Cyclohexanol → Cyclohexyl vinylcarbamate

HRID 1105745

Reaction equation

HRID 1105745 reaction equation
[CH:1]([N:3]=[C:4]=[O:5])=[CH2:2].[CH:6]1([OH:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.[N-]=C=O>C(OCC)(=O)C>[CH:1]([NH:3][C:4](=[O:5])[O:12][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[CH2:2]

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 77094Vinyl isocyanateHCID 105034IsocyanateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 85174Cyclohexyl vinylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

69 parts of vinyl isocyanate and 89.5 parts of ethyl acetate are introduced into a reaction vessel and heated to 40° C. A mixture of 110 parts of cyclohexanol and 89.5 parts of ethyl acetate (containing 0.02% of dibutyl-tin dilaurate as the catalyst) is added in the course of 1 hour. The mixture is then allowed to react for a further 2 hours at 40° C. A light yellow solution is obtained, from which the reaction product separates out, as crystals, on cooling. Blocked isocyanate content: 11.7%.

Workup

  1. additionis added in the course of 1 hour
  2. customto react for a further 2 hours at 40° C
  3. customA light yellow solution is obtained, from which the reaction product
  4. temperatureon cooling

Sources & evidence

ORD record
ord-6892c16d1cdb4ccfbcabd6cc81d7092c
Source dataset
uspto-grants-1982_01
Patent number
US04310398

Linked notes

Loading…