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2-Hydroxyethyl acrylate → Isophorone diisocyanate 2-hydroxyethyl acrylate

HRID 2259819
Notes
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Reaction equation

HRID 2259819 reaction equation
[O:1]=[C:2]=[N:3][CH:4]1[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:6]([CH3:16])([CH2:7][N:8]=[C:9]=[O:10])[CH2:5]1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.[C:54]([O:58][CH2:59][CH2:60][OH:61])(=[O:57])[CH:55]=[CH2:56]>C(C(C)=O)C(C)C>[O:1]=[C:2]=[N:3][CH:4]1[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:6]([CH3:16])([CH2:7][N:8]=[C:9]=[O:10])[CH2:5]1.[C:54]([O:58][CH2:59][CH2:60][OH:61])(=[O:57])[CH:55]=[CH2:56]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 131652-Hydroxyethyl acrylateHCID 169132Isophorone diisocyanateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 86740661Isophorone diisocyanate 2-hydroxyethyl acrylateYield 90%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

A 2-liter flask fitted with a stirrer, an air introduction tube, a condensing pipe and a thermostat was charged with 222 parts of isophorone diisocyanate and 50 parts of methyl isobutyl ketone. While blowing a dry air into a liquid phase, they were stirred and heated to 70° C. To the mixture was added 0.3 part of dibutyltin dilaurate, followed by adding dropwise 232 parts of 2-hydroxyethyl acrylate for 1 hour. Even after the dropwise addition, the mixture was heated and kept at 70° C. The reaction mixture was collected with the lapse of time and absorption of -NCO was ascertained by IR. A time when the absorption of -NCO disappeared was made the termination of the reaction. There resulted a blocked 90% isophorone diisocyanate/2-hydroxyethyl acrylate solution. The 70% solids content bubble viscosity (solvent composition: 10% of methyl isobutyl ketone and 20% of n-butyl acrylate) was GH.

Workup

  1. customA 2-liter flask fitted with a stirrer, an air introduction tube
  2. additionEven after the dropwise addition
  3. temperaturethe mixture was heated
  4. customkept at 70° C
  5. customThe reaction mixture was collected with the lapse of time and absorption of -NCO
  6. customA time when the absorption of -NCO
  7. customthe termination of the reaction

Sources & evidence

ORD record
ord-139977df1cd340d68616facac5967e21
Source dataset
uspto-grants-1995_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05475057

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes