Melamin

Melamine

HCID 7955CAS 108-78-1

Grundinformationen

Standard-SMILES
Nc1nc(N)nc(N)n1
InChIKey
JDSHMPZPIAZGSV-UHFFFAOYSA-N
Summenformel
C3H6N6
Durchschnittliche Molmasse
126,12 g/mol
Monoisotopische Masse
126,06539419

Überblick

Melamine appears as colorless to white monoclinic crystals or prisms or white powder. Sublimes when gently heated. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Melamine
IUPAC
1,3,5-triazine-2,4,6-triamine
Lokaler Name
Melamin
Englischer Name
Melamine
Summenformel
C3H6N6
Molmasse
126.12

Namen und Synonyme

MELAMINE1,3,5-Triazine-2,4,6-triamine108-78-1CyanuramideCyanurotriamideCyanurotriamineIsomelamineTheoharnCyanuric triamides-TriazinetriamineTeoharnTriaminotriazine
Weitere Namen anzeigen
Melamin1,3,5-Triazine-2,4,6-triamine (Melamine)Metformin EP Impurity DMELAMINE(P)
Hicophor PR2,4,6-Triamino-1,3,5-triazineAeroPluragardYukamelamine2,4,6-Triamino-s-triazineCymelVirset 656-4

Datenbank-Bezeichner

CAS
108-78-1、5432-64-4
PubChem CID
7955
DTXSID
DTXSID6020802
ChEMBL
CHEMBL1231106
ChEBI
CHEBI:27915
UNII
N3GP2YSD88
EC Number
203-615-4
Nikkaji
J2.428G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1,4
Polarare Oberfläche (TPSA)
117 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
0
Schwere Atome
9

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Triazines

Industrial compound

Polymers · 2 Einträge

Plastics -> PUR

Plastics -> Flame retardants

SpringerMaterials PropertiesBoiling point
Pesticides · 2 Einträge

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Pesticide (Melamine) -> USDA PDB

LogP · 3 Einträge

log Kow = -1.37

-1.37

-1.14

Density · 4 Einträge

1.573 at 61 °F (NTP, 1992) - Denser than water; will sink

1.573 at 14 °C

1574 kg/m³

1.573 @ 16°C

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · >300 °C (lit.)
Siedepunkt
224.22 °C · 224.22°C (rough estimate)
Dichte
1.573 · 1.573
Dampfdruck
66.65 hPa · 66.65 hPa (315 °C)
Brechungsindex
1.872 · 1.872
Flammpunkt
110 °C · >110°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

P203, P260, P280, P318, P319, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 67.5% (624 of 924) of all reports.

Warning

H351 (18.2%): Suspected of causing cancer [Warning Carcinogenicity]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 1,3,5-Triazine-2,4,6-triamine

Hazard Traits - Carcinogenicity

Regulation (EC) No 178/2002 (amended)

1,3,5-Triazine-2,4,6-triamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3,5-Triazine-2,4,6-triamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15978

Substance: Melamine

Other Safety InformationIMAP assessments - 1,3,5-Triazine-2,4,6-triamine: Human health tier I assessment
Fire Hazards · 2 Einträge

Literature sources indicate that this compound is nonflammable. (NTP, 1992)

Combustible under specific conditions. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. It may also cause irritation of the upper respiratory tract. Other symptoms may include urinary bladder stones, diuresis and crystalluria. Dermatitis has been reported. Kidney injury may occur.

Hazards Summary · 1 Eintrag

Toxic by ingestion; May cause kidney stones; A skin, eye, mucous membrane, and respiratory tract irritant; [CAMEO] An irritant; Effects in high-dose animal studies include abnormal liver function tests; [MSDSonline] No occupational morbidity or mortality reported; [AIHA] Melamine-contaminated pet food caused kidney stones and acute kidney failure in cats and dogs. [Reference #1]

FDA RequirementsMelamine is an indirect food additive for use only as a component of adhesives.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth.

