Water → HCID 18935929, compound

HRID 1460851Notes

Reaction equation

HRID 1460851 reaction equation
[C:1]1([O:6][CH:7]([O:10][C:11]2[CH2:15][CH2:14][CH2:13][CH:12]=2)[CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH:2]=1.[C:16](OC)(=[O:20])[C:17]([CH3:19])=[CH2:18].O>[OH-].[Li+].COC1C=CC(O)=CC=1.CO>[C:16]([O:9][CH2:8][CH:7]([O:6][C:1]1[CH2:5][CH2:4][CH2:3][CH:2]=1)[O:10][C:11]1[CH2:15][CH2:14][CH2:13][CH:12]=1)(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

7

Reactant 3

HCID 962Water3×HCID 6658Methyl MethacrylateHCID 57225440HCID 57225440, compound

Product 1

HCID 18935929HCID 18935929, compoundYield 84.7%

Reagents, catalysts & solvents 3

HCID 3939Lithium HydroxideCatalystHCID 90154-MethoxyphenolCatalystHCID 887MethanolSolvent

Procedure

In a 3000-liter reactor equipped with a stirrer, a thermometer, an air introducing pipe, a distillation column and a reflux condenser, 776 kg (4 kmoles) of dicyclopentenyloxyethyl alcohol, and 1200 kg (12 kmoles) of methyl methacrylate were placed and mixed well with stirring. The water content of the resulting mixture was 800 ppm. The water content was measured by using a Karl Fischer type digital microamount water content measuring device (mfd. by Mitsubishi Chemical Industries Ltd.). Subsequently, 3 kg of anhydrous lithium hydroxide as a catalyst and 390 g of hydroquinone monomethyl ether as a polymerization inhibitor were added to the reactor, and the reaction was carried out while introducing dried air at a rate of 4 m3/ hr and refluxing the methyl methacrylate through the distillation column. While removing methanol by-produced by the reaction from the distillation column, the reaction was continued until almost no methanol was distilled (about 8 hours), followed by removal of unreacted methyl methacrylate under reduced pressure. After cooling, the reaction solution was filtered under pressure (5 kg/cm2) using a filter paper (pore size 0.1 mm, area 5 m2) placing thereon 10 kg of diatomaceous earth to yield 943 kg of dicyclopentenyloxyethyl methacrylate. The filtering time was 2.5 hours.

Workup

  1. customIn a 3000-liter reactor equipped with a stirrer
  2. additiona thermometer, an air introducing pipe
  3. additionmixed well
  4. additionwhile introducing
  5. customdried air at a rate of 4 m3/ hr
  6. temperaturerefluxing the methyl methacrylate
  7. distillationthrough the distillation column
  8. customWhile removing methanol
  9. customby-produced by the reaction from the distillation column
  10. distillationwas distilled (about 8 hours)
  11. customfollowed by removal of unreacted methyl methacrylate under reduced pressure
  12. temperatureAfter cooling
  13. filtrationthe reaction solution was filtered under pressure (5 kg/cm2)

Sources & evidence

ORD record
ord-7ec54c50ac684398a89abbd7181b9137
Source dataset
uspto-grants-1991_12
Patent number
US05072027

Reaction notes

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