(+-)-alpha-Pinene → Vinyl isocyanate

HRID 848050Notes

Reaction equation

HRID 848050 reaction equation
[Br:1][CH:2]([NH:4][C:5](Br)=[O:6])[CH3:3].CC1C2C(C)(C)C(C2)CC=1>>[Br:1][CH:2]([N:4]=[C:5]=[O:6])[CH3:3].[CH:2]([N:4]=[C:5]=[O:6])=[CH2:3]

Participants

4

Reactant 2

HCID 6654(+-)-alpha-PineneHCID 12573468(1-Bromoethyl)carbamyl bromide

Product 2

HCID 77094Vinyl isocyanateYield 89%HCID 21886720HCID 21886720, compoundYield 10%

Procedure

A mixture of 231 parts of 1-bromoethylcarbamic acid bromide and 475 parts of α-pinene is heated at from 23° to 120° C. in the course of 1.5 hours, whilst stirring, and the reaction mixture is then subjected to fractional distillation. A total of 14.6 parts (10% of theory) of 1-bromoethyl isocyanate of freezing point -27.5° C. (decomposition) and 61.5 parts (89% of theory) of vinyl isocyanate of boiling point 38.5° C./1013 mbar is obtained.

Workup

  1. temperatureis heated at from 23° to 120° C. in the course of 1.5 hours
  2. distillationthe reaction mixture is then subjected to fractional distillation

Sources & evidence

ORD record
ord-6103ed3903304d68b8529afbb5aec749
Source dataset
uspto-grants-1981_10
Patent number
US04294773

Reaction notes

Loading…