2-Hydroxyethyl Methacrylate → Propylene glycol methyl ether acetate

HRID 574024

Reaction equation

HRID 574024 reaction equation
[C:1]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:13]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1)(=[O:15])[CH3:14].[C:25]([O:30][CH2:31][CH2:32][OH:33])(=[O:29])[C:26]([CH3:28])=[CH2:27].N(C(C)(CC)C([O-])=O)=NC(C)(CC)[C:37]([O-])=[O:38]>CCCCCCC.C(C(C)=O)C(C)C>[C:1]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:13]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1)(=[O:15])[CH3:14].[C:25]([O:30][CH2:31][CH2:32][OH:33])(=[O:29])[C:26]([CH3:28])=[CH2:27].[C:13]([O:16][CH:17]([CH3:24])[CH2:18][O:38][CH3:37])(=[O:15])[CH3:14].[CH3:25][O:30][CH2:31][CH2:32][O:33][CH2:10][CH2:9][O:8][CH2:7][CH3:12]

Participants

9

Reactant 4

HCID 133602-Hydroxyethyl MethacrylateHCID 758214-Ethenylphenyl acetateHCID 11041138Tetrahydropyranyl methacrylateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 3

HCID 7946Propylene glycol methyl ether acetateHCID 138471-Ethoxy-2-(2-methoxyethoxy)ethaneHCID 866576232-Tetrahydropyranyl methacrylate p-acetoxystyrene 2-hydroxyethyl methacrylate

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 71.5 g (0.42 mol) of 2-tetrahydropyranyl methacrylate, 19.5 g (0.12 mol) of p-acetoxystyrene, 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 a mixed solvent of propylene glycol monomethyl ether acetate and diethylene glycol ethyl methyl ether, and heptane and methyl isobutyl ketone contained in the solution were removed by distillation under reduced pressure to obtain Polymer A1-7 (2-tetrahydropyranyl methacrylate/p-acetoxystyrene/2-hydroxyethyl methacrylate) as a solution in a mixed solvent of propylene glycol monomethyl ether acetate and diethylene glycol ethyl methyl ether.

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 a mixed solvent of propylene glycol monomethyl ether acetate and diethylene glycol ethyl methyl ether, and heptane and methyl isobutyl ketone
  6. customwere removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0f00b9825d854a42998bbc8a14935fbe
Source dataset
uspto-grants-2015_05
Patent number
US09034440B2

Linked notes

Loading…