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Fire-resistant chemical used in dinnerware, insulation, and cleaning products

Melamine
Structural formula of melamine
Ball-and-stick model of the melamine molecule
Space-filling model of the melamine molecule
Names
Preferred IUPAC name
1,3,5-Triazine-2,4,6-triamine
Other names
2,4,6-Triamino-s-triazine
Cyanurotriamide
Cyanurotriamine
Cyanuramide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.288 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9) checkY
    Key: JDSHMPZPIAZGSV-UHFFFAOYSA-N checkY
  • InChI=1/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9)
    Key: JDSHMPZPIAZGSV-UHFFFAOYAF
  • Nc1nc(N)nc(N)n1
Properties
C3H6N6
Molar mass 126.123 g·mol−1
Appearance White solid
Density 1.573 g/cm3[1]
Melting point 343 °C (649 °F; 616 K) (decomposition)[1]
Boiling point Sublimes
3240 mg/ L (20 °C)[2]
Solubility very slightly soluble in hot alcohol[clarification needed], benzene, glycerol, pyridine
insoluble in ether, benzene, CCl4
log P −1.37
Acidity (pKa) 5.0 (conjugated acid)[3]
Basicity (pKb) 9.0 [3]
−61.8·10−6 cm3/mol
1.872[1]
Structure
Monoclinic
Thermochemistry
−1967 kJ/mol
Hazards
GHS labelling:[4]
GHS08: Health hazard
Warning
H351, H373
P203, P260, P280, P318, P319, P405, P501
500 °C (932 °F; 773 K)
Lethal dose or concentration (LD, LC):
3850 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)
Chemical compound
Marking of product made of Melamine

Melamine ⓘ is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass, and its derivatives have fire-retardant properties due to its release of nitrogen gas when burned or charred. Melamine can be combined with formaldehyde and other agents to produce melamine resins. Such resins are characteristically durable thermosetting plastic used in high-pressure decorative laminates such as Formica, melamine dinnerware including cooking utensils, plates, and plastic products,[5] laminate flooring, and dry erase boards. Melamine foam is used as insulation and soundproofing material, and in polymeric cleaning products such as Magic Eraser.

Melamine gained infamy when Chinese food producers Sanlu Group added it to baby formula in order to increase the apparent protein content, causing the 2008 Chinese milk scandal.[6][7] Ingestion of melamine may lead to reproductive damage, or bladder or kidney stones, and bladder cancer. It is also an irritant when inhaled or in contact with the skin or eyes. The United Nations' food standards body, the Codex Alimentarius Commission, has set the maximum amount of melamine allowed in powdered infant formula to 1 mg/kg and the amount of the chemical allowed in other foods and animal feed to 2.5 mg/kg. While not legally binding, the levels allow countries to ban importation of products with excessive levels of melamine.

Etymology

[edit]

The German word Melamin was coined by combining the words melam (a derivative of ammonium thiocyanate) and amine.[8][9] Melamine is, therefore, unrelated etymologically to the root melas (μέλας, meaning 'black' in Greek), from which the words melanin, a pigment, and melatonin, a hormone, are formed.

Uses

[edit]

Plastics and building materials

[edit]

In one large-scale application, melamine is combined with formaldehyde and other agents to produce melamine resins. Such resins are characteristically durable thermosetting plastic used in high-pressure decorative laminates such as Wilsonart, melamine dinnerware, laminate flooring, and dry erase boards.[10] Melamine cookware is not microwave-safe,[11] and can be identified from the fact it is "slightly heavier and noticeably thicker than its plastic counterparts."[12]

Melamine foam is used as insulation, soundproofing material and in polymeric cleaning products, such as Magic Eraser.

Melamine is one of the major components in Pigment Yellow 150, a colorant in inks and plastics.

Melamine also is used in the fabrication of melamine polysulfonate, used as a superplasticizer for making high-resistance concrete. Sulfonated melamine formaldehyde (SMF) is a polymer used as a cement admixture to reduce the water content in concrete while increasing the fluidity and the workability of the mix during handling and pouring. It results in concrete with a lower porosity and a higher mechanical strength, exhibiting an improved resistance to aggressive environments and a longer lifetime.

