Potassium Cyanate
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Potassium cyanate is an
inorganic compound An inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds⁠that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as ''inorganic chemistry''. Inorgan ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
KOCN (sometimes denoted KCNO). It is a colourless solid. It is used to prepare many other compounds including useful
herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...
. Worldwide production of the potassium and sodium salts was 20,000 tons in 2006.Peter M. Schalke1, "Cyanates, Inorganic Salts" Ullmann's Encyclopedia of Industrial Chemistry2006, Wiley-VCH, Weinheim. . Article Online Posting Date: July 15, 2006


Structure and bonding

The
cyanate The cyanate ion is an anion with the chemical formula . It is a resonance of three forms: (61%) ↔ (30%) ↔ (4%). Cyanate is the derived anion of isocyanic acid, H−N=C=O, and its lesser tautomer cyanic acid (a.k.a. cyanol), H−O−C ...
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...
is isoelectronic with
carbon dioxide Carbon dioxide is a chemical compound with the chemical formula . It is made up of molecules that each have one carbon atom covalent bond, covalently double bonded to two oxygen atoms. It is found in a gas state at room temperature and at norma ...
and with the
azide In chemistry, azide (, ) is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant ...
anion, being linear. The C-N distance is 121 pm, about 5 pm longer than for
cyanide In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This a ...
. Potassium cyanate is isostructural with potassium azide.


Uses

The potassium and sodium salts can be used interchangeably for the majority of applications. Potassium cyanate is often preferred to the sodium salt, which is less soluble in water and less readily available in pure form. Potassium cyanate is used as a basic raw material for various organic syntheses, including,
urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...
derivatives,
semicarbazide Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea. Synthesis The compound prepared by treating urea with hydrazine:Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazi ...
s,
carbamate In organic chemistry, a carbamate is a category of organic compounds with the general Chemical formula, formula and Chemical structure, structure , which are formally Derivative (chemistry), derived from carbamic acid (). The term includes orga ...
s and
isocyanate In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...
s. For example, it is used to prepare the drug hydroxyurea. It is also used for the
heat treatment Heat treating (or heat treatment) is a group of industrial, thermal and metalworking processes used to alter the physical, and sometimes chemical, properties of a material. The most common application is metallurgical. Heat treatments are a ...
of metals (e.g.,
Ferritic nitrocarburizing Ferritic nitrocarburizing or FNC, also known by the proprietary names "Tenifer", "Tufftride", Melonite, and "Arcor",Other trade names include Tuffride/ Tuffrider, QPQ, Sulfinuz, Sursulf, Meli 1, and Nitride, among others is a range of proprietar ...
).


Therapeutic uses

Potassium cyanate has been used to reduce the percentage of sickled erythrocytes under certain conditions and has also increased the number of deformalities. In an aqueous solution, it has prevented irreversibly the in vitro sickling of hemoglobins containing human erythrocytes during deoxygenization. Veterinarians have also found potassium cyanate useful in that the cyanate salts and isocyanates can treat parasite diseases in both birds and mammals.


Preparation and reactions

KOCN is prepared by heating
urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...
with
potassium carbonate Potassium carbonate is the inorganic compound with the formula . It is a white salt, which is soluble in water and forms a strongly alkaline solution. It is deliquescent, often appearing as a damp or wet solid. Potassium carbonate is mainly used ...
at 400 °C: :2 OC(NH2)2 + K2CO3 → 2 KOCN + (NH4)2CO3 The reaction produces a liquid. Intermediates and impurities include
biuret Biuret ( ) is a chemical compound with the chemical formula . It is a white solid that is soluble in hot water. A variety of organic derivatives are known. The term "biuret" also describes a family of organic compounds with the chemical formula , ...
,
cyanuric acid Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the chemical formula, formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a com ...
, and potassium allophanate (KO2CNHC(O)NH2), as well as unreacted starting urea, but these species are unstable at 400 °C. Protonation gives a 97:3 mixture (at room temperature) of two
tautomer In chemistry, tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the reloca ...
s, HNCO (
isocyanic acid Isocyanic acid is a chemical compound with the structural formula HNCO, which is often written as . It is a colourless, volatile and poisonous gas, condensing at 23.5 °C. It is the predominant tautomer and an isomer of cyanic acid ''( ...
) and NCOH (cyanic acid). This mixture is stable at high dilution but trimerizes on concentration to give
cyanuric acid Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the chemical formula, formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a com ...
.


Properties

Potassium carbonate crystals are destroyed by the melting process so that the urea can react with almost all potassium ions to convert to potassium cyanate at a higher rate than when in the form of a salt. This makes it easier to reach higher purities above 95%. It can also be made by oxidizing potassium cyanide at a high temperature in the presence of oxygen or easily reduced oxides, such as lead, tin, or manganese dioxide, and in aqueous solution by reacting with hypochlorites or hydrogen peroxide. Another way to synthesize it is to allow an alkali metal cyanide to react with oxygen in nickel containers under controlled conditions. It can be formed by the oxidation of ferrocyanide. Lastly, it can be made by heating potassium cyanide with lead oxide."Potassium cyanate" https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=11378442&loc=ec_rcs


References


External links


MSDS


{{Cyanates Potassium compounds Cyanates