Methacrylic Acid → 1-Ethoxyethyl Methacrylate (stabilized with MEHQ)

HRID 1025257Notes

Reaction equation

HRID 1025257 reaction equation
C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[CH:15]([O:17][CH2:18][CH3:19])=[CH2:16].[C:20]([OH:25])(=[O:24])[C:21]([CH3:23])=[CH2:22].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>>[C:20]([O:25][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

7

Reactant 6

HCID 4093Methacrylic AcidHCID 7108PhenothiazineHCID 8023Ethyl vinyl etherHCID 24436Sodium SulfateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 201933451-Ethoxyethyl Methacrylate (stabilized with MEHQ)

Procedure

0.5 parts of phenothiazine was added to 144.2 parts (2 molar equivalents) of ethyl vinyl ether, 86.1 parts (1 molar equivalent) of methacrylic acid was added dropwise to the reaction system while cooling to 10° C. or below, and stirring was then carried out at room temperature (25° C.) for 4 hours. 5.0 parts of pyridinium p-toluenesulfonate was added thereto, stirring was then carried out at room temperature for 2 hours, and the mixture was allowed to stand at room temperature overnight. 5 parts of sodium bicarbonate and 5 parts of sodium sulfate were added to the reaction mixture, stirring was carried out at room temperature for 1 hour, insoluble material was filtered, concentration under vacuum was then carried out at no greater than 40° C., and a yellow oily residue was distilled under vacuum, thus giving 134.0 parts of 1-ethoxyethyl methacrylate (MAEVE) as a colorless oily material, this being a fraction with a boiling point (bp.) of 43° C. to 45° C./7 mmHg.

Workup

  1. additionwas added dropwise to the reaction system
  2. temperaturewhile cooling to 10° C. or below
  3. customwas then carried out at room temperature
  4. custom(25° C.)
  5. customfor 4 hours
  6. stirringstirring
  7. waitto stand at room temperature overnight
  8. stirringstirring
  9. waitwas carried out at room temperature for 1 hour
  10. filtrationinsoluble material was filtered
  11. concentrationconcentration under vacuum
  12. customwas then carried out at no greater than 40° C.
  13. distillationa yellow oily residue was distilled under vacuum

Sources & evidence

ORD record
ord-032d3d47ebe343f49cd9e1ef87f6d838
Source dataset
uspto-grants-2014_05
Patent number
US08728708B2

Reaction notes

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