Acrylic Acid → Phenoxyethyl acrylate methyl methacrylate acrylic acid

HRID 1950661Notes

Reaction equation

HRID 1950661 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(C(C)=O)C.C(O)(C)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 KetoneSolvent4×

Conditions

Temperature
75 °C

Procedure

360.0 g of methyl ethyl ketone was placed in a 2 L three-necked flask equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas introduction tube, and the temperature of the methyl ethyl ketone was increased to 75° C. under nitrogen atmosphere. Thereafter, a mixed solution of 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 an azo polymerization initiator V-601 (tradename, manufactured by Wako Pure Chemical Industries Co., Ltd.) was dripped into the flask at a constant rate while maintaining the temperature inside the flask at 75° C., such that the dripping was completed in 2 hours. After the completion of the dripping, a solution of 0.72 g of V-601 (tradename, manufactured by Wako Pure Chemical Industries Co., Ltd.) in 36.0 g of methyl ethyl ketone was added thereto, and the contents of the flask were stirred for 2 hours while maintaining the liquid temperature at 75° C. Thereafter, a solution of 0.72 g of V-601 (tradename, manufactured by Wako Pure Chemical Industries Co., Ltd.) in 36.0 g of isopropanol was added thereto, and the contents of the flask were stirred for 2 hours while maintaining the liquid temperature at 75° C. Then, the liquid temperature was increased to 85° C., and stirring was further continued for 2 hours, as a result of which a resin solution of a copolymer of phenoxyethyl acrylate/methyl methacrylate/acrylic acid (at a ratio by mass of 50/45/5) was obtained.

Workup

  1. customequipped with a stirrer
  2. temperaturewhile maintaining the liquid temperature at 75° C
  3. stirringthe contents of the flask were stirred for 2 hours
  4. temperaturewhile maintaining the liquid temperature at 75° C
  5. temperatureThen, the liquid temperature was increased to 85° C.
  6. stirringstirring
  7. waitwas further continued for 2 hours

Sources & evidence

ORD record
ord-ec0863557be54b0d8dc74321f3f87c6c
Source dataset
uspto-grants-2013_03
Patent number
US08403473B2

Reaction notes

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