Acrylic Acid → Phenoxyethyl acrylate methyl methacrylate acrylic acid

HRID 1890128Notes

Reaction equation

HRID 1890128 reaction equation
[C:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:4])[CH:2]=[CH2:3].[C:15]([O:20][CH3:21])(=[O:19])[C:16]([CH3:18])=[CH2:17].[C:22]([OH:26])(=[O:25])[CH:23]=[CH2:24].N(C(C)(C)C(OC)=O)=NC(C)(C)C(OC)=O>C(O)(C)C.C(C(C)=O)C>[C:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].[C:15]([O:20][CH3:21])(=[O:19])[C:16]([CH3:18])=[CH2:17].[C:22]([OH:26])(=[O:25])[CH:23]=[CH2:24]

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 6658Methyl MethacrylateHCID 39485Phenoxyethyl acrylateHCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)3×

Product 1

HCID 86634647Phenoxyethyl acrylate methyl methacrylate acrylic acid

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6569Methyl Ethyl KetoneSolvent3×

Conditions

Temperature
75 °C

Procedure

In 2-liter three-necked flask equipped with a stirrer, a thermometer, a reflux cooling tube and a nitrogen gas inlet tube, 360.0 g of methyl ethyl ketone was fed, and the temperature was raised to 75° C. While the temperature inside the reaction vessel was maintained at 75° C., a mixed solution containing 180.0 g of phenoxyethyl acrylate, 162.0 g of methyl methacrylate, 18.0 g of acrylic acid, 72 g of methyl ethyl ketone, and 1.44 g of “V-601” (trade name, manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the flask at a constant rate so that the dropwise addition was completed in 2 hours. After completion of the dropwise addition, a solution containing 0.72 g of “V-601” and 36.0 g of methyl ethyl ketone was added to the flask, and the mixture was stirred for 2 hours at 75° C. Subsequently, a solution containing 0.72 g of “V-601” and 36.0 g of isopropanol was added to the flask, and the resulting mixture was stirred for 2 hours at 75° C. Subsequently, the temperature was raised to 85° C., and stirring was continued for another 2 hour. Thus, a resin solution of a phenoxyethyl acrylate/methyl methacrylate/acrylic acid (=50/45/5 [mass ratio]) copolymer was obtained.

Workup

  1. customIn 2-liter three-necked flask equipped with a stirrer
  2. temperaturea thermometer, a reflux cooling tube and a nitrogen gas inlet tube
  3. temperatureWhile the temperature inside the reaction vessel was maintained at 75° C.
  4. additionwas added dropwise to the flask at a constant rate so that the dropwise addition
  5. additionAfter completion of the dropwise addition
  6. additionwas added to the flask
  7. additionwas added to the flask
  8. stirringthe resulting mixture was stirred for 2 hours at 75° C
  9. temperatureSubsequently, the temperature was raised to 85° C.
  10. stirringstirring
  11. waitwas continued for another 2 hour

Sources & evidence

ORD record
ord-f29b34a3a61644e3959ed54edef9b3a2
Source dataset
uspto-grants-2013_08
Patent number
US08506069B2

Reaction notes

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