Isopropyl isocyanate → Vinyl isocyanate

HRID 1446974Notes

Reaction equation

HRID 1446974 reaction equation
[Cl:1][CH:2]([NH:4][C:5](Cl)=[O:6])[CH3:3].[CH:8]([N:11]=[C:12]=[O:13])([CH3:10])[CH3:9]>>[CH:2]([N:4]=[C:5]=[O:6])=[CH2:3].[Cl:1][CH2:9][CH2:8][N:11]=[C:12]=[O:13].[CH:8]([N:11]=[C:12]=[O:13])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 12573467(1-Chloroethyl)carbamyl chloride

Product 3

HCID 160352-Chloroethyl isocyanateYield 2%HCID 61277Isopropyl isocyanateHCID 77094Vinyl isocyanateYield 43%

Conditions

Temperature
70 °C

Procedure

57 parts of 1-chloroethylcarbamic acid chloride are introduced into 700 parts by volume of isopropyl isocyanate at 22° C., the mixture is heated to 70° C. in the course of 1.5 hours whilst passing a slight stream of nitrogen through it, and the reaction mixture is condensed in a cold trap at -70° C. 12 parts (43% of theory) of vinyl isocyanate of boiling point 38.5° C./1013 mbar, 0.85 part (2% of theory) of chloroethyl isocyanate of boiling point 92° C./1013 mbar and 218 parts of isopropyl isocyanate are obtained.

Workup

  1. customcondensed in a cold trap at -70° C

Sources & evidence

ORD record
ord-5b0347513819430dae10d2def020fd20
Source dataset
uspto-grants-1982_02
Patent number
US04314948

Reaction notes

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