Methacrylic Acid → Methyl methacrylate isobornyl methacrylate methacrylic acid

HRID 2279696Notes

Reaction equation

HRID 2279696 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(O)(C)C.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

7

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 2

HCID 3776IsopropanolSolventHCID 6569Methyl Ethyl KetoneSolvent4×

Conditions

Temperature
87 °C

Procedure

560.0 g of methyl ethyl ketone were placed in a 2 L three-necked flask equipped with a mechanical stirrer, a thermometer, a reflux condenser tube, and a nitrogen gas inlet tube, and heated to a temperature of 87° C. While maintaining the contents inside the reaction vessel in a refluxed state (thereafter, refluxing was continued until the reaction was completed), to this reaction vessel, a mixed solution of 278.4 g of methyl methacrylate, 243.6 g of isobornyl methacrylate, 58.0 g of methacrylic acid, 108 g of methyl ethyl ketone, and 2.32 g of “V-601” (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise at a constant speed so that the dropwise addition was completed in two hours. After the dropwise addition was completed, the resulting mixture was stirred for one hour. Thereafter, a solution of 1.16 g of “V-601” and 6.4 g of methyl ethyl ketone was added and the resulting mixture was stirred for two hours (process (1)). Subsequently, the process (1) was repeated for four times. Then, a solution of 1.16 g of “V-601” and 6.4 g of methyl ethyl ketone was further added, and stirring was continued for 3 hours. After completion of the polymerization reaction, the temperature of the resulting solution was lowered to 65° C. and then, 163.0 g of isopropanol were added thereto and the resulting mixture was cooled while leaving it standing still. In this way, a solution of a methyl methacrylate/isobornyl methacrylate/methacrylic acid copolymer (=48/42/10 [mass ratio]) was obtained.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureWhile maintaining the contents inside the reaction vessel in a refluxed state (thereafter,
  3. temperaturerefluxing
  4. additionAfter the dropwise addition
  5. stirringstirring
  6. waitwas continued for 3 hours
  7. customAfter completion of the polymerization reaction
  8. customwas lowered to 65° C.
  9. temperaturethe resulting mixture was cooled
  10. customwhile leaving it

Sources & evidence

ORD record
ord-d65013e2f54b402395a14c985cfa4ca8
Source dataset
uspto-grants-2015_09
Patent number
US09133359B2

Reaction notes

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