Melamine

Melamine Basic information
Product Name:Melamine
Synonyms:2,4,6-TRIAMINO-1,3,5-TRIAZINE FOR SYNTHE;1,3,5-Triazine-2,4,6-triamine (Melamine);MELAMINE(P);Melamine, synthesis grade;Melamine 5g [108-78-1];Melamine,2,4,6-Triamino-1,3,5-triazine, sym-Triaminotriazine;Melamine (250 mg) (2,4,6-Triamino-1,3,5-triazine);1,3,5-Triazin-2,4,6-triaMine
CAS:108-78-1
MF:C3H6N6
MW:126.12
EINECS:203-615-4
Product Categories:Building Blocks;Chemical Synthesis;Amines;Aromatics;Heterocyclic Building Blocks;Triazines;Heterocycles;Organics;Bases & Related Reagents;Nucleotides;Fine chemical;108-78-1
Mol File:108-78-1.mol
Melamine Structure
Melamine Chemical Properties
Melting point >300 °C (lit.)
Boiling point 224.22°C (rough estimate)
density 1.573
vapor pressure 66.65 hPa (315 °C)
refractive index 1.872
Fp >110°C
storage temp. no restrictions.
solubility water: soluble25mg/mL, clear to slightly hazy, colorless
pka5(at 25℃)
form Fine Crystalline Powder
color White
PH7-8 (32g/l, H2O, 20℃)
Water Solubility 3 g/L (20 ºC)
Merck 14,5811
BRN 124341
Stability:Stable. Incompatible with strong acids, strong oxidizing agents. Nonflammable.
InChIKeyJDSHMPZPIAZGSV-UHFFFAOYSA-N
LogP-1.22 at 20℃
CAS DataBase Reference108-78-1(CAS DataBase Reference)
IARC2B (Vol. Sup 7, 73, 119) 2019
NIST Chemistry Reference1,3,5-Triazine-2,4,6-triamine(108-78-1)
EPA Substance Registry SystemMelamine (108-78-1)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 43-44-20/21
Safety Statements 36/37
RIDADR 3263
WGK Germany 1
RTECS OS0700000
Autoignition Temperature>600 °C
TSCA Yes
PackingGroup III
HS Code 29336980
Hazardous Substances Data108-78-1(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 3161 mg/kg LD50 dermal Rabbit > 1000 mg/kg
MSDS Information
ProviderLanguage
1,3,5-Triazine-2,4,6-triamine English
SigmaAldrich English
Melamine Usage And Synthesis
DescriptionMelamine-formaldehyde resin (MFR) is an active ingredient of strong (reinforced) plasters. Sensitization was reported in a plaster-room technician, who applied resin-reinforced pIaster casts, and in dental technicians. MFR was contained in a strong dental pIaster used for mouldings. Used as a textile finish res in, it was also found to be an allergen in a women who replaced clothes in a store. MFR also releases formaldehyde, which may be the sensitizer.
Chemical PropertiesMelamine is a white solid organic compound whose molecules consist of a sixmembered heterocyclic ring of alternate carbon and nitrogen atoms with three amino groups attached to the carbons. Condensation polymerization with methanal or other aldehydes produces melamine resins, which are important thermosetting plastics.
UsesIt is used to make high-pressure laminating resins (e.g., decorative countertops), molded compounds (e.g., dinnerware), and surface coating resins (e.g., appliance finishes and automotive topcoats). Additional major products are textile and paper treatment resins. Miscellaneous uses include adhesive resins for gluing lumber, plywood, and flooring, and resins for leather tanning agents. Melamine, melamine cyanurate, other melamine salts, and guanidine compounds are currently the most used group of nitrogencontaining flame retardants. Melamine is used as a flame retardant additive for polypropylene and polyethylene. Melamine cyanurate is employed commercially as a flame retardant for polyamides and terephthalates.
UsesForms synthetic resins with formaldehyde.
DefinitionChEBI: Melamine is a trimer of cyanamide, with a 1,3,5-triazine skeleton. It has a role as a xenobiotic metabolite. It is functionally related to a cyanamide. It is a conjugate base of a melamine(1+).
Production MethodsThe compound now is synthesized from urea.
Definitionmelamine: A white crystalline compound,C3N6H6. Melamine is a cycliccompound having a six-memberedring of alternating C and N atoms,with three NH2 groups. It can becopolymerized with methanal to givethermosetting melamine resins,which are used particularly for laminatedcoatings.
Production MethodsMelamine is prepared almost exclusively by the urea process—the action of ammonia on urea. It is produced worldwide.
PreparationThe standard route to melamine is from urea. Urea is heated in the presence of ammonia at 250-350??C and 4--20 MPa. The reaction probably involves the simultaneous dehydration and hydration of urea to form cyanamide and ammonium carbamate; trimerization of the cyanamide then leads to melamine:

108-78-1 synthesis


Thus only 50% of the urea used gives melamine in one step and ammonium carbamate has to be separated and converted to urea for recycling. Despite this limitation, the urea route is the most economical of currently available routes.

General DescriptionColorless to white monoclinic crystals or prisms or white powder. Sublimes when gently heated.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileMelamine is incompatible with strong oxidizing agents and strong acids . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
HazardToxic by ingestion, skin, and eye irritant. Questionable carcinogen.
Fire HazardLiterature sources indicate that Melamine is nonflammable.
Contact allergensMelamine-formaldehyde resin (MFR) results from condensation of melamine and formaldehyde. It is anactive ingredient of strong (reinforced) plasters, such as industrial or some dental plasters used for molding.It is also used as a textile finish resin. MFR acts as an allergen generally because of formaldehyde releasing (see Chap. 40)
Safety ProfileModerately toxic by ingestion and intraperitoneal routes. An eye, skin, and mucous membrane irritant. Causes dermatitis in humans. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN-.
Potential ExposureManufactured from urea, melamine is used in the manufacture of plastics, melamineformaldehyde resins; rubber, synthetic textiles; laminates, adhesives, and molding compound
CarcinogenicityA bioassay of melamine was conducted in rats and mice by NTP. Male F344 rats and B6C3F1 mice were administered melamine in their diets at concentrations of 2250 or 4500 ppm daily for 103 weeks.Female rats were fed 4500 or 9000 ppm melamine. At the end of 111 weeks, surviving animals were killed and examined.
Purification MethodsCrystallise Melamine from water or dilute aqueous NaOH. It sublimes at ~240o on prolonged heating. [Beilstein 26 I 74, 26 II 132, 26 III/IV 1253.]
IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Melamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents such as hydrides, nitrides, alkali metals, and sulfides.
Trichloromelamine Chimassorb 119 2,4-DIAMINO-6-DIETHYLAMINO-1,3,5-TRIAZINE Melamine cyanurate CYROMAZIN (N-CYCLOPROPYL- 1,3,5-TRIAZINE-2,4,6-TRIAMINE) 2,2',2''-(1,3,5-triazine-2,4,6-triyltriimino)trisethanol BUTTPARK 1\01-14 Fluorescent brightener 71 TRIETHYLENEMELAMINE Melamine N,N-Di(2-propenyl)-1,3,5-triazine-2,4,6-triamine BUTTPARK 1\01-15 N,N,N'',N'',N ,N -HEXAKIS(METHOXYMETHYL)-1,3,5-TRIAZINE-2,4,6- TRIAMINE) 1,3,5-triazine-2,4,6-triamine polyphosphate 2-N-BUTYLAMINO-4,6-DIAMINO-1,3,5-TRIAZINE Fluorescent Brightener 28 1,3,5-Triazine BUTTPARK 1\01-20

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