N,N-Diethylacrylamide → N,N-diethyl acrylamide N,N-dimethylacrylamide

HRID 931867

Reaction equation

HRID 931867 reaction equation
[CH2:1]([N:3]([CH2:8][CH3:9])[C:4](=[O:7])[CH:5]=[CH2:6])[CH3:2].[CH3:10][N:11]([CH3:16])[C:12](=[O:15])[CH:13]=[CH2:14].N(C(C1NCCN=1)(C)C)=NC(C1NCCN=1)(C)C>>[CH2:1]([N:3]([CH2:8][CH3:9])[C:4](=[O:7])[CH:5]=[CH2:6])[CH3:2].[CH3:10][N:11]([CH3:16])[C:12](=[O:15])[CH:13]=[CH2:14]

Participants

4

Reactant 3

HCID 17583N,N-DiethylacrylamideHCID 17587N,N-DimethylacrylamideHCID 887152,2'-Azobis(2-(2-imidazolin-2-yl)propane)

Product 1

HCID 86674667N,N-diethyl acrylamide N,N-dimethylacrylamide

Procedure

In a 300 mL three-necked flask, N,N-diethyl acrylamide (DEAA, 19.22 g, 0.151 mol), N,N-dimethylacrylamide (DMA, 14.88 g, 0.150 mol), TAA (104.65 g) and a polymerization initiator VA-061 (Wako Pure Chemical Industries, Ltd., 0.0465 g, 0.186 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 25% 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 70° C. for 1.5 hours, followed by temperature rise to 75° C. and further stirring for 3.5 hours. After completion of the polymerization, the polymerization reaction solution was cooled to room temperature and the solvent was distilled off by an evaporator, and then washed once with each of n-hexane/methanol (=500 mL/0 mL, 250 mL/25 mL, 200 mL/30 mL and 200 mL/3 mL). 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: 90 kD, Mw: 327 kD (Mw/Mn=3.7).

Workup

  1. customequipped with a three-way
  2. customAfter degassing inside the three-necked flask
  3. customfollowed by temperature rise to 75° C.
  4. stirringfurther stirring for 3.5 hours
  5. customAfter completion of the polymerization
  6. customthe polymerization reaction solution
  7. distillationthe solvent was distilled off by an evaporator
  8. washwashed once with each of n-hexane/methanol (=500 mL/0 mL, 250 mL/25 mL, 200 mL/30 mL and 200 mL/3 mL)
  9. customThe solid component was dried overnight by a vacuum
  10. customdrying oven at 60° C
  11. additionLiquid nitrogen was charged
  12. customthe solid component was crushed by a spatula
  13. customdried by a vacuum
  14. customdrying oven at 60° C. for 3 hours

Sources & evidence

ORD record
ord-2e2b37e65cdd4fccbec7ba5b8f86e645
Source dataset
uspto-grants-2016_03
Patent number
US09297930B2

Linked notes

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