Fertilizers

[edit]

Melamine was once envisioned as fertilizer for crops during the 1950s and 1960s because of its high (66% by mass) nitrogen content.[13] However, melamine is much more expensive to produce than other common nitrogen fertilizers, such as urea. The mineralization (degradation to ammonia) for melamine is slow, making this product both economically and scientifically impractical for use as a fertilizer.[citation needed]

Melamine dinnerware
[edit]

Melamine and its salts are used as fire-retardant additives in paints, plastics, and paper.[14] A melamine fiber, Basofil, has low thermal conductivity, excellent flame resistance and is self-extinguishing; this makes it useful for flame-resistant protective clothing, either alone or as a blend with other fibres.[15]

[edit]

Melamine is sometimes illegally added to food products in order to increase the apparent protein content. Standard tests, such as the Kjeldahl and Dumas tests, estimate protein levels by measuring the nitrogen content, so they can be misled by the addition of nitrogen-rich, but non-proteinaceous compounds such as melamine. There are instruments available today that can differentiate melamine nitrogen from protein nitrogen.[16]

Medicine

[edit]

Melamine derivatives of arsenical drugs are potentially important in the treatment of African trypanosomiasis.[17]

Melamine use as non-protein nitrogen (NPN) for cattle was described in a 1958 patent.[18] In 1978, however, a study concluded that melamine "may not be an acceptable non-protein N source for ruminants" because its hydrolysis in cattle is slower and less complete than other nitrogen sources such as cottonseed meal and urea.[19]

Toxicity

[edit]

The short-term lethal dose of melamine is on a par with common table salt, with an LD50 of more than 3 grams per kilogram of bodyweight.[20] U.S. Food and Drug Administration (FDA) scientists explained that when melamine and cyanuric acid are absorbed into the bloodstream, they concentrate and interact in the urine-filled renal tubules, then crystallize and form large numbers of round, yellow crystals, which in turn block and damage the renal cells that line the tubes, causing the kidneys to malfunction[21] and lead to kidney stones, kidney failure, and death.[5] Signs of melamine toxicity can include irritability, blood in the urine, little to no urine, symptoms of kidney infection, or high blood pressure.[5]

The European Union set a standard for acceptable human consumption (tolerable daily intake or TDI) of melamine at 0.2 mg per kilogram of body mass[22] (previously 0.5 mg/kg), Canada declared a limit of 0.35 mg/kg, and the US FDA's limit was put at 0.063 mg/kg (previously 0.63 mg/kg). The World Health Organization's food safety director estimated that the amount of melamine a person could stand per day without incurring a bigger health risk, the TDI, was 0.2 mg per kilogram of body mass.[23]

Toxicity of melamine can be mediated by intestinal microbiota. In culture, Raoultella terrigena, which rarely colonizes mammalian intestines,[24] was shown to convert melamine to cyanuric acid directly. Rats colonized by R. terrigena showed greater melamine-induced kidney damage compared to those not colonized.[25]

Acute toxicity

[edit]

Melamine is reported to have an oral median lethal dose (LD50) of 3248 mg/kg based on rat data. It is also an irritant when inhaled or in contact with the skin or eyes. The reported dermal LD50 is greater than 1000 mg/kg for rabbits. A study by Soviet researchers in the 1980s suggested that melamine cyanurate, commonly used as a fire retardant,[26] could be more toxic than either melamine or cyanuric acid alone.[27] For rats and mice, the reported LD50 for melamine cyanurate was 4.1 g/kg (given inside the stomach) and 3.5 g/kg (via inhalation), compared to 6.0 and 4.3 g/kg for melamine and 7.7 and 3.4 g/kg for cyanuric acid respectively.

A toxicology study in animals conducted after recalls of contaminated pet food concluded that the combination of melamine and cyanuric acid in diet does lead to acute kidney injury in cats.[28] A 2008 study produced similar experimental results in rats and characterized the melamine and cyanuric acid in contaminated pet food from the 2007 outbreak.[29] A 2010 study from Lanzhou University attributed kidney failure in humans to uric acid stone accumulation after ingestion of melamine resulting in a rapid aggregation of metabolites such as cyanuric acid diamide (ammeline) and cyanuric acid.[30] A 2013 study demonstrated that melamine can be metabolized to cyanuric acid by gut bacteria. In particular, Klebsiella terrigena was determined to be a factor in melamine toxicity. In culture, K. terrigena was shown to convert melamine to cyanuric acid directly. Cyanuric acid was detected in the kidneys of rats administered melamine alone, and the concentration after Klebsiella colonization was increased.[25]

Chronic toxicity

[edit]

Ingestion of melamine may lead to reproductive damage, or bladder or kidney stones, which can lead to bladder cancer.[31][32][33][34]

A study in 1953 reported that dogs fed 3% melamine for a year had the following changes in their urine: (1) reduced specific gravity, (2) increased output, (3) melamine crystalluria, and (4) protein and occult blood.[35]

A survey commissioned by the American Association of Veterinary Laboratory Diagnosticians suggested that crystals formed in the kidneys when melamine combined with cyanuric acid, "don't dissolve easily. They go away slowly, if at all, so there is the potential for chronic toxicity."[36][37][38]

