Methacrylic Acid → Phenoxyethylmethacrylate methylmethacrylate methacrylic acid

HRID 1970660Notes

Reaction equation

HRID 1970660 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 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 added to a 1000-mL three-necked flask equipped with an agitator and a cooling tube, and was heated to 72° C. under a nitrogen atmosphere. To this, a solution of 0.85 g of dimethyl-2,2′-azobisisobutyrate, 50 g of phenoxyethyl methacrylate, 13 g of methacrylic acid and 37 g of methyl methacrylate dissolved in 50 g of methyl ethyl ketone was added dropwise over 3 hours. After the addition was completed, the mixture was reacted for one more hour, and then a solution of 0.42 g of dimethyl-2,2′-azobisisobutyrate dissolved in 2 g of methyl ethyl ketone was added. The temperature was raised to 78° C., and the mixture was heated for 4 hours. The obtained reaction solution was precipitated two times in excess of hexane, and the precipitated resin was dried to obtain 96.5 g of a phenoxyethyl methacrylate/methyl methacrylate/methacrylic acid copolymer (copolymerization ratio by mass percent=50/37/13) (resin dispersant P-1).

Workup

  1. customequipped with an agitator and a cooling tube
  2. additionwas added dropwise over 3 hours
  3. additionAfter the addition
  4. customthe mixture was reacted for one more hour
  5. additionwas added
  6. temperatureThe temperature was raised to 78° C.
  7. temperaturethe mixture was heated for 4 hours
  8. customThe obtained reaction solution
  9. customwas precipitated two times in excess of hexane
  10. customthe precipitated resin was dried

Sources & evidence

ORD record
ord-bcaa36e89f214a8f8281187476339849
Source dataset
uspto-grants-2013_04
Patent number
US08430493B2

Reaction notes

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