Community hub
Recent from talks
Contribute something to knowledge base
Content stats: 0 posts, 0 articles, 1 media, 0 notes
Members stats: 0 subscribers, 0 contributors, 0 moderators, 0 supporters
Subscribers
Supporters
Contributors
Moderators
Hub AI
Oxalic acid AI simulator
(@Oxalic acid_simulator)
Hub AI
Oxalic acid AI simulator
(@Oxalic acid_simulator)
Oxalic acid
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 is derived from early investigators who 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 is a much stronger acid than acetic acid. It is a reducing agent and its conjugate bases hydrogenoxalate (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.
The preparation of salts of oxalic acid from plants had been known since at least 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from wood sorrel, akin to kraft process. By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid from its salt in sorrel.
In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman produced oxalic 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 oxalic acid from natural sources were identical. The modern name was introduced (along with many other acid names) in 1787, by de Morveau, Lavoisier and co-authors.
In 1824, the German chemist Friedrich Wöhler obtained oxalic acid by reacting cyanogen with ammonia in aqueous solution. This experiment may represent the first synthesis of a natural product.
Oxalic acid is mainly manufactured by the oxidation of carbohydrates like glucose using nitric acid or air in the presence of vanadium pentoxide. Another process uses oxygen to regenerate the nitric acid, using a variety of precursors including glycolic acid and ethylene glycol. As of 2011, this process was only used by Mitsubishi in Japan. A newer method entails oxidative carbonylation of alcohols to give the diesters of oxalic acid:
These diesters are subsequently hydrolyzed to oxalic acid. Approximately 120,000 tonnes are produced annually.
Historically oxalic 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. Oxalic acid can also be formed by the heating of sodium formate in the presence of an alkaline catalyst.[better source needed]
Oxalic acid
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 is derived from early investigators who 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 is a much stronger acid than acetic acid. It is a reducing agent and its conjugate bases hydrogenoxalate (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.
The preparation of salts of oxalic acid from plants had been known since at least 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from wood sorrel, akin to kraft process. By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid from its salt in sorrel.
In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman produced oxalic 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 oxalic acid from natural sources were identical. The modern name was introduced (along with many other acid names) in 1787, by de Morveau, Lavoisier and co-authors.
In 1824, the German chemist Friedrich Wöhler obtained oxalic acid by reacting cyanogen with ammonia in aqueous solution. This experiment may represent the first synthesis of a natural product.
Oxalic acid is mainly manufactured by the oxidation of carbohydrates like glucose using nitric acid or air in the presence of vanadium pentoxide. Another process uses oxygen to regenerate the nitric acid, using a variety of precursors including glycolic acid and ethylene glycol. As of 2011, this process was only used by Mitsubishi in Japan. A newer method entails oxidative carbonylation of alcohols to give the diesters of oxalic acid:
These diesters are subsequently hydrolyzed to oxalic acid. Approximately 120,000 tonnes are produced annually.
Historically oxalic 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. Oxalic acid can also be formed by the heating of sodium formate in the presence of an alkaline catalyst.[better source needed]
Recent media
Recent media