Phenyl isocyanate → 1-Phenyl-3-[2-(3-isopropenylphenyl)-2-propyl]carbodiimide

HRID 2226668Notes

Reaction equation

HRID 2226668 reaction equation
CC1CCP(=O)(C2C=CC=CC=2)C=1.[CH3:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([N:26]=[C:27]=O)([CH3:25])[CH3:24])[CH:18]=1)=[CH2:16].[C:29]1([N:35]=C=O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(N=C=NC2C=CC=CC=2)C=CC=CC=1>>[C:29]1([N:35]=[C:27]=[N:26][C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:15]([CH3:14])=[CH2:16])[CH:18]=2)([CH3:25])[CH3:24])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 7672Phenyl isocyanateHCID 697221H-Phosphole, 2,3-dihydro-4-methyl-1-phenyl-, 1-oxideHCID 98693N,N'-Methanetetraylbis(benzenamine)HCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

Product 1

HCID 231929181-Phenyl-3-[2-(3-isopropenylphenyl)-2-propyl]carbodiimide

Procedure

We combined 0.3182 g 3-methyl-1-phenyl-2-phospholene-1-oxide (MPPO), m-TMI [2-(3-isopropenylphenyl)-2-propylisocyanate], and 19.31 g phenyl isocyanate. After heating at 140°-150° C. for 14 hours, IR showed nearly complete conversion of isocyanates to carbodiimides. GC-MS integrated ionization current shows a response of 265944 units for the title mixed product, 3558 units for the diphenyl carbodiimide, and 3602 units for the ditertiarycarbodiimide. Assuming that the detector sensitivity for the mixed product is the same, the selectivity for the mixed product is the average of the two other products, the reaction selectivity for the mixed product is 265944/(265944+3602+3558) or 97%, so the maximum yield of either mixed product is 3%.

Workup

  1. temperatureAfter heating at 140°-150° C. for 14 hours

Sources & evidence

ORD record
ord-65e5486786014b9a805d8a319a8a79f4
Source dataset
uspto-grants-1994_09
Patent number
US05349087

Reaction notes

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