(1-Chloroethyl)carbamyl chloride → Vinyl isocyanate

HRID 648143Notes

Reaction equation

HRID 648143 reaction equation
[Cl:1][CH:2]([NH:4][C:5](Cl)=[O:6])[CH3:3]>C(N=C=O)CCCCCN=C=O>[CH:2]([N:4]=[C:5]=[O:6])=[CH2:3].[Cl:1][CH:2]([N:4]=[C:5]=[O:6])[CH3:3]

Participants

4

Reactant 1

HCID 12573467(1-Chloroethyl)carbamyl chloride

Product 2

HCID 77094Vinyl isocyanateYield 53%HCID 125734821-Chloroethyl isocyanateYield 17.7%

Reagents, catalysts & solvents 1

HCID 13192Hexamethylene diisocyanateSolvent

Procedure

563 parts of 1-chloroethylcarbamyl chloride are dissolved in 2,800 parts by volume of hexamethylene diisocyanate. The solution, totalling 3,100 parts by volume, is introduced in 3 portions (500, 1,500 and 1,100 parts by volume) with different residence times (150, 310 and 225 minutes respectively) into a thin film evaporator operated under atmospheric pressure, with a counter-current of nitrogen. The jacket temperature is 73°-75° C. and the material passes over at 48°-54° C. The reaction product is collected in a receiver and two downstream cold traps, and the composition is determined by gas chromatography. 145.3 parts (53% of theory) of vinyl isocyanate, of boiling point 38.5° C./1,013 mbar, and 73.8 parts (17.7% of theory) of 1-chloroethyl isocyanate, of boiling point 92° C./1,013 mbar, are obtained.

Workup

  1. additionis introduced in 3 portions (500, 1,500 and 1,100 parts by volume) with different residence times (150, 310 and 225 minutes respectively)
  2. custominto a thin film evaporator
  3. customis 73°-75° C.
  4. customover at 48°-54° C
  5. customThe reaction product is collected in a receiver and two downstream cold traps

Sources & evidence

ORD record
ord-a1ab6149a73743ca952238e95e429dce
Source dataset
uspto-grants-1983_10
Patent number
US04411752

Reaction notes

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