ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Carboxylic acid esters and derivatives > 4,4'-Diphenylmethane diisocyanate
4,4'-Diphenylmethane diisocyanate Chemical Properties
- Melting point:38-44 °C
- Boiling point:392 °C
- Density 1.19
- vapor pressure 0.066 hPa (20 °C)
- refractive index 1.5906 (estimate)
- Flash point:196 °C
- storage temp. Refrigerator
- solubility 2g/l (decomposition)
- form neat
- Specific Gravity1.180
- explosive limit0.4%(V)
- Water Solubility decomposes
- FreezingPoint 37℃
- Sensitive Moisture Sensitive/Lachrymatory
- BRN 797662
- Exposure limitsTLV-TWA 0.051 mg/m3 (0.005 ppm) (ACGIH and NIOSH); ceiling (air) 0.204 mg/m3 (0.02 ppm)/10 min (NIOSH and OSHA); IDLH 102 mg/m3 (10 ppm).
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents. Reacts violently with alcohols.
- CAS DataBase Reference101-68-8(CAS DataBase Reference)
- IARC3 (Vol. 19, Sup 7, 71) 1999
- NIST Chemistry ReferenceBenzene, 1,1'-methylenebis[4-isocyanato-(101-68-8)
- EPA Substance Registry System4,4'-Methylenedi(phenyl isocyanate) (101-68-8)
- Hazard Codes Xn,T,C
- Risk Statements 42/43-36/37/38-20-48/20-40
- Safety Statements 45-36/37-23
- RIDADR 2206
- WGK Germany 1
- RTECS NQ9350000
- Autoignition Temperature>600 °C
- Hazard Note Toxic/Corrosive/Lachrymatory/Moisture Sensitive
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29291090
- Hazardous Substances Data101-68-8(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 9000 mg/kg
4,4'-Diphenylmethane diisocyanate Usage And Synthesis
- Description4,4'-Diphenylmethane-diisocyanate (MDI) is used in the manufacture of various polyurethane products - elastic and rigid foams, paints, lacquers, adhesives, binding agents, synthetics rubbers, and elastomeric fibers.
- Chemical Propertieswhite to light yellow flakes or crystals
- Chemical PropertiesMDI is a white to light-yellow, odorless flakes. A liquid above 37C.
- UsesDiphenylmethane-4,4-diisocyanate (MDI)is widely used in the production ofrigid urethane foam products, coatings, andelastomers..
- UsesDiphenyl methane diisocyanate (MDI) is widely used in polyurethane coatings, this product is made of polyurethane foam used as a warm (cold), building materials, vehicle, ship parts; masterwork can made car Block, buffer, synthetic leather, non plastic polyurethane, polyurethane elastic fiber, no plastic elastic fibers, films, adhesives.
- UsesDiphenylmethane-4,4-diisocyanate is used in the preparation of polyurethane resin and Spandex fibers; bonding of rubber to rayon; diisoeyanate in the production of polyurethane lacquers, foam plastics, rubber, and glues.
- DefinitionChEBI: A diisocyanate consisting of diphenylmethane with two isocyanate groups at the 4- and 4'-positions.
- PreparationPhosgene (800 g, 8 mol) (for a safe source) was dissolved in o-dichlorobenzene (2000 mL), and the resulting solution was cooled in an ice-salt bath. To the stirred solution, a hot solution of 4,4'-diaminodiphenylmethane (200 g, 1.01 mol) in o-dichlorobenzene (1000 mL) was slowly added through a heated dropping funnel. The rate of addition was regulated so that the temperature of the phosgene solution did not rise substantially above 0°C. The fine suspension that resulted was slowly heated and additional phosgene (700 g, 7.1 mol) was added at 130 °C until a clear solution appeared. After purging with carbon dioxide, the solvent was removed in vacuo and the product was purified by vacuum distillation. At 156–158 °C (0.1 mmHg), 215 g (0.85 mol, 84%) of 4,4’-diphenylmethane diisocyanate was obtained. Several procedures for the preparation of isocyanates with phosgene have been described. Nevertheless, many of them require the delivery of gaseous phosgene from an external source, such as a pressurized cylinder.