Metabolism

[edit]

Melamine is a metabolite of cyromazine, a pesticide.[39] It has been reported that cyromazine can also be converted to melamine in plants.[40][41]

Treatment of urolithiasis

[edit]

Fast diagnosis and treatment of acute obstructive urolithiasis may prevent the development of acute kidney failure. Urine alkalinization and stone liberalization have been reported to be the most effective treatments in humans.[30]

Contamination

[edit]

Melamine-formaldehyde resin tableware was evaluated by the Taiwan Consumers' Foundation to have 20 parts per million of free melamine that could migrate out of the plastic into acidic foods if held at 160 °F (71 °C) for two hours, such as if food were kept heated in contact with it in an oven.[5]

Regulation in food and feed

[edit]

The United Nations' food standards body, Codex Alimentarius Commission, has set the maximum amount of melamine allowed in powdered infant formula to 1 mg/kg and the amount of the chemical allowed in other foods and animal feed to 2.5 mg/kg. While not legally binding, the levels allow countries to ban importation of products with excessive levels of melamine.[42]

Synthesis and reactions

[edit]

Melamine was first synthesized by the German chemist Justus von Liebig in 1834. In early production, first calcium cyanamide was converted into dicyandiamide, which was heated above its melting temperature to produce melamine. Today most industrial manufacturers use urea in the following reaction to produce melamine:

6 (NH2)2CO → C3H6N6 + 6 NH3 + 3 CO2

In the first step, urea decomposes into cyanic acid and ammonia:

(NH2)2CO → HNCO + NH3

Cyanic acid polymerizes to cyanuric acid, which condenses with the liberated ammonia forming melamine. The released water reacts with cyanic acid, which helps to drive the reaction:

6 HNCO + 3 NH3 → C3H6N6 + 3 CO2 + 3 NH3

The above reaction can be carried out by either of two methods: catalyzed gas-phase production or high pressure liquid-phase production. In one method, molten urea is introduced onto a fluidized bed with catalyst for reaction. Hot ammonia gas is also present to fluidize the bed and inhibit deammonization. The effluent then is cooled. Ammonia and carbon dioxide in the off-gas are separated from the melamine-containing slurry. The slurry is further concentrated and crystallized to yield melamine.[43] Major manufacturers and licensors such as Orascom Construction Industries, BASF, and Eurotecnica have developed some proprietary methods.

The off-gas contains large amounts of ammonia. Therefore, melamine production is often integrated into urea production, which uses ammonia as feedstock.

Crystallization and washing of melamine generates a considerable amount of waste water, which may be concentrated into a solid (1.5–5% of the weight) for easier disposal. The solid may contain approximately 70% melamine, 23% oxytriazines (ammeline, ammelide, and cyanuric acid), 0.7% polycondensates (melem, melam, and melon).[44] In the Eurotecnica process, however, there is no solid waste and the contaminants are decomposed to ammonia and carbon dioxide and sent as off gas to the upstream urea plant; accordingly, the waste water can be recycled to the melamine plant itself or used as clean cooling water make-up.[45]

Melamine reacts with acid and related compounds to form melamine cyanurate and related crystal structures, which have been implicated as contaminants or biomarkers in Chinese protein adulterations.

Drug derivatives

[edit]

Melamine is part of the core structure for a number of drugs including almitrine, altretamine, cyromazine, ethylhexyl triazone, iscotrizinol, meladrazine, melarsomine, melarsoprol, tretamine, trinitrotriazine, and others.[46]

Production in mainland China

[edit]

Between the late 1990s and early 2000s, both consumption and production of melamine grew considerably in mainland China. By early 2006, melamine production in mainland China is reported to be in "serious surplus".47 Between 2002 and 2007, while the global melamine price remained stable, a steep increase in the price of urea (feedstock for melamine) has reduced the profitability of melamine manufacturing. Currently, China is the world's largest exporter of melamine, while its domestic consumption still grows by 10% per year. However, reduced profit has already caused other joint melamine ventures to be postponed there.

Detection in biological specimens

[edit]

The presence of melamine in urine specimens from children who consumed adulterated milk products has been determined by liquid chromatography-mass spectrometry.[96]

Melamine on metal surfaces

[edit]

It is reported that melamine molecules adsorbed on gold[97] or silver[98] surface tend to arrange into honeycomb or closed-packed structures. Such a self-assembly occurs due to the inter-molecular hydrogen bond interaction. This ordering was further investigated using classical Monte Carlo[99] and DFT[100] methods.

