Melamine Explained

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You are here Everything Explained.Today A-Z Contents M ME MEL MELA MELAMMelamine

Melamine is an organic base and a trimer of cyanamide , with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogengas when burned or charred, and has several other industrial uses. Melamineis also a metabolite of cyromazine, a pesticide. It is formed in the body of mammals that have ingested cyromazine. [1] It has been reported thatcyromazine can also be converted to melamine in plants. [2] [3]

Melamine combines with cyanuric acid and related compounds to formmelamine cyanurate and related crystal structures, which have beenimplicated as contaminants or biomarkers in Chinese protein adulteration s.

The German word melamin was coined by combining the words: melam (aderivative of ammonium thiocyanate) and amine.[4] [5] Melamine is,therefore, unrelated etymologically to the root melas ( μελας , meaning blackin Greek), from which the words melanin, a pigment, and melatonin , ahormone, are formed.

Melamine is combined with formaldehyde to produce melamine resin , a verydurable thermosetting plastic used in high pressure decorative laminate ssuch as Formica, melamine dinnerware, laminate flooring, and dry eraseboards.

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

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

Melamine also enters the fabrication of melamine poly-sulfonate used assuperplasticizer for making high-resistance concrete . Sulfonated melamineformaldehyde (SMF) is a polymer used as cement admixture to reduce thewater content in concrete while increasing the fluidity and the workability of the mix during its handling and pouring. It results in concrete with a lowerporosity and a higher mechanical strength, exhibiting an improved resistanceto aggressive environments and a longer lifetime.

The use of melamine as fertilizer for crops had been envisaged during the1950s and 1960s because of its high nitrogen content (2/3). However,melamine is much more expensive to produce than are other commonnitrogen fertilizers, such as urea . To be effective as a fertilizer, it is essentialthat the plant nutrients are released or made available in a manner thatmatches the needs of the growing crop. The nitrogen mineralization processfor melamine is extremely slow, making this product both economically andscientifically impractical for use as a fertilizer.

Melamine and its salts are used as fire-retardant additives in paints, plastics,and paper. [6]

mine Explained http://everything.explained.today/Melam

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Melamine derivatives of arsenical drugs are potentially important in thetreatment of African trypanosomiasis .[7]

Melamine use as non-protein nitrogen (NPN) for cattle was described in a1958 patent. [8] In 1978, however, a study concluded that melamine "maynot be an acceptable non-protein N source for ruminants" because itshydrolysis in cattle is slower and less complete than other nitrogen sourcessuch as cottonseed meal and urea. [9]

Melamine is sometimes illegally added to food products in order to increasethe apparent protein content. Standard tests, such as the Kjeldahl andDumas tests, estimate protein levels by measuring the nitrogen content, sothey can be misled by adding nitrogen-rich compounds such as melamine.An instrument (SPRINT) developed by the company CEM Corp allows thedetermination of protein content directly in some applications; theinstrument cannot be fooled by adding melamine in the sample. [10] [11]

Melamine is also used as a nitrogen and carbon source for N-doped carbonnanotube . N-CNTs can be prepared via Chemical Vapor Deposition (CVD)method by pyrolysizing melamine under an Ar atmosphere in a horizontalglass tube. A thin film of iron (5 nm) is first deposited on a Si/SiO 2 wafer.

N-CNT synthesis occurs at a furnace temperatures between 800 and980 °C. [12]

Melamine is described as "Harmful if swallowed, inhaled or absorbed throughthe skin. Chronic exposure may cause cancer or reproductive damage. Eye,skin and respiratory irritant". However, the short-term lethal dose is on a parwith common table salt with an LD50 of more than 3 grams per kilogram of bodyweight. [13] U.S. Food and Drug Administration (FDA) scientistsexplained 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 inturn block and damage the renal cells that line the tubes, causing thekidneys to malfunction. [14]

The European Union set a standard for acceptable human consumption(tolerable daily intake , TDI) of melamine at 0.2 mg per kg of body mass, [15](previously 0.5 milligrams), Canada declared a limit of 0.35 mg and the USFDA's limit was put at 0.063 mg daily (previously 0.63 mg). The WorldHealth Organization 's food safety director estimated that the amount of melamine a person could stand per day without incurring a bigger healthrisk, the TDI, was 0.2 mg per kg of body mass. [16]

Toxicity of melamine can be mediated by intestinal microbes. In culture,Klebsiella terrigena , which rarely colonizes mammalian intestines, [17] wasshown to convert melamine to cyanuric acid directly. Rats colonized by K.terrigena showed greater melamine-induced kidney damage compared tothose not colonized. [18]

Melamine is reported to have an oral LD 50 of 3248 mg/kg based on rat data.It is also an irritant when inhaled or in contact with the skin or eyes. Thereported dermal LD 50 is >1000 mg/kg for rabbits.A study by USSR


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researchers in the 1980s suggested that melamine cyanurate , commonlyused as a fire retardant, [19] could be more toxic than either melamine orcyanuric acid alone. [20] For rats and mice, the reported LD 50 for melaminecyanurate was 4.1 g/kg (given inside the stomach) and 3.5 g/kg (viainhalation), compared to 6.0 and 4.3 g/kg for melamine and 7.7 and 3.4g/kg for cyanuric acid, respectively.

