METHYLENEDIPHENYLENE DIISOCYANATE
4,4'-METHYLENEBIS(PHENYL ISOCYANATE)
CAS: 26447-40-5
Molecular Formula: C15H10N2O2
METHYLENEDIPHENYLENE DIISOCYANATE - Names and Identifiers
| Name | 4,4'-METHYLENEBIS(PHENYL ISOCYANATE) |
| Synonyms | BIS(4-ISOCYANATOPHENYL)METHANE METHYLENEDIPHENYLENE DIISOCYANATE METHYLENEBIS(P-PHENYL ISOCYANATE) METHYLENEDI-P-PHENYL DIISOCYANATE DIPHENYLMETHANE-4,4'-DIISOCYANATE METHYLENEDIPHENYL 4,4'-DIISOCYANATE 4,4'-METHYLENEBIS(PHENYL ISOCYANATE) METHYLENE DI-P-PHENYLENE DIISOCYANATE Benzene, 1,1'-methylenebis[isocyanato- |
| CAS | 26447-40-5 |
| EINECS | 247-714-0 |
METHYLENEDIPHENYLENE DIISOCYANATE - Physico-chemical Properties
| Molecular Formula | C15H10N2O2 |
| Molar Mass | 250.25 |
| Density | 1.18 |
| Melting Point | 42-45℃ |
| Appearance | Flakes |
| Color | White |
| Storage Condition | 2-8°C |
METHYLENEDIPHENYLENE DIISOCYANATE - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20 - Harmful by inhalation R36/37/38 - Irritating to eyes, respiratory system and skin. R42/43 - May cause sensitization by inhalation and skin contact. |
| Safety Description | S23 - Do not breathe vapour. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2811 |
METHYLENEDIPHENYLENE DIISOCYANATE - References
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| basic physical properties | Chinese name: diphenylmethane diisocyanate Chinese alias: diphenylmethane diisocyanate, 4,4 '-methylenebis (phenyl isocyanate), Diphenylmethane-4,4'-diisocyanate, bis(4-isocyanatophenyl)methane English name: Diphenylmethane-4,4 '-diisocyanate English alias: MDI, Diphenyl-methane-diisocyanate, Isonate, caredate30, methyllenediphenyl 4,4'-Diisocyanate, 4,4,4 '-methyllenediphenyl ate;hylenem50, desmodur44, Bis (4-isophenyl) methanane, 4,4'-diphenylmethanisocytanate, p,p'-diphenylhandianisanate, p, di-p-phenyl, flages, 4,4-Diphenylmethane Diisocyanate, PMDI, 4,4 '-MDI, 4,4'-methyllenebis, methyllene4, 4 '-diphenyl diisoanate Molecular formula: c15H10N2O2 Molecular Weight: 250.24 CAS number: 101-68-8 PSA:58.86 LogP:3.21 |
| physical and chemical properties | density: 1.19g/cm3 Melting Point: 38-44 ℃ freezing point: 37 ℃ Boiling Point: 392 ℃ viscosity: 4.9mPa · s(50 ℃) flash point: 213 ℃ refractive index: 1.5906(50 ℃) vapor pressure: 9.02E-06 mmHg (25°C) solubility: soluble in acetone, carbon tetrachloride, benzene, chlorobenzene, kerosene, nitrobenzene, dioxane, etc. Properties: white to light yellow chips or crystals taste: pungent odor (heated) hazard identification: Dangerous goods Sample: see figure below |
| Overview | diphenylmethane diisocyanate is a kind of polymer monomer with great commercial value, mainly used in polyurethane foam, rubber, raw materials for fibers, coatings, etc. |
| synthesis process | 1. Phosgene method [8-9] This method mainly consists of the following two main processes: condensation of aniline with formaldehyde and phosgenation of diamine condensates. (1) condensation process: aniline and 25% ~ 35% hydrochloric acid catalyst first react to generate aniline hydrochloride solution, and then add about 37% of formaldehyde aqueous solution, condensation reaction is carried out at 80 ℃ for 1~2H, reaction is carried out at elevated temperature up to about 100 ℃ for 1H, rearrangement reaction is carried out, and the solution is neutralized with caustic soda aqueous solution, and finally washed with water, layered, washed with water, (2) phosgenation: phosgenation reaction of the diamine condensate, in industry, it is usually divided into two stages: Low-temperature phosgenation and high-temperature phosgenation. In the low temperature phosgenation stage, the diamine is mainly reacted with phosgene and hydrogen chloride to form the corresponding diamine amide salt and hydrochloride. Please refer to the following figure for the specific process: Figure 1 Schematic diagram of condensation process between aniline and formaldehyde Figure 2 Schematic diagram of phosgenation process of diamine condensate Figure 3 process of preparing MDI by phosgene schematic diagram although the technology of this method is mature, phosgene is highly toxic, by-products corrosion equipment, residual chlorine products difficult to remove and environmental pollution and other shortcomings. 2. Thermal decomposition method Thermal decomposition method is the most promising green synthesis route for industrial application. Chen et al. studied the thermal decomposition reaction of 3% methyl diphenylmethane dicarbamate (MDC) at 260 ℃ with ultrafine ZnO as catalyst and dibutyl phthalate as solvent. The yield of DI was 52.1. With dibutyl phthalate as solvent and ZnO/Zn as Catalyst, the thermal decomposition of 2. 