Formaldehyde → Aniline

HRID 848688Notes

Reaction equation

HRID 848688 reaction equation
[CH2:1]([C:11]1[CH:16]=[CH:15][C:14]([N:17]=C=O)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][C:5]([N:8]=C=O)=[CH:4][CH:3]=1.C=O.NC1C=CC=CC=1>>[NH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1.[CH2:1]([C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1)[C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6115Aniline2×HCID 7570Diphenylmethane diisocyanate

Product 2

HCID 6115AnilineHCID 75774,4-Diaminodiphenylmethane

Procedure

A novel process for making 4,4'-methylene diphenyl diisocyanate and corresponding oligomer in improved selectivity and yield comprises condensing formaldehyde and aniline under neutral or basic conditions to yield an anil condensate, followed by reacting the anil condensate with additional aniline and a protonic salt of aniline to yield 4,4'-methylene dianiline and corresponding oligomer, then followed by conventional phosgenation.

Workup

  1. customyield
  2. customto yield an anil condensate

Sources & evidence

ORD record
ord-d36ad017a1f24fb896ab3b56239cb53d
Source dataset
uspto-grants-1981_10
Patent number
US04297294

Reaction notes

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