Melamine

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This article is about the chemical substance called melamine. The term "melamine" may also be used to refer to the plastic melamine resin.
Melamine
IUPAC name
Other names 2,4,6-Triamino-s-triazine
Cyanurotriamide
Cyanurotriamine
Cyanuramide
Identifiers
CAS number 108-78-1
PubChem 7955
SMILES
Properties
Molecular formula C3H6N6
Molar mass 126.12 g/mol
Appearance White solid
Density 1574 kg/m3
Melting point

345 °C, 618 K, 653 °F (decomposition[1])
Boiling point

Sublimes
Solubility in water 3.240 g/l (20 °C)[1]
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox references

Melamine (pronounced /ˈmɛ lə miːn/ melamine-pronunciation.ogg melamine (help·info)) is an organic base and a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred, and has several other industrial uses. Melamine is also a metabolite of cyromazine, a pesticide. It is formed in the body of mammals who have ingested cyromazine.[2] It has been reported that cyromazine can also be converted to melamine in plants.[3][4]

Melamine combines with cyanuric acid to form melamine cyanurate, which has been implicated in the Chinese protein export contaminations.

Contents

[edit] Etymology

The German word melamin was coined by combining the names of 2 other chemical products: Melam (a distillation derivative of ammonium thiocyanate) and Amine.[5][6]

Melamine etymology is thus not derived from the root mela (μελα, meaning black in Greek), such as, e.g., the pigment melanin, the hormone melatonin, or the melanotan peptides.

[edit] Uses

Melamine is combined with formaldehyde to produce melamine resin, a very durable thermosetting plastic used in Formica, and melamine foam, a polymeric cleaning product. The end products include countertops, dry erase boards, fabrics, glues, housewares and flame retardants. Melamine is one of the major components in Pigment Yellow 150, a colorant in inks and plastics.

Melamine also enters the fabrication of melamine poly-sulfonate used as superplasticizer for making high-resistance concrete. Sulfonated melamine formaldehyde (SMF) is a polymer used as cement admixture to reduce the water content in concrete while increasing the fluidity and the workability of the mix during its 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 life-time.

The use of melamine as fertilizer for crops had been envisaged during the '50s and '60s because of its high nitrogen content (2/3).[7] However melamine is much more expensive to produce than other common nitrogen fertilizers, such as urea. To be effective as a fertilizer, it is essential that the plant nutrients are released or made available in a manner that matches the needs of the growing crop. The nitrogen mineralization process for melamine is extremely slow, making this product both economically and scientifically impractical for use as a fertilizer.

Melamine derivatives of arsenical drugs are potentially important in the treatment of African trypanosomiasis.[8]

Melamine use as non-protein nitrogen (NPN) for cattle was described in a 1958 patent.[9] 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.[10]

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 adding nitrogen-rich compounds such as melamine.[11]

[edit] Toxicity

Melamine is described as being "Harmful if swallowed, inhaled or absorbed through the skin. Chronic exposure may cause cancer or reproductive damage. Eye, skin and respiratory irritant.” However, the toxic dose is on a par with common table salt with an LD50 of more than 3 grams per kilogram of bodyweight.[12] FDA scientists explained that when melamine and cyanuric acid are absorbed into the bloodstream, they concentrate and interact in the urine-filled renal microtubules, 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.[13]

The European Union set a standard for acceptable human consumption of melamine at 0.5 milligrams per kg of body mass, Canada declared a limit of 0.35 mg and the US FDA’s limit was put at 0.63 mg, but was later reduced to 0.063 mg daily. 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 "tolerable daily intake" (TDI), was 0.2 mg per kg of body mass.[14]

[edit] Acute toxicity

Melamine is reported to have an oral 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 >1000 mg/kg for rabbits.[15] In a 1945 study. A study by USSR researchers in the 1980s suggested that melamine cyanurate, commonly used as a fire retardant,[16] could be more toxic than either melamine or cyanuric acid alone.[17] 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 conducted after recalls of contaminated pet food concluded that the combination of melamine and cyanuric acid in diet does lead to acute renal failure in cats.[18]

[edit] Chronic toxicity

Ingestion of melamine may lead to reproductive damage, or bladder or kidney stones, which can lead to bladder cancer.[15][19][20][21][22]

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.[23]

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."[24][25][26]

[edit] Synthesis

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

6 (NH2)2CO → C3H6N6 + 6 NH3 + 3 CO2

It can be understood as two steps.

First, urea decomposes into cyanic acid and ammonia in an endothermic reaction:

(NH2)2CO → HCNO + NH3

Then, cyanic acid polymerizes to form melamine and carbon dioxide:

6 HCNO → C3H6N6 + 3 CO2

The second reaction is exothermic but the overall process is endothermic.

