p-Toluenesulfonic acid → 1,6-Hexanediol monomethyl ether acrylate

HRID 5202

Reaction equation

HRID 5202 reaction equation
COC.[CH3:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O.[C:13]([OH:17])(=[O:16])[CH:14]=[CH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[C:13]([O:17][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH3:4])(=[O:16])[CH:14]=[CH2:15]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 8254Dimethyl EtherHCID 126516996-Methoxyhexan-1-ol

Product 1

HCID 146930481,6-Hexanediol monomethyl ether acrylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

803.6 grams of the monomethyl ether described in Part (A) above were azeotropically esterified with 629.8 grams acrylic acid in 254.6 grams toluene in the presence of 24 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. 900 ppm p-methoxyphenol (MEHQ) was added and the solvent removed at 80° C. with maximum vacuum in the presence of an air sparge. Filter aid was added and the product filtered at 60° C. to give a clear, yellow liquid having a viscosity of 6.5 cps and a Gardener color of 3. Equipment used was a 2 liter flask, thermometer, Dean-Stark condenser and sparge tube.

Workup

  1. customwas collected
  2. customwere 95°-98° C.
  3. customnitrogen sparge in vacuo
  4. washOn completion, the product was washed
  5. addition900 ppm p-methoxyphenol (MEHQ) was added
  6. customthe solvent removed at 80° C. with maximum vacuum in the presence of an air
  7. customsparge
  8. filtrationFilter aid
  9. additionwas added
  10. filtrationthe product filtered at 60° C.
  11. customto give a clear, yellow liquid
  12. customthermometer, Dean-Stark condenser and sparge tube

Sources & evidence

ORD record
ord-a9a5f08948ef490a8633b44f5ca2f366
Source dataset
uspto-grants-1993_09
Patent number
US05243085

Linked notes

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