Dimethyl Sulfoxide → Acrylic acid hydroxyethyl methacrylate

HRID 2169669Notes

Reaction equation

HRID 2169669 reaction equation
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].CS(C)=O.N(C(C1NCCN=1)(C)C)=NC(C1NCCN=1)(C)C>C(O)C.O>[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6581Acrylic AcidHCID 133602-Hydroxyethyl MethacrylateHCID 887152,2'-Azobis(2-(2-imidazolin-2-yl)propane)

Product 1

HCID 10330472Acrylic acid hydroxyethyl methacrylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 200 mL three-necked flask, 2-hydroxyethyl methacrylate (HEMA, 11.4 g, 0.10 mol), acrylic acid (AA, 7.21 g, 0.10 mol), dimethyl sulfoxide (74.5 g) and a polymerization initiator VA-061 (Wako Pure Chemical Industries, Ltd., 0.016 g, 0.062 mmol) were charged, and then equipped with a three-way stop-cock, a reflux condenser tube, a thermometer and a mechanical stirrer. The concentration of the monomer was 20% by weight. After degassing inside the three-necked flask using a vacuum pump and repeating replacement by argon three times, stirring was carried out at 60° C. for 0.5 hours, followed by temperature rise to 70° C. and further stirring for 6.5 hours. After completion of the polymerization, the polymerization reaction solution was cooled to room temperature, and then the mixed solution was poured into water (1,000 mL)/ethanol (10 mL) and left to stand overnight. On the next day, the supernatant was discarded and the obtained solid component was further washed twice with 700 mL of water. The solid component was dried overnight by a vacuum drying oven at 60° C. Liquid nitrogen was charged and the solid component was crushed by a spatula, and then dried by a vacuum drying oven at 60° C. for 3 hours. The thus obtained copolymer had a molecular weight of Mn: 79 kD, Mw: 226 kD (Mw/Mn=2.9).

Workup

  1. customequipped with a three-way
  2. customAfter degassing inside the three-necked flask
  3. customfollowed by temperature rise to 70° C.
  4. stirringfurther stirring for 6.5 hours
  5. customAfter completion of the polymerization
  6. customthe polymerization reaction solution
  7. waitleft
  8. waitto stand overnight
  9. washthe obtained solid component was further washed twice with 700 mL of water
  10. customThe solid component was dried overnight by a vacuum
  11. customdrying oven at 60° C
  12. additionLiquid nitrogen was charged
  13. customthe solid component was crushed by a spatula
  14. customdried by a vacuum
  15. customdrying oven at 60° C. for 3 hours

Sources & evidence

ORD record
ord-6cd8b276fc7548c491fadd1953260db1
Source dataset
uspto-grants-2015_06
Patent number
US09046644B2

Reaction notes

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