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.[27] Major manufacturers and licensors such as DSM, 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 is a pollutant if discharged directly into the environment. The waste water 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).[28]

[edit] Recent production of melamine in mainland China

Between the late 1990s and early 2000s, both consumption and production of melamine grew considerably in mainland China. In the United States Geological Survey 2004 Minerals Survey Yearbook, in a report on worldwide nitrogen production, the author stated that "(mainland) China continued to plan and construct new ammonia and urea plants using coal gasification technology."[29]

By early 2006, melamine production in mainland China is reported to be in "serious surplus".[30] In April 2007, DSM's melamine industry update painted a grave global picture.[31] 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.

Surplus melamine has been an adulterant for feedstock and milk in mainland China for several years now because it can make diluted or poor quality material appear to be higher in protein content by elevating the total nitrogen content detected by some simple protein tests. Actions taken in 2008 by the Government of China has reduced the practice of adulteration, with the goal of eliminating it. Court trials began in December 2008 for six people linked to the scandal and ended in January 2009 with two of the convicts being sentenced to death.[32][33]

[edit] Poisoning and kidney failure caused by melamine cyanurate

[edit] 2007 Animal feed recalls

Further information: 2007 pet food recalls and Chinese protein export contamination

In 2007 a pet food recall was initiated by Menu Foods and other pet food manufacturers who had found their products had been contaminated and caused serious illnesses or deaths in some of the animals that had eaten them.[34][35][36] In March 2007, the US Food and Drug Administration reported finding white granular melamine in the pet food, in samples of white granular wheat gluten imported from a single source in China, Xuzhou Anying Biologic Technology[37] as well as in crystalline form in the kidneys and in urine of affected animals.[38] Further vegetable protein imported from China was later implicated.

In April 2007, The New York Times reported that the addition of "melamine scrap" into fish and livestock feed to give the false appearance of a higher level of protein was an "open secret" in many parts of mainland China, reporting that this melamine scrap was being produced by at least one plant processing coal into melamine.[39] Four days later, the New York Times reported that, despite the widely reported ban on melamine use in vegetable proteins in mainland China, at least some chemical manufacturers continued to report selling it for use in animal feed and in products for human consumption. Li Xiuping, a manager at Henan Xinxiang Huaxing Chemical in Henan Province, stated, "Our chemical products are mostly used for additives, not for animal feed. Melamine is mainly used in the chemical industry, but it can also be used in making cakes."[40] Shandong Mingshui Great Chemical Group, the company reported by the New York Times as producing melamine from coal, produces and sells both urea and melamine but does not list melamine resin as a product.[41]

Another recall incident in 2007 involved melamine which had been purposely added as a binder to fish and livestock feed manufactured in the United States. This was traced to suppliers in Ohio and Colorado.[42]

[edit] 2008 Chinese scandal

Further information: 2008 Chinese milk scandal

In September 2008, several companies were implicated in a scandal involving milk and infant formula which had been adulterated with melamine, leading to kidney stones and other renal failure, especially among young children. By 22 September, nearly 300,000 people had become ill, with more than 12,800 hospitalizations and four infant deaths.[43][44] In a study published in the New England Journal of Medicine,it was reported that melamine exposure increased the incidence of urinary tract stones by seven times in children.[45] Melamine may have been added to fool government protein content tests after water was added to fraudulently dilute the milk. Because of melamine's high nitrogen content (66% by mass versus approx. 10–12% for typical protein), it can cause the protein content of food to appear higher than the true value.[46][47] Officials estimate that about 20 percent of the dairy companies tested in China sell products tainted with melamine. On January 22, 2009, three of those involved in the scandal (including one conditional sentence) were sentenced to death in a Chinese court.[48]

In October 2008, "Select Fresh Brown Eggs" imported to Hong Kong from the Hanwei Group in Dalian in northeastern China, were found to be contaminated with nearly twice the legal limit of melamine. York Chow, the health secretary of Hong Kong, said he thought animal feeds might be the source of the contamination and announced that the Hong Kong Centre for Food Safety would henceforward be testing all mainland Chinese pork, farmed fish, animal feed, chicken meat, eggs, and offal products for melamine.[49]

[edit] Testing for melamine and cyanuric acid in food

Until the 2007 pet food recalls, melamine had not routinely been monitored in food, except in the context of plastic safety or insecticide residue. This could be due to the previously assumed low toxicity of melamine, and the relatively expensive methods of detection.

Following the 2008 health scare in China over powdered milk, the Joint Research Centre of the European Commission in Belgium set-up a website about methods to detect melamine.[50]

In October 2008, the U.S. Food and Drug Administration (FDA) issued new methods for the analysis of melamine and cyanuric acid in infant formulations in the Laboratory Information Bulletin No 4421.[51] Similar recommendations have been issued by other authorities, like the Japanese Ministry of Health, Labor and Welfare,[52] both based on liquid chromatography – mass spectrometry (LC/MS) detection after hydrophilic interaction liquid chromatography (HILIC) separation.[53]

The existing methods for melamine determination using a triple quadrupole liquid chromatography – mass spectrometry (LC/MS) after solid phase extraction (SPE) are often complex and time consuming. However, electrospray ionization methods coupled with mass spectrometry allow a rapid and direct analysis of samples with complex matrices: the native liquid samples are directly ionized under ambient conditions in their original solution. In December 2008, two new fast and inexpensive methods for detecting melamine in liquids have been published on-line in the Chem. Comm. Journal of the Royal Society of Chemistry (UK).[54]

Ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS) has been developed at ETH Zurich (Switzerland) by Zhu et al., (2008)[55][56] for a rapid detection of melamine in untreated food samples. Ultrasounds are used to nebulize the melamine-containing liquids into a fine spray. The spray is then ionised by extractive electrospray ionisation (EESI) and analysed using tandem mass spectrometry (MS/MS). An analysis requires 30 seconds per sample. The limit of detection of melamine is a few nanograms of melamine per gram of milk.

