Cyanuric acid


Cyanuric acid
Cyanuric acid
Identifiers
CAS number 108-80-5 YesY
PubChem 7956
ChemSpider 7668 YesY
KEGG C06554 YesY
ChEBI CHEBI:17696 YesY
ChEMBL CHEMBL243087 YesY
RTECS number XZ1800000
Jmol-3D images Image 1
Properties
Molecular formula C3H3N3O3
Molar mass 129.07 g/mol
Appearance white crystalline powder
Density 2.5 g/cm3
Melting point

decomp. 320–360 ºC

Solubility in water 0.27 g/100 ml (25 ºC)
Hazards
MSDS ICSC 1313
Related compounds
Related triazines Cyanuric fluoride
Cyanuric chloride
 YesY acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleaches, disinfectants, and herbicides. In 1997, worldwide production was 160 million kilograms.[1]

Contents

Properties and synthesis

Properties

Cyanuric acid is the cyclic trimer of the elusive species cyanic acid, HOCN. The two structures shown in the infobox readily interconvert; that is, they are tautomers. However, mixture with melamine forms melamine cyanurate, which locks cyanuric acid in the tri-keto tautomer and makes melamine cyanurate insoluble in water. The triol tautomer, which may have aromatic character, predominates in solution. The hydroxyl (-OH) groups assume phenolic character. Deprotonation with base affords a series of cyanurate salts:

[C(O)NH]3 \overrightarrow{\leftarrow} [C(O)NH]2[C(O)N]- + H+ (Ka = 10−7)
[C(O)NH]2[C(O)N]- \overrightarrow{\leftarrow} [C(O)NH][C(O)N]22- + H+ (Ka = 10−11)
[C(O)NH][C(O)N]22- \overrightarrow{\leftarrow} [C(O)N]33- + H+ (Ka = 10−14)

Synthesis

Cyanuric acid (CYA) was first synthesized by Friedrich Wöhler in 1829 by the thermal decomposition of urea and uric acid.[2] The current industrial route to CYA entails the thermal decomposition of urea, with release of ammonia. The conversion commences at approximately 175 °C:[1]

3 H2N-CO-NH2 → [C(O)NH]3 + 3 NH3

CYA crystallizes from water as the dihydrate.

Cyanuric acid can be produced by hydrolysis of crude or waste melamine followed by crystallization. Acid waste streams from plants producing these materials contain cyanuric acid and on occasion, dissolved amino-substituted triazines, namely, ammeline, ammelide, and melamine. In one method, an ammonium sulfate solution is heated to the "boil" and treated with a stoichiometric amount of melamine, by which means the cyanuric acid present precipitates as melamine-cyanuric acid complex. The various waste streams containing cyanuric acid and amino-substituted triazines may be combined for disposal and during upset conditions, undissolved cyanuric acid may be present in the waste streams. [3][4]

Intermediates and impurities

Intermediates in the dehydration include both isocyanic acid, biuret, and triuret:

H2N-CO-NH2 → HNCO + NH3
H2N-CO-NH2 + HNCO → H2N-CO-NH-CO-NH2
H2N-CO-NH-CO-NH2 + HNCO → H2N-CO-NH-CO-NH-CO-NH2

One impurity in the production of CYA is ammelide, especially as the reaction temperature exceeds 190 °C: 3 H2N-CO-NH-CO-NH2 → [C(O)]2(CNH2)(NH)2N + 2 NH3 + H2O The first appearance of ammelamide occurs prior to 225 °C and is suspected also to occur from decomposition of biuret but is produced at a slower rate than that of CYA.

Melamine, [C(NH2)N]3, formation occurs between 325 and 350 °C and only in very small quantities.[5]

Applications

Precursors to chlorinated cyanurates

Cyanuric acid is mainly used as a precursor to N-chlorinated cyanurates, which are used to disinfect water. The dichloro derivative is prepared by direct chlorination:

[C(O)NH]3 + 2 Cl2 + 2 NaOH → [C(O)NCl]2[C(O)NH]

This species is typically converted to its sodium salt, sodium dichloro-s-triazinetrione. Further chlorination gives trichloroisocyanuric acid, [C(O)NCl]3. These N-chloro compounds serve as disinfectants and algicides for swimming pool water.[1] It stabilizes the chlorine in the pool and prevents the chlorine from being quickly consumed by sunlight.

Precursors to crosslinking agents

Because of their trifunctionality, CYA is a precursor to crosslinking agents, especially for polyurethane resins.

Analysis

Testing for cyanuric acid concentration is commonly done with a turbidometric test, which uses a reagent, melamine, to precipitate the cyanuric acid. The relative turbidity of the reacted sample quantifies the CYA concentration. Referenced in 1957.[6] This test works because melamine combines with the cyanuric acid in the water to form a fine, insoluble, white precipitate (melamine cyanurate) that causes the water to cloud in proportion to the amount of cyanuric acid in it.

Animal feed

FDA permits a certain amount of cyanuric acid to be present in some non-protein nitrogen (NPN) additives used in animal feed and drinking water.[7] Cyanuric acid has been used as NPN. For example, Archer Daniels Midland manufactures an NPN supplement for cattle, which contains biuret, triuret, cyanuric acid and urea.[8]

2007 pet food recalls

Cyanuric acid is implicated in connection to the 2007 pet food recalls, the contamination and wide recall of many brands of cat and dog foods beginning in March 2007. Research has found evidence that cyanuric acid, a constituent of urine, together with melamine forms poorly soluble crystals which can cause renal failure (see Analysis section above).

