Hydroquinone → Ethylene glycol dimethacrylate

HRID 1452270

Reaction equation

HRID 1452270 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].C([Sn](Cl)(Cl)Cl)[CH2:9][CH2:10][CH3:11].C[O-].[Na+].[CH3:19][O:20][C:21]1C=CC(O)=CC=1.C1(C=CC(O)=CC=1)[OH:29]>CCCCCCC.C(O)CO>[C:1]([O:6][CH2:7][CH2:19][O:20][C:21](=[O:29])[C:10]([CH3:9])=[CH2:11])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 6658Methyl MethacrylateHCID 90154-MethoxyphenolHCID 14236Butyltin trichlorideHCID 10942334Sodium Methoxide

Product 1

HCID 7355Ethylene glycol dimethacrylateYield 93%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8900HeptaneSolvent

Procedure

A mixture of ethylene glycol (62.0 parts), methyl methacrylate (300 parts), heptane (50 parts), butyltin trichloride (7.0 parts), sodium methoxide (5.4 parts, 25% in methanol), 4-methoxyphenol (0.5 parts) and hydroquinone (0.5 parts) was heated as in Example 1. Methanol, heptane, and excess methyl methacrylate were removed from the crude product. To remove the tin catalyst and polymerization inhibitors, the crude product containing approximately 50% solvent was washed twice with 15% sodium hydroxide at 20% of batch weight. After reducing alkalinity by washing the product with a 15% sodium chloride brine solution, the organic layer was concentrated to yield 185 parts (93% yield based on ethylene glycol) of ethylene glycol dimethacrylate (EGDMA). The purity of the final product was greater than 98%. Analysis for residual tin was 160 ppm.

Workup

  1. temperaturewas heated as in Example 1
  2. customMethanol, heptane, and excess methyl methacrylate were removed from the crude product
  3. customTo remove
  4. customthe tin catalyst and polymerization inhibitors
  5. washwas washed twice with 15% sodium hydroxide at 20% of batch weight
  6. washby washing the product with a 15% sodium chloride brine solution
  7. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-c699d8b312b64b27b6ebbad83ba81f1e
Source dataset
uspto-grants-1997_02
Patent number
US05606103

Linked notes

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