Acrylic Acid → Phenoxyethyl acrylate methyl methacrylate acrylic acid

HRID 2273694Notes

Reaction equation

HRID 2273694 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 a 2-liter three-necked flask equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas inlet tube, 360.0 g of methyl ethyl ketone was inserted and the temperature was raised to 75° C. While the temperature inside the flask 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” (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise 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 this, and after the mixture was stirred for 2 hours at 75° C., a solution containing 0.72 g of “V-601” and 36.0 g of isopropanol was added thereto and stirred for 2 hours at 75° C. After this, the temperature was raised to 85° C. and stirring was continued for another 2 hours and a resin solution of a phenoxyethyl acrylate/methyl methacrylate/acrylic acid (=50/45/5 [mass ratio]) copolymer was obtained.

Workup

  1. customIn a 2-liter three-necked flask equipped with a stirrer
  2. temperatureWhile the temperature inside the flask was maintained at 75° C.
  3. additionwas added dropwise at a constant rate so that the dropwise addition
  4. additionAfter completion of the dropwise addition
  5. additionwas added to this, and after the mixture
  6. additionwas added
  7. stirringstirred for 2 hours at 75° C
  8. temperatureAfter this, the temperature was raised to 85° C.
  9. stirringstirring
  10. waitwas continued for another 2 hours

Sources & evidence

ORD record
ord-62aa6c7355a64ab5a7a6887dc3106789
Source dataset
uspto-grants-2015_09
Patent number
US09126449B2

Reaction notes

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