First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Fire Fighting Procedures · 2 Einträge

Powder, water spray, foam, carbon dioxide.

Melanine itself does not burn. Use any extinguishing agent suitable for surrounding fire. Poisonous gases including carbon monoxide, hydrogen cyanide, nitrogen oxides, and ammonia are produced in fire. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.

Storage Conditions · 1 Eintrag

Store in tightly closed containers in a cool, well vented area away form strong oxidizers and strong acids. Where possible, automatically pump liquid from drums or other storage containers to process containers. A regulated, marked area should be established where this chemical is handled, used, or stored in compliance with OSHA standard 1910.1045.

Cleanup Methods · 4 Einträge

Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Use HEPA vacuum or wet method to reduce dist during clean-up. Do not dry sweep. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place (extra personal protection: P2 filter respirator for harmful particles).

DISSOLVED CYANURIC ACID, CYANURATES, & OTHER DERIVATIVES (0.2-3.0%) CONTAINED IN WASTE WATER FROM THE MFR OF CHLORINATED CYANURIC ACIDS ARE REMOVED BY SLURRYING WITH POWDERED OR GRANULATED ACTIVE CARBON FOR 0.5-3 HR & FILTRATION.

ACID WASTEWATERS FROM MFR OF CYANURIC ACID & ITS CHLORINATED DERIVATIVES WHICH CONTAIN CYANURIC ACID, MELAMINE, AMMELINE, & AMMELIDE & HAVE PH 0-6, ARE HEATED TO 245-270 °C UNDER EVOLVED PRESSURE, WHICH MAY BE 1-30 ATM & ARE HYDROLYZED COMPLETELY.

Toxikologische Informationen

Interactions · 1 Eintrag

The major pet food recall associated with acute renal failure in dogs and cats focused initially on melamine as the suspect toxicant. In the course of the investigation, cyanuric acid was identified in addition to melamine in the offending food. The purpose of this study was to characterize the toxicity potential of melamine, cyanuric acid, and a combination of melamine and cyanuric acid in cats. In this pilot study, melamine was added to the diet of 2 cats at 0.5% and 1%, respectively. Cyanuric acid was added to the diet of 1 cat at increasing doses of 0.2%, 0.5%, and 1% over the course of 10 days. Melamine and cyanuric acid were administered together at 0%, 0.2%, 0.5%, and 1% to 1 cat per dose group. No effect on renal function was observed in cats fed with melamine or cyanuric acid alone. Cats dosed with a combination were euthanized at 48 hours after dosing because of acute renal failure. Urine and touch impressions of kidneys from all cats dosed with the combination revealed the presence of fan-shaped, birefringent crystals. Histopathologic findings were limited to the kidneys and included crystals primarily within tubules of the distal nephron, severe renal interstitial edema, and hemorrhage at the corticomedullary junction. The kidneys contained estimated melamine concentrations of 496 to 734 mg/kg wet weight and estimated cyanuric acid concentrations of 487 to 690 mg/kg wet weight. The results demonstrate that the combination of melamine and cyanuric acid is responsible for acute renal failure in cats.

Health Effects · 1 Eintrag

Studies ranging from skin irritation to carcinogenicity are available. Melamine is not genotoxic but it causes carcinomas of the urinary bladder at high doses. Melamine is not irritating to skin and eye, not sensitising and not teratogenic. (L1777)

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a log Kow of -1.37(2) and a regression-derived equation(3), indicates that melamine is expected to have very high mobility in soil(SRC). Volatilization of melamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 3.59X10-10 mm Hg(4), and water solubility, 3.23 mg/L(5). Melamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). No biodegradation using a standard 5-day BOD test(6) suggests that biodegradation may not be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a log Kow of -1.37(2) and a regression-derived equation(3), indicates that melamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.84X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 3.59X10-10 mm Hg(4), and water solubility, 3.23X10+3 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is(SRC). No biodegradation using a standard 5-day BOD test was observed(8), suggesting that biodegradation may not be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), melamine, which has a vapor pressure of 3.59X10-10 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase melamine may be removed from the air by wet or dry deposition(SRC).