5 % MDC solution was carried out at 250 ℃, and the yield of MDI was 67.3. At 275 ℃, with Zn/SBA 15 as catalyst, dibutyl terephthalate and diisooctyl phthalate as mixed solvent, 0.3% MDC was thermally decomposed to MDI, and the yield was 84.3. Zhao et al at 280 deg C with zinc powder as catalyst, nitrobenzene and tetrahydrofuran as mixed solvent, 2% MDC thermal decomposition to produce MDI yield was 87.3. Bo et al. disclose a process for the decomposition of organic polycarbamates into organic polyisocyanates and phenols, which provides high yields of organic polyisocyanates at low temperatures. Under the condition of solvent, although the yield is higher, and can reduce the occurrence of polymerization reaction. The specific process of the method is as follows: Figure 4 schematic diagram of preparation of MDI by thermal decomposition Figure 5 Schematic diagram of preparation of MDI by laboratory thermal decomposition |
| Content determination | Guo Qiaozhen et al. established an ultra performance liquid chromatography-tandem mass spectrometry method for the analysis of diphenylmethane diisocyanate. Diphenylmethane diisocyanate was derived into methyl diphenylmethane dicarbamate by using methanol as derivatization reagent. The content of diphenylmethane diisocyanate was determined by measuring the content of diphenylmethane dicarbamate. The experiment was conducted on a Waters acquisition BEH C18 ultra-high performance liquid chromatography column (2. 1mm X 50mm X 1.7μm); Column temperature 25 ℃; Sample temperature 20 ℃; Injection volume 1 μl; Mobile phase A is methanol, B is aqueous solution containing 0.100 (volume fraction) formic acid; linear gradient elution; Elution procedure: 0-2 min, A- 100%A; Flow rate 0.25/min. Mass spectrometry conditions: electrospray ionization ion source, capillary voltage 3. 5 kV, conical hole voltage 25V, RF lens voltage 0.3V, ion source temperature 100 degrees Celsius, the solvent temperature 200 degrees Celsius, the solvent gas flow rate of 600 L/ h, using the selected ion monitoring mode. Methyl diphenyl methane dicarbamate was completely separated from other compounds within 1. 5 min and detected by quadrupole mass spectrometry with selected ion monitoring mode. The linear range is 2-100μg/L, the detection limit is 1 μ/L, the correlation coefficient is 0.9994. |
| Main use | diphenylmethane diisocyanate (MDI) is the primary raw material for producing polyurethane (PU). Polyurethane materials produced by MDI are widely used in the production of automobile parts, soles, artificial leather, coatings, adhesives, thermal insulation materials, etc. Most of the MDI is used to produce foam, MDI is also widely used in elastomer, adhesive (dense) agents, coatings and plastics and other industries. |
| Storage Conditions | cool, ventilated, strictly waterproof, moisture-proof, avoid direct sunlight, away from fire, heat source. During long-term storage, the storage temperature should not exceed 20 ℃. |
| references | [1] Wang Qingyin. Preparation of diphenylmethane diisocyanate by solvent-free thermal decomposition of phenyl diphenylmethane dicarbamate catalyzed by nano-Cu2O [J]. Chinese Journal of catalysis, 2013(34) [2] Eckert,Heiner,Forster.Barba angewwandte Chemie.1987(99) [3] Guo Qiaozhen. Determination of diphenylmethane diisocyanate by UPLC-MS/MS [J]. Journal of Mass Spectrometry, 2011(32) [4] Yu Liming. Market Analysis of diphenylmethane diisocyanate at home and abroad [J].2008(26) [5] Zhao Xinqiang. Clean synthesis of diphenylmethane diisocyanate II. Catalytic synthesis and decomposition of methyl alkanedicarbamate [J]. Journal of Petroleum Processing, 2001(17) [6] Zhu Yinsheng. Green catalytic synthesis of diphenylmethane diisocyanate [J]. Guangdong Chemical Industry, 2009(36) [7] Qian bozhang. Market Analysis of diphenylmethane diisocyanate at home and abroad [J]. Shanghai Chemical Industry, 2012(137) [8] Zhang Qinhua. Study on the polymerization kinetics of diphenylmethane diisocyanate_MDI_[J]. Acta Chimica Sinica, 2011(69) [9]. Apparent kinetics of the thermal decomposition of diphenylmethane dicarbamate to diphenylmethane diisocyanate [J]. Journal of Chemistry of colleges and universities, 2011(32) [10] Wang Qing-yin. Preparation of diphenylmethane diisocyanate by solvent-free thermal decomposition of diphenylmethane diaminophenyl Ester catalyzed by Sb2O3 [J]. Molecular Catalysis, 2013(27) |
Last Update：2024-04-10 22:29:15
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