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{{Short description|Chemical compound belonging to the class of triazine}} |
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{{distinguish|text = ] (hydrogen cyanide, HCN), nor with ]}} |
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| verifiedrevid = 408408600 |
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| verifiedrevid = 443544577 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Cyanuric acid.png |
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| ImageFile = Cyanuric acid.png |
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| ImageSize = 250px |
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| ImageName = Structural formulae of both tautomers |
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| ImageName = Structural formulae of both tautomers |
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| ImageFileR2 = Cyanuric-acid-from-xtal-3D-balls.png |
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| ImageFileR2 = Cyanuric-acid-from-xtal-3D-balls.png |
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| ImageSizeR2 = 120px |
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| ImageNameR2 = Ball-and-stick model of the trione tautomer |
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| ImageNameR2 = Ball-and-stick model of the trione tautomer |
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| ImageCaptionR2=Isocyanuric (trione) tautomer |
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| ImageFileL2 = Cyanuric-acid-triol-3D-balls.png |
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| ImageFileL2 = Cyanuric-acid-triol-3D-balls.png |
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| ImageSizeL2 = 120px |
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| ImageSizeL2 = 120px |
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| ImageNameL2 = Ball-and-stick model of the triol tautomer |
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| ImageNameL2 = Ball-and-stick model of the triol tautomer |
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| ImageCaptionL2=Cyanuric (triol) tautomer |
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| IUPACName = 1,3,5-Triazinane-2,4,6-trione |
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| PIN = 1,3,5-Triazinane-2,4,6-trione<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 733 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}<!-- corrected according to http://www.chem.qmul.ac.uk/iupac/bibliog/BBerrors.html --></ref> |
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| OtherNames = 1,3,5-Triazinetriol; ''s''-Triazinetriol; 1,3,5-Triazine-2,4,6(1''H'',3''H'',5''H'')-trione; ''s''-Triazinetrione; Tricarbimide; Isocyanuric acid; Seudocyanuric acid |
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| OtherNames = 1,3,5-Triazine-2,4,6(1''H'',3''H'',5''H'')-trione<ref name=iupac2013 /><br />1,3,5-Triazinetriol<br />''s''-Triazinetriol<br />''s''-Triazinetrione<br />Tricarbimide<br />Isocyanuric acid<br />Pseudocyanuric acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C06554 |
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| KEGG = C06554 |
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| InChI = 1/C3H3N3O3/c7-1-4-2(8)6-3(9)5-1/h(H3,4,5,6,7,8,9) |
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| InChI = 1/C3H3N3O3/c7-1-4-2(8)6-3(9)5-1/h(H3,4,5,6,7,8,9) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZFSLODLOARCGLH-UHFFFAOYSA-N |
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| StdInChIKey = ZFSLODLOARCGLH-UHFFFAOYSA-N |
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| CASNo=108-80-5 |
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| CASNo =108-80-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 6202-04-6 |
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| PubChem=7956 |
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| CASNo1_Comment = (Dihydrate) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = H497R4QKTZ |
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| PubChem =7956 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7668 |
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| ChemSpiderID = 7668 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17696 |
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| ChEBI = 17696 |
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| SMILES = O=C1NC(=O)NC(=O)N1 |
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| SMILES = Oc1nc(O)nc(O)n1 |
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| RTECS = XZ1800000 |
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| SMILES_Comment = Cyanuric (triol) tautomer |
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| SMILES1 = O=C1NC(=O)NC(=O)N1 |
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| SMILES1_Comment = Isocyanuric (trione) tautomer |
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| RTECS = XZ1800000 |
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}} |
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}} |
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| Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>3</sub>H<sub>3</sub>N<sub>3</sub>O<sub>3</sub> |
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| Formula = C<sub>3</sub>H<sub>3</sub>N<sub>3</sub>O<sub>3</sub> |
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| MolarMass = 129.07 g/mol |
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| MolarMass = 129.07 g/mol |
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| Appearance = white crystalline powder |
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| Appearance = white crystalline powder |
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| Density = 2.5 g/cm<sup>3</sup> |
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| Density = 1.75 g/cm<sup>3</sup> |
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| MeltingPt = decomp. 320–360 ºC |
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| MeltingPtC = 320–360 |
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| MeltingPt_notes = decomposes |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = 0.27 g/100 ml (25 ºC) |
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| Solubility = 2700 mg/L (25 °C) |
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| MagSus = -61.5·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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}} |
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| Section7= {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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}} |
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| Section8= {{Chembox Related |
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| OtherFunctn = ]<br/>] |
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| Function = ]s |
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| OtherCpds = |
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}} |
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}} |
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|Section8={{Chembox Related |
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| OtherFunction = ]<br/>]<br/>] |
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| OtherFunction_label = ]s |
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| OtherCompounds = |
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}} |
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}} |
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}} |
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'''Cyanuric acid''' or '''1,3,5-triazine-2,4,6-triol''' is a ] with the ] (CNOH)<sub>3</sub>. Like many industrially useful chemicals, this ] has many synonyms. This white, odorless solid finds use as a precursor or a component of ]es, disinfectants, and herbicides. In 1997, worldwide production was 160 million kilograms.<ref name="Ullmann">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</ref> |
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'''Cyanuric acid''' or '''1,3,5-triazine-2,4,6-triol''' is a ] with the ] (CNOH)<sub>3</sub>. Like many industrially useful chemicals, this ] has many synonyms. This white, odorless solid finds use as a precursor or a component of ]es, disinfectants, and ]s. In 1997, worldwide production was 160 000 ]s.<ref name="Ullmann">Klaus Huthmacher, Dieter Most "Cyanuric Acid and Cyanuric Chloride" Ullmann's Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. doi 10.1002/14356007.a08 191</ref> |
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== Properties and synthesis == |
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== Properties and synthesis == |
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=== Properties === |
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=== Properties === |
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Cyanuric acid is the cyclic ] of the elusive species ], HOCN. The two ] shown in the infobox readily interconvert; that is, they are ]s. However, mixture with ] forms ], which locks cyanuric acid in the tri-keto tautomer and makes melamine cyanurate insoluble in water. The triol tautomer, which may have ] character, predominates in solution. The ] (-OH) groups assume ] character. Deprotonation with base affords a series of cyanurate ]s: |
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Cyanuric acid can be viewed as the cyclic ] of the elusive ] ], HOCN. The ring can readily interconvert between several ] via ]. Although the triol tautomer may have ] character, the keto form predominates in solution.<ref>{{cite journal |last1=Pérez-Manríquez |first1=Liliana |last2=Cabrera |first2=Armando |last3=Sansores |first3=Luis Enrique |last4=Salcedo |first4=Roberto |title=Aromaticity in cyanuric acid |journal=Journal of Molecular Modeling |date=7 September 2010 |volume=17 |issue=6 |pages=1311–1315 |doi=10.1007/s00894-010-0825-2|pmid=20820829 |pmc=3102184 }}{{open access}}</ref> The ] (-OH) groups assume ]ic character. Deprotonation with base affords a series of cyanurate ]s: |
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: <sub>3</sub> <math>\overrightarrow{\leftarrow}</math> <sub>2</sub><sup>-</sup> + H<sup>+</sup> (K<sub>a</sub> = 10<sup>−7</sup>) |
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: <sub>3</sub> ⇌ <sub>2</sub><sup>−</sup> + H<sup>+</sup> (pK<sub>a</sub> = 6.88)<ref name="CRC85">"Dissociation constants of organic acids and bases" CRC Handbook of Chemistry and physics, Internet Version 2005 (85th ed.)</ref> |