See also

[edit]

References

[edit]
  1. 1 2 3 Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). CRC Press. p. 3.516. ISBN 978-1-4398-5511-9.
  2. ↑ Melamine from PubChem
  3. 1 2 Jang, Y.H., Hwang, S., Chang, S.B., Ku, J. and Chung, D.S. (2009). "Acid Dissociation Constants of Melamine Derivatives from Density Functional Theory Calculations". The Journal of Physical Chemistry A. 113 (46): 13036–13040. Bibcode:2009JPCA..11313036J. doi:10.1021/jp9053583. PMID 19845385.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ↑ PubChem. "Melamine". pubchem.ncbi.nlm.nih.gov. Retrieved February 13, 2026.
  5. 1 2 3 4 Nutrition, Center for Food Safety and Applied (December 19, 2022). "Melamine in Tableware Questions and Answers". FDA. Archived from the original on December 21, 2022.
  6. ↑ Hau, Anthony Kai-Ching; Kwan, Tze Hoi; Li, Philip Kam-tao (2009). "Melamine Toxicity and the Kidney". Journal of the American Society of Nephrology. 20 (2): 245–250. doi:10.1681/asn.2008101065. PMID 19193777.
  7. ↑ Scholl, Peter F.; Bergana, Marti Mamula; Yakes, Betsy Jean; Xie, Zhuohong; Zbylut, Steven; Downey, Gerard; Mossoba, Magdi; Jablonski, Joseph; Magaletta, Robert; Holroyd, Stephen E.; Buehler, Martin (July 19, 2017). "Effects of the Adulteration Technique on the Near-Infrared Detection of Melamine in Milk Powder". Journal of Agricultural and Food Chemistry. 65 (28): 5799–5809. Bibcode:2017JAFC...65.5799S. doi:10.1021/acs.jafc.7b02083. ISSN 0021-8561. PMID 28617599.
  8. ↑ "Melamine". The American Heritage Dictionary of the English Language (Fourth ed.). 2000. Archived from the original on December 1, 2008. Retrieved September 28, 2008.
  9. ↑ Bann, Bernard; Miller, Samuel A. (1958). "Melamines and derivatives of melamine". Chemical Reviews. 58: 131–172. Bibcode:1958ChRv...58..131B. doi:10.1021/cr50019a004.
  10. ↑ Deim, H.; Matthias, G.; Wagner, R. A. (2012). "Amino Resins". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_115.pub2. ISBN 978-3-527-30673-2.
  11. ↑ "Melamine in Tableware Questions and Answers". United States: Food and Drug Administration. December 19, 2022. Archived from the original on December 21, 2022. Retrieved December 21, 2022. Foods and drinks should not be heated on melamine-based dinnerware in microwave ovens.
  12. ↑ "How Can You Identify Melamine Dishes?". bzyoo. June 9, 2023.
  13. ↑ Hauck, R. D.; Stephenson, H. F. (1964). "Fertilizer Nitrogen Sources, Nitrification of Triazine Nitrogen". Journal of Agricultural and Food Chemistry. 12 (2): 147–151. Bibcode:1964JAFC...12..147H. doi:10.1021/jf60132a014.
  14. ↑ Ashford, Robert D. (2011) Ashford's Dictionary of Industrial Chemicals, 3rd ed. Wavelength. p. 5713. ISBN 9780952267430.
  15. ↑ "Melamine Fibres". Polymer Properties Database.
  16. ↑ Moore, Jeffrey C.; Devries, Jonathan W.; Lipp, Markus; Griffiths, James C.; Abernethy, Darrell R. (2010). "Total Protein Methods and Their Potential Utility to Reduce the Risk of Food Protein Adulteration". Comprehensive Reviews in Food Science and Food Safety. 9 (4): 330–357. Bibcode:2010CRFSF...9..330M. doi:10.1111/j.1541-4337.2010.00114.x. PMID 33467839.
  17. ↑ Barrett, Michael P.; Gilbert, Ian H. (2006). "Targeting of Toxic Compounds to the Trypanosome's Interior". Advances in Parasitology. Vol. 63. pp. 125–183. doi:10.1016/S0065-308X(06)63002-9. ISBN 978-0-12-031763-9. PMID 17134653.
  18. ↑ Colby, Robert W. and Mesler, Robert J. Jr. (1958) "Ruminant feed compositions". U.S. patent 2,819,968.
  19. ↑ Newton, G. L.; Utley, P. R. (1978). "Melamine as a Dietary Nitrogen Source for Ruminants". Journal of Animal Science. 47 (6): 1338–1344. Bibcode:1978JAniS..47.1338N. doi:10.2527/jas1978.4761338x.
  20. ↑ "Melamine in milk by David Bradley". Sciencebase. September 17, 2008. Retrieved September 27, 2008.
