N-vinyl-2-pyrrolidone → HCID 21583951, compound

HRID 2051439Notes

Reaction equation

HRID 2051439 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[CH:13]([N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20])=[CH2:14].[CH:21]([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=[CH2:22]>O>[CH:21]([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=[CH2:22].[CH:13]([N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20])=[CH2:14]

Participants

5

Reactant 3

HCID 6917N-vinyl-2-pyrrolidoneHCID 24412Potassium PersulfateHCID 661711-Vinylimidazole

Product 1

HCID 21583951HCID 21583951, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

P(NVI-VP) was prepared by charging 1.4 gm of potassium persulfate and 450 ml of water into a 1 liter 3-neck round bottom flask equipped with an addition funnel, mechanical stirrer, condenser, thermometer, and nitrogen purge. The solution was stirred for 30 minutes while being purged with nitrogen and thereafter heated to 60° C. A mixture of 55 gms (0.5 mols) of N-vinylpyrrolidinone (VP) and 47 gms (0.5 mols) of N-vinylimidazole (NVI) was added over 1.25 hours. The reaction temperature was increased to 85° C. for 2 hours, then the mixture was allowed to cool to 25° C. and 1.0 gm. of azoisobutyronitrile (AIBN) was added. The mixture was then reheated to 85° C. and held there for 1 hour before cooling to 25° C. The polymer was precipitated by addition of 1,4 dioxane. After filtering, the polymer was dried overnight under vacuum at 60° C. The yield was 53.6 g of polymer (52.5%), ninh (EtOH, 30° C.)=0.885. The elemental analysis was 62.93% C, 7.31% H, 20.23% N, C/N=3.11. The polymer was calculated to be 47.1 mol.% NVI and 52.9 mol.% VP.

Workup

  1. customequipped with an addition funnel, mechanical stirrer, condenser
  2. customthermometer, and nitrogen purge
  3. customwhile being purged with nitrogen
  4. additionwas added over 1.25 hours
  5. temperatureThe reaction temperature was increased to 85° C. for 2 hours
  6. temperatureto cool to 25° C.
  7. customwas then reheated to 85° C.
  8. waitheld there for 1 hour
  9. temperaturebefore cooling to 25° C
  10. customThe polymer was precipitated by addition of 1,4 dioxane
  11. filtrationAfter filtering
  12. customthe polymer was dried overnight under vacuum at 60° C
  13. customThe yield was 53.6 g of polymer (52.5%), ninh (EtOH, 30° C.)=0.885

Sources & evidence

ORD record
ord-838c1d5c48a54a6b85153586f7e37040
Source dataset
uspto-grants-1991_05
Patent number
US05018380

Reaction notes

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