Methacrylic Acid → Phenoxyethylmethacrylate methylmethacrylate methacrylic acid

HRID 1890127Notes

Reaction equation

HRID 1890127 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.COC(=O)C(N=NC(C)(C)C(OC)=O)(C)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 204.5%

Reagents, catalysts & solvents 2

HCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)Catalyst2×HCID 6569Methyl Ethyl KetoneSolvent3×

Conditions

Temperature
70 °C

Procedure

In a 1000-ml three-necked flask equipped with a stirrer and a cooling tube, 90 g of methyl ethyl ketone was added and was heated to 70° C. in a nitrogen atmosphere, and to this, a solution prepared by dissolving 0.83 g of dimethyl-2,2′-azobisisobutyrate, 70 g of phenoxyethyl methacrylate, 10 g of methacrylic acid and 20 g of methyl methacrylate in 52 g of methyl ethyl ketone was added dropwise over 3 hours. After completion of the dropwise addition, the mixture was allowed to react for another one hour, and then a solution prepared by dissolving 0.44 g of dimethyl-2,2′-azobisisobutyrate in 2 g of methyl ethyl ketone was added thereto. The temperature of the mixture was raised to 80° C., and the mixture was heated for 5 hours. The reaction solution thus obtained was reprecipitated two times in excess hexane, and a resin precipitated therefrom was dried. Thus, 93.2 g of a phenoxyethyl methacrylate/methyl methacrylate/methacrylic acid (copolymerization ratio [mass ratio]=70/20/10) copolymer (resin dispersant P-1) was obtained.

Workup

  1. customIn a 1000-ml three-necked flask equipped with a stirrer and a cooling tube
  2. customto this, a solution prepared
  3. additionwas added dropwise over 3 hours
  4. additionAfter completion of the dropwise addition
  5. customto react for another one hour
  6. customa solution prepared
  7. additionwas added
  8. temperatureThe temperature of the mixture was raised to 80° C.
  9. temperaturethe mixture was heated for 5 hours
  10. customThe reaction solution thus obtained
  11. customwas reprecipitated two times in excess hexane
  12. customa resin precipitated
  13. customtherefrom was dried

Sources & evidence

ORD record
ord-af758f8f3a91431ca10aba052c3cb257
Source dataset
uspto-grants-2013_08
Patent number
US08506069B2

Reaction notes

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