Methacrylic Acid → Phenoxyethylmethacrylate methylmethacrylate methacrylic acid

HRID 400308

Reaction equation

HRID 400308 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.N(C(C)(C)C(OC)=O)=NC(C)(C)C(OC)=O>[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

6

Reactant 3

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 663572-Phenoxyethyl methacrylate

Product 1

HCID 67403649Phenoxyethylmethacrylate methylmethacrylate methacrylic acidYield 162.8%

Reagents, catalysts & solvents 2

HCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)Catalyst2×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 condenser tube, and was heated to 72° C. under a nitrogen atmosphere. Then, a solution obtained by dissolving 0.85 g of dimethyl 2,2′-azobisisobutyrate, 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 thereto dropwise over 3 hours. After the addition was completed, the mixture was further allowed to react for one hour, and then a solution obtained by dissolving 0.42 g of dimethyl 2,2′-azobisisobutyrate in 2 g of methyl ethyl ketone was added thereto. The temperature of the resulting mixture was elevated to 78° C., and the mixture was heated for 4 hours. The obtained reaction liquid was reprecipitated twice with an excess of hexane. The separated resin was dried, to obtain 96.5 g of a phenoxyethyl methacrylate/methyl methacrylate/methacrylic acid (copolymerization ratio [mass % ratio]=50/37/13) copolymer (polymer dispersant P-1).

Workup

  1. customequipped with a stirrer and a condenser tube
  2. customThen, a solution obtained
  3. additionwas added
  4. additionAfter the addition
  5. customto react for one hour
  6. customa solution obtained
  7. additionwas added
  8. customwas elevated to 78° C.
  9. temperaturethe mixture was heated for 4 hours
  10. customThe obtained reaction liquid
  11. customwas reprecipitated twice with an excess of hexane
  12. customThe separated resin was dried

Sources & evidence

ORD record
ord-403530f3ec0e45c78ad80f4e4b79c958
Source dataset
uspto-grants-2014_06
Patent number
US08740368B2

Linked notes

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