Toluene 2,4-Diisocyanate → HCID 131729226, compound

HRID 1662919Notes

Reaction equation

HRID 1662919 reaction equation
[CH3:1][CH:2]([OH:5])[CH2:3][OH:4].[CH2:6]([OH:14])[C:7]([CH2:12][OH:13])([CH2:10][OH:11])[CH2:8][OH:9].[CH3:15][C:16]1[C:17]([N:25]=[C:26]=[O:27])=[CH:18][C:19]([N:22]=[C:23]=[O:24])=[CH:20][CH:21]=1>>[CH3:1][CH:2]([OH:5])[CH2:3][OH:4].[CH2:6]([OH:14])[C:7]([CH2:12][OH:13])([CH2:10][OH:11])[CH2:8][OH:9].[CH3:15][C:16]1[C:17]([N:25]=[C:26]=[O:27])=[CH:18][C:19]([N:22]=[C:23]=[O:24])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 11443Toluene 2,4-DiisocyanateHCID 16212716HCID 16212716, compound

Product 1

HCID 131729226HCID 131729226, compound

Conditions

Temperature
65 °C

Procedure

An acetylenic derivative was prepared for use in a click reaction. About 15.75 grams (about 25 mmoles) of pentaerythritol propoxylate was slowly added to about 21.81 grams (about 125 mmoles) of 2,4-tolylene diisocyanate (TDI) at room temperature (about 21±5° C.). The mixture was then heated at about 65° C. for about 18 hours. The reaction mixture was washed seven times with petroleum ether. For each of the washings, about 45 mL of petroleum ether was added and the reaction mixture was stirred at about 65° C. for a period of time of from about 10 minutes to about 15 minutes. The mixture was decanted and the supernatant petroleum ether was removed with a pipette. The process was repeated six times; the resulting material was dried under a vacuum to provide a pentaerythritol propoxylate-TDI adduct. The material had a free isocyanate content of about 13.49%, as determined by titration. The pentaerythritol propoxylate-TDI adduct was of the formula depicted in FIG. 1, where n was from about 1 to about 15.

Workup

  1. washThe reaction mixture was washed seven times with petroleum ether
  2. additionFor each of the washings, about 45 mL of petroleum ether was added
  3. customThe mixture was decanted
  4. customthe supernatant petroleum ether was removed with a pipette
  5. customthe resulting material was dried under a vacuum

Sources & evidence

ORD record
ord-83b63af88e0b496697acd1b6cf99c4f1
Source dataset
uspto-grants-2011_10
Patent number
US08034396B2

Reaction notes

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