4,4-Diaminodiphenylmethane → Benzenamine, 4,4'-methylenebis[N-(1-methylpropyl)-

HRID 1511195Notes

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].C(C(C)=O)C>[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: 121 °C

Procedure

4,4′-Methylenebis(benzeneamine) (MDA; 2.0 g), granular Pt(S)/C (1.0 g, Johnson Matthey), and methyl ethyl ketone (50.0 g) were charged to a 100 mL autoclave. The autoclave was degassed three times with H2 and then the mixture was heated at 121° C. for 2 hours under 85 psig (6.87×105 Pa) of H2. The reaction mixture was cooled to 22° C. and degassed. The granular Pt(S)/C catalyst settled to the bottom of reactor as soon as the agitation was stopped, making it easier to decant the product solution and recover the catalyst. GC analysis showed a 95% yield of N,N′-di(2-butyl)-4,4′-methylenebis(benzeneamine), and less than 0.4 area % of over-alkylated side-product.

Workup

customThe autoclave was degassed three times with H2
temperatureThe reaction mixture was cooled to 22° C.
customdegassed
customto decant the product solution
customrecover the catalyst

Sources & evidence

ORD record: ord-181770cf99a24b6a8d316c2727ddf3bc
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212078B2

Reaction notes

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