Disodium oxalate
Encyclopedia
Disodium oxalate, often called simply sodium oxalate, is a sodium
Sodium
Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...

 salt of oxalic acid
Oxalic acid
Oxalic acid is an organic compound with the formula H2C2O4. This colourless solid is a dicarboxylic acid. In terms of acid strength, it is about 3,000 times stronger than acetic acid. Oxalic acid is a reducing agent and its conjugate base, known as oxalate , is a chelating agent for metal cations...

 with the molecular formula Na2C2O4. It is usually a white, crystalline, odorless powder, that decomposes at 250–270 °C
Celsius
Celsius is a scale and unit of measurement for temperature. It is named after the Swedish astronomer Anders Celsius , who developed a similar temperature scale two years before his death...

.

Disodium oxalate can act as a reducing agent
Reducing agent
A reducing agent is the element or compound in a reduction-oxidation reaction that donates an electron to another species; however, since the reducer loses an electron we say it is "oxidized"...

, and it may be used as a primary standard
Primary standard
A primary standard in metrology is a standard that is accurate enough that it is not calibrated by or subordinate to other standards. Primary standards are defined via other quantities like length, mass and time. Primary standards are used to calibrate other standards referred to as working...

 for standardizing potassium permanganate
Potassium permanganate
Potassium permanganate is an inorganic chemical compound with the formula KMnO4. It is a salt consisting of K+ and MnO4− ions. Formerly known as permanganate of potash or Condy's crystals, it is a strong oxidizing agent. It dissolves in water to give intensely purple solutions, the...

 (KMnO4) solutions.

The mineral
Mineral
A mineral is a naturally occurring solid chemical substance formed through biogeochemical processes, having characteristic chemical composition, highly ordered atomic structure, and specific physical properties. By comparison, a rock is an aggregate of minerals and/or mineraloids and does not...

 form of sodium oxalate is natroxalate. It is only very rarely found and restricted to extremely sodic conditions of ultra-alkaline pegmatite
Pegmatite
A pegmatite is a very crystalline, intrusive igneous rock composed of interlocking crystals usually larger than 2.5 cm in size; such rocks are referred to as pegmatitic....

s.

Preparation

Sodium oxalate can be prepared through the neutralization of oxalic acid with NaOH in a 1:2 acid-to-base molar ratio. Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces NaHC2O4, monobasic sodium oxalate or sodium hydrogenoxalate
Hydrogenoxalate
Hydrogenoxalate or hydrogen oxalate is an anion with chemical formula HC2O4− or HO2C–CO2−, derived from oxalic acid by the loss of a single proton; or, alternatively, from the oxalate anion C2O42− by addition of a proton....

.

Reactions

Sodium oxalate is used to standardize potassium permanganate
Potassium permanganate
Potassium permanganate is an inorganic chemical compound with the formula KMnO4. It is a salt consisting of K+ and MnO4− ions. Formerly known as permanganate of potash or Condy's crystals, it is a strong oxidizing agent. It dissolves in water to give intensely purple solutions, the...

 solutions. It is desirable that the temperature of the titration mixture is greater than 60 °C to ensure that all the permanganate added reacts quickly. The kinetics of the reaction is complex, and the manganate(II) ions formed catalyze the further reaction between permanganate and oxalic acid (formed in situ by the addition of excess sulfuric acid). The final equation is as follows:
5H2C2O4 + 2KMnO4 + 3H2SO4 → K2SO4 + 2MnSO4 + 10CO2 + 8H2O

Biological activity

Like several other oxalate
Oxalate
Oxalate , is the dianion with formula C2O42− also written 22−. Either name is often used for derivatives, such as disodium oxalate, 2C2O42−, or an ester of oxalic acid Oxalate (IUPAC: ethanedioate), is the dianion with formula C2O42− also written (COO)22−. Either...

s, sodium oxalate is toxic to humans. It can cause burning pain in the mouth, throat and stomach, bloody vomiting, headache, muscle cramps, cramps and convulsions, drop in blood pressure, heart failure, shock, coma, and possible death. Mean lethal dose by ingestion of oxalates is 10-15 grams (per MSDS).

Sodium oxalate, like citrate
Citrate
A citrate can refer either to the conjugate base of citric acid, , or to the esters of citric acid. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate.-Other citric acid ions:...

s, can also be used to remove calcium ions (Ca2+) from blood plasma. It also prevents blood from clotting. Note that by removing calcium ions from the blood, sodium oxalate can impair brain function, and deposit calcium oxalate in the kidneys.
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