Phenyl isocyanate → N,N'-Methanetetraylbis(benzenamine)

HRID 2419188Notes

Reaction equation

HRID 2419188 reaction equation
[C:1]1([N:7]=[C:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCCCCC>[C:1]1([N:7]=[C:8]=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 7672Phenyl isocyanate

Product 1

HCID 98693N,N'-Methanetetraylbis(benzenamine)

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 3.619 g. of the copolymer prepared as described in Example 2 and a solution of 30.5 g. of phenyl isocyanate in 100 ml. of n-hexane was heated under reflux for 9.25 hours. At the end of this time the solid catalyst was removed by filtration and the filtrate was evaporated to dryness to yield diphenyl carbodiimide. An infrared spectrum of the product revealed only a trace of unreacted isocyanate. In contrast, a solution of phenyl isocyanate in n-hexane, heated under reflux for the same length of time but in the absence of catalyst, showed no significant amount of absorption corresponding to carbodiimide linkages in the infrared spectrum.

Workup

  1. additionA mixture of 3.619 g
  2. customof the copolymer prepared
  3. temperatureunder reflux for 9.25 hours
  4. customAt the end of this time the solid catalyst was removed by filtration
  5. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f82096b729924bd9b054adc48fbe4e9d
Source dataset
uspto-grants-1978_08
Patent number
US04105643

Reaction notes

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