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: <sub>2</sub><sup>-</sup> <math>\overrightarrow{\leftarrow}</math> <sub>2</sub><sup>2-</sup> + H<sup>+</sup> (K<sub>a</sub> = 10<sup>−11</sup>) |
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: <sub>2</sub><sup>−</sup> ⇌ <sub>2</sub><sup>2−</sup> + H<sup>+</sup> (pK<sub>a</sub> = 11.40) |
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: <sub>2</sub><sup>2-</sup> <math>\overrightarrow{\leftarrow}</math> <sub>3</sub><sup>3-</sup> + H<sup>+</sup> (K<sub>a</sub> = 10<sup>−14</sup>) |
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: <sub>2</sub><sup>2−</sup> ⇌ <sub>3</sub><sup>3−</sup> + H<sup>+</sup> (pK<sub>a</sub> = 13.5) |
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Cyanuric acid is noted for its strong interaction with ], forming insoluble ]. This interaction locks the cyanuric acid into the tri-keto ]. Melamine cyanurate is cited as an example of ].<ref>{{cite book |last=Lehn |first=J. M. |title=Supramolecular Chemistry: Concepts and Perspectives |publisher=VCH |location=Weinheim |year=1995 }}</ref> |
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=== Synthesis === |
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=== Synthesis === |
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Cyanuric acid (CYA) was first synthesized by ] in 1829 by the thermal decomposition of ] and ].<ref>Wöhler, F. On the decomposition of urea and uric acid at high temperature. Ann Phys Chemie 1829 15:619-30</ref> The current industrial route to CYA entails the ] of urea, with release of ammonia. The conversion commences at approximately 175 °C:<ref name="Ullmann" /> |
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Cyanuric acid (CYA) was first synthesized by ] in 1829 by the thermal decomposition of ] and ].<ref>Wöhler, F. (1829) (On the decomposition of urea and uric acid at higher temperature), ''Annalen der Physik und Chemie'', 2nd series, '''15''' : 619-630.</ref> The current industrial route to CYA entails the ] of urea, with release of ]. The conversion commences at approximately 175 °C:<ref name="Ullmann" /> |
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: 3 H<sub>2</sub>N-CO-NH<sub>2</sub> → <sub>3</sub> + 3 NH<sub>3</sub> |
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: 3 H<sub>2</sub>N-CO-NH<sub>2</sub> → <sub>3</sub> + 3 NH<sub>3</sub> |
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CYA crystallizes from water as the dihydrate. |
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CYA crystallizes from water as the dihydrate. |
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Cyanuric acid can be produced by hydrolysis of crude or waste ] followed by crystallization. Acid waste streams from plants producing these materials contain cyanuric acid and on occasion, dissolved amino-substituted triazines, namely, ], 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 ]. 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. |
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Cyanuric acid can be produced by ] of crude or waste ] followed by ]. Acid waste streams from plants producing these materials contain cyanuric acid and on occasion, dissolved amino-substituted triazines, namely, ], ], and melamine. In one method, an ] solution is heated to the "boil" and treated with a ] amount of melamine, by which means the cyanuric acid present precipitates as ]. The various waste streams containing cyanuric acid and ]-substituted ]s may be combined for disposal, and during upset conditions undissolved cyanuric acid may be present in the ]. |
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<ref name="CYApat">{{cite web |
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<ref name="CYApat">{{cite web |
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| title=Process for preparing pure cyanuric acid |
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| title =Process for preparing pure cyanuric acid |
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| url=http://www.freepatentsonline.com/4278794.html |
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| url =http://www.freepatentsonline.com/4278794.html |
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| date=July 14, 1981 |
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| date =July 14, 1981 |
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| accessdate=2007-12-10}}</ref><ref name="CYApat2">{{cite web |
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| accessdate =2007-12-10}}</ref><ref name="CYApat2">{{cite web |
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| title=High pressure thermal hydrolysis process to decompose triazines in acid waste streams |
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| title =High pressure thermal hydrolysis process to decompose triazines in acid waste streams |
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| url=http://www.freepatentsonline.com/4013757.html |
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| url =http://www.freepatentsonline.com/4013757.html |
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| date=March 22, 1977 |
