Methacrylic Acid → Methacrylic Acid

HRID 1190761Notes

Reaction equation

HRID 1190761 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[C:9]([CH3:11])=[CH2:10].[C:21]([OH:26])(=[O:25])[C:22]([CH3:24])=[CH2:23].N(C(C)(C)C(OC)=O)=NC(C)(C)C(OC)=O>C(C(C)=O)C>[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:12])[C:9]([CH3:11])=[CH2:10].[C:21]([OH:26])(=[O:25])[C:22]([CH3:24])=[CH2:23]

Participants

7

Reactant 4

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 17236Benzyl methacrylateHCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)3×

Product 2

HCID 4093Methacrylic AcidHCID 10333664Methyl methacrylate benzylmethacrylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent4×

Conditions

Temperature
87 °C

Procedure

In a 2-liter three-neck flask equipped with a stirrer, a thermometer, a reflux condenser and a nitrogen gas introduction tube, 560.0 g of methyl ethyl ketone were placed and the surrounding temperature of the reaction container was increased to 87° C. While maintaining the refluxed state in the reaction container (refluxed until the reaction was completed), a mixed solution of 429.2 g of methyl methacrylate, 87.0 g of benzyl methacrylate, 29.0 g of PME-1000 (trade name, methoxypolyethylene glycol methacrylate (n=23), available from NOF Corporation), 34.8 g of methacrylic acid, 108.0 g of methyl ethyl ketone and 2.32 g of V-601 (trade name, available from Wako Pure Chemical Industries, Ltd.) was dropped therein at a constant rate so that the dropping was completed in 2 hours. After the completion of dropping, the mixture was stirred for 1 hour, and thereafter (1): a solution of 1.16 g of V-601 and 6.4 g of methyl ethyl ketone was further added and stirred for 2 hours. Subsequently, the process (1) was repeated 4 times, and a solution of 1.16 g of V-601 and 6.4 g of methyl ethyl ketone was further added and stirred for 3 hours. A resin solution of methyl methacrylate/benzyl methacrylate/PME-1000/methacrylic acid (=74/15/5/6 [mass ratio]) copolymer was thus obtained.

Workup

  1. customIn a 2-liter three-neck flask equipped with a stirrer
  2. temperatureWhile maintaining the refluxed state in the reaction container (
  3. temperaturerefluxed until the reaction
  4. additionwas dropped
  5. stirringstirred for 2 hours
  6. stirringstirred for 3 hours

Sources & evidence

ORD record
ord-f8fb59c02c824c2782bc320f384f15e1
Source dataset
uspto-grants-2014_03
Patent number
US08678577B2

Reaction notes

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