Safety

Cyanuric acid is classified as "essentially nontoxic".[1] The 50% oral median lethal dose (LD50) is 7700 mg/kg in rats.[9]

However, when cyanuric acid is administered together with melamine (which by itself is another low-toxicity substance), they may form extremely insoluble crystals,[10] leading to formation of kidney stones and potentially causing kidney failure and death -- as evidenced in dogs and cats during the 2007 pet food contamination and in children during the 2008 Chinese milk scandal cases.

See also

References

  1. ^ a b c d Klaus Huthmacher, Dieter Most "Cyanuric Acid and Cyanuric Chloride" Ullmann's Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. ISBN 10.1002/14356007.a08 191
  2. ^ Wöhler, F. On the decomposition of urea and uric acid at high temperature. Ann Phys Chemie 1829 15:619-30
  3. ^ "Process for preparing pure cyanuric acid". July 14, 1981. http://www.freepatentsonline.com/4278794.html. Retrieved 2007-12-10. 
  4. ^ "High pressure thermal hydrolysis process to decompose triazines in acid waste streams". March 22, 1977. http://www.freepatentsonline.com/4013757.html. Retrieved 2007-12-10. 
  5. ^ Shaber, Peter M. et al. "Study of the thermal decomposition of urea (pyrolysis) reaction and importance to cyanuric acid production," American Laboratory, August 1999: 13-21[1]
  6. ^ "Merck Turbidity Test". Merck. June 6, 2003. http://www.merckserono.net/servlet/PB/menu/1169010/index.html. Retrieved 2007-05-06. 
  7. ^ "21CFR573.220 Feed-grade biuret". U.S. Food and Drug Administration. April 1, 2006. http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=573.220. Retrieved 2007-05-06. 
  8. ^ "Roughage Buster Plus: ingredients". Archer Daniels Midland. http://www.admani.com/alliancebeef/RoughageBusterPlus.htm. Retrieved 2007-05-06. 
  9. ^ U.S. Food and Drug Administration, "Interim Melamine and Analogues Safety/Risk Assessment; Availability", Federal Register: May 30, 2007 (Volume 72, Number 103). Accessed 2008-09-27.
  10. ^ "Melamine and Cyanuric Acid Interaction May Play Part in Illness and Death from Recalled Pet Food", American Veterinary Medical Association (AVMA), Press Release, May 1, 2007. Accessed 2008-09-27.

External links


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Look at other dictionaries:

  • Cyanuric acid — (Chem.), an organic acid, {C3O3N3H3}, first obtained by heating uric acid or urea, and called {pyrouric acid}; afterwards obtained from {isocyanic acid}. It is a white crystalline substance, odorless and almost tasteless; called also… …   The Collaborative International Dictionary of English

  • cyanuric acid — [sī΄ə nyoorik] n. [ CYAN(O) + URIC] a white, crystalline acid, C3N3 (OH) 3, made by heating urea and used in making melamine, bleaches, etc …   English World dictionary

  • cyanuric acid — cianuro rūgštis statusas T sritis chemija formulė C₃N₃(OH)₃ atitikmenys: angl. cyanuric acid rus. циануровая кислота ryšiai: sinonimas – 1,3,5 triazin 2,4,6 triolis …   Chemijos terminų aiškinamasis žodynas

  • cyanuric acid — /saɪəˌnjurɪk ˈæsəd/ (say suyuh.nyoohrik asuhd) noun a heterocyclic substance, C3H3N3O3.2H20, obtained by heating urea or by the action of water on cyanuric chloride; tricyanic acid …   Australian English dictionary

  • cyanuric acid — noun Etymology: cyan + urea Date: 1838 a crystalline weak acid C3N3(OH)3 that yields cyanic acid when heated …   New Collegiate Dictionary

  • cyanuric acid — A cyclic product formed by heating urea; used industrially and as an herbicide. * * * cy·an·uric acid .sī ə .n(y)u̇r ik n a crystalline weak acid C3H3N3O3 used esp. in swimming pools to protect the available chlorine from dissipation by sunlight… …   Medical dictionary

  • cyanuric acid — noun a trimer of cyanic acid • Hypernyms: ↑acid …   Useful english dictionary

  • cyanuric acid — a white, crystalline, water soluble solid, C3H3O3N3·2H2O, used chiefly in organic synthesis. Also called tricyanic acid. [1875 80] * * * …   Universalium

  • cyanuric acid — noun An aromatic heterocyclic organic compound, CN(OH), that decomposes on heating to form cyanic acid; it is a prebiotic compound found in stellar dust clouds. Syn: tri …   Wiktionary

  • cyanuric acid — cy′a•nu′ric ac′id [[t]ˈsaɪ əˈnʊər ɪk, ˈnyʊər , ˌsaɪ [/t]] n. chem. a white crystalline solid, C3H3O3N3∙2H2O, used chiefly in organic synthesis • Etymology: 1875–80; cyan +uric …   From formal English to slang