Cyclohexanol → Cyclohexyl vinylcarbamate

HRID 371338

Reaction equation

HRID 371338 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>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

5

Reactant 3

HCID 7966CyclohexanolHCID 77094Vinyl isocyanateHCID 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 initially taken in a reaction vessel and are heated at 40° C. A mixture of 110 parts of cyclohexanol, 89.5 parts of ethyl acetate and 0.02% of dibutyltin dilaurate as the catalyst is added in the course of one hour, after which the mixture is allowed to continue reacting for a further 2 hours at 40° C. A pale yellow solution is obtained, from which, on cooling, the reaction product separates out in the form of crystals. Content of blocked isocyanate groups: 11.7%.

Workup

  1. additionis added in the course of one hour
  2. customA pale yellow solution is obtained, from which
  3. temperatureon cooling

Sources & evidence

ORD record
ord-19518ee734404747bb06682d89dd5fd3
Source dataset
uspto-grants-1985_07
Patent number
US04530978

Linked notes

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