Cyanide
Names | |
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Preferred IUPAC name
Cyanide | |
Systematic IUPAC name
Nitridocarbonate(II) | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
PubChem CID
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UNII | |
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Properties | |
CN− | |
Molar mass | 26.018 g·mol−1 |
Conjugate acid
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Hydrogen cyanide |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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The cyanide ion CN− is one of the most poisonous chemicals. It may cause death in minutes. |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In
In
Bonding
The cyanide ion −C≡N is
Occurrence
In nature
Cyanides are produced by certain
The Madagascar bamboo Cathariostachys madagascariensis produces cyanide as a deterrent to grazing. In response, the golden bamboo lemur, which eats the bamboo, has developed a high tolerance to cyanide.
The
Interstellar medium
The
Pyrolysis and combustion product
Hydrogen cyanide is produced by the combustion or pyrolysis of certain materials under oxygen-deficient conditions. For example, it can be detected in the exhaust of internal combustion engines and tobacco smoke. Certain plastics, especially those derived from acrylonitrile, release hydrogen cyanide when heated or burnt.[11]
Organic derivatives
In IUPAC nomenclature, organic compounds that have a −C≡N functional group are called nitriles.[12][13] An example of a nitrile is acetonitrile, CH3−C≡N. Nitriles usually do not release cyanide ions. A functional group with a hydroxyl −OH and cyanide −CN bonded to the same carbon atom is called cyanohydrin (R2C(OH)CN). Unlike nitriles, cyanohydrins do release poisonous hydrogen cyanide.
Reactions
Protonation
Cyanide is basic. The pKa of hydrogen cyanide is 9.21. Thus, addition of
Hydrolysis
Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes hydrolysis to give ammonia and formate, which are far less toxic than cyanide:[14]
- CN− + 2 H2O → HCO−2 + NH3
Cyanide hydrolase is an enzyme that catalyzes this reaction.
Alkylation
Because of the cyanide anion's high
- RX + CN− → RCN + X−
Redox
The cyanide ion is a
Metal complexation
The cyanide anion reacts with
Among the most important cyanide coordination compounds are the potassium ferrocyanide and the pigment Prussian blue, which are both essentially nontoxic due to the tight binding of the cyanides to a central iron atom.[20] Prussian blue was first accidentally made around 1706, by heating substances containing iron and carbon and nitrogen, and other cyanides made subsequently (and named after it). Among its many uses, Prussian blue gives the blue color to
Manufacture
The principal process used to manufacture cyanides is the
- 2 CH4 + 2 NH3 + 3 O2 → 2 HCN + 6 H2O
Sodium cyanide, the precursor to most cyanides, is produced by treating hydrogen cyanide with sodium hydroxide:[14]
- HCN + NaOH → NaCN + H2O
Toxicity
Many cyanides are highly toxic. The cyanide anion is an
The most hazardous compound is
Organic nitriles do not readily release cyanide ions, and so have low toxicities. By contrast, compounds such as trimethylsilyl cyanide (CH3)3SiCN readily release HCN or the cyanide ion upon contact with water.[25]
Antidote
Hydroxocobalamin reacts with cyanide to form cyanocobalamin, which can be safely eliminated by the kidneys. This method has the advantage of avoiding the formation of methemoglobin (see below). This antidote kit is sold under the brand name Cyanokit and was approved by the U.S. FDA in 2006.[26]
An older cyanide antidote kit included administration of three substances:
Sensitivity
Minimum risk levels (MRLs) may not protect for delayed health effects or health effects acquired following repeated sublethal exposure, such as hypersensitivity, asthma, or bronchitis. MRLs may be revised after sufficient data accumulates.[28]
Applications
Mining
Cyanide is mainly produced for the
The "pregnant liquor" containing these ions is separated from the solids, which are discarded to a
Aqueous cyanide is hydrolyzed rapidly, especially in sunlight. It can mobilize some heavy metals such as mercury if present. Gold can also be associated with arsenopyrite (FeAsS), which is similar to
Industrial organic chemistry
The second major application of alkali metal cyanides (after mining) is in the production of CN-containing compounds, usually nitriles. Acyl cyanides are produced from acyl chlorides and cyanide. Cyanogen, cyanogen chloride, and the trimer cyanuric chloride are derived from alkali metal cyanides.
