Potassium hydrogenoxalate
Encyclopedia
Potassium hydrogenoxalate, also known as potassium bioxalate, is a salt with formula KHC2O4 or K+·HO2C-CO2. It is one of the most common salts of the 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....

 anion, and can be obtained by reacting potassium hydroxide
Potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula KOH, commonly called caustic potash.Along with sodium hydroxide , this colorless solid is a prototypical strong base. It has many industrial and niche applications. Most applications exploit its reactivity toward acids and its corrosive...

 with 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...

 in 1:1 mole ratio.

The salt is also known as potassium hydrogen oxalate, potassium binoxalate, acid potassium oxalate, or monobasic potassium oxalate. In older literature, it was also called sorrel salt, sal acetosella, or (rather improperly) salt of lemon

Potassium hydrogenoxalate occurs in some plants, notably sorrel. It is a commercial product, used in photography, marble grinding, and to remove ink stains.

Properties

The anhydrous
Anhydrous
As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another...

 product is a white, odorless, crystalline solid, hygroscopic and soluble in water (2.5 g/100 g at room temperature). The solutions are basic. Below 50 °C the much less soluble potassium tetraoxalate forms and precipitates out of solution.

The monohydrate
Hydrate
Hydrate is a term used in inorganic chemistry and organic chemistry to indicate that a substance contains water. The chemical state of the water varies widely between hydrates, some of which were so labeled before their chemical structure was understood....

 KHC2O4·H2O starts losing the water at 100 °C.

The anhydrous salt was found to have remarkable elastic anisotropy
Elasticity (physics)
In physics, elasticity is the physical property of a material that returns to its original shape after the stress that made it deform or distort is removed. The relative amount of deformation is called the strain....

, due to its crystal structure
Crystal structure
In mineralogy and crystallography, crystal structure is a unique arrangement of atoms or molecules in a crystalline liquid or solid. A crystal structure is composed of a pattern, a set of atoms arranged in a particular way, and a lattice exhibiting long-range order and symmetry...

 that consists of relatively rigid columns of hydrogen-bonded
Hydrogen bond
A hydrogen bond is the attractive interaction of a hydrogen atom with an electronegative atom, such as nitrogen, oxygen or fluorine, that comes from another molecule or chemical group. The hydrogen must be covalently bonded to another electronegative atom to create the bond...

 hydrogenoxalate anions, joined into sheets by ionic
Ionic bond
An ionic bond is a type of chemical bond formed through an electrostatic attraction between two oppositely charged ions. Ionic bonds are formed between a cation, which is usually a metal, and an anion, which is usually a nonmetal. Pure ionic bonding cannot exist: all ionic compounds have some...

K–O bonds.

Toxicity

Potassium hydrogenoxalate is strongly irritating to eyes, mucoses and gastrointestinal tract. It may cause cardiac failure and death.
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