Methacrylic Acid → Methyl methacrylate isobornyl methacrylate methacrylic acid

HRID 75065

Reaction equation

HRID 75065 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]([OH:29])(=[O:28])[C:25]([CH3:27])=[CH2:26].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

6

Reactant 4

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

Product 1

HCID 131730598Methyl methacrylate isobornyl methacrylate methacrylic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent4×

Conditions

Temperature
75 °C

Procedure

540.0 g of methyl ethyl ketone was put in a 2 L three-neck flask including a mechanical stirrer, a thermometer, a reflux cooling tube, and a nitrogen gas-introducing tube, and the temperature thereof was increased to 75° C. While the internal pressure of the reaction container was being kept at 75° C., a mixed solution including 108 g of methyl methacrylate, 388.8 g of isobornyl methacrylate, 43.2 g of methacrylic acid, 108 g of methyl ethyl ketone, and 2.1 g of “V-601” (trade name, manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise thereto such that the dropwise addition was completed in 2 hours. After the dropwise addition ended, a solution including 1.15 g of “V-601” (described above) and 15.0 g of methyl ethyl ketone was added thereto, followed by stirring for 2 hours at 75° C. In addition, a solution including 0.54 g of “V-601” (described above) and 15.0 g of methyl ethyl ketone was added thereto, followed by stirring for 2 hours at 75° C. Thereafter, the temperature thereof was increased to 85° C. to continue stirring for 2 more hours, thereby obtaining a resin solution of a methyl methacrylate/isobornyl methacrylate/methacrylic acid (=20/72/8 [mass ratio]) copolymer.

Workup

  1. temperaturea thermometer, a reflux cooling tube, and a nitrogen gas-introducing tube
  2. customwas being kept at 75° C.
  3. additionwas added dropwise
  4. additionsuch that the dropwise addition
  5. additionAfter the dropwise addition
  6. additionwas added
  7. additionwas added
  8. stirringby stirring for 2 hours at 75° C
  9. temperatureThereafter, the temperature thereof was increased to 85° C.
  10. stirringto continue stirring for 2 more hours

Sources & evidence

ORD record
ord-93039fb6bd4141769c76244eb64ffeaf
Source dataset
uspto-grants-2014_09
Patent number
US08833918B2

Linked notes

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