- General DescriptionDiphenylmethane-4,4-diisocyanate is a light yellow colored solid. 4,4'-Diphenylmethane diisocyanate is not soluble in water. 4,4'-Diphenylmethane diisocyanate may be toxic by ingestion, inhalation, or skin absorption. If in a solution 4,4'-Diphenylmethane diisocyanate may or may not burn depending on the nature of the material and/or the solvent. It's used to make plastics.
- Air & Water Reactions4,4'-Diphenylmethane diisocyanate is not soluble in water.
- Reactivity ProfileIsocyanates and thioisocyanates, such as 4,4'-Diphenylmethane diisocyanate, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].
- Health HazardBreathlessness, chest discomfort, and reduced pulmonary function.
- Health HazardMDI can present a moderate to severe healthhazard, because of respiration of its vapors and particulates. It can contaminate the environment during foam application; concentrations in air were measured as high as5 mg/m3, mostly as particulates (ACGIH1986).
The toxic route is primarily inhalation.The vapor pressure of this compound atambient temperature is very low, 0.00014torr at 25°C. However, when heated to about75°C, the acute health hazard is greatlyenhanced (Hadengue and Philbert 1983). Theacute toxic symptoms were found to besimilar to those of toluene-2,4-diisocyanateand other aromatic isocyanates. Inhalation ofits vapors or particulates can cause bronchitis, coughing, fever, and an asthma-likesyndrome. Other symptoms were nausea,shortness of breath, chest pain, insomnia,and irritation of the eyes, nose, and throat.The immunologic response, however, variedamong humans. Exposure to 0.1–0.2 ppmfor 30 minutes is likely to manifest the acutetoxic effects in humans.
MDI is an eye and skin irritant. Contactwith skin can produce eczema. The acuteoral toxicity of this compound is very low,considerably lower than that of toluene-2,4-diisocyanate. The lethal dose for rats was31.7 g/kg.
MDI showed positive in mutagenic testingon Salmonella typhimurium. There is noreport that indicates its carcinogenicity.
- Fire HazardNoncombustible; flash point (open cup) 202°C (395°F). MDI reactions with strong oxidizers, acids, and bases can be vigorous.
- Contact allergensMDI is used in the manufacture of various polyurethane products: elastic and rigid foams, paints, lacquers, adhesives, binding agents, synthetic rubbers, and elastomeric fibers.
- Safety ProfilePoison by inhalation. Mildly toxic by ingestion. Human systemic effects by inhalation: increased immune response and body temperature. A skin and eye irritant. An allergic sensitizer. Questionable carcinogen. Mutation data reported. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx and SOx.
- Potential ExposureMDI is used in the production of polyurethane foams and plastics; polyurethane coatings; elastomers, and thermoplastic resins.
- ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
- IncompatibilitiesMay form explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive or flammable gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing the concentration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, caprolactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents such as hydrides, urethanes, ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acylchlorides may cause explosive polymerization. Attacks some plastics, rubber and coatings. May accumulate static electrical charges, and may cause ignition of its vapors. Unstable above 100F/38C. Polymerizes at temperatures above 204C. Contact with metals may evolve flammable hydrogen gas.
- Waste DisposalControlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).
4,4'-Diphenylmethane diisocyanate Preparation Products And Raw materials
- Benzyl isocyanate Isophorone diisocyanate Modified MDI DIISOCYANATE BENZOYL ISOCYANATE Tolylene-2,4-diisocyanate PHENYL VALERATE Methylene dithiocyanate ISOTHIOCYANATE, POLYMER-BOUND, 200-400 ISOCYANATE Phenyl isocyanate Diphenyl ether Phenyl salicylate Chlorodiphenylmethane Phenylacetic acid methylphenyl silicone resin Diphenylmethane Phenyl butyrate
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