  21. ↑ Weise, Elizabeth (August 5, 2007). "Poison pet food woes seem to hit cats harder". USA Today. Retrieved October 1, 2008.
  22. ↑ Harrington, Rory (April 15, 2010). "EFSA cuts melamine TDI by 60 per cent". FoodQualityNews.com. Retrieved April 16, 2010.
  23. ↑ Endreszl, Lara (December 10, 2008). "Safe Melamine Levels Named by World Health Organization". Health News. Archived from the original on March 18, 2009.
  24. ↑ Neergaard, Lauran (February 14, 2013). "Study Examines Why Most Survived China's Melamine Scare". Food Manufacturing News. Food Manufacturing. Retrieved February 22, 2013.
  25. 1 2 Zheng, X.; et al. (2013). "Melamine-induced renal toxicity is mediated by the gut microbiota". Science Translational Medicine. 5 (172): 172ra22. doi:10.1126/scitranslmed.3005114. PMID 23408055. S2CID 23408614.
  26. ↑ "Flame Retardants Center: Melamine Compounds". Specialchem4polymers.com. April 19, 2010. Archived from the original on September 22, 2008. Retrieved June 20, 2012.
  27. ↑ Babayan, A. A. and Aleksandryan, A. V. (1985). "Токсичные характеристики цианурата меламина, меламина и циануровой кислоты" [Toxicological characteristics of melamine cyanurate, melamine and cyanuric acid]. Zhurnal Eksperimental'noi I Klinicheskoi Meditsiny. 25: 345–249.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  28. ↑ Puschner, B.; Poppenga, R. H.; Lowenstine, L. J.; Filigenzi, M. S.; Pesavento, P. A. (2007). "Assessment of Melamine and Cyanuric Acid Toxicity in Cats". Journal of Veterinary Diagnostic Investigation. 19 (6): 616–24. doi:10.1177/104063870701900602. PMID 17998549.
  29. ↑ Dobson, R. L. M.; Motlagh, S.; Quijano, M.; Cambron, R. T.; Baker, T. R.; Pullen, A. M.; Regg, B. T.; Bigalow-Kern, A. S.; Vennard, T.; Fix, A.; Reimschuessel, R.; Overmann, G.; Shan, Y.; Daston, G. P. (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): 251–262. doi:10.1093/toxsci/kfn160. PMID 18689873.
  30. 1 2 3 Zhang, Xiangbo; Bai, Jinliang; Ma, Pengcheng; Ma, Jianhua; Wan, Jianghou; Jiang, Bin (2010). "Melamine-induced infant urinary calculi: A report on 24 cases and a 1-year follow-up". Urological Research. 38 (5): 391–5. doi:10.1007/s00240-010-0279-0. PMID 20517603. S2CID 23832448.
  31. ↑ "International Chemical Safety Card". Cdc.gov. Archived from the original on June 5, 2012. Retrieved June 20, 2012.
  32. ↑ OSHA – Chemical sampling information
  33. ↑ WHO – Some Chemicals that Cause Tumors of the Kidney or Urinary Bladder in Rodents and Some Other Substances[page needed]
  34. ↑ Heck, Henry d'A.; Tyl, Rochelle W. (1985). "The induction of bladder stones by terephthalic acid, dimethyl terephthalate, and melamine (2,4,6-triamino-s-triazine) and its relevance to risk assessment". Regulatory Toxicology and Pharmacology. 5 (3): 294–313. Bibcode:1985RToxP...5..294H. doi:10.1016/0273-2300(85)90044-3. PMID 3903881.
  35. ↑ Tusing, T.W. "Chronic Feeding – Dogs", cited by "Summary of toxicity data – trichloromelamine" by California Environmental Protection Agency, last revised on February 4, 2002, URL Archived June 25, 2007, at the Wayback Machine Retrieved September 5, 2007
  36. ↑ "Culprit in pet food deaths may be combination of contaminants". Michigan State University. November 29, 2007. Retrieved December 7, 2007.
  37. ↑ "Proceedings of the American Association of Veterinarian Laboratory Diagnosticians 50th Annual Conference" (PDF). AAVLD. October 2007. Archived from the original (PDF) on September 20, 2018. Retrieved May 16, 2021.
  38. ↑ "Researchers examine contaminants in food, deaths of pets". AVMA. November 2007. Archived from the original on November 22, 2007. Retrieved November 30, 2007.
  39. ↑ "Cyromazine" (PDF). European Medicines Agency. January 2001. Archived from the original (PDF) on October 10, 2008. Retrieved June 20, 2012.
