1,2,3-triazine-2,4,6(1H)-triamine
Melamine
CAS: 108-78-1;94977-27-2
Molecular Formula: C3H6N6
1,2,3-triazine-2,4,6(1H)-triamine - Names and Identifiers
| Name | Melamine |
| Synonyms | Melamine MELAMINE(P) Cyanuramide Melamine, synthesis grade 1,3,5-Triazin-2,4,6-triaMine 1,3,5-triazine-2,4,6-triamine 2,4,6-Triamino-1,3,5-triazine 1,2,3-triazine-4,5,6-triamine 1,2,3-triazine-2,4,6(1H)-triamine 1,3,5-Triazine-2,4,6-triamine (Melamine) 2,4,6-TRIAMINO-1,3,5-TRIAZINE FOR SYNTHE Melamine (250 mg) (2,4,6-Triamino-1,3,5-triazine) Melamine,2,4,6-Triamino-1,3,5-triazine, sym-Triaminotriazine |
| CAS | 108-78-1 94977-27-2 |
| EINECS | 203-615-4 |
| InChI | InChI=1/C3H8N6/c4-2-1-3(5)8-9(6)7-2/h1,7H,4,6H2,(H2,5,8) |
| InChIKey | JDSHMPZPIAZGSV-UHFFFAOYSA-N |
1,2,3-triazine-2,4,6(1H)-triamine - Physico-chemical Properties
| Molecular Formula | C3H6N6 |
| Molar Mass | 126.12 |
| Density | 1.573 |
| Melting Point | >300 °C (lit.) |
| Boling Point | 224.22°C (rough estimate) |
| Flash Point | >110°C |
| Water Solubility | 3 g/L (20 ºC) |
| Solubility | A small amount is soluble in water, ethylene glycol, glycerol and pyridine. Slightly soluble in ethanol, insoluble in ether, benzene, carbon tetrachloride. |
| Vapor Presure | 66.65 hPa (315 °C) |
| Appearance | White monoclinic crystal |
| Color | White |
| Merck | 14,5811 |
| BRN | 124341 |
| pKa | 5(at 25℃) |
| PH | 7-8 (32g/l, H2O, 20℃) |
| Storage Condition | no restrictions. |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. Nonflammable. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.872 |
| MDL | MFCD00006055 |
| Physical and Chemical Properties | density 1.573 |
| Use | Is the main raw material for the manufacture of melamine formaldehyde resin |
1,2,3-triazine-2,4,6(1H)-triamine - Risk and Safety
| Risk Codes | R43 - May cause sensitization by skin contact R44 - Risk of explosion if heated under confinement R20/21 - Harmful by inhalation and in contact with skin. |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | 3263 |
| WGK Germany | 1 |
| RTECS | OS0700000 |
| TSCA | Yes |
| HS Code | 29336980 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 3161 mg/kg LD50 dermal Rabbit > 1000 mg/kg |
1,2,3-triazine-2,4,6(1H)-triamine - Upstream Downstream Industry
| Raw Materials | silica gel Ammonia Urea Ammonia |
| Downstream Products | Boron nitride |
1,2,3-triazine-2,4,6(1H)-triamine - Reference
| Reference Show more | 1. [IF=10.588] Hongxue An et al."The behavior of melamine in biological wastewater treatment system."J Hazard Mater. 2017 Jan;322:445 2. [IF=10.588] Yong Guo et al."UV-light promoted formation of boron nitride-fullerene composite and its photodegradation performance for antibiotics under visible light irradiation."J Hazard Mater. 2021 May;410:124628 3. [IF=4.616] Ling Li et al."Point-of-care testing of melamine via gas pressure readout using polythymine-coated Au@Pt nanoparticles through specific triple hydrogen-bonding recognition."Analyst. 2021 Sep;146(19):5898-5903 4. [IF=3.591] Congcong Yan et al."Improved photoremoval performance of boron carbon nitride–pyromellitic dianhydride composite toward tetracycline and Cr(VI) by itself to change the solution pH."New J Chem. 2020 Jul;44(26):11105-11124 5. [IF=3.361] Mei Li et al."An electrochemical immunosensor coupling a bamboo-like carbon nanostructure substrate with toluidine blue-functionalized Cu(II)-MOFs as signal probes for a C-reactive protein assay."Rsc Adv. 2021 Feb;11(12):6699-6708 6. [IF=5.268] Bo Jiang et al."Precursor structure-determined fluorescence labeling for mesenchymal stem cells among four polyethylenimine-based carbon quantum dots."Colloid Surface B. 2022 May;213:112411 |
1,2,3-triazine-2,4,6(1H)-triamine - Reference Information
Open Data Unverified Data
