Glycidyl methacrylate → Propylene glycol methyl ether acetate

HRID 2191181Notes

Reaction equation

HRID 2191181 reaction equation
[C:1]([O:6][CH:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:14]([O:19][CH2:20][CH:21]1[O:23][CH2:22]1)(=[O:18])[C:15]([CH3:17])=[CH2:16].[CH2:24](C(C)=O)C(C)C.N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O>CCCCCCC>[C:1]([O:6][CH:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:14]([O:19][CH2:20][CH:21]1[O:23][CH2:22]1)(=[O:18])[C:15]([CH3:17])=[CH2:16].[C:14]([O:19][CH:20]([CH3:24])[CH2:21][O:23][CH3:22])(=[O:18])[CH3:15]

Participants

7

Reactant 4

HCID 7837Glycidyl methacrylateHCID 7909Methyl Isobutyl KetoneHCID 219175032,2'-Azobis(methyl 2-methylpropanate)HCID 219599501-Butoxyethyl methacrylate

Product 2

HCID 7946Propylene glycol methyl ether acetateHCID 866432061-n-Butoxyethyl methacrylate glycidyl methacrylate

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 67.1 g (0.36 mol) of 1-n-butoxyethyl methacrylate, 34.1 g (0.24 mol) of glycidyl 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 A-1 (1-n-butoxyethyl methacrylate/glycidyl 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-559355edd96d43b9b491feadc9f7fa28
Source dataset
uspto-grants-2012_12
Patent number
US08329380B2

Reaction notes

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