Phosgene → Cyclohexyl isocyanate

HRID 1455668Notes

Reaction equation

HRID 1455668 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH:5]1([NH2:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>ClC1C=CC=CC=1.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:5]1([N:11]=[C:1]=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 6371Phosgene5×HCID 7965Cyclohexylamine

Product 1

HCID 18502Cyclohexyl isocyanateYield 142.5%

Reagents, catalysts & solvents 2

HCID 13097Triphenylphosphine OxideCatalystHCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
79 °C

Procedure

500 g of chlorobenzene and 7 g of triphenylphosphine oxide (0.025 mol) were placed in the glass vessel and 47 g of gaseous phosgene was introduced at room temperature. The reaction mixture was subsequently heated to 78° C., with vigorous phosgene reflux being established. While stirring vigorously at 78-80° C., a total of 99.2 g of cyclohexylamine (1 mol) dissolved in 200 g of chlorobenzene and at the same time a further 116 g of phosgene were introduced over a period of 3 hours. After addition was complete, the system was maintained at 78-80° C. for a further one hour without introduction of phosgene to allow further reaction to occur and the residual unreacted phosgene was subsequently stripped out at 40° C. by means of nitrogen. The reaction mixture obtained was a fluid suspension from which the solid obtained was separated by filtration. 1.9 g of solid were able to be isolated in this way. The filtered crude product was worked up by distillation. Removal of the solvent and fractional distillation gave 84.6 g of cyclohexyl isocyanate (0.677 mol). This corresponds to 67.7% of the theoretical yield.

Workup

  1. additionwas introduced at room temperature
  2. temperaturereflux
  3. additionwere introduced over a period of 3 hours
  4. additionAfter addition
  5. customreaction
  6. customwas subsequently stripped out at 40° C. by means of nitrogen
  7. customThe reaction mixture obtained
  8. customobtained
  9. customwas separated by filtration
  10. customto be isolated in this way
  11. filtrationThe filtered crude product
  12. distillationwas worked up by distillation
  13. customRemoval of the solvent and fractional distillation

Sources & evidence

ORD record
ord-d4298122423f48bd8cd09ca0b02ff7b0
Source dataset
uspto-grants-2009_01
Patent number
US07482481B2

Reaction notes

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