Phosgene → Cyclohexyl isocyanate

HRID 1349378Notes

Reaction equation

HRID 1349378 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.CC1C=CC(S(N)(=O)=O)=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 249.7%

Reagents, catalysts & solvents 2

HCID 6269P-ToluenesulfonamideCatalystHCID 7964ChlorobenzeneSolvent2×

Procedure

500 g of chlorobenzene and 4.3 g of p-toluenesulfonamide (0.025 mol) were placed in the glass vessel and 33 g of gaseous phosgene was introduced at room temperature. The reaction mixture was subsequently heated to 79° C., with vigorous phosgene reflux being established. While stirring vigorously at 78–81° C., a total of 99.2 g of cyclohexylamine (1 mol) dissolved in 200 g of chlorobenzene and at the same time a further 122 g of phosgene were introduced over a period of 3 hours. After addition was complete, the system was maintained at 78–81° 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 50° C. by means of nitrogen. The reaction mixture obtained was a fluid suspension from which the solid obtained was separated by filtration. <0.5 g of solid was able to be isolated in this way. Cyclohexyl isocyanate was worked up by distillation. Removal of the solvent and fractional distillation gave 105.1 g of cyclohexyl isocyanate (0.833 mol). This corresponds to 83.3% 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 50° 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. distillationCyclohexyl isocyanate was worked up by distillation
  12. customRemoval of the solvent and fractional distillation

Sources & evidence

ORD record
ord-02b3d40a31a14c0592a9cefea1bfe82d
Source dataset
uspto-grants-2007_05
Patent number
US07211689B2

Reaction notes

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