| LogP | -1.22 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 2B (Vol. Sup 7, 73, 119) 2019 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | melamine, commonly known as "melamine", "protein essence", "melamine (Chinese pinyin: mà'àn)", it is a triazine nitrogen-containing heterocyclic organic compound, often used as a chemical raw material. It is a white monoclinic crystal, almost tasteless, slightly soluble in water (3.1g/L normal temperature), soluble in formaldehyde, acetic acid, hot ethylene glycol, glycerin, pyridine, etc., insoluble in acetone, ethers, harmful to the body, and cannot be used for food processing or food additives. However, some unscrupulous businesses mix melamine into milk products in order to increase the nitrogen level when testing protein content. |
| application prospect | melamine is an important nitrogen heterocyclic organic chemical intermediate using urea as raw material. it is more and more favored by people due to its environmental protection performance and wide range of uses. it is widely used in wood processing, plastics, coatings, water reducing agents, papermaking, adhesives, textiles, leather, electrical appliances, medicine, flame retardants and other industries. After decades of development, my country has developed its own unique semi-dry technology, and at the same time it has digested and absorbed foreign advanced technology and equipment, further enhancing the overall strength of the domestic trimethenamine industry. At present, China has become the world's largest melamine production base and export country. Figure 1 shows the current situation of global trimeric amine capacity distribution |
| preparation | melamine production unit adopts pressurized gas phase quenching method. liquid urine in urea unit area is used as raw material to generate melamine and by-product tail gas (ammonia, carbon dioxide) through catalytic reaction. excess ammonia and carbon dioxide are sent to urea combined production unit to co-produce urea, and the generated urea continues to be sent to melamine unit to realize recycling production of raw materials. In the post-crystallization section of melamine, after the process gas from the crystallizer is separated by the finished cyclone separator, all the process gas at 210 ℃ enters the top of the liquid urine washing tower, and comes into contact with the sprayed liquid urine downstream. After heat exchange by the liquid urine cooler to 133~138 ℃, it enters the gas collecting box through five columnar cyclone separators to perform gas-liquid separation to remove the melamine and low-temperature by-products entrained therein, the gas is separated by the carrier gas cyclone separator and then enters the carrier gas compressor. Part of the gas is used as the circulating carrier gas, and the other part of the gas enters the air-conditioning fan and is sent to the crystallizer. The excess melamine tail gas is sent to the urea absorption system through the tail gas compressor Recycling. |
| use | is the main raw material for the manufacture of melamine formaldehyde resin used as an organic element analysis reagent, and also used in the synthesis of organic and resin used as a tanning agent and filler for leather processing. melamine resin can be prepared by condensation polymerization with formaldehyde, which can be used in plastic and coating industry, and can also be used as anti-folding and anti-shrinkage treatment agent for textile products. Its modified resin can be used as metal coating with bright color, durability and good hardness. It can also be used for strong and heat-resistant decorative sheet, moisture-proof paper and gray leather tanning agent, adhesive for synthetic fireproof laminate, fixing agent or hardener of waterproof agent, etc. 582 melamine resin prepared from melamine, formaldehyde and butanol. Used as a leveling agent for solvent-based polyurethane coatings with excellent effect. Industrial additives are widely used in plastics, coatings, textiles and papermaking. Recently tested items: milk powder, feed enterprises add melamine to increase protein content. The addition of chemicals with high nitrogen content can create the illusion that the protein content is up to standard in the test. Therefore, melamine is also called "protein essence". A large amount of ingestion will damage the reproductive and urinary systems of humans and animals, resulting in kidney and bladder stones, and renal function failure and death. Standard sample for determination of nitrogen by organic microanalysis, organic synthesis, synthetic resin. |
