Methacrylic Acid → Methyl methacrylate isobornyl methacrylate methacrylic acid

HRID 627820Notes

Reaction equation

HRID 627820 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

Methyl ethyl ketone (540.0 g) was placed in a 2 L-volume three-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser, and a nitrogen gas introduction tube, and was heated to 75° C. Thereafter, while the temperature inside the flask was maintained at 75° C., a mixture solution of methyl methacrylate (108 g), isobornyl methacrylate (388.8 g), methacrylic acid (43.2 g), methyl ethyl ketone (108 g), and “V-601” (manufactured by Wako Pure Chemical Industries Ltd.) (2.1 g) was added dropwise into the flask (reaction container) at a constant rate such that the dropwise addition was completed in 2 hours. After the dropwise addition was completed, a solution of “V-601” (1.15 g) in methyl ethyl ketone (15.0 g) was added into the flask, and the resultant mixture in the flask stirred at 75° C. for 2 hours. A solution of “V-601” (0.54 g) in methyl ethyl ketone (15.0 g) was further added thereto, and the contents of the flask were stirred at 75° C. for 2 hours. Then, the temperature inside the flask was increased to 85° C., and stirring was continued for another 2 hours, as a result of which a resin solution of methyl methacrylate/isobornyl methacrylate/methacrylic acid (=20/72/8 [mass ratio]) copolymer was obtained.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThereafter, while the temperature inside the flask was maintained at 75° C.
  3. additionAfter the dropwise addition
  4. temperatureThen, the temperature inside the flask was increased to 85° C.
  5. stirringstirring
  6. waitwas continued for another 2 hours

Sources & evidence

ORD record
ord-522d8d11330c499bb9ca07d3a5224d4f
Source dataset
uspto-grants-2016_04
Patent number
US09309422B2

Reaction notes

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