Methacrylic Acid → Phenoxyethylmethacrylate methylmethacrylate methacrylic acid

HRID 452281

Reaction equation

HRID 452281 reaction equation
[C:1]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:16]([OH:21])(=[O:20])[C:17]([CH3:19])=[CH2:18].[C:22]([O:27][CH3:28])(=[O:26])[C:23]([CH3:25])=[CH2:24]>C(C(C)=O)C>[C:1]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:22]([O:27][CH3:28])(=[O:26])[C:23]([CH3:25])=[CH2:24].[C:16]([OH:21])(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 663572-Phenoxyethyl methacrylate

Product 1

HCID 67403649Phenoxyethylmethacrylate methylmethacrylate methacrylic acidYield 162.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent3×

Conditions

Temperature
72 °C

Procedure

88 g of methyl ethyl ketone was placed in a 1000-ml three-necked flask equipped with a stirrer and a cooling tube, heated to 72° C. under a nitrogen atmosphere. A solution prepared by dissolving 0.85 g of dimethyl-2,2′-azobisisobutylate, 50 g of phenoxyethyl methacrylate, 13 g of methacrylic acid, and 37 g of methyl methacrylate in 50 g of methyl ethyl ketone was added dropwise thereto over a period of 3 hours. After completion of the addition, the reaction was further continued for one hour, and then a solution prepared by dissolving 0.42 g of dimethyl-2,2′-azobisisobutylate in 2 g of methyl ethyl ketone was added thereto, and the solution was heated at 78° C. for 4 hours. The reaction solution thus obtained was reprecipitated twice in excess amounts of hexane, and the precipitated resin was dried to obtain 96.5 g of a phenoxyethyl methacrylate/methyl methacrylate/methacrylic acid (copolymerization ratio [mass ratio %]=50/37/13) copolymer (resin dispersant P-1).

Workup

  1. customequipped with a stirrer and a cooling tube
  2. customA solution prepared
  3. additionwas added dropwise
  4. additionAfter completion of the addition
  5. waitthe reaction was further continued for one hour
  6. customa solution prepared
  7. additionwas added
  8. temperaturethe solution was heated at 78° C. for 4 hours
  9. customThe reaction solution thus obtained
  10. customwas reprecipitated twice in excess amounts of hexane
  11. customthe precipitated resin was dried

Sources & evidence

ORD record
ord-9adf0412aab44df5b9fcbc40d49cc7e2
Source dataset
uspto-grants-2013_07
Patent number
US08491113B2

Linked notes

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