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| date =March 22, 1977 |
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| accessdate=2007-12-10}}</ref> |
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| accessdate =2007-12-10}}</ref> |
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=== Intermediates and impurities === |
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=== Intermediates and impurities === |
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Intermediates in the dehydration include both ], ], and triuret: |
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Intermediates in the dehydration include both ], ], and ]: |
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: H<sub>2</sub>N-CO-NH<sub>2</sub> → HNCO + NH<sub>3</sub> |
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: H<sub>2</sub>N-CO-NH<sub>2</sub> → HNCO + NH<sub>3</sub> |
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: H<sub>2</sub>N-CO-NH-CO-NH<sub>2</sub> + HNCO → H<sub>2</sub>N-CO-NH-CO-NH-CO-NH<sub>2</sub> |
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: H<sub>2</sub>N-CO-NH-CO-NH<sub>2</sub> + HNCO → H<sub>2</sub>N-CO-NH-CO-NH-CO-NH<sub>2</sub> |
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As temperature exceeds 190 °C, other reactions begin to dominate the process. |
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One impurity in the production of CYA is ], especially as the reaction temperature exceeds 190 °C: |
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3 H<sub>2</sub>N-CO-NH-CO-NH<sub>2</sub> → <sub>2</sub>(CNH<sub>2</sub>)(NH)<sub>2</sub>N + 2 NH<sub>3</sub> + H<sub>2</sub>O |
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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. |
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The first appearance of ] occurs prior to 225 °C and is suspected also to occur from decomposition of biuret but is produced at a lower rate than that of CYA or ammelide. |
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], <sub>3</sub>, formation occurs between 325 and 350 °C and only in very small quantities.<ref> 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</ref> |
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: 3 H<sub>2</sub>N-CO-NH-CO-NH<sub>2</sub> → <sub>2</sub>(CNH<sub>2</sub>)(NH)<sub>2</sub>N + 2 NH<sub>3</sub> + H<sub>2</sub>O |
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Melamine, <sub>3</sub>, formation occurs between 325–350 °C and only in very small quantities.<ref>{{cite journal |url=http://www.iscpubs.com/articles/al/a9908sch.pdf |author=Shaber, Peter M.|display-authors=etal|journal=American Laboratory|date=August 1999|title=Study of the thermal decomposition of urea (pyrolysis) reaction and importance to cyanuric acid production |pages=13–21|accessdate=2007-05-08 |url-status=dead |archiveurl=https://web.archive.org/web/20070928121342/http://www.iscpubs.com/articles/al/a9908sch.pdf |archivedate=2007-09-28 }}</ref> |
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===N-substituted isocyanurates from isocyanates=== |
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N-substituted isocyanurates can be synthesised by the trimerisation of ]s. This is utilised industrially in the formation of ]s. |
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== Applications == |
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== Applications == |
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Cyanuric acid is used as a ] stabilizer / buffer in ]s. It binds to ] and releases it slowly, extending the time needed to deplete each dose of ]. A chemical equilibrium exists between the acid with free chlorine and its chlorinated form.<ref name=byrossi>{{Cite web |date=2021-05-18 |title=What Is Pool Stabilizer |url=https://byrossi.com/pool-stabilizer/ |access-date=2022-07-27 |language=en-US}}</ref> |
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=== Precursors to chlorinated cyanurates === |
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=== Precursors to chlorinated cyanurates === |
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Cyanuric acid is mainly used as a ] to ''N''-chlorinated cyanurates, which are used to disinfect water. The dichloro derivative is prepared by direct chlorination: |
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: <sub>3</sub> + 2 Cl<sub>2</sub> + 2 NaOH → <sub>2</sub> + 2 NaCl + 2 {{H2O-nl}} |
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This species is typically converted to its sodium salt, ]. Further chlorination gives ], <sub>3</sub>.<ref name="Ullmann" /> |
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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: |
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These ''N''-chloro compounds serve as disinfectants and ] for swimming pool water.<ref name="Ullmann" /> The aforementioned equilibrium stabilizes the chlorine in the pool and prevents the chlorine from being quickly consumed by ].<ref name=byrossi/> |
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: <sub>3</sub> + 2 Cl<sub>2</sub> + 2 NaOH → <sub>2</sub> |
