Water → Mono-methoxy diethylene glycol monoacrylate

HRID 344843Notes

Reaction equation

HRID 344843 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].CC1C=CC(S(O)(=O)=[O:22])=CC=1.O>C1(C)C=CC=CC=1>[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].[CH3:1][O:2][CH:3]([OH:22])[CH2:4][O:5][CH2:6][CH2:7][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 8134Diethylene Glycol Monomethyl Ether

Product 1

HCID 87063345Mono-methoxy diethylene glycol monoacrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

682 grams Methyl Carbitol (diethylene glycol monomethyl ether, Union Carbide) were azeotropically esterified with 598.9 grams acrylic acid in 272 grams toluene in the presence of 22.8 grams P-toluenesulfonic acid and inhibitors until no more water was collected. Conditions were 95°-98° C., nitrogen sparge in vacuo. On completion, the product was washed and neutralized with sodium carbonate. 1,300 ppm p-methoxyphenol were added and solvent removed at 80° C. at maximum vacuum with an air sparge. Filter aid was added and the product filtered to clarity at 50° C. The final product was a clear, light yellow liquid, viscosity 6 cps with a Gardner 1 color.

Workup

  1. customwas collected
  2. customwere 95°-98° C.
  3. customnitrogen sparge in vacuo
  4. washOn completion, the product was washed
  5. addition1,300 ppm p-methoxyphenol were added
  6. customsolvent removed at 80° C. at maximum vacuum with an air
  7. customsparge
  8. filtrationFilter aid
  9. additionwas added
  10. filtrationthe product filtered to clarity at 50° C

Sources & evidence

ORD record
ord-eb89a74469d242a68750f562be305a08
Source dataset
uspto-grants-1991_10
Patent number
US05053554

Reaction notes

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