A toxicology study in animals conducted after recalls of contaminated petfood concluded that the combination of melamine and cyanuric acid in dietdoes lead to acute renal failure in cats. [21] A 2008 study produced similarexperimental results in rats and characterized the melamine and cyanuricacid in contaminated pet food from the 2007 outbreak. [22] A 2010 studyfrom Lanzhou University attributed renal failure in humans to uric acid stoneaccumulation after ingestion of melamine resulting in a rapid aggregation of metabolites such as cyanuric acid diamide ( ammeline ) and cyanuric acid.

Ingestion of melamine may lead to reproductive damage , or bladder orkidney stone s, which can lead to bladder cancer .[23] [24] [25] [26] [27]

A study in 1953 reported that dogs fed 3% melamine for a year had thefollowing changes in their urine: (1) reduced specific gravity, (2) increasedoutput , (3) melamine crystalluria, and (4) protein and occult blood.[28]

A survey commissioned by the American Association of VeterinaryLaboratory Diagnosticians suggested that crystals formed in the kidneyswhen melamine combined with cyanuric acid, "don't dissolve easily. They goaway slowly, if at all, so there is the potential for chronic toxicity." [29] [30][31]

Fast diagnosis and treatment of acute obstructive urolithiasis may preventthe development of acute renal failure . Urine alkalinization and stoneliberalization have been reported to be the most effective treatments inhumans.

The United Nations' food standards body, Codex Alimentarius Commission,has set the maximum amount of melamine allowed in powdered infantformula to 1 mg/kg and the amount of the chemical allowed in other foodsand animal feed to 2.5 mg/kg. While not legally binding, the levels allowcountries to ban importation of products with excessive levels of melamine. [32]

Melamine was first synthesized by the German chemist Justus von Liebig in1834. In early production, first calcium cyanamide is converted intodicyandiamide, then heated above its melting temperature to producemelamine. However, today most industrial manufacturers use urea in thefollowing reaction to produce melamine:


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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 endothermicreaction :

(NH2)2CO → HCNO + NH3

Then, cyanic acid polymerizes to form cyanuric acid which condenses withthe liberated ammonia forming melamine which releases water which thenreacts with cyanic acid present(which helps to drive the reaction) generatingcarbon dioxide and ammonia.

6 HCNO + 3 NH3 → C3H6N6 + 3 CO2 + 3NH3

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

The above reaction can be carried out by either of two methods: catalyzedgas-phase production or high pressure liquid-phase production. In onemethod, molten urea is introduced onto a fluidized bed with catalyst forreaction. Hot ammonia gas is also present to fluidize the bed and inhibit

deammonization. The effluent then is cooled. Ammonia and carbon dioxide inthe off-gas are separated from the melamine-containing slurry. The slurry isfurther concentrated and crystallized to yield melamine. [33] Majormanufacturers and licensors such as Orascom Construction Industries , BASF,and Eurotecnica have developed some proprietary methods.

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

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). [34] In the Eurotecnicaprocess, however, there is no solid waste and the contaminants aredecomposed to ammonia and carbon dioxide and sent as off gas to theupstream urea plant; accordingly, the waste water can be recycled to themelamine plant itself or used as clean cooling water make-up. [35]

Between the late 1990s and early 2000s, both consumption and productionof melamine grew considerably in mainland China . By early 2006, melamineproduction in mainland China is reported to be in "serious surplus". [36]Between 2002 and 2007, while the global melamine price remained stable, asteep increase in the price of urea (feedstock for melamine) has reduced theprofitability of melamine manufacturing. Currently, China is the world'slargest exporter of melamine, while its domestic consumption still grows by10% per year. However, reduced profit has already caused other jointmelamine ventures to be postponed there.

Surplus melamine has been an adulterant for feedstock and milk in mainlandChina for several years now because it can make diluted or poor qualitymaterial appear to be higher in protein content by elevating the total


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nitrogen content detected by some simple protein tests. Actions taken in2008 by the Government of China have reduced the practice of adulteration,with the goal of eliminating it. Court trials began in December 2008 for sixpeople linked to the scandal and ended in January 2009 with two of theconvicts being sentenced to death and executed. [37] [38]

Melamine has been involved in several food recalls after the discovery of severe kidney damage to children and pets poisoned by melamine-adulterated food.