Medical uses
The cyanide compound
Illegal fishing and poaching
Cyanides are illegally used to capture live fish near coral reefs for the aquarium and seafood markets. The practice is controversial, dangerous, and damaging but is driven by the lucrative exotic fish market.[31]
Poachers in Africa have been known to use cyanide to poison waterholes, to kill elephants for their ivory.[32]
Pest control
Cyanides are used as insecticides for fumigating ships.[36] Cyanide salts are used for killing ants,[37] and have in some places been used as rat poison[38] (the less toxic poison arsenic is more common).[39]
Niche uses
Potassium ferrocyanide is used to achieve a blue color on cast bronze sculptures during the final finishing stage of the sculpture. On its own, it will produce a very dark shade of blue and is often mixed with other chemicals to achieve the desired tint and hue. It is applied using a torch and paint brush while wearing the standard safety equipment used for any patina application: rubber gloves, safety glasses, and a respirator. The actual amount of cyanide in the mixture varies according to the recipes used by each foundry.
Cyanide is also used in
Although usually thought to be toxic, cyanide and cyanohydrins increase germination in various plant species.[40][41]
Human poisoning
Deliberate cyanide poisoning of humans has occurred many times throughout history.[42] Common salts such as
Food additive
Because of the high stability of their complexation with
Chemical tests for cyanide
Cyanide is quantified by potentiometric titration, a method widely used in gold mining. It can also be determined by titration with silver ion. Some analyses begin with an air-purge of an acidified boiling solution, sweeping the vapors into a basic absorber solution. The cyanide salt absorbed in the basic solution is then analyzed.[45]
Qualitative tests
Because of the notorious toxicity of cyanide, many methods have been investigated. Benzidine gives a blue coloration in the presence of
References
- .
- ^ "Environmental and Health Effects of Cyanide". International Cyanide Management Institute. 2006. Archived from the original on 30 November 2012. Retrieved 4 August 2009.
- ISBN 0-7506-3365-4.[page needed]
- ISBN 0-13-035471-6.[page needed]
- ^ "ToxFAQs for Cyanide". Agency for Toxic Substances and Disease Registry. July 2006. Retrieved 2008-06-28.
- PMID 10669009.
- PMID 9431670.
- (PDF) from the original on 2020-11-23.
- PMID 16599455. Archived from the original(PDF) on 2008-09-11. Retrieved 2008-08-23.
- doi:10.1086/186961.
- ^ a b Anon (June 27, 2013). "Facts about cyanide:Where cyanide is found and how it is used". CDC Emergency preparedness and response. Centers for Disease Control and Prevention. Retrieved 10 December 2016.
- IUPAC Gold Book nitriles
- ^ NCBI-MeSH Nitriles
- ^ ISBN 978-3527306732.
- ISBN 978-3527306732.
- ^ Young, C. A., & Jordan, T. S. (1995, May). Cyanide remediation: current and past technologies. In: Proceedings of the 10th Annual Conference on Hazardous Waste Research (pp. 104–129). Kansas State University: Manhattan, KS. https://engg.ksu.edu/HSRC/95Proceed/young.pdf
- ^ Dmitry Yermakov. "Cyanide Destruction | SRK Consulting". srk.com. Retrieved 2 March 2021.
- ^ Botz Michael M. Overview of cyanide treatment methods. Elbow Creek Engineering, Inc. http://www.botz.com/MEMCyanideTreatment.pdf
- ^ Sharpe, A. G. The Chemistry of Cyano Complexes of the Transition Metals; Academic Press: London, 1976[page needed]
- ISBN 978-0-12-352651-9.
