N-(4-Methyl-2-pentanylidene)hydroxylamine → HCID 131717678, compound

HRID 2259820Notes

Reaction equation

HRID 2259820 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].[CH2:62]([C:66]([CH3:69])=[N:67][OH:68])[CH:63]([CH3:65])[CH3:64]>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].[CH2:62]([C:66]([CH3:69])=[N:67][OH:68])[CH:63]([CH3:65])[CH3:64]

Participants

6

Reactant 4

HCID 7756N-(4-Methyl-2-pentanylidene)hydroxylamineHCID 131652-Hydroxyethyl acrylateHCID 169132Isophorone diisocyanateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 131717678HCID 131717678, compoundYield 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 116 parts of 2-hydroxyethyl acrylate for 1 hour. Even after the dropwise addition, the temeprature was kept at 70° C. for 1 hour. Subsequently, 115 parts of methyl isobutyl ketoxime was added dropwise for 1 hour. Even after the dropwise addition, heating was conducted to keep the temperature at 70° C. The reaction mixture was collected with the lapse of time. Absorption of -NCO was ascertained by IR. A time when absorption of -NCO disappeared was made the termination of the reaction. There was obtained a blocked 90% isophorone diisocyanate/2-hydroxyethyl acrylate/methyl isobutyl ketoxime solution. The 70% solids content buble viscosity (solvent composition: 10% of methyl isobutyl ketone and 20% of n-butyl acrylate) was DE.

Workup

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

Sources & evidence

ORD record
ord-4a75e6b46eaa427bb2a8ad29f0d66d8b
Source dataset
uspto-grants-1995_12
Patent number
US05475057

Reaction notes

Loading…