4,4-Diaminodiphenylmethane → 4,4'-Bis(sec-butylamino)diphenylmethane

HRID 1511194Notes

Reaction equation

[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1>[Pt].CC(=O)CC>[CH3:9][CH:1]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][CH:5]([CH2:6][CH3:7])[CH3:4])=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

4,4′-Methylenebis(benzeneamine) (MDA; 1.20 g), Pt(S)/C (1.20 g), and 2-butanone (methyl ethyl ketone, MEK; 50.0 g) were charged to an autoclave. The autoclave was degassed three times with H2 at 22° C. and the mixture was heated to 120° C. under 14 psig (1.98×105 Pa) H2 without stirring. At 120° C., with stirring, the autoclave was pressurized to 85 psig (6.87×105 Pa) with H2 over a period of twelve minutes. The reaction mixture was then cooled to 22° C. GC analysis showed 100% conversion of MDA, and a 96% yield of N,N′-di(2-butyl)-4,4′-methylenebis(benzeneamine).

Workup

customThe autoclave was degassed three times with H2 at 22° C.
stirringAt 120° C., with stirring
waitthe autoclave was pressurized to 85 psig (6.87×105 Pa) with H2 over a period of twelve minutes
temperatureThe reaction mixture was then cooled to 22° C

Sources & evidence

ORD record: ord-e05cebe9378c461080f19ef4bdd9b6d8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212078B2

Reaction notes

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