Methyl Isobutyl Ketone → Propylene glycol methyl ether acetate

HRID 1425630Notes

Reaction equation

HRID 1425630 reaction equation
[C:1]([O:6][CH:7]([O:9][CH2:10][CH3:11])[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:16])[C:13]([CH3:15])=[CH2:14].C(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][CH3:11])[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:12]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:7]([O:9][CH:10]([CH3:11])[CH2:12][O:17][CH3:18])(=[O:6])[CH3:8]

Participants

7

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 17236Benzyl methacrylateHCID 201933451-Ethoxyethyl Methacrylate (stabilized with MEHQ)HCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 2

HCID 7946Propylene glycol methyl ether acetateHCID 68475471HCID 68475471, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 66.4 g (0.42 mol) of 1-ethoxyethyl methacrylate, 31.7 g (0.18 mol) of benzyl 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′-10 (1-ethoxyethyl methacrylate/benzyl 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-c5d58c09ebfb4a01b949652279047abc
Source dataset
uspto-grants-2015_01
Patent number
US08932800B2

Reaction notes

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