Methacrylic Acid → Phenoxyethylmethacrylate methylmethacrylate methacrylic acid

HRID 1471204

Reaction equation

HRID 1471204 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]>COC(=O)C(N=NC(C)(C)C(OC)=O)(C)C.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

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 6569Methyl Ethyl KetoneSolvent3×HCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)Solvent2×

Conditions

Temperature
72 °C

Procedure

88 g of methyl ethyl ketone was added to a 1000 ml three-necked flask that included a stirrer and condenser and heated in a nitrogen atmosphere to 72° C., and a solution in which 0.85 g of dimethyl-2,2′-azobisisobutyrate, 50 g of phenoxyethyl methacrylate, 13 g of methacrylic acid, and 37 g of methyl methacrylate were dissolved in 50 g of methyl ethyl ketone was added dropwise thereto over three hours. After reacting for another hour after the end of the dropwise addition, a solution in which 0.42 g of dimethyl-2,2′-azobisisobutyrate was dissolved in 2 g of methyl ethyl ketone was added, heated to and maintained at 78° C. for four hours. The obtained reaction solution was reprecipitated twice in an excess amount of hexane and the precipitated resin was dried, whereby 96.5 g of a phenoxyethyl methacrylate/methyl methacrylate/methacrylic acid (copolymer ratio [mass ratio]=50/37/13) copolymer (water-insoluble resin P-1) was obtained.

Workup

  1. additionwas added dropwise
  2. waitAfter reacting for another hour
  3. additionafter the end of the dropwise addition
  4. additionwas added
  5. temperatureheated to and
  6. temperaturemaintained at 78° C. for four hours
  7. customThe obtained reaction solution
  8. customwas reprecipitated twice in an excess amount of hexane
  9. customthe precipitated resin was dried

Sources & evidence

ORD record
ord-1a5364f734454e22abd8b580cd685aea
Source dataset
uspto-grants-2015_04
Patent number
US09010916B2

Linked notes

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