Methacrylic Acid → Methyl methacrylate isobornyl methacrylate methacrylic acid

HRID 539390Notes

Reaction equation

HRID 539390 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 introduced into a 2-L three-necked flask equipped with a mechanical stirrer, a thermometer, a reflux cooling tube and a nitrogen gas inlet tube, and the temperature of the content was raised to 75° C. While the temperature inside the reaction vessel was maintained at 75° C., a mixed solution containing 216.0 g of methyl methacrylate, 270.0 g of isobornyl methacrylate, 54.0 g of methacrylic acid, 108 g of methyl ethyl ketone, and 2.16 g of “V-601” (trade name, manufactured by Wako Pure Chemical Industries, Ltd.; polymerization initiator), was added dropwise to the reaction vessel at a constant rate so that the dropwise addition was completed in 2 hours. After completion of the dropwise addition, a solution containing 1.08 g of “V-601” and 15.0 g of methyl ethyl ketone was added to the flask, and the mixture was stirred for 2 hours at 75° C. Subsequently, a solution containing 0.54 g of “V-601” and 15.0 g of methyl ethyl ketone was further added to the flask, and the mixture was stirred for 2 hours at 75° C. Subsequently, the mixture was heated to 85° C. and was continuously stirred for another 2 hours. Thus, a resin solution of a methyl methacrylate/isobornyl methacrylate/methacrylic acid (=40/50/10 [mass ratio]) copolymer was obtained.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturea thermometer, a reflux cooling tube and a nitrogen gas inlet tube
  3. temperatureWhile the temperature inside the reaction vessel was maintained at 75° C.
  4. additiona mixed solution containing
  5. additionwas added dropwise to the reaction vessel at a constant rate so that the dropwise addition
  6. additionAfter completion of the dropwise addition
  7. additionwas added to the flask
  8. additionwas further added to the flask
  9. stirringthe mixture was stirred for 2 hours at 75° C
  10. temperatureSubsequently, the mixture was heated to 85° C.
  11. stirringwas continuously stirred for another 2 hours

Sources & evidence

ORD record
ord-86b2f71070bd4e8896855437643e8075
Source dataset
uspto-grants-2014_10
Patent number
US08870339B2

Reaction notes

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