4,4'-Methylenedianiline Chemical Properties
- Melting point:89-91 °C(lit.)
- Boiling point:242 °C2 mm Hg(lit.)
- Density 1.15
- refractive index 1.5014 (estimate)
- Flash point:430 °F
- solubility water: soluble
- form neat
- Water Solubility Slightly soluble. <0.1 g/100 mL at 19 ºC
- Merck 14,2980
- BRN 474706
- CAS DataBase Reference101-77-9(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzenamine, 4,4'-methylenebis-(101-77-9)
- IARC2B (Vol. 39, Sup 7) 1987
- EPA Substance Registry System4,4'-Methylenedianiline (101-77-9)
- Hazard Codes T,N
- Risk Statements 45-39/23/24/25-43-48/20/21/22-51/53-68
- Safety Statements 53-45-61
- RIDADR UN 2651 6.1/PG 3
- WGK Germany 3
- RTECS BY5425000
- TSCA Yes
- HazardClass 6.1
- PackingGroup III
- HS Code 29215900
- Hazardous Substances Data101-77-9(Hazardous Substances Data)
- ToxicityLD50 oral in rabbit: 620mg/kg
4,4'-Methylenedianiline Usage And Synthesis
- Chemical Properties4,4'-Methylenedianiline is a light brown crystalline solid with a faint amine odor. lt is very slightly soluble in water and soluble in alcohol, benzene,and ether. lt is combustible when exposed to heat or flame. When heated to decomposition，it emits toxic fumes of aniline and nitrogen oxides (NOx). The dihydrochloride is a crystalline solid that is soluble in water.
4,4'-Methylenedianiline is primarily used to produce 4,4-'methylenedianiline diisocyanate and other polymeric isocyanates which are used to manufacture polyurethane foams.
- Uses4,4'-Methylenedianiline is used in the production of polyurethane foams and epoxy resins. Potential contributor in pulmonary arterial hypertension (PAH) in rats through alteration of the serotenergic transport system. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants. Dyes and metabolites, Environmental Testing.
Production of methylene diphenyl diisocyanate (MDI), which is used to produce polyurethanes; hardening agent for epoxy resins, anticorrosive materials, printed circuit parts, dyestuff intermediates, filament-wound pipe, and wire coatings
- Preparation93 g (1 mole) of aniline are dissolved in 96 % alcohol and to the cooled solution with proper stirring 120 g (1 mole) of 40 % formaldehyde solution are gradually added. After the addition is completed a second molecular portion of aniline, 93 g (1 mole) of aniline are added and the reaction is continued until the odor of formaldehyde has disappeared. The complete the reaction the mixture is refluxed for 2 hours. 130 g (1 mole) of aniline hydrochloride are then added, and boiling continued for a further 12 hours. The alcohol is distilled off, the residue made alkaline with the solution of sodium hydroxide and the excess of aniline removed by distillation with superheated steam. The residual oil, which consists of 4,4′-diaminodiphenylmethane, is then purified by solution in dilute hydrochloric acid and reprecipitation with dilute alkali. The 4,4′-diaminodiphenylmethane base is filtered off, washed and dried.
Organic medical chemicals, by M. Barrowliff, 188-189, 1921
- DescriptionDiaminodiphenylmethane is an aromatic diamine used as a curing agent in epoxy res ins of t11e bisphenol A type, as in the production of plastics, isocyanates, adhesives, elastomers, polyuret11ane (elastic and rigid foams, paints, lacquers, adhesives, binding agents, synt11etics rubbers, and elastomeric fibers) and butyl rubber. Diaminodiphenylmet11ane is also a by-product of azo dyes. It is also possibly formed by hydrolysis of diphenylmethane-4A'-diisocyanate.
- Chemical Properties4,4’-Diaminodiphenylmethane is a pale yellow crystalline solid (turns light brown on contact with air) with a faint amine-like odor.
- Chemical Propertieswhite to yellow or beige flakes or crystals
- Uses4,4'-methylenedianiline be used as organic intermediates. Mainly used for the synthesis of polyimide and as curing agent of epoxy resin.
- UsesAs chemical intermediate in production of isocyanates and polyisocyantes for preparation of polyurethane foams, Spandex fibers; as curing agent for epoxy resins and urethane elastomers; in production of polyamides; in the determination of tungsten and sulfates; in preparation of azo dyes; as corrosion inhibitor.
