Methyl Ethyl Ketone → 4,4'-Bis(sec-butylamino)diphenylmethane

HRID 1511196Notes

Reaction equation

HRID 1511196 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.[CH2:16]([C:18]([CH3:20])=O)[CH3:17]>[Pt].O>[CH:16]([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:1]([CH2:2][CH3:3])[CH3:9])=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)([CH2:18][CH3:20])[CH3:17]

Participants

5

Reactant 2

HCID 6569Methyl Ethyl KetoneHCID 75774,4-Diaminodiphenylmethane

Product 1

HCID 1106404,4'-Bis(sec-butylamino)diphenylmethaneYield 96%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Conditions

Temperature
136 °C

Procedure

4,4′-Methylenebis(benzeneamine) (19.8 g, 0.1 mol), methyl ethyl ketone (20.0 g, 0.28 mol), Pt(S)/C (2.0 g), and water (28.0 g; formed a second phase) were charged into reactor. The reactor was purged 3 times with H2 at 22° C. The reaction mixture was then stirred at 800 rpm at 136° C. under H2 for 2.5 hours. GC showed 100% conversion of 4,4′-methylenebis(benzeneamine), and a 96-97% yield of N,N′-di-sec-butyl-4,4′-methylenebis(benzeneamine).

Workup

  1. customformed a second phase)
  2. additionwere charged into reactor
  3. customThe reactor was purged 3 times with H2 at 22° C

Sources & evidence

ORD record
ord-417eb1719b714b9899cedfebac1ab15a
Source dataset
uspto-grants-2012_07
Patent number
US08212078B2

Reaction notes

Loading…