Huang et al., (2008)[57][58] have also developed at Purdue University (US) a simpler instrumentation and a faster method by using a low-temperature plasma probe to ionize the samples. The major obstacles being solved, the ESI-MS technique allows now high-throughput analysis of melamine traces in complex mixtures.

The Melaminometer[59][60] uses a synthetic biology design for detecting melamine and related chemical analogues such as cyanuric acid. The ongoing project is hosted at OpenWetWare as open source biology in collaboration with DIYbio. The Melaminometer approach aims to provide a very low cost (sub-$1) biological method of detecting the FDA-listed substances without use of costly instrumentation or training. A rapid and sensitive melamine colorimetric visualization assay has been developed and is ready for the marketing.[61]This is a practical method for use in home and in field.


Because melamine resin is often used in food packaging and tableware, melamine at ppm level (1 part per million) in food and beverage has been reported due to migration from melamine-containing resins.[62] Small amounts of melamine have also been reported in foodstuff as a metabolite product of cyromazine, an insecticide used on animals and crops.[63]

The Food Safety and Inspection Service (FSIS) of the United States Department of Agriculture (USDA) provides a test method for analyzing cyromazine and melamine in animal tissues.[64][65] In 2007, the FDA began using a high performance liquid chromatography test to determine the melamine, ammeline, ammelide, and cyanuric acid contamination in food.[66] Another procedure is based on surface-enhanced Raman spectroscopy (SERS).[67][68]

[edit] Legal maximum limits accepted for human food

Member States of the European Union are required under Commission Decision 2008/757/EC[69] to ensure that all composite products containing at least 15 % of milk product, originating from China, are systematically tested before import into the Community and that all such products which are shown to contain melamine in excess of 2.5 mg/kg are immediately destroyed.

[edit] See also

[edit] References

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  2. ^ Report on cyromazine of the European Medicines Agency
  3. ^ Lori 0. Lim, Susan J. Scherer, Kenneth D. Shuler, and John P. Toth. Disposition of Cyromazine in Plants under Environmental Conditions J. Agric. Food Chem. 1990, 38, 860–864 [1]
  4. ^ FAO report on cyromazine
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  7. ^ Hauck, R.D.; H.F. Stephenson (1964). "Nitrification of triazine nitrogen". Fertilizer Nitrogen Sources 12 (2): 147. 
  8. ^ Barrett MP, Gilbert IH (2006). "Targeting of toxic compounds to the trypanosome's interior". Adv. Parasitol. 63: 125–83. doi:10.1016/S0065-308X(06)63002-9. PMID 17134653. 
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  11. ^ "Protein Pretense", Alison Snyder, Scientific American Magazine, August 2008 [2] |accessdate=2008-09-19
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  15. ^ a b MSDS
  16. ^ Flame Retardants Center: Melamine Compounds
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  35. ^ AVMA: Pet food recall
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  63. ^ J.V. Sancho, M. Ibanez, S. Grimalt, O.J. Pozo, F. Hernandez, "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 Vol.530, p237–243 (2005) Abstract accessed 05-06-2007.
  64. ^ "Cyromazine and Melamine" (PDF). USDA FSIS. July 1991. http://www.fsis.usda.gov/ophs/clg/Cyromazine.pdf. Retrieved on 2007-04-27. 
  65. ^ "Chemistry Laboratory Guidebook". USDA FSIS. http://www.fsis.usda.gov/science/Chemistry_Lab_Guidebook/index.asp. Retrieved on 2007-04-27. 
  66. ^ "HPLC Determination of Melamine, Ammeline, Ammelide, and Cyanuric Acid Contamination in Wheat Gluten and Rice Protein Concentrate". FDA. 25 April 2007. http://acs.confex.com/acs/mwrm07/techprogram/P51682.HTM. Retrieved on 2007-05-09. 
  67. ^ 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. 
  68. ^ Mengshi Lin, Lili He, Joseph Awika, Liyi Yang, David R. Ledoux, Hao Li, Azlin Mustapha, (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–T134. doi:10.1111/j.1750-3841.2008.00901.x. http://www3.interscience.wiley.com/cgi-bin/fulltext/121385682/PDFSTART. 
  69. ^ European Commission decision (2008/798/EC) imposing special conditions governing the import of products containing milk or milk products originating from China

[edit] External links

Sister project Look up melamine in
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