- Uses4,4'-Diaminodiphenyl-methane is used in the determination of tungsten and sulfates; in the preparation of azo dyes; cross-linking agent for epoxy resins; in the preparation of isocyanates and polyisocyanates; in the rubber industry as a curative for neoprene, as an anti-frosting agent (antioxidant) in footwear; raw material in preparation of poly(amide-imide) resins (used in magnet-wire enamels); curing agent for epoxy res ins and urethane elastomers; corrosion inhibitor; rubber additive (accelerator, antidegradant, retarder) in tires and heavy rubber products; in adhesives and glues, laminates, paints and inks, PVC products, handbags, eyeglass frames, plastic jewelry, electric encapsulators, surface coatings, spandex clothing, hairnets, eyelash curlers, earphones, balls, shoe soles, face masks.
- DefinitionChEBI: An aromatic amine that is diphenylmethane substituted at the 4-position of each benzene ring by an amino group.
- General DescriptionA tan flake or lump solid with a faint fishlike odor. May be toxic by inhalation or ingestion, and may be irritating to skin. Insoluble in water.
- Air & Water ReactionsOxidizes slowly in air in a reaction catalyzed by light. Somewhat hygroscopic. Insoluble in water.
- Reactivity Profile4,4'-Methylenedianiline polymerizes if heated above 257° F. Incompatible with strong oxidizing agents. 4,4'-Methylenedianiline is also incompatible with acids. Catalyzes isocyanate-alcohol and epoxide reactions. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
- Health HazardTOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
- Fire HazardCombustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
- Safety ProfileConfirmed carcinogen with experimental tumorigenic data. Human poison by ingestion. Poison by subcutaneous and intraperitoneal routes. Human systemic effects by ingestion: rigidity, jaundice, other liver changes. An eye irritant. Mutation data reported. It is not rapidly absorbed through the skin. Combustible when exposed to heat or flame. When heated to decomposition it emits highly toxic fumes of aniline and NOx.
- Potential ExposureUsed as an intermediate and as a curing agent. Approximately 99% of the DDM produced is con- sumed in its crude form (occasionally containing not more than 50% DDM and ply-DDM) at its production site by reac- tion with phosgene in the preparation of isocyanates and poly- isocyanates. These isocyanates and polyisocyanates are employed in the manufacture of rigid polyurethane foams which find application as thermal insulation. Polyisocyanates are also used in the preparation of the semiflexible polyure- thane foams used for automotive safety cushioning. DDM is also used as: an epoxy hardening agent; a raw material in the production of polyurethane elastomers; in the rubber industry as a curative for Neoprene and as an antifrosting agent (anti- oxidant) in footwear; a raw material in the production of Quana nylon; and a raw material in the preparation of poly (amide-imide) resins (used in magnet wire enamels).
- Carcinogenicity4,4′-Methylenedianiline and its dihydrochloride salt are reasonably anticipated to be human carcinogens based on sufficient evidence of carcinogenicity from studies in experimental animals.
- ShippingUN2651 4,40 -Diaminodiphenyl methane, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- Purification MethodsCrystallise the amine from water, 95% EtOH or *benzene. [Beilstein 13 IV 390.]
- IncompatibilitiesDust forms and explosive mixture with air. May polymerize in temperatures .125℃ . A weak base. Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong acids. Flammable gas- eous hydrogen may be generated in combination with strong reducing agents, such as hydrides .
- Waste DisposalControlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).
4,4'-Methylenedianiline Preparation Products And Raw materials
- CRYSTAL VIOLET Pigment Violet 3 Basic Red 9 ACID FUCHSIN CALCIUM SALT 4,4'-Bis(diethylamino) benzophenone 4,4'-DIAMINO-2,2'-DINITRODIPHENYLMETHANE Pigment Blue 61 4,4'-Bis(dimethylamino)benzhydrol Arnolds base, N,N,Nμ,Nμ-Tetramethyl-4,4μ-diaminodiphenylmethane, N,N,Nμ,Nμ-Tetramethyl-4,4μ-methylenedianiline,N,N,N',N'-TETRAMETHYL-4,4'-METHYLENEDIANILINE Michler's ketone Tris Base Biphenyl 1,3-Diaminoguanidine monohydrochloride 4-Aminobenzoic acid 1,5-Diphenylcarbazide 4,4'-Methylenedianiline Aniline Aminodiphenylmethane
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