4-Methoxyphenol → 2-Hydroxyethyl acrylate

HRID 1500595Notes

Reaction equation

HRID 1500595 reaction equation
[C:1]([O:5][CH2:6][CH2:7][OH:8])(=[O:4])[CH:2]=[CH2:3].[O:9]=[C:10]=[N:11][CH:12]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:14]([CH3:24])([CH2:15][N:16]=[C:17]=[O:18])[CH2:13]1.COC1C=CC(O)=CC=1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[NH2:11][C:1]([O:5][CH2:6][CH3:7])=[O:4].[O:9]=[C:10]=[N:11][CH:12]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:14]([CH3:24])([CH2:15][N:16]=[C:17]=[O:18])[CH2:13]1.[C:1]([O:5][CH2:6][CH2:7][OH:8])(=[O:4])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 131652-Hydroxyethyl acrylateHCID 169132Isophorone diisocyanateHCID 9809426Di-n-butyldilauryltin

Product 3

HCID 131652-Hydroxyethyl acrylateHCID 169132Isophorone diisocyanateHCID 21863578Urethane acrylate

Procedure

Into a 1-liter separable flask were put 232 parts (2 mol) of 2-hydroxyethyl acrylate (manufactured by Nippon Shokubai, trade name: BHEA), 222 parts (1 mol) of isophorone diisocyanate and 0.09 parts of hydroquinone monomethyl ether. With stirring, air was introduced into the liquid through a glass tube, and the liquid temperature was made to be 70° C. Thereto was added 0.09 parts of dibutyltin dilaurate and while the reaction temperature was adjusted to be between 70 and 80° C., reaction was performed for 6 hours to give a urethane acrylate of isophorone diisocyanate and 2-hydroxyethyl acrylate.

Workup

  1. customInto a 1-liter separable flask were put
  2. additionair was introduced into the liquid through a glass tube
  3. customto be 70° C
  4. customto be between 70 and 80° C.
  5. customreaction

Sources & evidence

ORD record
ord-c2ca2a2ab27d4f2d8537aa835f311d51
Source dataset
uspto-grants-2015_12
Patent number
US09206117B2

Reaction notes

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