Phosgene → 2-Ethylhexyloxycarbonyl isocyanate

HRID 867979Notes

Reaction equation

HRID 867979 reaction equation
[C:1](=[O:12])([O:3][CH2:4][CH:5]([CH2:10][CH3:11])[CH2:6][CH2:7][CH2:8][CH3:9])[NH2:2].[C:13](Cl)(Cl)=[O:14]>CCCCCCCCCCCCCCCCCCCNC=O.ClC1C=CC=CC=1>[CH2:10]([CH:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][O:3][C:1]([N:2]=[C:13]=[O:14])=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 6371Phosgene3×HCID 94289Carbamic acid, 2-ethylhexyl ester

Product 1

HCID 139080002-Ethylhexyloxycarbonyl isocyanateYield 85%

Reagents, catalysts & solvents 2

HCID 17845310MethylstearylformamideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
-78 °C

Procedure

138.6 g of 2-ethylhexyl carbamate were initially introduced in melted form and 93 g of phosgene were passed into the melt at 80° C. within 3.25 hours, the gas outlet stream being passed through a reflux condenser cooled to -78° C. 800 g of chlorobenzene and 5.0 g of methylstearylformamide were then added, the mixture was heaLed to 120° C., and 48 g of phosgene were passed into the mixture within 3 hours. The mixture was stirred for a further 1 hour at 130° C. and excess phosgene was subsequently blown out using nitrogen. Subsequent distillation produced 135.5 g (=85% of theory) of 2-ethylhexyloxycarbonyl isocyanate having a boiling point of 45°-60° C. at 0.13-0.4 mbar.

Workup

  1. customthe gas outlet stream being passed through a reflux condenser
  2. customwas heaLed to 120° C.
  3. distillationSubsequent distillation

Sources & evidence

ORD record
ord-a698b358b4e5427e8ede694b582186b2
Source dataset
uspto-grants-1988_10
Patent number
US04777283

Reaction notes

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