Methacrylic Acid → Propylene glycol methyl ether acetate

HRID 574032Notes

Reaction equation

HRID 574032 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:33]([O-])=[O:34]>CCCCCCC.C(C(C)=O)C(C)C>[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].[C:1]([O:6][CH:7]([CH3:10])[CH2:8][O:34][CH3:33])(=[O:5])[CH3:2]

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

Into a 500 ml-volume three-neck flask, 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 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 A′1-8 (tert-butyl methacrylate/benzyl methacrylate/methacrylic acid) 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-403fb000166f44be9a06ee7e6076727c
Source dataset
uspto-grants-2015_05
Patent number
US09034440B2

Reaction notes

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