Methacrylic Acid → 3,4-Epoxycyclohexylmethyl methacrylate benzyl methacrylate methacrylic acid

HRID 574027

Reaction equation

HRID 574027 reaction equation
[C:1]([O:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH:11]2[O:14][CH:10]2[CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:15]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])[C:16]([CH3:18])=[CH2:17].[C:28]([OH:33])(=[O:32])[C:29]([CH3:31])=[CH2:30].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][CH2:7][CH:8]1[CH2:13][CH2:12][CH:11]2[O:14][CH:10]2[CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:15]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:19])[C:16]([CH3:18])=[CH2:17].[C:28]([OH:33])(=[O:32])[C:29]([CH3:31])=[CH2:30]

Participants

7

Reactant 4

HCID 4093Methacrylic AcidHCID 17236Benzyl methacrylateHCID 14645478(7-Oxabicyclo(4.1.0)heptan-3-yl)methyl 2-methylprop-2-enoateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 1

HCID 866555463,4-Epoxycyclohexylmethyl methacrylate benzyl methacrylate methacrylic acid

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 58.9 g (0.30 mol) of 3,4-epoxycyclohexylmethyl methacrylate (Cyclomer M100, produced by Daicel Chemical Industries, Ltd.), 31.7 g (0.18 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 diethylene glycol dimethyl ether, and heptane and methyl isobutyl ketone contained in the solution were removed by distillation under reduced pressure to obtain Polymer A2-3 (3,4-epoxycyclohexylmethyl methacrylate/benzyl methacrylate/methacrylic acid) as a diethylene glycol dimethyl ether 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 diethylene glycol dimethyl ether
  6. customwere removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f0b569f1ff9d4984a01f8dd1979814df
Source dataset
uspto-grants-2015_05
Patent number
US09034440B2

Linked notes

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