(1-Chloroethyl)carbamyl chloride → Vinyl isocyanate

HRID 1446975Notes

Reaction equation

HRID 1446975 reaction equation
Cl[CH:2]([NH:4][C:5](Cl)=[O:6])[CH3:3]>C(N=C=O)C>[CH:2]([N:4]=[C:5]=[O:6])=[CH2:3].[CH2:2]([N:4]=[C:5]=[O:6])[CH3:3]

Participants

4

Reactant 1

HCID 12573467(1-Chloroethyl)carbamyl chloride

Product 2

HCID 8022Ethyl isocyanateHCID 77094Vinyl isocyanateYield 50.5%

Reagents, catalysts & solvents 1

HCID 8022Ethyl isocyanateSolvent

Procedure

57 parts of 1-chloroethylcarbamic acid chloride are dissolved in 520 parts of ethyl isocyanate at 22° C. and dry nitrogen is blown through the solution, a Raschig ring column being used to achieve a preliminary separation of the 3-component mixture (ethyl isocyanate, vinyl isocyanate and 1-chloroethyl isocyanate) in the column. The reaction mixture is subjected to fractional distillation for 3 hours. 14 parts (50.5% of theory) of vinyl isocyanate of boiling point 38.5° C./1013 mbar and 466 parts of ethyl isocyanate of boiling point 60° C./1013 mbar are obtained.

Workup

  1. customa preliminary separation of the 3-component mixture (ethyl isocyanate, vinyl isocyanate and 1-chloroethyl isocyanate) in the column
  2. distillationThe reaction mixture is subjected to fractional distillation for 3 hours

Sources & evidence

ORD record
ord-a430a44bbaa94ba3898a7c3b08cc9245
Source dataset
uspto-grants-1982_02
Patent number
US04314948

Reaction notes

Loading…