| production method | is obtained by reacting dicyandiamide with ammonia at 200 ℃ in methanol solvent. This method consumes 1180kg of dicyandiamide (98%) and 30kg of liquid ammonia per ton of products. Compared with this method, urea method has low cost and is widely used at present. Urea with ammonia as the carrier, silica gel as the catalyst, in 380-400 ℃ temperature boiling reaction, first decomposition to generate cyanic acid, and further condensation to generate melamine. The generated trimeric amine gas is cooled and trapped to obtain a crude product, which is then dissolved to remove impurities and recrystallize to obtain a finished product. The production of melamine by urea method consumes about 3800kg of urea and 500kg of liquid ammonia per ton of products. |
| spontaneous combustion temperature | >600°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:43:38
1,2,3-triazine-2,4,6(1H)-triamine - Nature
Open Data Verified Data
white crystals. Heat sublimation. Non-flammable. Soluble in methanol, Formaldehyde, Acetic Acid, thermal ethylene glycol, glycerol, pyridine, insoluble in ether, benzene, carbon tetrachloride. At high temperatures can be decomposed to produce highly toxic cyanide gas.
Last Update：2024-01-02 23:10:35
1,2,3-triazine-2,4,6(1H)-triamine - Preparation Method
Open Data Verified Data
melamine urea as raw material, ammonia as liquefied carrier gas, silica gel as catalyst for gas-solid catalytic reaction, using semi-dry atmospheric method, melamine is synthesized at 380~400 ℃, and melamine is crystallized in a coagulator. The crude product is dissolved, filtered and crystallized to make a finished product, or dicyandiamide is used in methanol solvent, it was obtained by reaction with ammonia at 200 °c.
Last Update：2022-01-01 09:30:38
1,2,3-triazine-2,4,6(1H)-triamine - Market Development
Melamine to urea as raw material, the production of 1 tons of melamine about 3 tons of urea. China is the world's largest producer of urea, urea production and low prices, even in the national implementation of high tariffs to curb urea exports, the annual urea exports still reach (300~700) the rich urea resources make China's melamine production has a unique advantage. China's melamine production capacity expansion is serious, resulting in Chinese melamine enterprises competitive, industry product prices rose Fatigue.
Last Update：2023-08-16 21:38:17
1,2,3-triazine-2,4,6(1H)-triamine - Use
Open Data Verified Data
used as tanning agent and filler in leather processing. Widely used in plastics, wood, paper, textile, coatings and other industries, is the manufacture of advanced coatings, laminates, molding powder, adhesives, textile and paper processing agents, insulating materials of raw materials.
Last Update：2022-01-01 09:30:38
1,2,3-triazine-2,4,6(1H)-triamine - Main use
melamine resin can be prepared by condensation polymerization with formaldehyde, which can be used in plastic and coating industry, and can also be used as anti-folding and anti-shrinkage treatment agent for textile products. The modified resin can be used as a metal coating with bright color, durability and good hardness. It can also be used for strong, heat-resistant decorative sheet, moisture-proof paper and gray leather tanning agent, synthetic fire-resistant layer board adhesive, waterproof agent fixing agent or hardening agent. 582 melamine resin was prepared from melamine, formaldehyde and butanol. Used as a leveling agent for solvent-based polyurethane coatings, the effect is particularly good.