  40. ↑ Lim, Lori O.; Scherer, Susan J.; Shuler, Kenneth D.; Toth, John P. (1990). "Disposition of cyromazine in plants under environmental conditions". Journal of Agricultural and Food Chemistry. 38 (3): 860–864. Bibcode:1990JAFC...38..860L. doi:10.1021/jf00093a057.
  41. ↑ "Cyromazine" (PDF). Pesticide Residues in Food, 1992 Evaluations: Residues. Food & Agriculture Org. 1993. pp. 265–. ISBN 978-92-5-103341-8. Archived from the original (PDF) on October 21, 2012.
  42. ↑ "International experts limit melamine levels in food". World Health Organization. July 6, 2010. Archived from the original on July 7, 2010. Retrieved July 7, 2010. Establishment of maximum levels will help governments differentiate between low levels of unavoidable melamine occurrence that do not cause health problems, and deliberate adulteration – thereby protecting public health without unnecessary impediments to international trade.
  43. ↑ Kirk-Othmer (1978). Kirk-Othmer encyclopedia of chemical technology. Vol. 7 (3rd ed.). Wiley. pp. 303–304. ISBN 978-0-471-48516-2.
  44. ↑ Lahalih, Shawqui M.; Absi-Halabi, M. (1989). "Recovery of solids from melamine waste effluents and their conversion to useful products". Industrial & Engineering Chemistry Research. 28 (4): 500–504. doi:10.1021/ie00088a020. ISSN 0888-5885.
  45. ↑ "How a golden chemical became greener". Nitrogen+Syngas. No. 293. May–June 2008. Archived from the original on February 2, 2017.
  46. ↑ Matsui, Kohji (1972). "Syntheses and Reactions of s-Triazine Derivatives". Journal of Synthetic Organic Chemistry, Japan (in Japanese). 30 (1): 19–35. doi:10.5059/yukigoseikyokaishi.30.19. ISSN 0037-9980.
  47. ↑ Ruilin, Wang (January 6, 2006). "Melamine capacity is serious surplus". China Chemical Reporter. Retrieved April 21, 2007.
  48. ↑ "Tainted milk trial opens in China". BBC. December 26, 2008. Retrieved January 7, 2009.
  49. ↑ "Chinese Milk Scam Duo Face Death". BBC. January 22, 2009. Retrieved January 22, 2009.
  50. ↑ Dry food added to pet food recall list. CNN. March 30, 2007
  51. ↑ "Pet food recall". AVMA. April 11, 2007. Archived from the original on April 15, 2007. Retrieved June 20, 2012.
  52. ↑ "Natural Balance FAQ". Archived from the original on September 30, 2007.
  53. ↑ Melamine Pet Food Recall – Frequently Asked Questions. FDA.gov (Updated October 7, 2009)
  54. ↑ "FDA: Pet food recall". Fda.gov. Archived from the original on April 7, 2007. Retrieved June 20, 2012.
  55. ↑ Barboza, David; Barrionuevo, Alexei (April 30, 2007). "Filler in Animal Feed Is Open Secret in China". The New York Times. Retrieved April 30, 2007.
  56. ↑ Barboza, David & Barrionuevo, Alexei (May 3, 2007). "China Makes Arrest in Pet Food Case". The New York Times. Retrieved May 3, 2007.
  57. ↑ "Products". Shandong Mingshui Great Chemical Group. Archived from the original on July 26, 2005. Retrieved April 30, 2007.
  58. ↑ Scott McDonald (September 21, 2008). "Nearly 53,000 Chinese children sick from milk". The Pantagraph. ISSN 2641-7634. Archived from the original on May 16, 2021. Retrieved May 16, 2021.
  59. ↑ Jane Macartney, China baby milk scandal spreads as sick toll rises to 13,000[dead link], The Times (September 22, 2008)
  60. ↑ "Toxicological and Health Aspects of Melamine and Cyanuric Acid" (PDF). WHO. 2009. Retrieved August 13, 2009.
  61. ↑ Guan, Na; Fan, Qingfeng; Ding, Jie; Zhao, Yiming; Lu, Jingqiao; Ai, Yi; Xu, Guobin; Zhu, Sainan; Yao, Chen; Jiang, Lina; Miao, Jing; Zhang, Han; Zhao, Dan; Liu, Xiaoyu; Yao, Yong (2009). "Melamine-Contaminated Powdered Formula and Urolithiasis in Young Children". New England Journal of Medicine. 360 (11): 1067–74. doi:10.1056/NEJMoa0809550. PMID 19196669.
  62. ↑ "Fonterra says somebody sabotaged milk". The New Zealand Herald. September 15, 2008. Retrieved September 22, 2008.
