| Identification | Back Directory | [Name]
2,2'-methylenedianiline | [CAS]
6582-52-1 | [Synonyms]
Einecs 229-512-4 2,2'-methylenedianiline 2,2'-methylenedianiline Aniline, 2,2'-methylenedi- 2,2'-Diaminodiphenylmethane 2,2'-Methylenebis(benzeneamine) Benzenamine, 2,2'-methylenebis- 2-[(2-aminophenyl)methyl]aniline | [EINECS(EC#)]
229-512-4 | [Molecular Formula]
C13H14N2 | [MDL Number]
MFCD01109641 | [MOL File]
6582-52-1.mol | [Molecular Weight]
198.26 |
| Chemical Properties | Back Directory | [Melting point ]
134-135 °C | [Boiling point ]
153-155 °C(Press: 3 Torr) | [density ]
0.9877 g/cm3 | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Acetonitrile (Slightly), Chloroform (Slightly) | [form ]
Solid | [pka]
4.27±0.10(Predicted) | [color ]
Light Brown to Brown | [EPA Substance Registry System]
Benzenamine, 2,2'-methylenebis- (6582-52-1) |
| Hazard Information | Back Directory | [Uses]
2,2''-Methylenedianiline is used in the production of rigid polyurethane foams. | [Synthesis]
The general procedure for the synthesis of 2-(4-aminobenzyl)aniline, 2,2'-methylenedianiline and 4,4'-diaminodiphenylmethane from formaldehyde and aniline hydrochloride is as follows:
1. hydrochloric acid from tank 2 (at a concentration of 30.8 wt%, which is a by-product of the MDI unit) and aniline from tank 3 are transported via pump 6 in a ratio of hydrochloric acid to aniline at a molar ratio of 0.36:1 to a venturi mixer 5, wherein mixing is carried out and reaction is carried out to generate aniline hydrochloride. Subsequently, the generated aniline hydrochloride is pumped into a recirculation tube and mixed with the recirculating solution from the condensing mixing vessel 1 to form a mixed solution.
2. The mixed solution is introduced into a heat exchanger 7, where the heat of reaction is removed, cooled to 38°C, and then conveyed to the inlet of a high gravity rotary bed reactor 8.
3. at the same time, the formaldehyde solution (with a concentration of 37 wt%) from the storage tank 4 was fed through the other feed port of the high gravity rotary bed reactor 8, controlling the molar ratio of formaldehyde to aniline to be 0.40:1. in the high gravity rotary bed reactor 8, the formaldehyde solution was fully mixed with the premixed solution and underwent a pre-condensation reaction under the following reaction conditions: temperature 35°C, reaction time 0.5 sec, rotor speed 1000 rpm.
4. The mixed solution after reaction flows into the condensation reactor 1 for further pre-condensation reaction under the following conditions: temperature 42°C, stirring speed 110 rpm, reaction residence time 20 minutes.
5. Subsequently, the temperature of the reaction solution was raised to above 90 °C for a molecular rearrangement reaction with a reaction residence time of about 2 h. A solution of diphenylmethylene diamine hydrochloride and polymethylene polyphenylene polyamine hydrochloride was finally obtained.
6. Of the reaction mixture from the condensing reactor 1, 92 vol% was returned to the recirculation tubes as a recirculating solution and flowed through the heat exchanger 7, while the remaining 8 vol% was discharged and neutralized with a sodium hydroxide solution at a concentration of 42 wt%.
7. The brine phase was separated from the polyamine organic phase, the polyamine organic phase was washed with water and purified to give a final mixture of diphenylmethylene diamine and polymethylene polyphenylene polyamine. The product composition is detailed in Table 2. | [References]
[1] Patent: EP2145874, 2010, A1. Location in patent: Page/Page column 6 |
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Struchem Co., Ltd.
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0512-63009836 18994340901 |
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www.beidapharma.com |
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