Hexamethylene diisocyanate → Vinyl isocyanate

HRID 1446972Notes

Reaction equation

HRID 1446972 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 2

HCID 13192Hexamethylene diisocyanate2×HCID 12573467(1-Chloroethyl)carbamyl chloride

Product 2

HCID 77094Vinyl isocyanateYield 36.8%HCID 125734821-Chloroethyl isocyanateYield 16.1%

Conditions

Temperature
-100 °C

Procedure

A solution of 57 parts of 1-chloroethylcarbamic acid chloride in 100 parts by volume of hexamethylene diisocyanate is introduced slowly in the course of half an hour, at 100° C., under the surface of 572 parts of hexamethylene diisocyanate. At the same time nitrogen is blown through the solution and the exit gas is cooled to -100° C. in a cold trap. After the reaction, the reaction mixture is subjected to fractional distillation. 10.2 parts (36.8% of theory) of vinyl isocyanate of boiling point 38.5° C./1013 mbar and 6.8 parts (16.1% of theory) of 1-chloroethyl isocyanate of boiling point 92° C./1013 mbar are obtained.

Workup

  1. customAfter the reaction
  2. distillationthe reaction mixture is subjected to fractional distillation

Sources & evidence

ORD record
ord-c95c66a28ffd435287f690039ee8c5d0
Source dataset
uspto-grants-1982_02
Patent number
US04314948

Reaction notes

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