2-Isocyanatoethyl methacrylate → Bisphenol A

HRID 2294757Notes

Reaction equation

HRID 2294757 reaction equation
[CH3:1][C:2]([C:14]1[CH:19]=[CH:18][C:17]([O:20]CCO)=[CH:16][CH:15]=1)([C:4]1[CH:9]=[CH:8][C:7]([O:10]CCO)=[CH:6][CH:5]=1)[CH3:3].C(OCCN=C=O)(=O)C(C)=C>>[OH:10][C:7]1[CH:6]=[CH:5][C:4]([C:2]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)([CH3:3])[CH3:1])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 354092-Isocyanatoethyl methacrylateHCID 61909Bisphenol A bis(2-hydroxyethyl)ether

Product 1

HCID 6623Bisphenol A

Procedure

A total of 200 g (0.345 mol) of dry Photonol 7025 is placed into a 1L three neck flask equipped with mechanical agitation, and gas-inlet tube. The system is flushed with dry nitrogen and then dry oxygen. To the BPA are added 375 g of dry acetonitrile and allowed to mix until the BPA has completely dissolved. Subsequently 2 drops of stannous octoate and 500 ppm MEHQ are, added. Via a dropping funnel are added 107.1 g (0.690 mol) of isocyanatoethyl methacrylate. The reaction is allowed to proceed at room temperature for 24-28 hours. The progress of the reaction is followed by the disappearance of the NCO absorption at 2270 cm-1 in the infrared spectra. The acetonitrile is removed under reduced pressure, and the resultant viscous liquid dicapped SPA 890 is used as is.

Workup

  1. customequipped with mechanical agitation, and gas-inlet tube
  2. customThe system is flushed with dry nitrogen
  3. additionTo the BPA are added 375 g of dry acetonitrile
  4. additionto mix until the BPA
  5. dissolutionhas completely dissolved
  6. additionadded
  7. customThe progress of the reaction is followed by the disappearance of the NCO absorption at 2270 cm-1 in the infrared spectra
  8. customThe acetonitrile is removed under reduced pressure

Sources & evidence

ORD record
ord-282b2c83d7c04b7e852cd75281113f2e
Source dataset
uspto-grants-1997_11
Patent number
US05690953

Reaction notes

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