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Potassium cyanide is a compound 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 ...
KCN. This colorless crystalline salt, similar in appearance to
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or do ...
, is highly soluble in water. Most KCN is used in gold mining,
organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
, and
electroplating Electroplating, also known as electrochemical deposition or electrodeposition, is a process for producing a metal coating on a solid substrate through the reduction of cations of that metal by means of a direct electric current. The part to be ...
. Smaller applications include
jewellery Jewellery ( UK) or jewelry ( U.S.) consists of decorative items worn for personal adornment, such as brooches, rings, necklaces, earrings, pendants, bracelets, and cufflinks. Jewellery may be attached to the body or the clothes. From a w ...
for chemical
gilding Gilding is a decorative technique for applying a very thin coating of gold over solid surfaces such as metal (most common), wood, porcelain, or stone. A gilded object is also described as "gilt". Where metal is gilded, the metal below was tradi ...
and buffing.Andreas Rubo, Raf Kellens, Jay Reddy, Joshua Wooten, Wolfgang Hasenpusch "Alkali Metal Cyanides" in Ullmann's Encyclopedia of Industrial Chemistry 2006 Wiley-VCH, Weinheim, Germany. Potassium cyanide is highly
toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a sub ...
. The moist solid emits small amounts of
hydrogen cyanide Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on a ...
due to
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
, which may smell like
bitter almonds The almond (''Prunus amygdalus'', syn. ''Prunus dulcis'') is a species of tree native to Iran and surrounding countries, including the Levant. The almond is also the name of the edible and widely cultivated seed of this tree. Within the genu ...
. Not everyone, however, can smell cyanide; the ability to do so is a
genetic trait Genetics is the study of genes, genetic variation, and heredity in organisms.Hartl D, Jones E (2005) It is an important branch in biology because heredity is vital to organisms' evolution. Gregor Mendel, a Moravian Augustinian friar working i ...
. The taste of potassium cyanide has been described as acrid and bitter, with a burning sensation similar to lye.


Production

KCN is produced by treating
hydrogen cyanide Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on a ...
with an aqueous solution of
potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...
, followed by evaporation of the solution in a vacuum: About 50,000 tons of potassium cyanide are produced yearly.


Historical production

Before 1900 and the invention of the
Castner process The Castner process is a process for manufacturing sodium metal by electrolysis of molten sodium hydroxide at approximately 330 °C. Below that temperature, the melt would solidify; above that temperature, the molten sodium would start to dissol ...
, potassium cyanide was the most important source of
alkali metal The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names ...
cyanides. In this historical process, potassium cyanide was produced by decomposing
potassium ferrocyanide Potassium ferrocyanide is the inorganic compound with formula K4 e(CN)6�3H2O. It is the potassium salt of the coordination complex e(CN)6sup>4−. This salt forms lemon-yellow monoclinic crystals. Synthesis In 1752, the French chemist Pie ...
:


Structure

In aqueous solution, KCN is dissociated into hydrated potassium (K+) ions and
cyanide Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of ...
(CN) ions. The common form of solid KCN, stable at ambient pressure and temperature, has the same cubic crystal structure as
sodium chloride Sodium chloride , commonly known as salt (although sea salt also contains other chemical salts), is an ionic compound with the chemical formula NaCl, representing a 1:1 ratio of sodium and chloride ions. With molar masses of 22.99 and 35. ...
, with each potassium ion surrounded by six cyanide ions, and vice versa. Despite the cyanide ions being diatomic, and thus less symmetric than chloride, they rotate so rapidly, their time-averaged shape is spherical. At low temperature and high pressure, this free rotation is hindered, resulting in a less symmetric crystal structure with the cyanide ions arranged in sheets. .


Applications

KCN and sodium cyanide (NaCN) are widely used in
organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
for the preparation of
nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including me ...
s and
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...
s, particularly in the
von Richter reaction The von Richter reaction, also named von Richter rearrangement, is a name reaction in the organic chemistry. It is named after Victor von Richter, who discovered this reaction in year 1871. It is the reaction of aromatic In chemistry, aromati ...
. It also finds use for the synthesis of hydantoins, which can be useful synthetic intermediates, when reacted with a carbonyl compound such as an
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl gro ...
or
ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double b ...
in the presence of ammonium carbonate. KCN is used as a photographic fixer in the wet plate
collodion process The collodion process is an early photographic process. The collodion process, mostly synonymous with the "collodion wet plate process", requires the photographic material to be coated, sensitized, exposed, and developed within the span of about ...
. The KCN dissolves silver where it has not been made insoluble by the developer. This reveals and stabilizes the image, making it no longer sensitive to light. Modern wet plate photographers may prefer less toxic fixers, often opting for
sodium thiosulfate Sodium thiosulfate (sodium thiosulphate) is an inorganic compound with the formula . Typically it is available as the white or colorless pentahydrate, . The solid is an efflorescent (loses water readily) crystalline substance that dissolves well ...
, but KCN is still used.