  63. ↑ "Toxic milk toll rockets in China". BBC News. September 15, 2008. Retrieved September 22, 2008.
  64. ↑ Tran, Tini (September 17, 2008). "6,200 Chinese babies ill, 3 die from tainted milk". Yahoo! News. Archived from the original on September 21, 2008. Retrieved September 22, 2008.
  65. ↑ "Three Death Sentences in Chinese Milk Scandal". Quality Assurance Magazine. BNP Media. January 22, 2009. Retrieved December 26, 2025.
  66. ↑ "Hong Kong widens China food tests". BBC News. October 27, 2008. Retrieved October 27, 2008.
  67. ↑ "Melamine tainted milk re-emerges in northwest China plant". Xinhua. July 9, 2010. Archived from the original on July 11, 2010. Retrieved July 9, 2010.
  68. ↑ Wines, Michael (July 9, 2010). "Tainted Dairy Products Seized in Western China". New York Times. Retrieved July 9, 2010.
  69. ↑ Langman, Craig B. (2009). "Melamine, Powdered Milk, and Nephrolithiasis in Chinese Infants". The New England Journal of Medicine. 360 (11): 1139–41. doi:10.1056/NEJMe0900361. PMID 19196666.
  70. ↑ Sun, N.; Shen, Y.; Sun, Q.; Li, X. R.; Jia, L. Q.; Zhang, G. J.; Zhang, W. P.; Chen, Z.; Fan, J. F.; Jiang, Y. P.; Feng, D. C.; Zhang, R. F.; Zhu, X. Y.; Xiao, H. Z. (2009). "Diagnosis and treatment of melamine-associated urinary calculus complicated with acute renal failure in infants and young children". Chinese Medical Journal. 122 (3): 245–51. doi:10.3760/cma.j.issn.0366-6999.2009.03.002. PMID 19236798.
  71. ↑ Li, Gang; Jiao, Shufang; Yin, Xiangjun; Deng, Ying; Pang, Xinghuo; Wang, Yan (2009). "The risk of melamine-induced nephrolithiasis in young children starts at a lower intake level than recommended by the WHO". Pediatric Nephrology. 25 (1): 135–41. doi:10.1007/s00467-009-1298-3. PMID 19727838. S2CID 360958.
  72. ↑ Liu, J.-m.; Ren, A.; Yang, L.; Gao, J.; Pei, L.; Ye, R.; Qu, Q.; Zheng, X. (2010). "Urinary tract abnormalities in Chinese rural children who consumed melamine-contaminated dairy products: A population-based screening and follow-up study". Canadian Medical Association Journal. 182 (5): 439–43. doi:10.1503/cmaj.091063. PMC 2842835. PMID 20176755.
  73. ↑ "About melamine". Irmm.jrc.ec.europa.eu. February 2, 2012. Archived from the original on February 12, 2012. Retrieved June 20, 2012.
  74. ↑ Breidbach, A., Bouten, K., Kroger, K., Ulberth, F. "Melamine Proficiency Test 2009". ec.europa.eu Archived October 15, 2009, at the Wayback Machine
  75. ↑ U.S. FDA Laboratory Information Bulletin No 4421 – "US FDA/CFSAN - Determination of Melamine and Cyanuric Acid Residues in Infant Formula using LC-MS/MS - Lib. 4421". Archived from the original on October 10, 2008. Retrieved October 16, 2008.
  76. ↑ Japanese Ministry of Health, Labor and Welfare. forth.go.jp
  77. ↑ Zwitterionic HILIC separation of melamine and cyanuric acid – "Strategies for Determination of Melamine by HILIC". October 3, 2008. Archived from the original on October 6, 2008. Retrieved October 16, 2008.
  78. ↑ Hodge, James (December 12, 2008). "Dairy detection: monitoring melamine in milk". Chemical Science. No. 2. Royal Chemical Society, RCS Publishing. Retrieved January 4, 2009.
  79. ↑ Zhu, Liang; Gamez, Gerardo; Chen, Huanwen; Chingin, Konstantin; Zenobi, Renato (2009). "Rapid detection of melamine in untreated milk and wheat gluten by ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS)". Chemical Communications (5): 559–61. doi:10.1039/b818541g. PMID 19283290.
  80. ↑
  81. ↑ Huang, Guangming; Ouyang, Zheng; Cooks, R. Graham (2009). "High-throughput trace melamine analysis in complex mixtures". Chemical Communications (5): 556–8. doi:10.1039/b818059h. PMID 19283289.
  82. ↑ Melaminometer
  83. ↑ McKenna, Phil (January 7, 2009). "Rise of the garage genome hackers". New Scientist. Retrieved February 17, 2009.