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This species is typically converted to its sodium salt, ]. Further chlorination gives ], <sub>3</sub>. These ''N''-chloro compounds serve as disinfectants and algicides for swimming pool water.<ref name="Ullmann" /> It stabilizes the chlorine in the pool and prevents the chlorine from being quickly consumed by sunlight. |
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=== Precursors to crosslinking agents === |
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=== Precursors to crosslinking agents === |
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Because of its trifunctionality, CYA is a precursor to ], especially for ] resins and ] ]. |
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The experimental ] drug teroxirone (triglycidyl isocyanurate) is formed by reacting cyanuric acid with 3 equivalents of ]. It works by cross-linking DNA.<ref>M. Budnowski, Angew. Chem., 7, 827 (1968).</ref> |
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Because of their trifunctionality, CYA is a precursor to crosslinking agents, especially for polyurethane resins. |
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== Analysis == |
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== Analysis == |
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Testing for cyanuric acid concentration is commonly done with a ], which uses a reagent, melamine, to precipitate the cyanuric acid. The relative ] of the reacted sample quantifies the CYA concentration. Referenced in 1957, this test<ref name="Mercktest">{{cite web |
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|url=http://www.merckserono.net/servlet/PB/menu/1169010/index.html |
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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.<ref name="Mercktest">{{ cite web|url=http://www.merckserono.net/servlet/PB/menu/1169010/index.html |
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| title=Merck Turbidity Test|date=June 6, 2003 |
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|title=Merck Turbidity Test |
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|date=June 6, 2003 |
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| publisher=] |
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|publisher=] |
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| accessdate=2007-05-06}}</ref> |
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|accessdate=2007-05-06 |
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|archive-url=https://web.archive.org/web/20070701125445/http://www.merckserono.net/servlet/PB/menu/1169010/index.html |
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This test works because melamine combines with the cyanuric acid in the water to form a fine, insoluble, white precipitate (]) that causes the water to cloud in proportion to the amount of cyanuric acid in it. |
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|archive-date=July 1, 2007 |
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|url-status=dead |
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}} (dead link 8 April 2018)</ref> works because melamine combines with the cyanuric acid in the water to form a fine, white ] of the insoluble complex ] that causes the ] in proportion to the amount of cyanuric acid in it. More recently, a sensitive method has been developed for analysis of cyanuric acid in ].<ref>Panuwet P, Wade EL, Nguyen JV, Montesano MA, Needham LL, Barr DB. Quantification of cyanuric acid residue in human urine using high performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 2010 878(28):2916-2922.</ref> |
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== Animal feed == |
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== Animal feed == |
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FDA permits a certain amount of cyanuric acid to be present in some ] (NPN) additives used in ] and ].<ref name="FDAcyan">{{ cite web |
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| url =http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=573.220 |
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FDA permits a certain amount of cyanuric acid to be present in some ] (NPN) additives used in animal feed and drinking water.<ref name="FDAcyan">{{ cite web |
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| title =21CFR573.220 Feed-grade biuret |
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| url=http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=573.220 |
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| date =April 1, 2006 |
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| title=21CFR573.220 Feed-grade biuret |
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| publisher =] |
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| date=April 1, 2006 |
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| accessdate =2007-05-06}}</ref> Cyanuric acid has been used as NPN. For example, ] manufactures an NPN supplement for cattle, which contains biuret, triuret, cyanuric acid and ].<ref name="RoughageBusterPlus">{{ cite web |
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| publisher=] |
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|url=http://www.admani.com/alliancebeef/RoughageBusterPlus.htm |