Potassium gold cyanide

In gold mining, KCN forms the water-soluble salt potassium gold cyanide (or gold potassium cyanide) and potassium hydroxide from gold metal in the presence of oxygen (usually from the surrounding air) and water: :4 Au + 8 KCN + O2 + 2 H2O → 4 K u(CN)2+ 4 KOH A similar process uses NaCN to produce sodium gold cyanide (NaAu(CN2)).


Toxicity

Potassium cyanide is a potent inhibitor of
cellular respiration Cellular respiration is the process by which biological fuels are oxidised in the presence of an inorganic electron acceptor such as oxygen to produce large amounts of energy, to drive the bulk production of ATP. Cellular respiration may be des ...
, acting on mitochondrial cytochrome c oxidase, hence blocking
oxidative phosphorylation Oxidative phosphorylation (UK , US ) or electron transport-linked phosphorylation or terminal oxidation is the metabolic pathway in which cells use enzymes to oxidize nutrients, thereby releasing chemical energy in order to produce adenosine t ...
. Lactic acidosis then occurs as a consequence of anaerobic metabolism. Initially, acute cyanide poisoning causes a red or ruddy complexion in the victim because the tissues are not able to use the
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements ...
in the blood. The effects of potassium cyanide and sodium cyanide are identical, and symptoms of poisoning typically occur within a few minutes of ingesting the substance: the person loses consciousness, and
brain death Brain death is the permanent, irreversible, and complete loss of brain function which may include cessation of involuntary activity necessary to sustain life. It differs from persistent vegetative state, in which the person is alive and some aut ...
eventually follows. During this period the victim may suffer convulsions. Death is caused by
cerebral hypoxia Cerebral hypoxia is a form of hypoxia (reduced supply of oxygen), specifically involving the brain; when the brain is completely deprived of oxygen, it is called ''cerebral anoxia''. There are four categories of cerebral hypoxia; they are, in ...
. The expected LD100 dose (human) for potassium cyanide is 200–300 mg while the median lethal dose LD50 is estimated at 140 mg. A number of prominent persons who were killed or died by
suicide Suicide is the act of intentionally causing one's own death. Mental disorders (including depression, bipolar disorder, schizophrenia, personality disorders, anxiety disorders), physical disorders (such as chronic fatigue syndrome), and ...
using potassium cyanide include: *
Viktor Meyer Viktor Meyer (8 September 18488 August 1897) was a German chemist and significant contributor to both organic and inorganic chemistry. He is best known for inventing an apparatus for determining vapour densities, the Viktor Meyer apparatus, and ...
, 19th-century German chemist, died by suicide in 1897 after taking cyanide *
Gustav Wied Gustav Johannes Wied (6 March 1858 – 24 October 1914) was a Danish writer. He was generally known as a satirical critic of society in his time and he deliberately used his writing talents to expose the establishment, bourgeoisie and rulin ...
, Danish novelist, poet, and playwright, in 1914 * Pritilata Waddedar, an Indian revolutionary nationalist, took cyanide in 1932 to avoid capture by British police * Badal Gupta, a revolutionary from Bengal, who is noted for launching an attack on the Writers' Building in Kolkata, consumed cyanide in 1930 immediately after the attack. He died at the age of 18. * Wallace Carothers, polymer chemist who died by suicide in 1937 after battling depression for years * Infamous personalities of
Nazi Germany Nazi Germany (lit. "National Socialist State"), ' (lit. "Nazi State") for short; also ' (lit. "National Socialist Germany") (officially known as the German Reich from 1933 until 1943, and the Greater German Reich from 1943 to 1945) was ...
, such as
Erwin Rommel Johannes Erwin Eugen Rommel () (15 November 1891 – 14 October 1944) was a German field marshal during World War II. Popularly known as the Desert Fox (, ), he served in the ''Wehrmacht'' (armed forces) of Nazi Germany, as well as servi ...
,
Hitler Adolf Hitler (; 20 April 188930 April 1945) was an Austrian-born German politician who was dictator of Nazi Germany, Germany from 1933 until Death of Adolf Hitler, his death in 1945. Adolf Hitler's rise to power, He rose to power as the le ...
's longtime companion Eva Braun,
Joseph Goebbels Paul Joseph Goebbels (; 29 October 1897 – 1 May 1945) was a German Nazi politician who was the '' Gauleiter'' (district leader) of Berlin, chief propagandist for the Nazi Party, and then Reich Minister of Propaganda from 1933 to ...
