Methyl Methacrylate → HCID 67172764, compound

HRID 2353813Notes

Reaction equation

HRID 2353813 reaction equation
[C:1]([O:6]C)(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16]>COC1C=CC(O)=CC=1.C(N(C(CC)C)C1C=CC(N)=CC=1)(CC)C>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16]

Participants

5

Reactant 2

HCID 6658Methyl MethacrylateHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Product 1

HCID 67172764HCID 67172764, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 14849096N1,N1-Bis(1-methylpropyl)-1,4-benzenediamineCatalyst

Procedure

A 750 ml reactor with Oldershaw column and liquid distributor was initially charged with 280 mg of hydroquinone monomethyl ether (350 ppm), 600 g (6.0 mol) of methyl methacrylate (MMA) and 194 g (1.5 mol) of N-hydroxyethylpyrrolidone, which were stirred at a stirrer speed (anchor stirrer) of 400 rpm and an air supply of 1.5 l/h. Subsequently, 6.37 g (30 mmol; 2.0 mol % based on N-hydroxyethylpyrrolidone) of anhydrous potassium phosphate were added, the vacuum was established (300 mbar) and the suspension was heated (the jacket temperature was adjusted to 120° C. by means of thermostat control). After approx. 20 minutes, the suspension began to boil (t=0 min). During the reaction, distillate was removed continuously (reflux:efflux ratio was 25:1) and the temperature in the bottom rose from approx. 63° C. to 79° C. After 300 min, the reaction was ended and the vacuum was removed. The suspension was cooled and then filtered through a pressure suction filter (30 ml of methyl methacrylate were added to flush the residue). 492 g of crude product were obtained, which were admixed with 200 ppm of N,N-di-sec-butyl-p-phenylenediamine (98 mg) and were distilled with a supply of air. This first removed the excess methyl methacrylate and then afforded the product of value (130° C., 1.3 mbar). 273 g (92%) of N-hydroxyethylpyrrolidone methacrylate (N-(2-(methacryloyl)ethyl)pyrrolidone) were obtained in high purity (GC analysis: 99.6%). The color number was 50 (APHA color number).

Workup

  1. additionSubsequently, 6.37 g (30 mmol; 2.0 mol % based on N-hydroxyethylpyrrolidone) of anhydrous potassium phosphate were added
  2. temperaturethe suspension was heated (the jacket temperature
  3. customwas adjusted to 120° C. by means of thermostat control
  4. custom(t=0 min)
  5. customDuring the reaction, distillate
  6. customwas removed continuously
  7. temperature(reflux:efflux ratio was 25:1)
  8. custombottom rose from approx. 63° C. to 79° C
  9. waitAfter 300 min
  10. customthe vacuum was removed
  11. temperatureThe suspension was cooled
  12. filtrationfiltered through a pressure suction
  13. filtrationfilter (30 ml of methyl methacrylate
  14. additionwere added
  15. customto flush the residue)
  16. custom492 g of crude product were obtained
  17. distillationwere distilled with a supply of air
  18. customThis first removed the excess methyl methacrylate
  19. customafforded the product of value (130° C., 1.3 mbar)

Sources & evidence

ORD record
ord-31ed745506024315bb34799e23adea1c
Source dataset
uspto-grants-2010_07
Patent number
US07750100B2

Reaction notes

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