Melamine cyanurate, also known as melamine–cyanuric acid adduct or melamine–cyanuric acid complex, is a crystalline complex formed from a 1:1 mixture of melamine and cyanuric acid. The substance is not a salt despite its non-systematic name melamine cyanurate. The complex is held together by an extensive two-dimensional network of hydrogen bonds between the two compounds, reminiscent of the guanine–cytosine base pairs found in DNA.[2] Melamine cyanurate forms spoke-like crystals from aqueous solutions [3] and has been implicated as a causative agent for toxicity seen in the Chinese protein export contamination and the 2007 pet food recall.[3] This complex is cited as an example of supramolecular chemistry.[4]
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| Names | |
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| Preferred IUPAC name
1,3,5-Triazinane-2,4,6-trione—1,3,5-triazine-2,4,6-triamine (1/1) | |
| Other names
Melamine–cyanuric acid compound, melamine–cyanuric acid adduct, melamine cyanurate, melamine isocyanurate
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.048.687 |
| MeSH | melamine cyanurate |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H9N9O3
(C3H6N6·C3H3N3O3) | |
| Molar mass | 255.19 g/mol |
| none | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses
editMelamine cyanurate is used as a flame retardant, most commonly in polybutylene terephthalate (PBT), polyamide 6 (nylon 6) and polyamide 6,6 (nylon 6:6).[5] It is also used to fireproof in polyester fabrics.
Toxicity
editIt has been considered to be more toxic than either melamine or cyanuric acid alone.[6]
LD50 in rats and mice (ingested):
- 4.1 g/kg – Melamine cyanurate
- 6.0 g/kg – Melamine[clarification needed]
- 7.7 g/kg – Cyanuric acid
A toxicology study conducted after recent pet food recalls concluded that the combination of melamine and cyanuric acid in diet does lead to acute kidney injury in cats.[7] A 2008 study produced similar experimental results in rats and characterized the melamine and cyanuric acid in contaminated pet food from the 2007 outbreak.[8]
See also
editReferences
edit- ^ EPA: Substance : Archived 2008-09-22 at the Wayback Machine
- ^ Perdigão LM, Champness NR, Beton PH (2006). "Surface self-assembly of the cyanuric acid-melamine hydrogen bonded network". Chem. Commun. (5): 538–540. doi:10.1039/b514389f. PMID 16432575.538-540&rft.date=2006&rft_id=info:doi/10.1039/b514389f&rft_id=info:pmid/16432575&rft.aulast=Perdigão&rft.aufirst=LM&rft.au=Champness, NR&rft.au=Beton, PH&rfr_id=info:sid/en.wikipedia.org:Melamine cyanurate" class="Z3988">
- ^ a b Lili He; Yang Liu; Mengshi Lin; Joseph Awika; David R Ledoux; Hao Li; Azlin Mustapha (2008). "A new approach to measure melamine, cyanuric acid, and melamine cyanurate using surface enhanced Raman spectroscopy coupled with gold nanosubstrates". Sens. & Instrumen. Food Qual. 2: 66–71. doi:10.1007/s11694-008-9038-0. S2CID 93425738.66-71&rft.date=2008&rft_id=info:doi/10.1007/s11694-008-9038-0&rft_id=https://api.semanticscholar.org/CorpusID:93425738#id-name=S2CID&rft.au=Lili He&rft.au=Yang Liu&rft.au=Mengshi Lin&rft.au=Joseph Awika&rft.au=David R Ledoux&rft.au=Hao Li&rft.au=Azlin Mustapha&rfr_id=info:sid/en.wikipedia.org:Melamine cyanurate" class="Z3988">
- ^ Lehn, J. M. (1995). Supramolecular Chemistry: Concepts and Perspectives. Weinheim: VCH.
- ^ Gijsman, Pieter; Steenbakkers, Rieky; Fürst, Christian; Kersjes, Joyce (2002). "Differences in the flame retardant mechanism of melamine cyanurate in polyamide 6 and polyamide 66". Polymer Degradation and Stability. 78 (2): 219–224. doi:10.1016/S0141-3910(02)00136-2.219-224&rft.date=2002&rft_id=info:doi/10.1016/S0141-3910(02)00136-2&rft.aulast=Gijsman&rft.aufirst=Pieter&rft.au=Steenbakkers, Rieky&rft.au=Fürst, Christian&rft.au=Kersjes, Joyce&rfr_id=info:sid/en.wikipedia.org:Melamine cyanurate" class="Z3988">
- ^ A.A. Babayan, A.V.Aleksandryan, "Toxicological characteristics of melamine cyanurate, melamine and cyanuric acid", Zhurnal Eksperimental'noi i Klinicheskoi Meditsiny, Vol.25, 345-9 (1985). Original article in Russian.
- ^ Puschner et al. (November 2007). Assessment of melamine and cyanuric acid toxicity in cats. Journal of Veterinary Diagnostic Investigation. Retrieved on 2007-11-16.
- ^ Dobson; et al. (August 2008). "Identification and characterization of toxicity of contaminants in pet food leading to an outbreak of renal toxicity in cats and dogs". Toxicological Sciences. 106 (1): 251–62. doi:10.1093/toxsci/kfn160. PMID 18689873.251-62&rft.date=2008-08&rft_id=info:doi/10.1093/toxsci/kfn160&rft_id=info:pmid/18689873&rft.au=Dobson&rft_id=https://doi.org/10.1093%2Ftoxsci%2Fkfn160&rfr_id=info:sid/en.wikipedia.org:Melamine cyanurate" class="Z3988">