Sulfuric Acid → Glyceryl methacrylate

HRID 722666

Reaction equation

HRID 722666 reaction equation
[CH2:1]([O:5][C:6](=[O:10])[C:7]([CH3:9])=[CH2:8])[CH:2]1[O:4][CH2:3]1.C[O:12]C1C=CC(O)=CC=1.S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O>[C:6]([O:5][CH2:1][CH:2]([CH2:3][OH:12])[OH:4])(=[O:10])[C:7]([CH3:9])=[CH2:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7837Glycidyl methacrylateHCID 90154-MethoxyphenolHCID 24436Sodium Sulfate

Product 1

HCID 65442Glyceryl methacrylateYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a two phase mixture of 86 g (0.6 mol) of comercial glycidylmethacrylate containing 200 ppm of MEHQ and 500 ml of water is added 2 ml of concentrated sulfuric acid at ambient temperature. After stirring approximately 18 hours, the mixture appeared as a clear homogenous solution. To the resultant solution is added sufficient sodium sulfate to cause separation of an oil. The 2 phase mixture is extracted sequentially with 5 portions of 150 ml each of chloroform and the combined chloroform extracts are dried over solid sodium sulfate. After filtering the solid sodium sulfate, the solvent is removed by evaporation to give 77 g (80%) of glycerol mono-methacrylate as a clear colorless oil. The monomer can be used without further purification or can be further purified by chromatography to separate trace amounts of glycerol di-methacrylate.

Workup

  1. customseparation of an oil
  2. extractionThe 2 phase mixture is extracted sequentially with 5 portions of 150 ml each of chloroform
  3. dry with materialthe combined chloroform extracts are dried over solid sodium sulfate
  4. filtrationAfter filtering the solid sodium sulfate
  5. customthe solvent is removed by evaporation

Sources & evidence

ORD record
ord-3c76a2f843a94fe98f011185866b09ce
Source dataset
uspto-grants-2006_11
Patent number
US07138457B2

Linked notes

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