The main raw material for the manufacture of melamine formaldehyde resin is used as an organic elemental analysis reagent, and also used in the synthesis of organic and resin as tanning agent and filler in leather processing. Melamine resin can be prepared by condensation polymerization with formaldehyde, which can be used in plastic and coating industry, and can also be used as anti-folding and anti-shrinkage treatment agent for textile products. The modified resin can be used as a metal coating with bright color, durability and good hardness.
melamine resin made by condensation polymerization with formaldehyde is widely used in the manufacture and processing of wooden building formwork. It can be used for the waterproof of the template surface and the adhesion of the wood core board, and increase the number of repeated use of the template.
Last Update：2023-08-16 21:39:23
1,2,3-triazine-2,4,6(1H)-triamine - Safety
Open Data Verified Data
mouse oral LD50:4550mg/kg; Rat oral 3000mg/kg. Avoid contact with oxidants and acids. Staff should be well protected, if accidentally touch the skin and eyes, should immediately rinse with a large amount of flowing water.
Last Update：2022-01-01 09:30:39
1,2,3-triazine-2,4,6(1H)-triamine - Limit standard
Chinese standard
China National Food Quality Supervision and Inspection Center in 2008 September 13, pointed out that melamine is a chemical raw material, is not allowed to add to food, so there is no such standard restrictions as pesticide residues. On October 8, the Ministry of Health, the Ministry of Industry and Information Technology, the Ministry of Agriculture, the State Administration for Industry and Commerce and the State Administration for Quality Supervision and Inspection Quarantine jointly issued an announcement to formulate temporary management values for melamine in milk and dairy products:
the limit of melamine in infant formula is 1 mg/kg, products higher than 1 mg/kg are not allowed to be sold. Liquid milk (including raw milk), milk powder, other formula milk powder melamine limit value of 2.5mg/kg, more than 2.5mg/kg products shall not be sold. Milk containing more than 15% of the other food melamine limit value of 2.5mg/kg, more than 2.5mg/kg products shall not be sold.
International standard
On 5 July 2012, the United Nations Codex Alimentarius Commission, which is responsible for setting food safety standards, set a new standard for melamine in milk. The content of melamine in liquid milk should not exceed 0.15 mg per kg. The Codex Alimentarius Commission says the new standards for melamine levels will help governments to better protect consumer rights and health.
Last Update：2023-08-16 21:39:38
1,2,3-triazine-2,4,6(1H)-triamine - Expanding reading-how melamine is added to milk
Fang Zhouzi popular science writer
Many people drink milk to supplement calcium, but if you pay attention to the labels on the domestic fresh milk packaging, calcium content is generally not listed, the indicated nutrient content is only two kinds: fat and protein. Fresh milk is full fat, low fat, fat points, the fat content is different, and in the fat is regarded as a health killer today, the average person will not care about whether the fat content is up to standard. Protein is the main nutrient in milk, fresh milk packaging will be filled with protein content of 100 or more than 2.9 grams, in order to show that meet the national standards for fresh milk (100 or more than 2.95 grams).
The protein content of raw milk is generally more than 3%, so it can generally meet the national standard, unless the raw milk is mixed with water. It is necessary to detect the content of protein in the acquisition of raw milk in order to guard against the price of water to sell milk. According to the chemical nature of the protein, there are several detection methods, each with advantages and disadvantages. The Kjeldahl method, which is commonly used in the food industry and has been designated as a national standard, is used. This is the late 19th century Danish John Kedar invented the method, the principle is very simple: protein contains nitrogen, the sample is treated with strong acid, so that the nitrogen in the protein release, determination of nitrogen content, the protein content can be calculated. Milk protein nitrogen rate of about 16%, according to national standards, the measured nitrogen content multiplied by 6.38, is the protein content.
so the Kjeldahl method is not actually measuring the protein content, but by measuring the nitrogen content to calculate the protein content, obviously, if there are other compounds in the sample containing nitrogen, This method is not accurate. Under normal circumstances, this is not a problem, because the main component of food is only protein contains nitrogen, other major components (carbohydrates, fats) do not contain nitrogen, therefore, the Kjeldahl method is a very accurate method for the determination of protein content. But if a person to the sample to steal other substances containing nitrogen, you can get a false Kjeldahl method of high protein content, with the water of milk as raw milk.
