Phosgene → 2-Isocyanatoethyl methacrylate

HRID 1277747Notes

Reaction equation

HRID 1277747 reaction equation
[C:1]([C:4]1[O:5][CH2:6][CH2:7][N:8]=1)([CH3:3])=[CH2:2].[C:9](Cl)(Cl)=[O:10].[OH-:13].[Na+]>O.C(Cl)Cl>[C:4]([O:5][CH2:6][CH2:7][N:8]=[C:9]=[O:10])(=[O:13])[C:1]([CH3:3])=[CH2:2]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 826512-Isopropenyl-2-oxazoline

Product 1

HCID 354092-Isocyanatoethyl methacrylateYield 84.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 20 gallon glass-lined jacketed reactor equipped with a recycle line and heat exchanger was charged with 9,979 g of methylene chloride (two gallon) and 11,340 g (3 gallons) of water. The recycle pump was started and the reactor cooled to approximately 0° C. A solution of 2-isopropenyl-2-oxazoline (2,268 g) in 7,598 g of water, a solution of phosgene (2,977 g) in 11,340 g of methylene chloride, and a solution of 35 percent sodium hydroxide (approximately 9,525 g) were added simultaneously to the reactor with stirring and cooling during a time period of approximately 65 minutes. The reaction temperature rose to approximately 16° C. during the course of the addition. Stirring at 116 rpm was continued for an additional 3 minutes. The aqueous and organic layers were allowed to separate and the organic layer recovered. The organic layer was then dried by passing it through 3 angstrom molecular sieves and inhibited with 25 g of phenothiazine and concentrated under reduced pressure. A final vacuum distillation at 46°-47° C./0.4 mm Hg gave 2,681 g of 2-isocyanatoethyl methacrylate for an 84.7 percent yield. In three other duplicate runs, the yields range from 78 percent to the above 84.7 percent yield. This is an average of 82 percent over the 4 runs.

Workup

  1. customequipped with a recycle line
  2. temperatureheat exchanger
  3. temperaturecooling during a time period of approximately 65 minutes
  4. additionThe reaction temperature rose to approximately 16° C. during the course of the addition
  5. stirringStirring at 116 rpm
  6. customto separate
  7. customthe organic layer recovered
  8. customThe organic layer was then dried
  9. concentrationconcentrated under reduced pressure
  10. distillationA final vacuum distillation at 46°-47° C./0.4 mm Hg

Sources & evidence

ORD record
ord-3b885308ba334b768e965e351a3db3cd
Source dataset
uspto-grants-1981_07
Patent number
US04278809

Reaction notes

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