Methacryloyl chloride → Methacrylic Acid

HRID 1939855Notes

Reaction equation

[CH:1]12[CH2:7]C(C=[CH:6]1)C[CH:2]2[OH:8].[C:9](Cl)(=[O:13])[C:10]([CH3:12])=[CH2:11]>>[C:2]([O-:8])(=[O:13])[C:1]([CH3:7])=[CH2:6].[C:9]([OH:13])(=[O:8])[C:10]([CH3:12])=[CH2:11]

Participants

Reactant 2

HCID 13528Methacryloyl chloride

HCID 96066Bicyclo(2.2.1)hept-5-en-2-ol

Product 2

HCID 4093Methacrylic Acid

HCID 87595Methacrylate

Procedure

Methacrylate (36 g) obtained by condensation of 5-norbornene-2-ol and methacrylic acid chloride and 4 g of methacrylic acid were dissolved in 360 g of methyl ethyl ketone, and the solution was heated at 70° C. Then, 0.40 g of 2,2-azobis(2,4-dimethylvaleronitrile) was added thereto, followed by heating reaction for 8 hours. After cooled to room temperature, the resulting reaction solution was slowly added dropwise to 10 liters of water, and precipitated crystals were filtered, washed and dried, thereby obtaining 18.72 g (yield: 46.8%) of a copolymer having an average molecular weight of 56,000 which is composed of 83.3 mol % of repeating unit (III-2) and 16.7 mol % of methacrylic acid.

Sources & evidence

ORD record: ord-14dbe8ed8fcd42e28eb39a03cc87ce29
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698372

Reaction notes

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