...
large amounts, oxalicacid may be considered slightly toxic, interfering with proper digestion and kidney function. However, oxalicacid is also present...
of the family Amaranthaceae, including quinoa, contain high levels of oxalicacid. The plant's growth is highly variable due to the number of different...
[citation needed] In the laboratory, formic acid can be obtained by heating oxalicacid in glycerol and extraction by steam distillation. Glycerol acts as a...
chemiluminescence in a glowstick. This chemical is the double ester of phenol with oxalicacid. Upon reaction with hydrogen peroxide, 1,2-dioxetanedione is formed,...
chloroacetic acid with sodium hydroxide followed by re-acidification. Other methods, not noticeably in use, include hydrogenation of oxalicacid, and hydrolysis...
including other names, ids, toxicity and safety. Acids from the two-carbon oxalicacid to the ten-member sebacic acid may be remembered using the mnemonic 'Oh...
intramolecular hydrogen bonds, e.g. in oxalicacid, where the distances exceed 2.4 Å. In even a slight presence of water, carbonic acid dehydrates to carbon dioxide...
21 October 2013. Gadd, Geoffrey M. "Fungal production of citric and oxalicacid: importance in metal speciation, physiology and biogeochemical processes"...
to dimerise to form oxalicacid. Acid anhydride Acid chloride Amide Amino acid Ester List of carboxylic acids Dicarboxylic acid Pseudoacid Thiocarboxy...
selectively reduced with reducing agents such as sulfur dioxide, hydrazine, oxalicacid, etc. The equation for the reduction of oxidized gold (Au3+) by sulfur...
and insoluble in diethyl ether. Oxamide is the diamide derived from oxalicacid, and the hydrate of cyanogen. Oxamide is produced from hydrogen cyanide...
acid anodizing process was patented by Gower and O'Brien in 1927. Sulfuric acid soon became and remains the most common anodizing electrolyte. Oxalic...
ascorbic acid will undergo further oxidative decomposition to various products including diketogulonic acid, xylonic acid, threonic acid and oxalicacid. Reactive...
oxalate (in archaic terminology, oxalate of lime) is a calcium salt of oxalicacid with the chemical formula CaC2O4 or Ca(COO)2. It forms hydrates CaC2O4·nH2O...
have been studied computationally. It can be viewed as the anhydride of oxalicacid or the two-fold ketone of ethylene oxide. It is an oxide of carbon (an...
contain above average levels of oxalicacid, particularly in older plants, and people who are sensitive to oxalicacid should avoid the genus as it is...
examples of weak acids include acetic acid and phosphorous acid. An acid such as oxalicacid ( HOOC − COOH {\displaystyle {\ce {HOOC-COOH}}} ) is said...
first came under question in 1824, when Friedrich Wöhler synthesized oxalicacid, a compound known to occur only in living organisms, from cyanogen. A...
removal acids are oxalicacid. Oxalicacid, also called ethanedioic acid, belongs to the carboxylic acid family. Oxalicacid is used widely as an acid rinse...
during the titration. A calculated titration curve for oxalicacid is shown at the right. Oxalicacid has pKa values of 1.27 and 4.27. Therefore, the buffer...
all of them, acidify the soil by excreting oxalicacid, a product of their respiratory metabolism. Oxalicacid precipitates calcium, forming insoluble crystals...
research. Wikimedia Commons has media related to Phytic acid. Antinutrient Essential nutrient Oxalicacid Schlemmer, U.; Frølich, W.; Prieto, R. M.; Grases...