Hexamethylene diisocyanate → Vinyl isocyanate

HRID 648139

Reaction equation

HRID 648139 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 12573482HCID 12573482, compoundYield 16.1%

Conditions

Temperature
-100 °C

Procedure

A solution of 57 parts of 1-chloroethylcarbamyl chloride in 100 parts by volume of hexamethylene diisocyanate is introduced slowly at 100° C., in the course of half an hour, 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. by means of a cold trap. The reaction mixture is subjected to fractional distillation. 10.2 parts (36.8% of theory) of vinyl isocyanate of boiling point 38.5° C./1,013 mbar and 6.8 parts (16.1% of theory) of 1-chloroethyl isocyanate of boiling point 92° C./1,013 mbar are obtained.

Workup

  1. distillationThe reaction mixture is subjected to fractional distillation

Sources & evidence

ORD record
ord-73014b2f188142b98e7d79a3a57c6fbf
Source dataset
uspto-grants-1983_10
Patent number
US04411752

Linked notes

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