Food Survey Values · 1 Eintrag

On March 15, 2007, the Food and Drug Administration (FDA) learned that certain pet foods were sickening and killing cats and dogs. FDA found contaminants in vegetable proteins imported into the United States from China and used as ingredients in pet food(1). Melamine was found in wheat gluten imported from China and used in pet food made by Menu Foods, which recalled 60 million cans and pouches of dog and cat food in mid-March of 2007. A portion of the tainted pet food was used to produce farm animal feed and fish feed. FDA and the U.S. Department of Agriculture discovered that some animals that ate the tainted feed had been processed into human food. All tainted pet food, animal and fish feed, and vegetable proteins continue to be recalled and destroyed (2007)(1).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesOral (L1775) ; inhalation (L1775) ; dermal (L1775)

Regulatorische Informationen

FDA RequirementsMelamine is an indirect food additive for use only as a component of adhesives.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
3263
hs_code
29336980
RTECS-Nr.
OS0700000
risk_code
43-44-20/21

Chemie und Industrie

Pharmakologische Informationen

Biological Half-Life · 1 Eintrag

... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. ... The elimination-phase half-life calculated from plasma data, 2.7 hr, was in good agreement with the urinary-excretion half-life of 3.0 hr. ...

Metabolism/Metabolites · 4 Einträge

Toxicokinetic studies in rats given 14C-labelled cyromazine as single and repeated oral doses showed that the active substance is rapidly and almost completely absorbed from the gastrointestinal tract and distributed to all organs and tissues. ... Cyromazine was incompletely metabolized, essentially by methylation, hydroxylation or Ndealkylation. The major component present was cyromazine, which accounted for 71-72% of the radiolabel; a further 7% was attributable to melamine, 8-11% to hydroxy-cyromazine and methylcyromazine.

... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. ... Radioactivity in plasma or urine co-chromatographed with that of the dosing solution, indicating that melamine is not metabolized in the male Fischer 344 rat.

Crystalluria was due to excretion of dimelamine-monophosphate crystals.

Melamine is not metabolized and is rapidly eliminated via urine in a study with oral application to rats. (L1777)

Absorption, Distribution and Excretion · 4 Einträge

... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. Within the first 24 hr, 90% of the administered dose was excreted in the urine. Negligible radioactivity appeared in breath and feces. There was little difference in blood, liver or plasma concentrations of 14C, suggesting that melamine distributes in body water. The only organs showing radioactivity levels much higher than plasma were the kidney and bladder. The bladder level was by far the highest, a finding probably due either to back diffusion from urine or to contamination of bladder tissue with urine. Virtually no residual radioactivity was observed in tissues examined at 24 hr or later. The elimination-phase half-life calculated from plasma data, 2.7 hr, was in good agreement with the urinary-excretion half-life of 3.0 hr. The renal clearance of melamine was 2.5 mL/min.

... Following oral administration of 250 mg/kg melamine to rats, 50% of the mother compound was excreted with the urine within 6 hrs. ... Crystals found in the urine were composed of dimelamine monophosphate, amounting to nearly 20% of the administered dose. After feeding melamine to dogs, 60 - 86.5% of the mother compound was recovered in the urine within 24 hrs. ...

Doses of 2.4 g/kg cause diuresis & elimination of fine crystals of dimelamine monophosphate in urine.

After administration of a single oral dose of 0.38 mg (14)C-melamine to adult male Fischer 344/N rats, 90% of the administered dose was excreted in the urine within the first 24 hours. Negligible radioactivity was detected in exhaled air and feces; and radioactivity was concentrated in the kidney and bladder. Virtually no residual radioactivity was observed in tissue after 24 hours or more. Chromatography of the radioactivity found in plasma or urine indicated that melamine is not metabolized in rats.

