Ethyl isocyanate → 1-Chloroethyl isocyanate

HRID 648144Notes

Reaction equation

HRID 648144 reaction equation
[Cl:1][CH:2]([NH:4][C:5](Cl)=[O:6])[CH3:3].[CH2:8]([N:10]=[C:11]=[O:12])[CH3:9].C(N=C=O)=C>>[Cl:1][CH:2]([N:4]=[C:5]=[O:6])[CH3:3].[CH2:8]([N:10]=[C:11]=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 77094Vinyl isocyanateHCID 12573467(1-Chloroethyl)carbamyl chloride

Product 2

HCID 8022Ethyl isocyanateHCID 125734821-Chloroethyl isocyanateYield 23.8%

Conditions

Temperature
90 °C

Procedure

A mixture of 57 parts of 1-chloroethylcarbamyl chloride, 156 parts of ethyl isocyanate and 841 parts of hexamethylene diisocyante is heated to 90° C. in the course of 3 hours, whilst passing a stream of nitrogen at 22° C. through the mixture. A mixture of 11.8 parts (42.5% of theory) of vinyl isocyanate, of boiling point 38.5° C./1,013 mbar, 10.1 parts (23.8% of theory) of 1-chloroethyl isocyanate of boiling point 92° C./1,013 mbar and 149 parts of ethyl isocyanate is obtained in the distillation receiver.

Workup

  1. customat 22° C.

Sources & evidence

ORD record
ord-d985f1816af24f6d83e0642a457867a7
Source dataset
uspto-grants-1983_10
Patent number
US04411752

Reaction notes

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