(1-Chloroethyl)carbamyl chloride → Vinyl isocyanate

HRID 648142Notes

Reaction equation

HRID 648142 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-chloroethylcarbamyl 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 in order to achieve a preliminary separation of the 3-component mixture in the column (ie. into ethyl isocyanate, vinyl isocyanate and 1-chloroethyl isocyanate). The reaction mixture is subjected to fractional distillation in the course of 3 hours. 14 parts (50.5% of theory) of vinyl isocyanate of boiling point 38.5° C./1,013 mbar and 466 parts of ethyl isocyanate of boiling point 60° C./1,013 mbar are obtained.

Workup

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

Sources & evidence

ORD record
ord-2b6c0909b0fc490bba002d54e5afc09a
Source dataset
uspto-grants-1983_10
Patent number
US04411752

Reaction notes

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