In 2007, a pet food recall was initiated by Menu Foods and other pet foodmanufacturers who had found their products had been contaminated andcaused serious illnesses or deaths in some of the animals that had eatenthem. [39] [40] [41] In March 2007, the US Food and Drug Administrationreported 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[42] as well as in crystalline form in the kidneysand in urine of affected animals. [43] Further vegetable protein imported fromChina was later implicated.

In April 2007, The New York Times reported that the addition of "melaminescrap" into fish and livestock feed to give the false appearance of a higherlevel of protein was an "open secret" in many parts of mainland China,reporting that this melamine scrap was being produced by at least one plantprocessing coal into melamine. [44] Four days later, the New York Timesreported that, despite the widely reported ban on melamine use in vegetableproteins in mainland China, at least some chemical manufacturers continuedto report selling it for use in animal feed and in products for human

consumption. Li Xiuping, a manager at Henan Xinxiang Huaxing Chemical inHenan Province, stated, "Our chemical products are mostly used foradditives, not for animal feed. Melamine is mainly used in the chemicalindustry, but it can also be used in making cakes." [45] Shandong MingshuiGreat Chemical Group, the company reported by the New York Times asproducing melamine from coal, produces and sells both urea and melaminebut does not list melamine resin as a product. [46]

Another recall incident in 2007 involved melamine which had been purposelyadded as a binder to fish and livestock feed manufactured in the UnitedStates. This was traced to suppliers in Ohio and Colorado. [47]

In September 2008, several companies, including Nestlé, were implicated ina scandal involving milk and infant formula which had been adulterated withmelamine, leading to kidney stones and other renal failure , especially amongyoung children. By December 2008, nearly 300,000 people had become ill,with more than 50,000 infant hospitalizations and six infant deaths. [48] [49][50] In a study published in the New England Journal of Medicine , it wasreported that melamine exposure increased the incidence of urinary tractstones by seven times in children. [51] Melamine may have been added tofool government protein content tests after water was added to fraudulentlydilute the milk. Because of melamine's high nitrogen content (66% by mass


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versus approx. 10–12% for typical protein), it can cause the protein contentof food to appear higher than the true value. [52] [53] Officials estimate thatabout 20 percent of the dairy companies tested in China sell products taintedwith melamine. On January 22, 2009, three of those involved in the scandal(including one conditional sentence) were sentenced to death in a Chinesecourt. [54]

In October 2008, "Select Fresh Brown Eggs" imported to Hong Kong fromthe Hanwei Group in Dalian in northeastern China, were found to becontaminated with nearly twice the legal limit of melamine. York Chow, thehealth secretary of Hong Kong, said he thought animal feeds might be thesource of the contamination and announced that the Hong Kong Centre forFood Safety would henceforward be testing all mainland Chinese pork,farmed fish, animal feed, chicken meat, eggs, and offal products formelamine. [55]

As of July 2010, Chinese authorities were still reporting some seizures of melamine-contaminated dairy product in some provinces, though it wasunclear whether these new contaminations constituted wholly newadulterations or were the result of illegal reuse of material from the 2008adulterations. [56] [57]

On characterization and treatment of urinary stones in affected infants, theNew England Journal of Medicine printed an editorial in March 2009, alongwith reports on cases from Beijing, Hong Kong and Taipei. [58]

Urinary calculi specimens were collected from 15 cases treated in Beijing andwere analyzed as unknown objects for their components at Beijing Instituteof Microchemistry using infrared spectroscopy , nuclear magnetic resonance ,and high performance liquid chromatography . The result of the analysisshowed that the calculus was composed of melamine and uric acid, and themolecular ratio of uric acid to melamine was around 2:1. [59]

In a 2009 study of 683 children diagnosed in Beijing in 2008 withnephrolithiasis and 6,498 children without nephrolithiasis aged < 3 years,investigators found that in children exposed to melamine levels < 0.2 mg/kgper day, the risk for nephrolithiasis was 1.7 times higher than in thosewithout melamine exposure, suggesting that the risk of melamine-inducednephrolithiasis in young children starts at a lower intake level than the levelsrecommended by the World Health Organization .[60]

In a study published in 2010, researchers from Beijing University studyingultrasound images of infants who fell ill in the 2008 contamination found thatwhile most children in a rural Chinese area recovered, 12 per cent stillshowed kidney abnormalities six months later. "The potential for long-termcomplications after exposure to melamine remains a serious concern," the

report said. "Our results suggest a need for further follow-up of affectedchildren to evaluate the possible long-term impact on health, including renalfunction."[61] Another 2010 follow-up study from Lanzhou Universityattributed the uric acid stone accumulation after ingestion of melamine to arapid aggradation of metabolites such as cyanuric acid diamide ( ammeline)and cyanuric acid and reported that urine alkalinization and stoneliberalization were the most effective treatments. [62]

Until the 2007 pet food recalls , melamine had not routinely been monitored


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in food, except in the context of plastic safety or insecticide residue. Thiscould be due to the previously assumed low toxicity of melamine, and therelatively expensive methods of detection.