- .
- .
- ISBN 978-1-57259-153-0.
- ^ ISBN 978-0-7817-7906-7.
- ^ "MSDS of trimethylsilyl cyanide" (PDF). Gelest Inc. 2008. Archived (PDF) from the original on 2022-10-10. Retrieved 2022-08-16.
- ^ Cyanide Toxicity~treatment at eMedicine
- .
- ^ Toxicological Profile for Cyanide (PDF) (Report). U.S. Department of Health and Human Services. 2006. pp. 18–19. Archived (PDF) from the original on 2004-03-31.
- S2CID 132571397. Retrieved 24 April 2022.
- PMID 19868035. Retrieved 2008-06-28.
- ^ Dzombak, David A; Ghosh, Rajat S; Wong-Chong, George M. Cyanide in Water and Soil. CRC Press, 2006, Chapter 11.2: "Use of Cyanide for Capturing Live Reef Fish".
- ^ Poachers kill 80 elephants with cyanide in Zimbabwe ABC News, 25 September 2013. Retrieved 30 October 2015.
- doi:10.1002/wsb.361.
- ^ Green, Wren (July 2004). "The use of 1080 for pest control" (PDF). New Zealand Department of Conservation. Retrieved 8 June 2011.
- ^ Shapiro, Lee; et al. (21 March 2011). "Effectiveness of cyanide pellets for control of dama wallabies (Macropus eugenii)" (PDF). New Zealand Journal of Ecology. 35 (3). Archived (PDF) from the original on 2015-02-03.
- ^ "Sodium Cyanide". PubChem. National Center for Biotechnology Information. 2016. Retrieved 2 September 2016.
Cyanide and hydrogen cyanide are used in electroplating, metallurgy, organic chemicals production, photographic developing, manufacture of plastics, fumigation of ships, and some mining processes.
- ^ "Reregistration Eligibility Decision (RED) Sodium Cyanide" (PDF). EPA.gov. 1 September 1994. p. 7. Archived (PDF) from the original on 2022-10-10. Retrieved 2 September 2016.
Sodium cyanide was initially registered as a pesticide on December 23, 1947, to control ants on uncultivated agricultural and non-agricultural areas.
- ^ "Tariff Information, 1921: Hearings on General Tariff Revision Before the Committee on Ways and Means, House of Representatives". AbeBooks.com. US Congress, House Committee on Ways and Means, US Government Printing Office. 1921. p. 3987. Retrieved 2 September 2016.
Another field in which cyanide is used in growing quantity is the eradication of rats and other vermin – especially in the fight against typhus.
- ^ "Deadliest Poisons Used by Man". PlanetDeadly.com. 18 November 2013. Archived from the original on 11 May 2016. Retrieved 2 September 2016.
- PMID 16658492.
- S2CID 2533762.
- ISBN 978-0-16-081320-7., Extract p. 41
- ISBN 978-3-527-27766-7.
- ISBN 978-3527306732.
- ISBN 978-3527306732.
- PMID 7423496.
External links
- ATSDR medical management guidelines for cyanide poisoning (US)
- HSE recommendations for first aid treatment of cyanide poisoning (UK)
- Hydrogen cyanide and cyanides (CICAD61)
- IPCS/CEC Evaluation of antidotes for poisoning by cyanides
- National Pollutant Inventory – Cyanide compounds fact sheet
- Eating apple seeds is safe despite the small amount of cyanide
- Toxicological Profile for Cyanide, U.S. Department of Health and Human Services, July 2006
- Safety data (French)
- Institut national de recherche et de sécurité (1997). "Cyanure d'hydrogène et solutions aqueuses". Fiche toxicologique n° 4, Paris: INRS, 5 pp. (PDF file, (in French))
- Institut national de recherche et de sécurité (1997). "Cyanure de sodium. Cyanure de potassium". Fiche toxicologique n° 111, Paris: INRS, 6 pp. (PDF file, (in French))