Methacrylic Acid → Propylene glycol methyl ether acetate

HRID 1618843Notes

Reaction equation

HRID 1618843 reaction equation
[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])[C:2]([CH3:4])=[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]([OH:29])(=[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:6][CH:7]([CH3:10])[CH2:8][O:15][CH3:11])(=[O:5])[CH3:2].[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])[C:2]([CH3:4])=[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]([OH:29])(=[O:28])[C:25]([CH3:27])=[CH2:26]

Participants

8

Reactant 4

HCID 4093Methacrylic AcidHCID 11448tert-Butyl methacrylateHCID 17236Benzyl methacrylateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 2

HCID 7946Propylene glycol methyl ether acetateHCID 20574609HCID 20574609, compound

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

A 500 ml three-necked flask was charged with 51.2 g (0.36 mol) of tert-butyl methacrylate, 21.1 g (0.12 mol) of benzyl methacrylate, 10.3 g (0.12 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 propylene glycol monomethyl ether acetate. The heptane and methyl isobutyl ketone contained in the solution were distilled off in vacuum, thereby obtaining a propylene glycol monomethyl ether acetate solution of polymer A′1-8 (tert-butyl methacrylate/benzyl 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 propylene glycol monomethyl ether acetate
  6. distillationwere distilled off in vacuum

Sources & evidence

ORD record
ord-0ff9f5a7fbec4fd886e6bcca3b3cb750
Source dataset
uspto-grants-2014_07
Patent number
US08771907B2

Reaction notes

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