Following the deaths of children in China from powdered milk in 2008, theJoint Research Centre (JRC) of the European Commission in Belgium set up awebsite about methods to detect melamine. [63] In May 2009, the JRCpublished the results of a study that benchmarked the ability of labs aroundthe world to accurately measure melamine in food. The study concluded thatthe majority of labs can effectively detect melamine in food. [64]

In October 2008, the U.S. Food and Drug Administration (FDA) issued newmethods for the analysis of melamine and cyanuric acid in infantformulations in the Laboratory Information Bulletin No 4421. [65] Similarrecommendations have been issued by other authorities, like the JapaneseMinistry of Health, Labor and Welfare, [66] both based on liquidchromatography – mass spectrometry ( LC/MS) detection after hydrophilicinteraction liquid chromatography ( HILIC) separation. [67]

The existing methods for melamine determination using a triple quadrupoleliquid 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 arapid and direct analysis of samples with complex matrices: the native liquidsamples are directly ionized under ambient conditions in their originalsolution. In December 2008, two new fast and inexpensive methods fordetecting melamine in liquids have been published on-line in the Chem.Comm. Journal of the Royal Society of Chemistry (UK).

Ultrasound-assisted extractive electrospray ionization mass spectrometry(EESI-MS) has been developed at ETH Zurich (Switzerland) by Zhu et al. ,(2008) [68] for a rapid detection of melamine in untreated food samples.Ultrasounds are used to nebulize the melamine-containing liquids into a finespray. The spray is then ionised by extractive electrospray ionisation (EESI)and analysed using tandem mass spectrometry (MS/MS). An analysisrequires 30 seconds per sample. The limit of detection of melamine is a fewnanograms of melamine per gram of milk.

Huang et al. , (2008) have also developed at Purdue University (US) asimpler instrumentation and a faster method by using a low-temperatureplasma probe to ionize the samples. The major obstacles being solved, theESI-MS technique allows now high-throughput analysis of melamine traces incomplex mixtures. [69]

The Melaminometer[70] [71] was a hypothetical design for a synthetic biologycircuit, to used for detecting melamine and related chemical analogues suchas cyanuric acid. The conceptual project is hosted at OpenWetWare as opensource biology in collaboration with DIYbio and has been discussed in variousnewspapers in the context of homebrew biotechnology. As of October 2009,the design has not been verified.

Because melamine resin is often used in food packaging and tableware,melamine at ppm level (1 part per million) in food and beverage has beenreported due to migration from melamine-containing resins. [72] Smallamounts of melamine have also been reported in foodstuff as a metaboliteproduct of cyromazine, an insecticide used on animals and crops. [73]

The Food Safety and Inspection Service (FSIS) of the United States


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Department of Agriculture (USDA) provides a test method for analyzingcyromazine and melamine in animal tissues. [74] [75] In 2007, the FDA beganusing a high performance liquid chromatography test to determine themelamine, ammeline , ammelide , and cyanuric acid contamination in food. [76]another procedure is based on surface-enhanced Raman spectroscopy(SERS). [77] [78]

Member States of the European Union are required under CommissionDecision 2008/757/EC [79] to ensure that all composite products containing atleast 15% of milk product, originating from China, are systematically testedbefore import into the Community and that all such products which areshown to contain melamine in excess of 2.5 mg/kg are immediatelydestroyed.

Melamine has been determined in urine specimens from children whoconsumed adulterated milk products by liquid chromatography-massspectrometry. [80]

It is reported that melamine molecules adsorbed on Au(111) [81] orAg(111) [82] surface tend to arrange into honeycomb or closed-packedstructures. Such a self-assembly occurs due to the inter-molecular hydrogenbond interaction. This ordering was further investigated using classical MonteCarlo[83] and DFT[84] methods.

Zhao Lianhai

[https://fscimage.fishersci.com/msds/96668.htm Melamine MaterialsSafety Data Sheet (MSDS)]OECD Screening Information Data Set (SIDS): Melamine (HighProduction Volume Chemicals Screening Information PDF, 89 pages).FDA Web Page with Information on Pet Food Recall (due to Melaminecontamination)European Commission decision (2008/798/EC) imposing specialconditions governing the import of products containing milk or milkproducts originating from ChinaStatement on melamine from the International Fertilizer IndustryAssociationToxicological and Health Aspects of Melamine and Cyanuric Acid:Report of a WHO Expert Meeting In collaboration with FAOMelmac Central's History on Melamine .


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