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| accessdate=2007-05-06}}</ref> Cyanuric acid has been used as NPN. For example, ] manufactures an NPN supplement for cattle, which contains ], ], cyanuric acid and ].<ref name="RoughageBusterPlus">{{ cite web |
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|title=Roughage Buster Plus: ingredients |
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| url=http://www.admani.com/alliancebeef/RoughageBusterPlus.htm |
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|publisher=] |
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| title=Roughage Buster Plus: ingredients |
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|accessdate=2007-05-06 |
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| publisher=] |
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|url-status=dead |
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| accessdate=2007-05-06}}</ref> |
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|archiveurl=https://web.archive.org/web/20070212001426/http://www.admani.com/alliancebeef/RoughageBusterPlus.htm |
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|archivedate=2007-02-12 |
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=== 2007 pet food recalls === |
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=== 2007 pet food recalls === |
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{{main|2007 pet food recalls#Melamine and cyanuric acid in pet sickness}} |
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{{main|2007 pet food recalls#Melamine and cyanuric acid in pet sickness}} |
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Cyanuric acid is implicated in connection to the ], 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 ] forms poorly soluble crystals which can cause renal failure (see Analysis section above). |
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Cyanuric acid is implicated in connection to the ], 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 ] (see Analysis section above). |
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== Safety == |
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== Safety == |
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Cyanuric acid is classified as "essentially nontoxic".<ref name="Ullmann" /> The 50% oral median lethal dose (]) is 7700 mg/kg in rats.<ref>], , {{webarchive |url=https://web.archive.org/web/20071216000052/http://www.cfsan.fda.gov/~dms/melamra.html |date=December 16, 2007 }} ]: May 30, 2007 (Volume 72, Number 103). Accessed 2008-09-27.</ref> |
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However, when cyanuric acid is present together with ] (which by itself is another low-toxicity substance), it will form an ] and rather ] complex,<ref> {{webarchive |url=https://web.archive.org/web/20070518221740/http://www.avma.org/press/releases/070501_petfoodrecall.asp |date=May 18, 2007 }}, American Veterinary Medical Association (AVMA), Press Release, May 1, 2007. Accessed 2008-09-27.</ref> as evidenced in dogs and cats during the ] and in children during the ] cases. |
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Cyanuric acid is classified as "essentially nontoxic".<ref name="Ullmann" /> |
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The 50% oral median lethal dose (]) is 7700 mg/kg in rats.<ref>], ]: May 30, 2007 (Volume 72, Number 103). Accessed 2008-09-27.</ref> |
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However, when cyanuric acid is administered together with ] (which by itself is another low-toxicity substance), they may form extremely insoluble crystals,<ref>, American Veterinary Medical Association (AVMA), Press Release, May 1, 2007. Accessed 2008-09-27.</ref> leading to formation of ] and potentially causing ] and ] -- as evidenced in dogs and cats during the ] and in children during the ] cases. |
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== See also == |
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== Natural occurrence == |
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An impure copper salt of the acid, with the formula Cu(C<sub>3</sub>N<sub>3</sub>O<sub>3</sub>H<sub>2</sub>)<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub>, is currently the only known isocyanurate mineral, called ]. It was found in a ] deposit in ]. It is very rare.<ref>Mindat, http://www.mindat.org/min-42755.html</ref> |
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* ] |
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== References == |
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== References == |
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== External links == |
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== External links == |
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* {{ICSC|1313|13}} |
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* {{ICSC|1313|13}} |
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* - News & developments updated regularly |
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* {{Webarchive|url=https://web.archive.org/web/20081020030853/http://www.oregonvma.org/news/recallnews.asp |date=2008-10-20 }} – News and developments updated regularly |
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