A commonly used nitrogen-containing substance that mimics proteins is urea. However, the nitrogen content of urea is not very high (46.6%), dissolved in water will give a pungent ammonia taste, easy to be detected, and with a simple detection method (Griess reagent method) you can find out whether the milk added urea. So the counterfeit was changed to melamine. Melamine nitrogen content of up to 66.6% (the higher the nitrogen content means the more protein can be imputed), white and tasteless, there is no simple detection method (to use "high performance liquid chromatography" this high-tech to detect), is an ideal protein substitute. Melamine is an important chemical raw material, widely used in the production of synthetic resins, plastics, coatings, etc., the current price is about 1 tons of 12000 yuan. In the process of producing melamine, waste residue will appear, and the waste residue also contains 70% melamine. Counterfeit is used to counterfeit protein melamine residue, some "biotechnology companies" in the online marketing "Protein essence", in fact, is melamine residue. In feed, dairy products to add "Protein essence" as protein.
how is melamine added to milk? There are two possible pathways. One is the addition of a milk station to raw milk. This has certain limitations because melamine is slightly soluble in water, The solubility at room temperature was 3.1g/L. That is, 100 of water can dissolve 0.31 grams of melamine, nitrogen 0.2 grams, equivalent to 1.27 grams of protein, which can be calculated, to achieve 100 or more 2.95 grams of protein requirements, 100 ml of milk can only be mixed with a maximum of 75 ml of water (with the addition of 0.54g of melamine). Another way is to add melamine in the milk powder manufacturing process, which is not limited by the solubility, you want to add how much can be.
The reason why melamine is used by outlaw as "Protein essence" may be because it is very low in toxicity and can not be killed by eating. Oral melamine in rats, semi-lethal dose (commonly used indicators of toxicology, which can cause half of the subjects died) is about 3 grams per kilogram of body weight, and salt. No obvious poisoning phenomenon was observed in rats, rabbits and dogs fed with large doses. Melamine into the body does not seem to be metabolized, but from the urine in the sample, but animal experiments also show that long-term feeding melamine can appear to melamine as the main component of kidney stones, bladder stones. We can't test it on humans, and even if a person with kidney stones has taken food containing melamine, it is difficult to determine that melamine is the culprit unless the patient has a single source of food, for example, only to eat the formula of the baby-did not expect that there is really the risk of the baby to do the test to prove that it can eat the dead!
some people think that since the defect of the protein detection method has led to the fatal fraud, it is better to simply cancel the protein detection and insist on the milk and water. In fact, the defect of Kjeldahl method is not difficult to make up, as long as more than one step: The samples were first treated with trichloroacetic acid. Trichloroacetic acid allows proteins to form a precipitate, after filtration, the nitrogen content of the precipitate and filtrate were measured, you can know the true content of protein and the nitrogen content of the protein. This is the common sense of biochemistry, and it has become the international standard (ISO 8968) for the detection of nitrogen content in milk. The "Protein essence" Fraud has appeared in China for some years, and the "Sanlu milk powder" incident is just an "industry secret" in front of the public. Only by improving the national standards and blocking the loopholes can we regain people's confidence in the domestic dairy industry. (Originally entitled "Protein essence" hoax ")
Last Update：2023-08-16 21:39:42
1,2,3-triazine-2,4,6(1H)-triamine - Preparation Method
From dicyandiamide in methanol solvent, at 200 deg C and ammonia reaction. This method needs to consume 1180kg of Dicyandiamide (98%) and 30kg of liquid ammonia per ton of product. Compared with this method, the cost of urea method is low, and it is more used. Urea with ammonia as the carrier, silica gel as catalyst, boiling reaction at 380-400 ℃ temperature, the first decomposition of cyanic acid, and further condensation of melamine. The generated tripolyamine gas is cooled and trapped to obtain a crude product, which is then dissolved to remove impurities and recrystallized to obtain a finished product. The production of melamine by urea method consumes about 3800kg of urea and 500kg of liquid ammonia per ton of product.
