Methacrylic Acid → Methacrylic Acid

HRID 1943508Notes

Reaction equation

HRID 1943508 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:8][C:9]([C:11]([O:13][CH:14]1[C@@:19]2([CH3:23])[C:20]([CH3:22])([CH3:21])[C@H:16]([CH2:17][CH2:18]2)[CH2:15]1)=[O:12])=[CH2:10].[C:24]([O-:29])(=[O:28])[C:25]([CH3:27])=[CH2:26].C(O)(=O)C(C)=C.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].[CH3:10][C:9]([C:11]([O:13][CH:14]1[C@@:19]2([CH3:23])[C:20]([CH3:22])([CH3:21])[C@H:16]([CH2:17][CH2:18]2)[CH2:15]1)=[O:12])=[CH2:8].[C:24]([OH:29])(=[O:28])[C:25]([CH3:27])=[CH2:26]

Participants

8

Reactant 5

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)3×HCID 87595MethacrylateHCID 71311141Isobornylmethacrylate

Product 2

HCID 4093Methacrylic AcidHCID 131730279HCID 131730279, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent4×

Conditions

Temperature
75 °C

Procedure

360.0 g of methyl ethyl ketone was placed in a 2 L three necked flask equipped with a stirrer, a thermometer, a reflux condenser tube, and a nitrogen gas introducing tube, and the temperature was raised to 75° C. Thereafter, while maintaining the temperature inside the flask at 75° C., a mixed solution containing 162.0 g of methyl methacrylate, 126.0 g of isobornylmethacrylate, 50.4 g of “PME-100” (trade name, manufactured by NOF CORPORATION, methoxypolyethyleneglycol methacrylate (n=2)), 21.6 g of methacrylic acid, 72 g of methyl ethyl ketone, and 1.44 g of V-601 (trade name, manufactured by Wako Pure Chemical Ind. Ltd.) was added dropwise at a constant rate so that the dropwise addition was completed in 2 hours. After completion of the dropping, a solution containing 0.72 g of V-601 (described above) and 36.0 g of methyl ethyl ketone was added, and stirred at 75° C. for 2 hours. Further, a solution containing 0.72 g of V-601 (described above) and 36.0 g of methyl ethyl ketone was added, and stirred at 75° C. for 2 hours. Thereafter, the temperature was raised to 85° C., and the stirring was continued for further 2 hours, thereby obtaining a resin solution of a methyl methacrylate/isobornylmethacrylate/PME-100/methacrylic acid (=45/35/14/6 [mass ratio]) copolymer.

Workup

  1. customequipped with a stirrer
  2. additiona thermometer, a reflux condenser tube, and a nitrogen gas introducing tube
  3. temperatureThereafter, while maintaining the temperature inside the flask at 75° C.
  4. additionwas added dropwise at a constant rate so that the dropwise addition
  5. additionwas added
  6. additionwas added
  7. stirringstirred at 75° C. for 2 hours
  8. temperatureThereafter, the temperature was raised to 85° C.
  9. waitthe stirring was continued for further 2 hours

Sources & evidence

ORD record
ord-d6af1df9b59743beb0c7aae675d80aaa
Source dataset
uspto-grants-2013_03
Patent number
US08393724B2

Reaction notes

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