2-Hydroxyethyl Methacrylate → Propylene glycol methyl ether acetate

HRID 574021Notes

Reaction equation

HRID 574021 reaction equation
[C:1]([O:5][CH:6]([O:8][CH2:9][CH3:10])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[C:11]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[C:12]([CH3:14])=[CH2:13].[C:24]([O:29][CH2:30][CH2:31][OH:32])(=[O:28])[C:25]([CH3:27])=[CH2:26].N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O>CCCCCCC.C(C(C)=O)C(C)C>[C:1]([O:5][CH:6]([O:8][CH2:9][CH3:10])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[C:11]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:15])[C:12]([CH3:14])=[CH2:13].[C:24]([O:29][CH2:30][CH2:31][OH:32])(=[O:28])[C:25]([CH3:27])=[CH2:26].[C:6]([O:8][CH:9]([CH3:10])[CH2:11][O:16][CH3:17])(=[O:5])[CH3:7]

Participants

8

Reactant 4

HCID 133602-Hydroxyethyl MethacrylateHCID 17236Benzyl methacrylateHCID 205502781-Ethoxyethyl acrylateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 2

HCID 7946Propylene glycol methyl ether acetateHCID 673209541-Ethoxyethyl acrylate benzyl methacrylate 2-hydroxyethyl methacrylate

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 51.9 g (0.36 mol) of 1-ethoxyethyl acrylate, 31.7 g (0.18 mol) of benzyl methacrylate, 7.8 g (0.06 mol) of 2-hydroxyethyl methacrylate and 300 ml of methyl isobutyl ketone were charged. A catalytic amount of 2,2′-azobis(methyl 2-methylpropionate) was added thereto as a radical polymerization initiator, and polymerization was allowed to proceed at 80° C. for 6 hours in a nitrogen stream. The reaction solution was cooled and then poured in a large amount of heptane to precipitate a polymer. The crystal was collected by filtration and dissolved in propylene glycol monomethyl ether acetate, and heptane and methyl isobutyl ketone contained in the solution were removed by distillation under reduced pressure to obtain Polymer A1-4 (1-ethoxyethyl acrylate/benzyl methacrylate/2-hydroxyethyl methacrylate) as a propylene glycol monomethyl ether acetate solution.

Workup

  1. customas a radical polymerization initiator, and polymerization
  2. temperatureThe reaction solution was cooled
  3. customto precipitate a polymer
  4. filtrationThe crystal was collected by filtration
  5. dissolutiondissolved in propylene glycol monomethyl ether acetate
  6. customwere removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0ec0b5bc367441248bcb991e6883b25c
Source dataset
uspto-grants-2015_05
Patent number
US09034440B2

Reaction notes

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