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

HRID 469154Notes

Reaction equation

HRID 469154 reaction equation
[CH2:1]([O:3][CH:4]=[CH2:5])[CH3:2].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[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:1]([O:3][CH2:4][CH3:5])[CH3:2])(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

7

Conditions

Temperature
25 °C

Procedure

In 144.2 parts by weight (2 mol equivalent) of ethylvinyl ether, 0.5 parts by weight of phenothiazine were added. Then, 86.1 parts by weight (1 mol equivalent) of methacrylic acid were added dropwise while cooling the reaction system at 10° C. or less, and the mixture was stirred for 4 hours at room temperature (25° C.). After adding 5.0 parts by weight of pyridinium p-toluenesulfonate, the mixture was stirred for 2 hours at room temperature and allowed to stand overnight at room temperature. To the reaction solution, 5 parts by weight of sodium hydrogen carbonate and 5 parts by weight of sodium sulfate were added, and the mixture was stirred for 1 hour at room temperature. After removing insoluble substances by filtering, the resultant solution was concentrated under reduced pressure at 40° C. or lower. The residue, a yellow oily substance, was distilled under reduced pressure, thereby obtaining a colorless oily substance, i.e., 134.0 parts by weight of 1-ethoxyethyl methacrylate (MAEVE) as a fraction having a boiling point (b.p.) of 43 to 45° C. at 7 mmHg.

Workup

  1. temperaturewhile cooling the reaction system at 10° C. or less
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. waitto stand overnight at room temperature
  4. stirringthe mixture was stirred for 1 hour at room temperature
  5. customAfter removing insoluble substances
  6. filtrationby filtering
  7. concentrationthe resultant solution was concentrated under reduced pressure at 40° C.
  8. distillationThe residue, a yellow oily substance, was distilled under reduced pressure

Sources & evidence

ORD record
ord-04a524dad57441f386aec8bb530611e2
Source dataset
uspto-grants-2014_01
Patent number
US08628907B2

Reaction notes

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