Methacrylic Acid → 1-Benzyloxyethyl methacrylate 2-hydroxyethyl methacrylate methacrylic acid

HRID 1618832Notes

Reaction equation

HRID 1618832 reaction equation
[C:1]([O:6][CH:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:17]([O:22][CH2:23][CH2:24][OH:25])(=[O:21])[C:18]([CH3:20])=[CH2:19].[C:26]([OH:31])(=[O:30])[C:27]([CH3:29])=[CH2:28].N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O>CCCCCCC.C(C(C)=O)C(C)C>[C:1]([O:6][CH:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:17]([O:22][CH2:23][CH2:24][OH:25])(=[O:21])[C:18]([CH3:20])=[CH2:19].[C:26]([OH:31])(=[O:30])[C:27]([CH3:29])=[CH2:28]

Participants

7

Reactant 4

HCID 4093Methacrylic AcidHCID 133602-Hydroxyethyl MethacrylateHCID 218349871-Benzyloxyethyl methacrylateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 1

HCID 866555411-Benzyloxyethyl methacrylate 2-hydroxyethyl methacrylate methacrylic acid

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

A 500 ml three-necked flask was charged with 105.7 g (0.48 mol) of 1-benzyloxyethyl methacrylate, 7.8 g (0.06 mol) of 2-hydroxyethyl methacrylate, 5.2 g (0.06 mol) of methacrylic acid and 300 ml of methyl isobutyl ketone. A catalytic amount of 2,2′-azobis(methyl 2-methylpropionate) as a radical polymerization initiator was added to the mixture, and polymerization was performed in a nitrogen stream at 80° C. for six hours. The obtained reaction liquid was cooled, and poured in a large volume of heptane, thereby precipitating a polymer. The polymer crystal was collected by filtration, and dissolved in diethylene glycol dimethyl ether. The heptane and methyl isobutyl ketone contained in the solution were distilled off in vacuum, thereby obtaining a diethylene glycol dimethyl ether solution of polymer A1-2 (1-benzyloxyethyl methacrylate/2-hydroxyethyl methacrylate/methacrylic acid).

Workup

  1. customThe obtained reaction liquid
  2. temperaturewas cooled
  3. customprecipitating a polymer
  4. filtrationThe polymer crystal was collected by filtration
  5. dissolutiondissolved in diethylene glycol dimethyl ether
  6. distillationwere distilled off in vacuum

Sources & evidence

ORD record
ord-59b0283b764642e0aaec2b3c29fbe1c8
Source dataset
uspto-grants-2014_07
Patent number
US08771907B2

Reaction notes

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