  84. ↑ Marcus, Wohlsen (December 26, 2008). "Amateurs are trying genetic engineering at home". Copyright 2008 The Associated Press. Retrieved February 17, 2009.
  85. ↑ Ishiwata H, Inoue T, Yamazaki T, Yoshihira K (1987). "Liquid chromatographic determination of melamine in beverages". Journal of the Association of Official Analytical Chemists. 70 (3): 457–460. doi:10.1093/jaoac/70.3.457. PMID 3610957.
  86. ↑ Sancho, J.V.; Ibáñez, M.; Grimalt, S.; Pozo, Ó.J.; Hernández, F. (2005). "Residue determination of cyromazine and its metabolite melamine in chard samples by ion-pair liquid chromatography coupled to electrospray tandem mass spectrometry". Analytica Chimica Acta. 530 (2): 237–243. Bibcode:2005AcAC..530..237S. doi:10.1016/j.aca.2004.09.038. INIST 16514561.
  87. ↑ "Cyromazine and Melamine" (PDF). USDA FSIS. July 1991. Archived from the original (PDF) on June 16, 2007. Retrieved April 27, 2007.
  88. ↑ "Chemistry Laboratory Guidebook". USDA FSIS. Retrieved April 27, 2007.
  89. ↑ "HPLC Determination of Melamine, Ammeline, Ammelide, and Cyanuric Acid Contamination in Wheat Gluten and Rice Protein Concentrate". U.S. Food and Drug Administration. April 25, 2007. Archived from the original on December 20, 2008. Retrieved May 9, 2007.
  90. ↑ He, Lili; Liu, Yang; Lin, Mengshi; Awika, Joseph; Ledoux, David R.; Li, Hao; Mustapha, Azlin (2008). "A new approach to measure melamine, cyanuric acid, and melamine cyanurate using surface enhanced Raman spectroscopy coupled with gold nanosubstrates". Sensing and Instrumentation for Food Quality and Safety. 2: 66–71. doi:10.1007/s11694-008-9038-0. S2CID 93425738.
  91. ↑ Lin, M.; He, L.; Awika, J.; Yang, L.; Ledoux, D.R.; Li, H.; Mustapha, A. (2008). "Detection of Melamine in Gluten, Chicken Feed, and Processed Foods Using Surface Enhanced Raman Spectroscopy and HPLC". Journal of Food Science. 73 (8): T129-34. Bibcode:2008JFooS..73901.xL. doi:10.1111/j.1750-3841.2008.00901.x. PMID 19019134.
  92. ↑ "The requested document does not exist. - EUR-Lex". eur-lex.europa.eu.
  93. ↑ Li, Saiwei; Wang, Yue; Tacken, Gemma M. L.; Liu, Yumei; Sijtsema, Siet J. (August 1, 2021). "Consumer trust in the dairy value chain in China: The role of trustworthiness, the melamine scandal, and the media". Journal of Dairy Science. 104 (8): 8554–8567. doi:10.3168/jds.2020-19733. ISSN 0022-0302. PMID 33896642.
  94. ↑ Zhang, Zhe; Godefroy, Samuel B.; Lyu, Hanyang; Sun, Baoguo; Fan, Yongxiang (November 1, 2018). "Transformation of China's food safety standard setting system – Review of 50 years of change, opportunities and challenges ahead". Food Control. 93: 106–111. doi:10.1016/j.foodcont.2018.05.047. ISSN 0956-7135.
  95. ↑ Baselt RC (2014). Disposition of toxic drugs and chemicals in man. Seal Beach, Ca.: Biomedical Publications. pp. 1213–1214. ISBN 978-0-9626523-9-4.
  96. ↑ Silly, Fabien; Shaw, Adam Q.; Castell, Martin R.; Briggs, G. A. D.; Mura, Manuela; Martsinovich, Natalia; Kantorovich, Lev (2008). "Melamine Structures on the Au(111) Surface". J. Phys. Chem. C. 112 (30): 11476–11480. doi:10.1021/jp8033769.
  97. ↑ Schmitz, Christoph H.; Ikonomov, Julian; Sokolowski, Moritz (2011). "Two commensurate hydrogen-bonded monolayer structures of melamine on Ag(111)". Surface Science. 605 (1–2): 1–6. Bibcode:2011SurSc.605....1S. doi:10.1016/j.susc.2010.09.006.
  98. ↑ Šimėnas, M.; Tornau, E. E. (2014). "A model of melamine molecules ordering on metal surfaces". J. Chem. Phys. 141 (5): 054701. Bibcode:2014JChPh.141e4701A. doi:10.1063/1.4891245. PMID 25106594.
  99. ↑ Mura, M.; Martsinovich, N.; Kantorovich, L. (2008). "Theoretical study of melamine superstructures and their interaction with the Au(111) surface". Nanotechnology. 19 (46) 465704. Bibcode:2008Nanot..19T5704M. doi:10.1088/0957-4484/19/46/465704. PMID 21836259. S2CID 25890258.
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