Tetrachloroethylene → Di-p-tolylcarbodiimide

HRID 2083268Notes

Reaction equation

HRID 2083268 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=O)=[CH:3][CH:2]=1.[N-:11]=[C:12]=O.C1(P2(=O)[CH2:24][CH2:23][C:22]([CH3:25])=[CH:21]2)C=CC=CC=1.Cl[C:28](Cl)=C(Cl)Cl>>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[N:11][C:12]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:28]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 31373TetrachloroethyleneHCID 693254-Methylphenyl isocyanateHCID 697221H-Phosphole, 2,3-dihydro-4-methyl-1-phenyl-, 1-oxideHCID 105034Isocyanate2×

Product 1

HCID 69763Di-p-tolylcarbodiimideYield 77%

Procedure

p-Tolylisocyanate (150 parts) was stirred under a nitrogen atmosphere at 115° C with 2,2,2-diazabicyclo-octane equivalent to the acidity of the isocyanate (0.14 parts) and 1-phenyl-3-methyl-phospholene-1-oxide (0.75 parts of a 0.1% solution in perchloroethylene) an amount of 5 ppm on the isocyanate. After 8 hours, examination by infra-red showed all isocyanate groups to have disappeared. The red-brown single phase liquid was distilled in vacuo to give 96.2 parts (77% of theory) of di-p-tolylcarbodiimide.

Workup

  1. distillationThe red-brown single phase liquid was distilled in vacuo

Sources & evidence

ORD record
ord-d56affcc338d4d87b1d39049214f4902
Source dataset
uspto-grants-1978_04
Patent number
US04085140

Reaction notes

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