Verwendung und Herstellung

Uses · 6 Einträge

Used as a co-monomer with formaldehyde to make high pressure laminate resins, molding compounds and surface coating resins, textile and paper treating resins, adhesive resins for gluing lumber, plywood, and flooring; Also used as a flame retardant additive for polypropylene and polyethylene, a leather tanning agent, a rust remover, a metal surface cleaner, an etching agent in the semiconductor industry, and a reagent in numerous fluorination processes; [HSDB]

Metal Degreasing [Category: Clean]

Melamine, melamine cyanurate, other melamine salts and guanidine compounds are currently the most used group of nitrogen-containing 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 (PET/PBT) and is being developed for use in epoxy and polyurethane resins. Melamine phosphate is also used as a flame retardant for terephthalates (PET/PBT) and is currently being developed for use in epoxy and polyurethane flame retardant formulations. Also in the development stages for use as flame-retardant additives are melamine salts and melamine formaldehyde for their application in thermoset resins.

Melamine resins, organic syntheses, leather tanning.

TO MAKE HIGH PRESSURE LAMINATE RESINS, MOLDING COMPOUNDS & SURFACE COATING RESINS, TEXTILE & PAPER TREATING RESINS, ADHESIVE RESINS FOR GLUING LUMBER, PLYWOOD, & FLOORING

COMONOMER WITH FORMALDEHYDE FOR AMINO RESIN PRODN

U.S. Exports · 3 Einträge

(1972) NEGLIGIBLE

(1975) NEGLIGIBLE

(1983) NEGLIGIBLE

U.S. Imports · 3 Einträge

(1972) 5.31X10+9 GRAMS

(1975) 2.88X10+9 GRAMS

(1983) 8.76X10+9 g

U.S. Production · 6 Einträge

2023: 100,000,000 - <500,000,000 lb

1990/1991 97,000 TONS/ANNUALLY

(1983) 8.17X10+10 g

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4119]

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

For more U.S. Production (Complete) data for MELAMINE (7 total), please visit the HSDB record page.

Consumption Patterns · 5 Einträge

Over 95% of global output is used to make thermosetting resins for use in laminates, protective coatings, moulding compounds, textile finishes and paper coatings with applications in the automotive, appliance, dinnerware, furniture, fabric and wood panelling industries. The rest is mostly consumed as melamine crystal or salts for flame retardant or moisture-resistan applications.

AS A COMONOMER IN THE PRODN OF AMINO RESINS IN THE FOLLOWING APPLICATIONS: 36% IN HIGH PRESSURE LAMINATES; 22.5% IN MOLDING COMPDS; 15.5% IN SURFACE COATINGS; 7% IN TEXTILE PRINTING; 8% IN PAPER TREATING; 11% IN MISC APPLICATIONS (1974)

26% FOR LAMINATES; 22% FOR COATINGS; 20% FOR MOLDING COMPOUNDS; 13% FOR PAPER COATINGS; 5% FOR ADHESIVES; 3% FOR TEXTILE TREATMENT RESINS; 7% OTHER (1985)

CHEMICAL PROFILE: Melamine. Surface coatings, 29%; laminates, 22%; exports, 14%; paper coatings, 13%; molding compounds, 6%; textile treatment resins, 5%; adhesives, 4%; flame retardants, 3%; miscellaneous uses (including tanning and pigment cross-linking agents), 4%.

CHEMICAL PROFILE: Melamine. Demand: 1987: 132 million lb; 1988: 135 million lb; 1992 /projected/: 149 million lb.

Consumer UsesFiller
Anwendungen · 2 Einträge

BeschreibungMelamine-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.

VerwendenIt 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.

Darstellung · 1 Eintrag

synthetischeThe standard route to melamine is from urea. Urea is heated in the presence of ammonia at 250-350C 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: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.

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