Acetone → N,N'-diisopropyl-4,4'-methylenebis(benzeneamine)

HRID 500036

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.[CH3:16][C:17]([CH3:19])=O.[C:20]1(C)[CH:25]=CC=C[CH:21]=1>[Pt]>[CH:17]([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:20]([CH3:25])[CH3:21])=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)([CH3:19])[CH3:16]

Participants

Conditions

Temperature: 22 °C

Procedure

4,4′-Methylenebis(benzeneamine) (8.0 g, 40 mmol), acetone (10.0 g, 172 mmol), Pt(S)/C (0.5 g), and toluene (50.0g) were charged into reactor. The reactor was purged 3 times with 110 psig (8.60×105 Pa) of H2 at 22° C. The reaction mixture was then stirred at 22° C. under 110 psig (8.60×105 Pa) of H2 overnight. GC (conditions: 180° C./5 minutes/10° C.-minutes rate/270° C./RT=9.37 minutes) showed 100% conversion of 4,4′-methylenebis(benzeneamine), and a 98% yield of N,N′-diisopropyl-4,4′-methylenebis(benzeneamine). The structure of the product was confirmed by GC-MS. No tertiary diamine was detected either by GC or by GC-MS.

Workup

customThe reactor was purged 3 times with 110 psig (8.60×105 Pa) of H2 at 22° C
customGC (conditions: 180° C./5 minutes/10° C.-minutes rate/270° C./RT=9.37 minutes)

Sources & evidence

ORD record: ord-b381ecc26f9f428699735f10065d7368
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767858B2

Linked notes

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