Bieber,+Eric1

= Oxalic Acid ** Oxalic acid ** is the chemical compound with the formula that can be written in a number of equivalent ways, C2O4H2, C2O2(OH)2, and as HOOCCOOH. In terms of acid strength, it is about 3,000 times stronger than acetic acid. Typically oxalic acid occurs as the dihydrate with the formula C2O4H2·2H 2 O. (Wikipedia) (Wikipedia http://upload.wikimedia.org/wikipedia/commons/1/17/Oxalic-acid-3D-balls.png) (Wikipedia http://upload.wikimedia.org/wikipedia/commons/3/3d/Oxalic-acid-3D-vdW.png) http://web.tradekorea.com/upload_file2/sell/45/S00007545/Oxalic_Acid.jpg Uses =

Oxalic acid is used in the restoration of old wood. Its reducing properties are utilized in platinotype, the early photographic platinum/palladium printing process. Vaporized oxalic acid, or a 6% solution of oxalic acid in sugar syrup, is used by some beekeepers as a miticide against the parasitic Varroa mite. (Wikipedia)

It is a white solid used in removal of certain kinds of stains, in removing calcium ions from solutions, and in tanning leather. It occurs naturally and is toxic. The most common uses of oxalic acid are in tanning leather and removing rust and ink stains. In stain removal, it acts as a reducing agent and is relied on by most dry cleaners for this purpose. Iron rust stains contain iron in its oxidized form (Fe III); the oxalic acid reduces it to its colorless reduced form (Fe II).Oxalic acid is also used to clean metals in many industries and is also used in the purification of glycerol (glycerin). In many industrial processes oxalic acid is used to remove calcium ions from solutions. The reaction of calcium ions with oxalic acidproduces an insoluble solid, calcium oxalate. (World of Chemistry)

**Major Sources**

The potassium and calcium salts of oxalic acid are found naturally in cabbage, spinach, and rhubarb leaves, and are also found in the bark of some species of eucalyptus trees. Few people ingest toxic amounts of oxalic acid directly. However, if a child or pet swallows antifreeze (which typically contains ethylene glycol), enzymes in the body will metabolize the ethylene glycol to oxalic acid, which is the reason antifreeze is toxic. (World of Chemistry)

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 acidand ethylene glycol. A newer method entails oxidative carbonylation of alcohols to give the diesters of oxalic acid: 4 ROH + 4 CO + O2 → 2 (CO2R)2 + 2 H2O These diesters are subsequently hydrolyzed to oxalic acid. Approximately 120M kg are produced annually. (wikipedia) 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. (Wikipedia)

**Properties**

pKa 2 |||| 1.27 4.28 ||
 * PHYSICAL STATE |||| white crystals ||
 * MELTING POINT |||| 101 - 102 C ||
 * BOILING POINT |||| 149 - 160 C (sublimes) ||
 * SPECIFIC GRAVITY |||| 1.6 - 1.7 ||
 * SOLUBILITY IN WATER |||| 1 g/7ml ||
 * pKa 1
 * NFPA RATINGS |||| Health: 3; Flammability: 1; Reactivity: 0 ||
 * FLASH POINT |||| 163 C ||
 * STABILITY |||| Stable under ordinary conditions ||

Good wiki. You have a lot of information that is helpful. I don't think I've ever heard of oxalic acid. It's interesting that it is used for stain removal. I wonder if it used in any laundry detergents. It's strange that it can be formed from ethylene glycol, which makes antifreeze toxic. I was slightly confused about the reactions and how it is formed, but otherwise your post was good. Meredith