Last Update：2024-04-10 22:29:15
1,2,3-triazine-2,4,6(1H)-triamine - Precautions
risk
Health hazard: no report of occupational poisoning. Note that this product can decompose at high temperatures to produce highly toxic cyanide gas.
explosion hazard: the product is not flammable.
first aid measures
Skin Contact: remove contaminated clothing and rinse with plenty of running water.
eye contact: lift the eyelid and rinse with running water or saline. The patient visited hospital.
inhalation: from site to fresh air. The patient visited hospital.
ingestion: drink enough warm water to induce vomiting. The patient visited hospital.
fire fighting measures
hazard characteristics: decomposition by heat gives off highly toxic cyanide gas.
harmful combustion products: carbon monoxide, carbon dioxide, nitrogen oxides, hydrogen cyanide.
fire extinguishing method: fire-fighting personnel must wear a filter-type gas mask (full face mask) or an isolated respirator, and wear full-body fire protection clothing to fire in the upward wind direction. Move the container from the fire to the open space as far as possible.
leakage treatment
emergency treatment: on Isolation, the leakage was contaminated area, and access was restricted. Emergency personnel are advised to wear dust masks (full face mask) and anti-virus clothing. Collect the dry, clean, capped containers with a clean shovel and transfer them to a safe place. If there is a large amount of leakage, it will be collected, recovered or transported to the waste disposal site for disposal.
operational disposition
precautions for operation: closed operation and full ventilation. Operators must be specially trained and strictly follow the operating procedures. It is recommended that operators wear self-priming filter type dust masks, chemical safety glasses, anti-virus penetration work clothes and rubber gloves. Dust should be avoided. Avoid contact with oxidants and acids. Handling should be light and light unloading, to prevent packaging and container damage. Emergency treatment equipment for leakage shall be provided. Harmful substances may remain in the empty container.
Storage Considerations: Store in a cool, ventilated warehouse. Keep away from fire and heat source. It should be stored separately from oxidants and acids, and mixed storage should not be avoided. The storage area shall be provided with suitable materials for containment of the leakage.
risk terms
R20/21Harmful by inhalation and in contact with skin.
inhalation and skin contact are harmful.
R44Risk of explosion if heated under confinement.
closed heating is explosive.
toxicity
melamine was considered to be slightly toxic, with oral LD50 in rats greater than 3 g/kg body weight. Animal long-term intake of melamine will cause reproductive, urinary system damage, bladder, kidney stones, and can further induce bladder cancer. The general adult body will discharge most of the melamine, but if used with cyanuric acid, it will form insoluble melamine cyanurate, causing serious kidney stones.
The International Chemical Safety Manual, Vol. 3, and the International Chemical Safety Card, organized by the International Programme for chemical safety and the European Commission, 1994, also describe only: long-term or repeated large intake of melamine may affect the kidney and bladder, resulting in stones. The mechanism of melamine forming kidney stones is not very clear. Some studies suggest that melamine is often mixed with cyanuric acid with similar structure, and melamine will combine with cyanuric acid to form crystal deposition after ingestion of human body into renal cells, this results in kidney stones and blockage of renal tubules, and may lead to kidney failure.
Last Update：2024-04-10 22:29:15
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View History
Raw Materials for 1,2,3-triazine-2,4,6(1H)-triamine
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