Methacrylic Acid → Phenoxyethylmethacrylate methylmethacrylate methacrylic acid

HRID 535206Notes

Reaction equation

HRID 535206 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 a further hour after the end of 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 thereto, and heated to and maintained at 78° C. for four hours. The obtained reaction solution was reprecipitated twice in excess hexane and the precipitated resin was dried to obtain 96.5 g of a phenoxyethyl methacrylate/methyl methacrylate/methacrylic acid (copolymer ratio [mass ratio]=50/37/13) copolymer (Water-Insoluble Resin P-1)

Workup

  1. additionwas added dropwise
  2. waitAfter reacting for a further hour
  3. additionafter the end of 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 excess hexane
  9. customthe precipitated resin was dried

Sources & evidence

ORD record
ord-7a404a5dd9b54053b4faa604a9c77488
Source dataset
uspto-grants-2014_10
Patent number
US08857969B2

Reaction notes

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