, Heinrich Himmler, and Hermann Göring *
World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the World War II by country, vast majority of the world's countries—including all of the great power ...
–era British agents (as purpose-made suicide pills) *
Alan Turing Alan Mathison Turing (; 23 June 1912 – 7 June 1954) was an English mathematician, computer scientist, logician, cryptanalyst, philosopher, and theoretical biologist. Turing was highly influential in the development of theoretical ...
, a computer scientist who died of cyanide poisoning in 1954 * Ramon Sampedro, Spanish tetraplegic and activist whose assisted suicide in 1998 provoked a national debate about Euthanasia, and was the subject of the Oscar-winning film "
The Sea Inside ''The Sea Inside'' ( es, Mar adentro) is a 2004 Spanish psychological drama film co-written and directed by Alejandro Amenábar, who also co-produced, scored and edited. It is based on the real-life story of Ramón Sampedro (played by Javier Bard ...
" * Ronald Clark O' Bryan, a Texas optician who killed his son by lacing a pixy stick with potassium cyanide in 1974 * Peoples Temple, the 1978 cult suicide in ( Jonestown), Guyana * Members of the
LTTE The Liberation Tigers of Tamil Eelam (LTTE; ta, தமிழீழ விடுதலைப் புலிகள், translit=Tamiḻīḻa viṭutalaip pulikaḷ, si, දෙමළ ඊළාම් විමුක්ති කොටි, t ...
involved in the assassination of Indian prime minister
Rajiv Gandhi Rajiv Gandhi (; 20 August 1944 – 21 May 1991) was an Indian politician who served as the sixth prime minister of India from 1984 to 1989. He took office after the 1984 assassination of his mother, then Prime Minister Indira Gandhi, to beco ...
in 1991 * Jason Altom, a promising graduate student in the lab of Nobel Prize–winning chemist EJ Corey at Harvard, died after drinking potassium cyanide in 1998 * John B. Mclemore, an Alabamian man whose life and 2015 suicide were the subject of the popular podcast "
S-Town ''S-Town'' is an American investigative journalism podcast hosted by Brian Reed and created by the producers of '' Serial'' and ''This American Life''. All seven chapters were released on March 28, 2017. The podcast was downloaded a record-breaki ...
" *
Slobodan Praljak Slobodan Praljak (; 2 January 1945 – 29 November 2017) was a Bosnian Croat who served in the Croatian Army and the Croatian Defence Council, an army of the Croatian Republic of Herzeg-Bosnia, between 1992 and 1995. Praljak was found guilty of ...
, a wartime general in Republic of Croatia, died by suicide by drinking from a vial containing potassium cyanide during the reading of his appeal judgment in
The Hague The Hague ( ; nl, Den Haag or ) is a city and municipality of the Netherlands, situated on the west coast facing the North Sea. The Hague is the country's administrative centre and its seat of government, and while the official capital o ...
on
International Criminal Tribunal for the former Yugoslavia The International Criminal Tribunal for the former Yugoslavia (ICTY) was a body of the United Nations that was established to prosecute the war crimes that had been committed during the Yugoslav Wars and to try their perpetrators. The tribunal ...
(ICTY) on 29 November 2017. It is used by professional
entomologist Entomology () is the scientific study of insects, a branch of zoology. In the past the term "insect" was less specific, and historically the definition of entomology would also include the study of animals in other arthropod groups, such as ara ...
s as a killing agent in collecting jars, as
insect Insects (from Latin ') are pancrustacean hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body ( head, thorax and abdomen), three pa ...
s succumb within seconds to the HCN fumes it emits, thereby minimizing damage to even highly fragile specimens. KCN can be detoxified most efficiently with
hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3 ...
or with a solution of sodium hypochlorite. Such solutions should be kept alkaline whenever possible so as to eliminate the possibility of generation of hydrogen cyanide: : KCN + H2O2 → K OCN + H2O


References


External links


International Chemical Safety Card 0671


( CICAD 61)
National Pollutant Inventory - Cyanide compounds fact sheet



CSST (Canada)

NIST Standard Reference Database
* Institut national de recherche et de sécurité (1997).
Cyanure de sodium. Cyanure de potassium
. ''Fiche toxicologique n° 111'', Paris:INRS, 6pp. {{Authority control Cyanides Photographic chemicals Potassium compounds