ChemicalBook--->CAS DataBase List--->6582-52-1

6582-52-1

6582-52-1 Structure

6582-52-1 Structure
IdentificationBack 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 PropertiesBack 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)
Safety DataBack Directory
[TSCA ]

TSCA listed
Hazard InformationBack Directory
[Uses]

2,2''-Methylenedianiline is used in the production of rigid polyurethane foams.
[Synthesis]

Formaldehyde

50-00-0

Aniline hydrochloride

142-04-1

2,4'-DIAMINODIPHENYLMETHANE

1208-52-2

2,2'-methylenedianiline

6582-52-1

4,4'-Methylenedianiline

101-77-9

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
Spectrum DetailBack Directory
[Spectrum Detail]

2,2'-methylenedianiline(6582-52-1)1HNMR
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